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Volumn 17, Issue 7, 2004, Pages 839-856

Biologically relevant chemical reactions of M-alkylguanine residues in DNA

Author keywords

[No Author keywords available]

Indexed keywords

DNA; DOUBLE STRANDED DNA; GUANINE DERIVATIVE; IMIDAZOLE DERIVATIVE; MONOMER; NUCLEOSIDE; SINGLE STRANDED DNA;

EID: 3242727654     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx049965c     Document Type: Review
Times cited : (224)

References (198)
  • 1
    • 0019598899 scopus 로고
    • Molecular electrostatic potential of the nucleic acids
    • Pullman, A., and Pullman, B. (1981) Molecular electrostatic potential of the nucleic acids. Q. Rev. Biophys. 14, 289-380.
    • (1981) Q. Rev. Biophys. , vol.14 , pp. 289-380
    • Pullman, A.1    Pullman, B.2
  • 2
    • 0018358626 scopus 로고
    • N-nitroso alkylating agents: Formation and persistence of alkyl derivatives in mammalian nucleic acids as contributing factors in carcinogenesis
    • Singer, B. (1979) N-nitroso alkylating agents: formation and persistence of alkyl derivatives in mammalian nucleic acids as contributing factors in carcinogenesis. J. Natl. Cancer. Inst. 62, 1329-1339.
    • (1979) J. Natl. Cancer. Inst. , vol.62 , pp. 1329-1339
    • Singer, B.1
  • 3
    • 0016412950 scopus 로고
    • The chemical effects of nucleic acid alkylation and their relationship to mutagenesis and carcinogenesis
    • Singer, B. (1975) The chemical effects of nucleic acid alkylation and their relationship to mutagenesis and carcinogenesis. Prog. Nucleic Acid Res. Mol. Biol. 15, 219-284.
    • (1975) Prog. Nucleic Acid Res. Mol. Biol. , vol.15 , pp. 219-284
    • Singer, B.1
  • 5
    • 0025288239 scopus 로고
    • Distribution of methyl and ethyl adducts following alkylation with monofunctional alkylating agents
    • Beranek, D. T. (1990) Distribution of methyl and ethyl adducts following alkylation with monofunctional alkylating agents. Mutat. Res. 231, 11-30.
    • (1990) Mutat. Res. , vol.231 , pp. 11-30
    • Beranek, D.T.1
  • 6
    • 0030591663 scopus 로고    scopus 로고
    • DNA adducts from chemotherapeutic agents
    • Lawley, P. D. (1996) DNA adducts from chemotherapeutic agents. Mutat. Res. 355, 13-40.
    • (1996) Mutat. Res. , vol.355 , pp. 13-40
    • Lawley, P.D.1
  • 7
    • 0026673948 scopus 로고
    • Relevance of urinary DNA adducts as markers of carcinogen exposure
    • Shuker, D. E. G., and Farmer, P. B. (1992) Relevance of urinary DNA adducts as markers of carcinogen exposure. Chem. Res. Toxicol. 5, 450-460.
    • (1992) Chem. Res. Toxicol. , vol.5 , pp. 450-460
    • Shuker, D.E.G.1    Farmer, P.B.2
  • 9
    • 0027493111 scopus 로고
    • Endogenous DNA adducts: Potential and paradox
    • Marnett, L. J., and Burcham, P. C. (1993) Endogenous DNA adducts: potential and paradox. Chem. Res. Toxicol. 6, 771-785.
    • (1993) Chem. Res. Toxicol. , vol.6 , pp. 771-785
    • Marnett, L.J.1    Burcham, P.C.2
  • 10
    • 0033711931 scopus 로고    scopus 로고
    • 1 adduct by the exonuclease deficient Klenow fragment of DNA polymerase I
    • 1 adduct by the exonuclease deficient Klenow fragment of DNA polymerase I. Chem. Res. Toxicol. 13, 1158-1164.
    • (2000) Chem. Res. Toxicol. , vol.13 , pp. 1158-1164
    • Johnston, D.S.1    Stone, M.P.2
  • 11
    • 0035067203 scopus 로고    scopus 로고
    • The chemistry and biology of aflatoxin B: From mutational spectrometry to carcinogenesis
    • Smela, M. E., Currier, S. S., Bailey, E. A., and Essigmann, J. M. (2001) The chemistry and biology of aflatoxin B: from mutational spectrometry to carcinogenesis. Carcinogenesis 22, 535-545.
    • (2001) Carcinogenesis , vol.22 , pp. 535-545
    • Smela, M.E.1    Currier, S.S.2    Bailey, E.A.3    Essigmann, J.M.4
  • 12
  • 13
    • 0000167527 scopus 로고    scopus 로고
    • Pluramycins. Old drugs having modern friends in structural biology
    • Hansen, M. R., and Hurley, L. H. (1996) Pluramycins. Old drugs having modern friends in structural biology. Acc. Chem. Res. 29, 249-258.
    • (1996) Acc. Chem. Res. , vol.29 , pp. 249-258
    • Hansen, M.R.1    Hurley, L.H.2
  • 14
    • 0037015442 scopus 로고    scopus 로고
    • Role of the azinomycin naphthoate and central amide in sequence-dependent DNA alkylation and cytotoxicity of epoxide-bearing substructures
    • Coleman, R. S., Burk, C. H., Navarro, A., Brueggemeier, R. W., and Diaz-Cruz, E. S. (2002) Role of the azinomycin naphthoate and central amide in sequence-dependent DNA alkylation and cytotoxicity of epoxide-bearing substructures. Org. Lett. 4, 3545-3548.
    • (2002) Org. Lett. , vol.4 , pp. 3545-3548
    • Coleman, R.S.1    Burk, C.H.2    Navarro, A.3    Brueggemeier, R.W.4    Diaz-Cruz, E.S.5
  • 15
    • 0034596974 scopus 로고    scopus 로고
    • A synthetic azinomycin analogue with demonstrated DNA cross-linking activity: Insights into the mechanism of action of this class of antitumor agent
    • Hartley, J. A., Hazrati, A., Kelland, L. R., Khanim, R., Shipman, M., Suzenet, F., and Walker, L. F. (2000) A synthetic azinomycin analogue with demonstrated DNA cross-linking activity: insights into the mechanism of action of this class of antitumor agent. Angew. Chem., Int. Ed. 39, 3467-3470.
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 3467-3470
    • Hartley, J.A.1    Hazrati, A.2    Kelland, L.R.3    Khanim, R.4    Shipman, M.5    Suzenet, F.6    Walker, L.F.7
  • 17
    • 1842691080 scopus 로고    scopus 로고
    • S-(2-Chloroethyl)-glutathione-generated p53 mutation spectra are influenced by differential repair rates more than sites of initial DNA damage
    • Valadez, J. G., and Guengerich, F. P. (2004) S-(2-Chloroethyl)- glutathione-generated p53 mutation spectra are influenced by differential repair rates more than sites of initial DNA damage. J. Biol. Chem. 279, 13435-13446.
    • (2004) J. Biol. Chem. , vol.279 , pp. 13435-13446
    • Valadez, J.G.1    Guengerich, F.P.2
  • 19
    • 0025572690 scopus 로고
    • Induction of G-C to A-T transitions by the acridine half-mustard ICR-191 supports a mispairing mechanism for mutagenesis by some bulky mutagens
    • Sahasrabudhe, S. R., Luo, X., and Humayun, M. Z. (1990) Induction of G-C to A-T transitions by the acridine half-mustard ICR-191 supports a mispairing mechanism for mutagenesis by some bulky mutagens. Biochemistry 29, 10899-10905.
    • (1990) Biochemistry , vol.29 , pp. 10899-10905
    • Sahasrabudhe, S.R.1    Luo, X.2    Humayun, M.Z.3
  • 20
    • 0033791629 scopus 로고    scopus 로고
    • Mechanisms of DNA damage by leinamycin
    • Gates, K. S. (2000) Mechanisms of DNA damage by leinamycin. Chem. Res. Toxicol. 13, 953-956.
    • (2000) Chem. Res. Toxicol. , vol.13 , pp. 953-956
    • Gates, K.S.1
  • 21
    • 3242732998 scopus 로고    scopus 로고
    • Chemical properties of the leinamycin-guanine adduct in DNA
    • Nooner, T., Dutta, S., and Gates, K. S. (2004) Chemical properties of the leinamycin-guanine adduct in DNA. Chem. Res. Toxicol. 17, 942-949.
    • (2004) Chem. Res. Toxicol. , vol.17 , pp. 942-949
    • Nooner, T.1    Dutta, S.2    Gates, K.S.3
  • 22
    • 0345724295 scopus 로고
    • Action of alkylating agents on deoxyribonucleic acid and guanylic acid
    • Lawley, P. D., and Wallick, C. A. (1957) Action of alkylating agents on deoxyribonucleic acid and guanylic acid. Chem. Ind. (London) 633.
    • (1957) Chem. Ind. (London) , pp. 633
    • Lawley, P.D.1    Wallick, C.A.2
  • 23
    • 3242740612 scopus 로고
    • Studies on the chemically reactive groups in deoribonucleic acid
    • Reiner, B., and Zamenhof, S. (1957) Studies on the chemically reactive groups in deoribonucleic acid. J. Biol. Chem. 228, 475-486.
    • (1957) J. Biol. Chem. , vol.228 , pp. 475-486
    • Reiner, B.1    Zamenhof, S.2
  • 26
    • 0030780379 scopus 로고    scopus 로고
    • Two new puriniums and three new pyrimidines from Heterostemma brownii
    • Lin, Y.-L., Huang, R.-L., Chang, C.-M., and Kuo, Y.-H. (1997) Two new puriniums and three new pyrimidines from Heterostemma brownii. J. Nat. Prod. 60, 982-985.
    • (1997) J. Nat. Prod. , vol.60 , pp. 982-985
    • Lin, Y.-L.1    Huang, R.-L.2    Chang, C.-M.3    Kuo, Y.-H.4
  • 27
    • 3242720003 scopus 로고
    • Constitution of herbipoline, a new purine base of animal origin
    • Ackermann, D., and List, P. H. (1957) Constitution of herbipoline, a new purine base of animal origin. Naturwissenschaften 44, 513-514.
    • (1957) Naturwissenschaften , vol.44 , pp. 513-514
    • Ackermann, D.1    List, P.H.2
  • 28
    • 78651135051 scopus 로고
    • Further studies on the alkylation of nucleic acids and their constituent nucleotides
    • Lawley, P. D., and Brookes, P. (1963) Further studies on the alkylation of nucleic acids and their constituent nucleotides. Biochem. J. 89, 127-138.
    • (1963) Biochem. J. , vol.89 , pp. 127-138
    • Lawley, P.D.1    Brookes, P.2
  • 29
    • 3242700929 scopus 로고
    • Synthesis of a purine ribonucleoside thiobetaine, 7-methyl-6- thioguanosine
    • Broom, A. D., and Robins, R. K. (1964) Synthesis of a purine ribonucleoside thiobetaine, 7-methyl-6-thioguanosine. J. Heterocycl. Chem. 1, 113-114.
    • (1964) J. Heterocycl. Chem. , vol.1 , pp. 113-114
    • Broom, A.D.1    Robins, R.K.2
  • 30
    • 0014956982 scopus 로고
    • Extreme lability of the C-8 proton: A consequence of 7-methylation of guanine residues in model compounds and in DNA and its analytical application
    • Tomasz, M. (1970) Extreme lability of the C-8 proton: a consequence of 7-methylation of guanine residues in model compounds and in DNA and its analytical application. Biochim. Biophys. Acta 199, 18-28.
    • (1970) Biochim. Biophys. Acta , vol.199 , pp. 18-28
    • Tomasz, M.1
  • 31
    • 0015526720 scopus 로고
    • Mechanism of the isotopic exchange of the C-8 hydrogen of purines in nucleosides and deoxyribonucleic acid
    • Tomasz, M., Olson, J., and Mercado, C. M. (1972) Mechanism of the isotopic exchange of the C-8 hydrogen of purines in nucleosides and deoxyribonucleic acid. Biochemistry 11, 1235-1241.
    • (1972) Biochemistry , vol.11 , pp. 1235-1241
    • Tomasz, M.1    Olson, J.2    Mercado, C.M.3
  • 33
    • 0035023205 scopus 로고    scopus 로고
    • Characterization of nucleoside and DNA adducts formed by S-(1-acetoxymethyl)-glutathione and implications for dihalomethane-glutathione conjugates
    • Marsch, G. A., Mundkowski, R. G., Morris, B. J., Manier, M. L., Hartman, M. K., and Guengerich, F. P. (2001) Characterization of nucleoside and DNA adducts formed by S-(1-acetoxymethyl)-glutathione and implications for dihalomethane-glutathione conjugates. Chem. Res. Toxicol. 14, 600-608.
    • (2001) Chem. Res. Toxicol. , vol.14 , pp. 600-608
    • Marsch, G.A.1    Mundkowski, R.G.2    Morris, B.J.3    Manier, M.L.4    Hartman, M.K.5    Guengerich, F.P.6
  • 35
    • 0032723198 scopus 로고    scopus 로고
    • Looking for stable carbenes: The difficulty in starting anew
    • Arduengo, A. J. (1999) Looking for stable carbenes: the difficulty in starting anew. Acc. Chem. Res. 32, 913-921.
    • (1999) Acc. Chem. Res. , vol.32 , pp. 913-921
    • Arduengo, A.J.1
  • 36
    • 0007069262 scopus 로고
    • 13C-H coupling constants. Evidence for stabilization of heterocyclic ylides by sulfur
    • 13C-H coupling constants. Evidence for stabilization of heterocyclic ylides by sulfur. J. Am. Chem. Soc. 91, 1113-1119.
    • (1969) J. Am. Chem. Soc. , vol.91 , pp. 1113-1119
    • Haake, P.1    Bausher, L.P.2    Miller, W.B.3
  • 38
    • 0008355413 scopus 로고
    • Thiazolium C(2)-proton exchange: General-base catalysis, direct proton transfer, and acid inhibition
    • Washabaugh, M. W., and Jencks, W. P. (1989) Thiazolium C(2)-proton exchange: general-base catalysis, direct proton transfer, and acid inhibition. J. Am. Chem. Soc. 111, 674-683.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 674-683
    • Washabaugh, M.W.1    Jencks, W.P.2
  • 39
    • 3142640259 scopus 로고
    • Mechanism of thiamine action. IV. Evidence from studies on model systems
    • Breslow, R. (1958) Mechanism of thiamine action. IV. Evidence from studies on model systems. J. Am. Chem. Soc. 80, 3719-3726.
    • (1958) J. Am. Chem. Soc. , vol.80 , pp. 3719-3726
    • Breslow, R.1
  • 40
    • 0014937072 scopus 로고
    • Novel assay of 7-alkylation of guanine residues in DNA. Application to nitrogen mustard, triethyleneamind and mitomycin C
    • Tomasz, M. (1970) Novel assay of 7-alkylation of guanine residues in DNA. Application to nitrogen mustard, triethyleneamind and mitomycin C. Biochim. Biophys. Acta 213, 288-295.
    • (1970) Biochim. Biophys. Acta , vol.213 , pp. 288-295
    • Tomasz, M.1
  • 41
    • 0016297364 scopus 로고
    • The reaction of anthramycin with DNA. II. Studies of kinetics and mechanism
    • Kohn, K. W., Glaubiger, D., and Spears, C. L. (1974) The reaction of anthramycin with DNA. II. Studies of kinetics and mechanism. Biochim. Biophys. Acta 361, 288-302.
    • (1974) Biochim. Biophys. Acta , vol.361 , pp. 288-302
    • Kohn, K.W.1    Glaubiger, D.2    Spears, C.L.3
  • 42
    • 0019394787 scopus 로고
    • PBD antibiotics. Proposed structures and characteristics of the in vitro DNA adducts of anthramycin, tomaymycin, sibiromycin and neothramycins A and B
    • Petrusek, R. L., Anderson, G. L., Garner, T. F., Quinton, F. L., Fannin, L., Kaplan, D. J., Zimmer, S. G., and Hurley, L. H. (1981) PBD antibiotics. Proposed structures and characteristics of the in vitro DNA adducts of anthramycin, tomaymycin, sibiromycin and neothramycins A and B. Biochemistry 20, 1111-1119.
    • (1981) Biochemistry , vol.20 , pp. 1111-1119
    • Petrusek, R.L.1    Anderson, G.L.2    Garner, T.F.3    Quinton, F.L.4    Fannin, L.5    Kaplan, D.J.6    Zimmer, S.G.7    Hurley, L.H.8
  • 43
    • 0026615736 scopus 로고
    • 3H]-guanine-labeled deoxyribonucleic acid to study alkylating agent reaction kinetics and stability
    • 3H]-guanine-labeled deoxyribonucleic acid to study alkylating agent reaction kinetics and stability. Anal. Biochem. 206, 161-167.
    • (1992) Anal. Biochem. , vol.206 , pp. 161-167
    • Mattes, W.B.1
  • 46
    • 0030037074 scopus 로고    scopus 로고
    • Molecular details of the structure of a psorospermin-DNA covalent/intercalation complex and associated sequence selectivity
    • Hansen, M., Lee, S.-J., Cassady, J. M., and Hurley, L. H. (1996) Molecular details of the structure of a psorospermin-DNA covalent/intercalation complex and associated sequence selectivity. J. Am. Chem. Soc. 118, 5553-5561.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 5553-5561
    • Hansen, M.1    Lee, S.-J.2    Cassady, J.M.3    Hurley, L.H.4
  • 47
    • 37049053144 scopus 로고
    • The alkylation of guanine and guanylic acid
    • Brookes, P., and Lawley, P. D. (1961) The alkylation of guanine and guanylic acid. J. Chem. Soc. 3923-3928.
    • (1961) J. Chem. Soc. , pp. 3923-3928
    • Brookes, P.1    Lawley, P.D.2
  • 48
    • 0014944029 scopus 로고
    • Synthesis and chemical properties of monomers and polymer containing 7-methylguanine and an investigation of their substrate or template properties form bacterial deoxyribonucleic acid or ribonucleic acid polymerases
    • Hendler, S., Furer, E., and Srinivasan, P. R. (1970) Synthesis and chemical properties of monomers and polymer containing 7-methylguanine and an investigation of their substrate or template properties form bacterial deoxyribonucleic acid or ribonucleic acid polymerases. Biochemistry 9, 4141-4153.
    • (1970) Biochemistry , vol.9 , pp. 4141-4153
    • Hendler, S.1    Furer, E.2    Srinivasan, P.R.3
  • 49
    • 0028122670 scopus 로고
    • Spectroscopic and thermodynamic characterization of the interaction of N7-guanyl thioether derivatives of d(TGCTG*CAAG) with potential complements
    • Persmark, M., and Guengerich, F. P. (1994) Spectroscopic and thermodynamic characterization of the interaction of N7-guanyl thioether derivatives of d(TGCTG*CAAG) with potential complements. Biochemistry 33, 8662-8672.
    • (1994) Biochemistry , vol.33 , pp. 8662-8672
    • Persmark, M.1    Guengerich, F.P.2
  • 50
    • 0036019716 scopus 로고    scopus 로고
    • Comparison of the acid-base properties of purine derivatives in aqueous solution. Determination of intrinsic proton affinities of various basic sites
    • Kampf, G., Kapinos, L. E., Griesser, R., Lippert, B., and Sigel, H. (2002) Comparison of the acid-base properties of purine derivatives in aqueous solution. Determination of intrinsic proton affinities of various basic sites. J. Chem. Soc. Perkin Trans. 2, 1320-1327.
    • (2002) J. Chem. Soc. Perkin Trans. , vol.2 , pp. 1320-1327
    • Kampf, G.1    Kapinos, L.E.2    Griesser, R.3    Lippert, B.4    Sigel, H.5
  • 51
    • 0003875539 scopus 로고
    • (Lister, J. H., Ed.) Purines, Wiley-Interscience, New York
    • Lawley, P. D. (1971) In The Chemistry of Heterocyclic Compounds (Lister, J. H., Ed.) Vol. Purines, pp 439-528, Wiley-Interscience, New York.
    • (1971) The Chemistry of Heterocyclic Compounds , pp. 439-528
    • Lawley, P.D.1
  • 52
    • 34548290664 scopus 로고
    • Acidic dissociation of 7,9-dialkylguanines and its possible relation to mutagenic properties of alkylating agents
    • Lawley, P. D., and Brookes, P. (1961) Acidic dissociation of 7,9-dialkylguanines and its possible relation to mutagenic properties of alkylating agents. Nature 192, 1081-1082.
    • (1961) Nature , vol.192 , pp. 1081-1082
    • Lawley, P.D.1    Brookes, P.2
  • 53
    • 0023154067 scopus 로고
    • DNA base modification: Ionized base pairs and mutagenesis
    • Sowers, L. C., Shaw, B. R., Veigl, M. L., and Sedwick, W. D. (1987) DNA base modification: ionized base pairs and mutagenesis. Mutat. Res. 177, 201-218.
    • (1987) Mutat. Res. , vol.177 , pp. 201-218
    • Sowers, L.C.1    Shaw, B.R.2    Veigl, M.L.3    Sedwick, W.D.4
  • 54
    • 0029789765 scopus 로고    scopus 로고
    • Self-complimentarity of 7,9-dimethylguanine: A base pair containing three hydrogen bonds
    • Metzger, S., and Lippert, B. (1996) Self-complimentarity of 7,9-dimethylguanine: A base pair containing three hydrogen bonds. Angew. Chem., Int. Ed. Engl. 35, 1228-1229.
    • (1996) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 1228-1229
    • Metzger, S.1    Lippert, B.2
  • 55
    • 0024797864 scopus 로고
    • Formation of acyclic and cyclic guanine adducts in DNA reacted with a-acetoxy-N-nitrosopyrrolidine
    • Wang, M., Chung, F.-L., and Hecht, S. S. (1989) Formation of acyclic and cyclic guanine adducts in DNA reacted with a-acetoxy-N-nitrosopyrrolidine. Chem. Res. Toxicol. 2, 423-428.
    • (1989) Chem. Res. Toxicol. , vol.2 , pp. 423-428
    • Wang, M.1    Chung, F.-L.2    Hecht, S.S.3
  • 56
    • 0030610333 scopus 로고    scopus 로고
    • A cyclic N7, C-8 guanine adduct of N-nitrosopyrrolidine (NPYR): Formation in nucleic acids and excretion in the urine of NPYR-treated rats
    • Wang, M., and Hecht, S. S. (1997) A cyclic N7, C-8 guanine adduct of N-nitrosopyrrolidine (NPYR): formation in nucleic acids and excretion in the urine of NPYR-treated rats. Chem. Res. Toxicol. 10, 772-778.
    • (1997) Chem. Res. Toxicol. , vol.10 , pp. 772-778
    • Wang, M.1    Hecht, S.S.2
  • 58
    • 0018620965 scopus 로고
    • DNA glycosylases, endonucleases for apurinic/apyridinic sites, and base excision repair
    • Lindahl, T. (1979) DNA glycosylases, endonucleases for apurinic/apyridinic sites, and base excision repair. Prog. Nucleic Acids Res. Mol. Biol. 22, 135-192.
    • (1979) Prog. Nucleic Acids Res. Mol. Biol. , vol.22 , pp. 135-192
    • Lindahl, T.1
  • 59
    • 0015504248 scopus 로고
    • Rate of depurination of native deoxyribonucleic acid
    • Lindahl, T., and Nyberg, B. (1972) Rate of depurination of native deoxyribonucleic acid. Biochemistry 11, 3610-3618.
    • (1972) Biochemistry , vol.11 , pp. 3610-3618
    • Lindahl, T.1    Nyberg, B.2
  • 60
    • 0015753524 scopus 로고
    • Heat-induced depyrimidination of deoxyribonucleic acid in solution
    • Lindahl, T., and Karlstrom, O. (1973) Heat-induced depyrimidination of deoxyribonucleic acid in solution. Biochemistry 12, 5151-5154.
    • (1973) Biochemistry , vol.12 , pp. 5151-5154
    • Lindahl, T.1    Karlstrom, O.2
  • 61
    • 0001639581 scopus 로고
    • Studies on depurination of DNA by heat
    • Greer, S., and Zamenhof, S. (1962) Studies on depurination of DNA by heat. J. Mol. Biol. 4, 123-141.
    • (1962) J. Mol. Biol. , vol.4 , pp. 123-141
    • Greer, S.1    Zamenhof, S.2
  • 62
    • 0015493356 scopus 로고
    • Acidic hydrolysis of deoxycytidine and deoxyuridine derivatives. The general mechanism of deoxyribonucleoside hydrolysis
    • Shapiro, R., and Danzig, M. (1972) Acidic hydrolysis of deoxycytidine and deoxyuridine derivatives. The general mechanism of deoxyribonucleoside hydrolysis. Biochemistry 11, 23-29.
    • (1972) Biochemistry , vol.11 , pp. 23-29
    • Shapiro, R.1    Danzig, M.2
  • 63
    • 0028557428 scopus 로고
    • Mechanistic studies on depurination and apurinic chain breakage in oligodeoxyribonucleotides
    • Suzuki, T., Ohsumi, S., and Makino, K. (1994) Mechanistic studies on depurination and apurinic chain breakage in oligodeoxyribonucleotides. Nucleic Acids Res. 22, 4997-5003.
    • (1994) Nucleic Acids Res. , vol.22 , pp. 4997-5003
    • Suzuki, T.1    Ohsumi, S.2    Makino, K.3
  • 64
    • 0017194965 scopus 로고
    • RNA double-helical fragments at atomic resolution. II. The crystal structure of sodium guanylyl-3′,5′-cytidine nonahydrate
    • Rosenberg, J. M., Seeman, N. C., Day, R. O., and Rich, A. (1976) RNA double-helical fragments at atomic resolution. II. The crystal structure of sodium guanylyl-3′,5′-cytidine nonahydrate. J. Mol. Biol. 104, 145-167.
    • (1976) J. Mol. Biol. , vol.104 , pp. 145-167
    • Rosenberg, J.M.1    Seeman, N.C.2    Day, R.O.3    Rich, A.4
  • 65
    • 0014961477 scopus 로고
    • Kinetics and mechanism of acid-catalyzed hydrolysis of some purine nucleosides
    • Zoltewicz, J. A., Clark, D. F., Sharpless, T. W., and Grahe, G. (1970) Kinetics and mechanism of acid-catalyzed hydrolysis of some purine nucleosides. J. Am. Chem. Soc. 92, 1741-1750.
    • (1970) J. Am. Chem. Soc. , vol.92 , pp. 1741-1750
    • Zoltewicz, J.A.1    Clark, D.F.2    Sharpless, T.W.3    Grahe, G.4
  • 66
    • 0015527189 scopus 로고
    • Contribution to the mechanism of the acid-catalyzed hydrolysis of purine nucleosides
    • Hevesi, L., Wolfson-Davidson, E., Nagy, J. B., Nagy, O. B., and Bruylants, A. (1972) Contribution to the mechanism of the acid-catalyzed hydrolysis of purine nucleosides. J. Am. Chem. Soc. 94, 4715-4720.
    • (1972) J. Am. Chem. Soc. , vol.94 , pp. 4715-4720
    • Hevesi, L.1    Wolfson-Davidson, E.2    Nagy, J.B.3    Nagy, O.B.4    Bruylants, A.5
  • 67
    • 0015518292 scopus 로고
    • Kinetics and mechanism of the hydrolysis of guanosine and 7-methylguanosine nucleosides in perchloric acid
    • Zoltewicz, J. A., and Clark, D. F. (1972) Kinetics and mechanism of the hydrolysis of guanosine and 7-methylguanosine nucleosides in perchloric acid. J. Org. Chem. 37, 1193-1197.
    • (1972) J. Org. Chem. , vol.37 , pp. 1193-1197
    • Zoltewicz, J.A.1    Clark, D.F.2
  • 68
    • 33845185675 scopus 로고
    • IUPAC recommendations for the representation of reaction mechanisms
    • Guthrie, R. D., and Jencks, W. P. (1989) IUPAC recommendations for the representation of reaction mechanisms. Acc. Chem. Res. 22, 343-349.
    • (1989) Acc. Chem. Res. , vol.22 , pp. 343-349
    • Guthrie, R.D.1    Jencks, W.P.2
  • 69
    • 0023015325 scopus 로고
    • Mutagenesis by apurinic/apyrimidinic sites
    • Loeb, L. A., and Preston, B. D. (1986) Mutagenesis by apurinic/apyrimidinic sites. Annu. Rev. Genet. 20, 201-230.
    • (1986) Annu. Rev. Genet. , vol.20 , pp. 201-230
    • Loeb, L.A.1    Preston, B.D.2
  • 72
    • 0015504253 scopus 로고
    • Rate of chain breakage at apurinic sites in double-stranded deoxyribonucleic acid
    • Lindahl, T., and Andersson, A. (1972) Rate of chain breakage at apurinic sites in double-stranded deoxyribonucleic acid. Biochemistry 11, 3618-3623.
    • (1972) Biochemistry , vol.11 , pp. 3618-3623
    • Lindahl, T.1    Andersson, A.2
  • 73
    • 0017169898 scopus 로고
    • A study of DNA spontaneous degradation
    • Crine, P., and Verly, W. G. (1976) A study of DNA spontaneous degradation. Biochim. Biophys. Acta 442, 50-57.
    • (1976) Biochim. Biophys. Acta , vol.442 , pp. 50-57
    • Crine, P.1    Verly, W.G.2
  • 74
    • 0028104053 scopus 로고
    • Chemistry of thermal degradation of abasic sites in DNA. Mechanistic investigation on thermal DNA strand cleavage of alkylated DNA
    • Sugiyama, H., Fujiwara, T., Ura, A., Tashiro, T., Yamamoto, K., Kawanishi, S., and Saito, I. (1994) Chemistry of thermal degradation of abasic sites in DNA. mechanistic investigation on thermal DNA strand cleavage of alkylated DNA. Chem. Res. Toxicol. 7, 673-683.
    • (1994) Chem. Res. Toxicol. , vol.7 , pp. 673-683
    • Sugiyama, H.1    Fujiwara, T.2    Ura, A.3    Tashiro, T.4    Yamamoto, K.5    Kawanishi, S.6    Saito, I.7
  • 75
    • 0028997295 scopus 로고
    • Novel reagents for chemical cleavage at abasic sites and UV photoproducts in DNA
    • McHugh, P. J., and Knowland, J. (1995) Novel reagents for chemical cleavage at abasic sites and UV photoproducts in DNA. Nucleic Acids Res. 23, 1664-1670.
    • (1995) Nucleic Acids Res. , vol.23 , pp. 1664-1670
    • McHugh, P.J.1    Knowland, J.2
  • 76
    • 0018846636 scopus 로고
    • Sequencing end-labeled DNA with base-specific chemical cleavages
    • Maxam, A. M., and Gilbert, W. (1980) Sequencing end-labeled DNA with base-specific chemical cleavages. Methods Enzymol. 65, 499-560.
    • (1980) Methods Enzymol. , vol.65 , pp. 499-560
    • Maxam, A.M.1    Gilbert, W.2
  • 77
    • 0022521735 scopus 로고
    • Mechanism of DNA strand breakage by piperidine at sites of N7 alkylation
    • Mattes, W. B., Hartley, J. A., and Kohn, K. W. (1986) Mechanism of DNA strand breakage by piperidine at sites of N7 alkylation. Biochim. Biophys. Acta 868, 71-76.
    • (1986) Biochim. Biophys. Acta , vol.868 , pp. 71-76
    • Mattes, W.B.1    Hartley, J.A.2    Kohn, K.W.3
  • 78
    • 0025277052 scopus 로고
    • 9-Amino-ellipticine inhibits the apurinic site-dependent base excision-repair pathway
    • Lefrancois, M., Bertrand, J.-R., and Malvy, C. (1990) 9-Amino-ellipticine inhibits the apurinic site-dependent base excision-repair pathway. Mutat. Res. 236, 9-17.
    • (1990) Mutat. Res. , vol.236 , pp. 9-17
    • Lefrancois, M.1    Bertrand, J.-R.2    Malvy, C.3
  • 79
    • 0001574268 scopus 로고
    • A new class of artificial nucleases that recognize and cleave apurinic sites in DNA with great selectivity and efficiency
    • Fkyerat, A., Demeunynck, M., Constant, J.-F., Michon, P., and Lhomme, J. (1993) A new class of artificial nucleases that recognize and cleave apurinic sites in DNA with great selectivity and efficiency. J. Am. Chem. Soc. 115, 9952-9959.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 9952-9959
    • Fkyerat, A.1    Demeunynck, M.2    Constant, J.-F.3    Michon, P.4    Lhomme, J.5
  • 80
    • 0017194182 scopus 로고
    • All oxygens in nucleic acids react with carcinogenic ethylating agents
    • Singer, B. (1976) All oxygens in nucleic acids react with carcinogenic ethylating agents. Nature 264, 333-339.
    • (1976) Nature , vol.264 , pp. 333-339
    • Singer, B.1
  • 81
    • 0017904587 scopus 로고
    • 4-alkyl pyrimidine nucleosides: Stability of the glycosyl bond and of the alkyl group as a function of pH
    • 4-alkyl pyrimidine nucleosides: Stability of the glycosyl bond and of the alkyl group as a function of pH. Biochemistry 17, 1246-1250.
    • (1978) Biochemistry , vol.17 , pp. 1246-1250
    • Singer, B.1    Kroger, M.2    Carrano, M.3
  • 82
    • 0021326895 scopus 로고
    • Substituent-induced effects on the stability of benzylated guanosines: Model systems for the factors influencing the stability of carcinogen-modified nucleic acids
    • Moschel, R. C., Hudgins, W. R., and Dipple, A. (1984) Substituent-induced effects on the stability of benzylated guanosines: model systems for the factors influencing the stability of carcinogen-modified nucleic acids. J. Org. Chem. 49, 363-372.
    • (1984) J. Org. Chem. , vol.49 , pp. 363-372
    • Moschel, R.C.1    Hudgins, W.R.2    Dipple, A.3
  • 83
    • 0021893487 scopus 로고
    • The influence of N7-substitutents on the stability of N7-alkylated guanosines
    • Muller, N., and Eisenbrand, G. (1985) The influence of N7-substitutents on the stability of N7-alkylated guanosines. Chem.-Biol. Interact. 53, 173-181.
    • (1985) Chem.-Biol. Interact. , vol.53 , pp. 173-181
    • Muller, N.1    Eisenbrand, G.2
  • 84
    • 0342549837 scopus 로고
    • Effect of the structure of the glycon on the acid-catalyzed hydrolysis of adenine nucleosides
    • York, J. L. (1981) Effect of the structure of the glycon on the acid-catalyzed hydrolysis of adenine nucleosides. J. Org. Chem. 46, 2171-2173.
    • (1981) J. Org. Chem. , vol.46 , pp. 2171-2173
    • York, J.L.1
  • 85
    • 0015528979 scopus 로고
    • Solvolysis of adenine nucleosides. II. Effects of sugars and adenine substituents on alkaline solvolyses
    • Garrett, E. R., and Mehta, P. J. (1972) Solvolysis of adenine nucleosides. II. Effects of sugars and adenine substituents on alkaline solvolyses. J. Am. Chem. Soc. 94, 8542-8547.
    • (1972) J. Am. Chem. Soc. , vol.94 , pp. 8542-8547
    • Garrett, E.R.1    Mehta, P.J.2
  • 86
    • 0026337154 scopus 로고
    • Imidazole ring opening of 7-methylguanosine at physiological pH
    • Barbarella, G., Tugnoli, V., and Zambianchi, M. (1991) Imidazole ring opening of 7-methylguanosine at physiological pH. Nucleosides Nucleotides 10, 1759-1769.
    • (1991) Nucleosides Nucleotides , vol.10 , pp. 1759-1769
    • Barbarella, G.1    Tugnoli, V.2    Zambianchi, M.3
  • 89
    • 0028804386 scopus 로고
    • A designed inhibitor of base-excision repair
    • Scharer, O. D., and Verdine, G. L. (1995) A designed inhibitor of base-excision repair. J. Am. Chem. Soc. 117, 10781-10782.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 10781-10782
    • Scharer, O.D.1    Verdine, G.L.2
  • 91
    • 0026751642 scopus 로고
    • Synthesis of suitably protected phosphoramidites of 2′-fluoro- 2′-deoxyguanosine and 2′-amino-2′-deoxyguanosine for incorporation into oligoribonucleotides
    • Benseler, F., Williams, D. M., and Eckstein, F. (1992) Synthesis of suitably protected phosphoramidites of 2′-fluoro-2′-deoxyguanosine and 2′-amino-2′-deoxyguanosine for incorporation into oligoribonucleotides. Nucleosides Nucleotides 11, 1333-1351.
    • (1992) Nucleosides Nucleotides , vol.11 , pp. 1333-1351
    • Benseler, F.1    Williams, D.M.2    Eckstein, F.3
  • 92
    • 0000137138 scopus 로고
    • Correlation between preferred sugar ring conformation and activity of nucleoside analogues against human immunodeficiency virus
    • Van Roey, P., Salerno, J. M., Chu, C. K., and Schinazi, R. F. (1989) Correlation between preferred sugar ring conformation and activity of nucleoside analogues against human immunodeficiency virus. Proc. Natl. Acad. Sci. U.S.A. 86, 3929-3933.
    • (1989) Proc. Natl. Acad. Sci. U.S.A. , vol.86 , pp. 3929-3933
    • Van Roey, P.1    Salerno, J.M.2    Chu, C.K.3    Schinazi, R.F.4
  • 93
    • 0024235149 scopus 로고
    • Depurination and imidazole ring-opening in nucleosides and DNA alkylated by styrene oxide
    • Vodicka, P., and Hemminki, K. (1988) Depurination and imidazole ring-opening in nucleosides and DNA alkylated by styrene oxide. Chem.-Biol. Interact. 68, 117-126.
    • (1988) Chem.-Biol. Interact. , vol.68 , pp. 117-126
    • Vodicka, P.1    Hemminki, K.2
  • 94
    • 0026607008 scopus 로고
    • Sequence-selective depurination, DNA interstrand cross-linking and DNA strand break formation associated with alkylated DNA
    • Prakash, A. S., and Gibson, N. W. (1992) Sequence-selective depurination, DNA interstrand cross-linking and DNA strand break formation associated with alkylated DNA. Carcinogenesis 13, 425-431.
    • (1992) Carcinogenesis , vol.13 , pp. 425-431
    • Prakash, A.S.1    Gibson, N.W.2
  • 95
    • 0028147058 scopus 로고
    • Molecular basis of nitrogen mustard effects on transcription processes: Role of depurination
    • Masta, A., Gray, P. J., and Phillips, D. R. (1994) Molecular basis of nitrogen mustard effects on transcription processes: role of depurination. Nucleic Acids Res. 22, 3880-3886.
    • (1994) Nucleic Acids Res. , vol.22 , pp. 3880-3886
    • Masta, A.1    Gray, P.J.2    Phillips, D.R.3
  • 97
    • 0035900960 scopus 로고    scopus 로고
    • Coupling of substrate recognition and catalysis by a human base-excision repair protein
    • Norman, D. P. G., Bruner, S. D., and Verdine, G. L. (2001) Coupling of substrate recognition and catalysis by a human base-excision repair protein. J. Am. Chem. Soc. 123, 359-360.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 359-360
    • Norman, D.P.G.1    Bruner, S.D.2    Verdine, G.L.3
  • 98
    • 0345270445 scopus 로고    scopus 로고
    • Powering DNA repair through substrate electrostatic interactions
    • Jiang, Y. L., Ichikawa, Y., Song, F., and Stivers, J. T. (2003) Powering DNA repair through substrate electrostatic interactions. Biochemistry 42, 1922-1929.
    • (2003) Biochemistry , vol.42 , pp. 1922-1929
    • Jiang, Y.L.1    Ichikawa, Y.2    Song, F.3    Stivers, J.T.4
  • 99
    • 0027697091 scopus 로고
    • Intramolecular catalysis in the depurination of a 7-methylguanosine
    • Van Arman, S. A., and Czarnik, A. W. (1993) Intramolecular catalysis in the depurination of a 7-methylguanosine. Bioorg. Med. Chem. 1, 369-374.
    • (1993) Bioorg. Med. Chem. , vol.1 , pp. 369-374
    • Van Arman, S.A.1    Czarnik, A.W.2
  • 100
    • 0035909316 scopus 로고    scopus 로고
    • Uracil-DNA glycosylase acts by substrate catalysis
    • Dinner, A. R., Blackburn, G. M., and Karplus, M. (2001) Uracil-DNA glycosylase acts by substrate catalysis. Nature 413, 752-755.
    • (2001) Nature , vol.413 , pp. 752-755
    • Dinner, A.R.1    Blackburn, G.M.2    Karplus, M.3
  • 101
    • 0042342532 scopus 로고    scopus 로고
    • A mechanistic perspective on the chemistry of DNA repair glycosylases
    • Stivers, J. T., and Jiang, Y. J. (2003) A mechanistic perspective on the chemistry of DNA repair glycosylases. Chem. Rev. 103, 2729-2759.
    • (2003) Chem. Rev. , vol.103 , pp. 2729-2759
    • Stivers, J.T.1    Jiang, Y.J.2
  • 102
    • 37049065759 scopus 로고
    • Methylation of guanosine and related compounds with diazomethane
    • Haines, J. A., Reese, C. B., and Todd, L. (1962) Methylation of guanosine and related compounds with diazomethane. J. Chem. Soc. 5281.
    • (1962) J. Chem. Soc. , pp. 5281
    • Haines, J.A.1    Reese, C.B.2    Todd, L.3
  • 103
    • 0001656758 scopus 로고
    • Ring cleavage of purine nucleosides to yield possible biogenetic precursors of pteridines and riboflavin
    • Townsend, L. B., and Robins, R. K. (1963) Ring cleavage of purine nucleosides to yield possible biogenetic precursors of pteridines and riboflavin. J. Am. Chem. Soc. 85, 242-243.
    • (1963) J. Am. Chem. Soc. , vol.85 , pp. 242-243
    • Townsend, L.B.1    Robins, R.K.2
  • 105
    • 0019978718 scopus 로고
    • Alkaline opening of imidazole ring of 7-methyguanosine. 1. Analysis of the resulting pyrimidine derivatives
    • Chetsanga, C. J., Bearie, B., and Makaroff, C. (1982) Alkaline opening of imidazole ring of 7-methyguanosine. 1. Analysis of the resulting pyrimidine derivatives. Chem.-Biol. Interact. 41, 217-233.
    • (1982) Chem.-Biol. Interact. , vol.41 , pp. 217-233
    • Chetsanga, C.J.1    Bearie, B.2    Makaroff, C.3
  • 106
    • 0019972273 scopus 로고
    • Alkaline opening of imidazole ring of 7-methylguanosine. 2. Further studies on reaction mechanisms and products
    • Chetsanga, C. J., and Makaroff, C. (1982) Alkaline opening of imidazole ring of 7-methylguanosine. 2. Further studies on reaction mechanisms and products. Chem.-Biol. Interact. 41, 235-249.
    • (1982) Chem.-Biol. Interact. , vol.41 , pp. 235-249
    • Chetsanga, C.J.1    Makaroff, C.2
  • 107
    • 0017315175 scopus 로고
    • Chemical transformations of 7,9-disubstituted purines and related heterocycles. Selective reduction of imines and immonium salts
    • Hecht, S. M., Adams, B. L., and Kozarich, J. W. (1976) Chemical transformations of 7,9-disubstituted purines and related heterocycles. Selective reduction of imines and immonium salts. J. Org. Chem. 13, 2303-2311.
    • (1976) J. Org. Chem. , vol.13 , pp. 2303-2311
    • Hecht, S.M.1    Adams, B.L.2    Kozarich, J.W.3
  • 108
    • 0023959751 scopus 로고
    • 7-Methylguanine nucleotides and their structural analogues; protolytic equilibria, complexing with magnesium(II) ion and kinetics for alkaline opening of the imidazole ring
    • Darzynkiewicz, E., Labadi, I., Haber, D., Burger, K., and Lonnberg, H. (1988) 7-Methylguanine nucleotides and their structural analogues; protolytic equilibria, complexing with magnesium(II) ion and kinetics for alkaline opening of the imidazole ring. Acta Chem. Scand. B B42, 86-92.
    • (1988) Acta Chem. Scand. B , vol.B42 , pp. 86-92
    • Darzynkiewicz, E.1    Labadi, I.2    Haber, D.3    Burger, K.4    Lonnberg, H.5
  • 111
    • 0014170213 scopus 로고
    • Stabilization of nitrogen mustard alkylations and interstrand cross-links in DNA by alkali
    • Kohn, K. W., and Spears, C. L. (1967) Stabilization of nitrogen mustard alkylations and interstrand cross-links in DNA by alkali. Biochim. Biophys. Acta 145, 734-741.
    • (1967) Biochim. Biophys. Acta , vol.145 , pp. 734-741
    • Kohn, K.W.1    Spears, C.L.2
  • 112
    • 0022457419 scopus 로고
    • Chemical reclosure of opened imidazole ring of guanine
    • Chetsanga, C. J., and Mavunga, I. (1986) Chemical reclosure of opened imidazole ring of guanine. Chem.-Biol. Interact. 58, 117-123.
    • (1986) Chem.-Biol. Interact. , vol.58 , pp. 117-123
    • Chetsanga, C.J.1    Mavunga, I.2
  • 113
    • 0024349808 scopus 로고
    • Depurination from DNA of 7-methylguanine, 7-(2-aminoethyl)-guanine and ring-opened 7-methylguanines
    • Hemminki, K., Peltonen, K., and Vodicka, P. (1989) Depurination from DNA of 7-methylguanine, 7-(2-aminoethyl)-guanine and ring-opened 7-methylguanines. Chem.-Biol. Interact. 70, 289-303.
    • (1989) Chem.-Biol. Interact. , vol.70 , pp. 289-303
    • Hemminki, K.1    Peltonen, K.2    Vodicka, P.3
  • 114
    • 0017716393 scopus 로고
    • 1-DNA or -ribosomal RNA adducts formed in hepatic microsome-mediated reactions and in rat liver microsomes
    • 1-DNA or -ribosomal RNA adducts formed in hepatic microsome-mediated reactions and in rat liver microsomes. Cancer Res. 37, 4430-4438.
    • (1977) Cancer Res. , vol.37 , pp. 4430-4438
    • Lin, J.-K.1    Miller, J.A.2    Miller, E.C.3
  • 116
    • 0019519786 scopus 로고
    • Quantitative comparison of covalent aflatoxin-DNA adducts formed in rat and mouse livers and kidneys
    • Croy, R. G., and Wogan, G. N. (1981) Quantitative comparison of covalent aflatoxin-DNA adducts formed in rat and mouse livers and kidneys. J. Natl. Cancer Inst. 66, 761-768.
    • (1981) J. Natl. Cancer Inst. , vol.66 , pp. 761-768
    • Croy, R.G.1    Wogan, G.N.2
  • 118
    • 0020646831 scopus 로고
    • Identification of N5-methyl-N5-formyl-2,5,6-triamino-4-hydroxypyrimidine as a major adduct in rat liver DNA after treatment with the carcinogens, N,N-dimethylnitrosamine or 1,2-dimethylhydrazine
    • Beranek, D. T., Weiss, C. C., Evans, F. E., Chetsanga, C. J., and Kadlubar, F. F. (1983) Identification of N5-methyl-N5-formyl-2,5,6-triamino-4- hydroxypyrimidine as a major adduct in rat liver DNA after treatment with the carcinogens, N,N-dimethylnitrosamine or 1,2-dimethylhydrazine. Biochem. Biophys. Res. Commun. 110, 625-631.
    • (1983) Biochem. Biophys. Res. Commun. , vol.110 , pp. 625-631
    • Beranek, D.T.1    Weiss, C.C.2    Evans, F.E.3    Chetsanga, C.J.4    Kadlubar, F.F.5
  • 119
    • 0021220884 scopus 로고
    • Characterization of the purine ring-opened 7-methylguanine and its persistence in rat bladder epithelial DNA after treatment with the carcinogen N-methylnitrosourea
    • Kadlubar, F. F., Beranek, D. T., Weiss, C. C., Evans, F. E., Cox, R., and Irving, C. C. (1984) Characterization of the purine ring-opened 7-methylguanine and its persistence in rat bladder epithelial DNA after treatment with the carcinogen N-methylnitrosourea. Carcinogenesis 5, 587-592.
    • (1984) Carcinogenesis , vol.5 , pp. 587-592
    • Kadlubar, F.F.1    Beranek, D.T.2    Weiss, C.C.3    Evans, F.E.4    Cox, R.5    Irving, C.C.6
  • 120
    • 0037867770 scopus 로고    scopus 로고
    • Imidazole ring-opened DNA purines and their biological significance
    • Tudek, B. (2003) Imidazole ring-opened DNA purines and their biological significance. J. Biochem. Mol. Biol. 36, 12-19.
    • (2003) J. Biochem. Mol. Biol. , vol.36 , pp. 12-19
    • Tudek, B.1
  • 121
    • 0037177990 scopus 로고    scopus 로고
    • Fapy-dG instructs Klenow Exo- to misincorporate deoxyadenosine
    • Wiederholt, C. J., and Greenberg, M. M. (2002) Fapy-dG instructs Klenow Exo- to misincorporate deoxyadenosine. J. Am. Chem. Soc. 124, 7278-7279.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 7278-7279
    • Wiederholt, C.J.1    Greenberg, M.M.2
  • 123
    • 0037012380 scopus 로고    scopus 로고
    • Synthesis and characterization of oligodeoxynucleotides containing formamidopyrimidine lesions and nonhydrolyzable analogues
    • Haraguchi, K., Delaney, M. O., Wiederholt, C. J., Sambandam, A., Hantosi, Z., and Greenberg, M. M. (2002) Synthesis and characterization of oligodeoxynucleotides containing formamidopyrimidine lesions and nonhydrolyzable analogues. J. Am. Chem. Soc. 124, 3263-3269.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 3263-3269
    • Haraguchi, K.1    Delaney, M.O.2    Wiederholt, C.J.3    Sambandam, A.4    Hantosi, Z.5    Greenberg, M.M.6
  • 124
    • 0026802570 scopus 로고
    • Detection of non B-DNA structures at specific sites in supercoiled plasmid DNA and chromatin with haloacetaldehyde and diethyl pyrocarbonate
    • Kohwi-Shigamatsu, T., and Kohwi, Y. (1992) Detection of non B-DNA structures at specific sites in supercoiled plasmid DNA and chromatin with haloacetaldehyde and diethyl pyrocarbonate. Methods Enzymol. 212, 155-180.
    • (1992) Methods Enzymol. , vol.212 , pp. 155-180
    • Kohwi-Shigamatsu, T.1    Kohwi, Y.2
  • 125
    • 0018830298 scopus 로고
    • 1 modified deoxyribonucleic acid in vitro
    • 1 modified deoxyribonucleic acid in vitro. Biochemistry 19, 1692-1698.
    • (1980) Biochemistry , vol.19 , pp. 1692-1698
    • Wang, T.-C.1    Cerutti, P.2
  • 126
    • 0021760535 scopus 로고
    • Two rotameric forms of open ring 7-methylguanine are present in alkylated polynucleotides
    • Boiteux, S., Belleney, J., Roques, B. P., and Laval, J. (1984) Two rotameric forms of open ring 7-methylguanine are present in alkylated polynucleotides. Nucleic Acids Res. 12, 5429-5439.
    • (1984) Nucleic Acids Res. , vol.12 , pp. 5429-5439
    • Boiteux, S.1    Belleney, J.2    Roques, B.P.3    Laval, J.4
  • 127
    • 0027947380 scopus 로고
    • Chemical determination of oxidative DNA damage by gas chromatography-mass spectrometry
    • Dizdaroglu, M. (1994) Chemical determination of oxidative DNA damage by gas chromatography-mass spectrometry. Methods Enzymol. 234, 3-16.
    • (1994) Methods Enzymol. , vol.234 , pp. 3-16
    • Dizdaroglu, M.1
  • 128
    • 0025240665 scopus 로고
    • Homogeneous E. coli FPG protein. A DNA glycosylase which excises imidazole ring-opened purines and nicks DNA at apurinic/apyrimidinic sites
    • Boiteux, S., O'Connor, T. R., Lederer, F., Gouyette, A., and Laval, J. (1990) Homogeneous E. coli FPG protein. A DNA glycosylase which excises imidazole ring-opened purines and nicks DNA at apurinic/apyrimidinic sites. J. Biol. Chem. 265, 3916-3922.
    • (1990) J. Biol. Chem. , vol.265 , pp. 3916-3922
    • Boiteux, S.1    O'Connor, T.R.2    Lederer, F.3    Gouyette, A.4    Laval, J.5
  • 129
    • 0026533905 scopus 로고
    • Substrate specificity of purine lesions in DNA produced by ionizing radiation and photosensitization
    • Boiteux, S., Gajewski, E., Laval, J., and Dizdaroglu, M. (1992) Substrate specificity of purine lesions in DNA produced by ionizing radiation and photosensitization. Biochemistry 31, 106-110.
    • (1992) Biochemistry , vol.31 , pp. 106-110
    • Boiteux, S.1    Gajewski, E.2    Laval, J.3    Dizdaroglu, M.4
  • 130
    • 0034637604 scopus 로고    scopus 로고
    • Recognition of formamidopyrimidine by Escherichia coli and mammalian thymine glycol glycosylases
    • Asagoshi, K., Yamada, T., Okada, Y., Terato, H., Ohyama, Y., Seki, S., and Ide, H. (2000) Recognition of formamidopyrimidine by Escherichia coli and mammalian thymine glycol glycosylases. J. Biol. Chem. 275, 24781-24786.
    • (2000) J. Biol. Chem. , vol.275 , pp. 24781-24786
    • Asagoshi, K.1    Yamada, T.2    Okada, Y.3    Terato, H.4    Ohyama, Y.5    Seki, S.6    Ide, H.7
  • 131
    • 0031407602 scopus 로고    scopus 로고
    • Fpg protein releases a ring-opened N-7 guanine adduct from DNA that has been modified by sulfur mustard
    • Li, Q., Laval, J., and Ludlum, D. B. (1997) Fpg protein releases a ring-opened N-7 guanine adduct from DNA that has been modified by sulfur mustard. Carcinogenesis 18, 1035-1038.
    • (1997) Carcinogenesis , vol.18 , pp. 1035-1038
    • Li, Q.1    Laval, J.2    Ludlum, D.B.3
  • 133
    • 0001434563 scopus 로고
    • Isolation and characterization of the radiation-induced degradation products of 2′-deoxyguanosine in oxygen-free aqueous solutions
    • Berger, M., and Cadet, J. (1985) Isolation and characterization of the radiation-induced degradation products of 2′-deoxyguanosine in oxygen-free aqueous solutions. Z. Naturforsch. 40B, 1519-1531.
    • (1985) Z. Naturforsch. , vol.40 B , pp. 1519-1531
    • Berger, M.1    Cadet, J.2
  • 134
    • 0023199083 scopus 로고
    • Reaction of acid-activated mitomycin C with calf thymus DNA and model guanines: Elucidation of the base-catalyzed degradation of N7-alkylguanine nucleosides
    • Tomasz, M., Lipman, R., Lee, M. S., Verdine, G. L., and Nakanishi, K. (1987) Reaction of acid-activated mitomycin C with calf thymus DNA and model guanines: elucidation of the base-catalyzed degradation of N7-alkylguanine nucleosides. Biochemistry 26, 2010-2027.
    • (1987) Biochemistry , vol.26 , pp. 2010-2027
    • Tomasz, M.1    Lipman, R.2    Lee, M.S.3    Verdine, G.L.4    Nakanishi, K.5
  • 135
    • 0035812375 scopus 로고    scopus 로고
    • 6-(2-Deoxy-α,β-D-erythro-pentofuranosyl)-2, 6-diamino-4-hydroxy-5-formamidopyrimidine)
    • 6-(2-Deoxy-α,β-D-erythro- pentofuranosyl)-2,6-diamino-4-hydroxy-5-formamidopyrimidine). J. Am. Chem. Soc. 123, 8636-8637.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 8636-8637
    • Haraguchi, K.1    Greenberg, M.M.2
  • 136
    • 0037016581 scopus 로고    scopus 로고
    • Synthesis, stability, and conformation of the formamidopyrimidine G DNA lesion
    • Bergdorf, L. T., and Carrel, T. (2002) Synthesis, stability, and conformation of the formamidopyrimidine G DNA lesion. Chem. Eur. J. 8, 293-301.
    • (2002) Chem. Eur. J. , vol.8 , pp. 293-301
    • Bergdorf, L.T.1    Carrel, T.2
  • 137
    • 0015928956 scopus 로고
    • Reaction of diethyl pyrocarbonate with nucleic acid components. Bases and nucleosides derived from guanine, cytosine, and uracil
    • Vincze, A., Henderson, E. L., McDonald, J. J., and Leonard, N. J. (1973) Reaction of diethyl pyrocarbonate with nucleic acid components. Bases and nucleosides derived from guanine, cytosine, and uracil. J. Am. Chem. Soc. 95, 2677-2682.
    • (1973) J. Am. Chem. Soc. , vol.95 , pp. 2677-2682
    • Vincze, A.1    Henderson, E.L.2    McDonald, J.J.3    Leonard, N.J.4
  • 138
    • 0015247071 scopus 로고
    • Reaction of diethyl pyrocarbonate with nucleic acid components. Adenosine
    • Leonard, N. J., McDonald, J. J., Henderson, E. L., and Reichmann, M. E. (1971) Reaction of diethyl pyrocarbonate with nucleic acid components. Adenosine. Biochemistry 10, 3335-3342.
    • (1971) Biochemistry , vol.10 , pp. 3335-3342
    • Leonard, N.J.1    McDonald, J.J.2    Henderson, E.L.3    Reichmann, M.E.4
  • 139
    • 0027393763 scopus 로고
    • Mass spectrometric investigation of the presence of 7-methyl ring-opened guanine derivatives in urine
    • Barak, R., Vincze, A., Bel, P., Dutta, S. P., and Chedda, G. B. (1993) Mass spectrometric investigation of the presence of 7-methyl ring-opened guanine derivatives in urine. Chem.-Biol. Interact. 86, 29-40.
    • (1993) Chem.-Biol. Interact. , vol.86 , pp. 29-40
    • Barak, R.1    Vincze, A.2    Bel, P.3    Dutta, S.P.4    Chedda, G.B.5
  • 140
    • 0019434111 scopus 로고
    • Release of 7-methylguanine residues from alkylated DNA by extracts of Micrococcus luteus and Escherichia coli
    • Laval, J., Pierre, J., and Laval, F. (1981) Release of 7-methylguanine residues from alkylated DNA by extracts of Micrococcus luteus and Escherichia coli. Proc. Natl. Acad. Sci. U.S.A. 78, 852-855.
    • (1981) Proc. Natl. Acad. Sci. U.S.A. , vol.78 , pp. 852-855
    • Laval, J.1    Pierre, J.2    Laval, F.3
  • 141
    • 0018387063 scopus 로고
    • Elease of 7-methylguanine residues whose imidazole rings have been opened from damaged DNA by a DNA glycosylase from Escherichia coli
    • Chetsanga, C. J., and Lindahl, T. R. (1979) elease of 7-methylguanine residues whose imidazole rings have been opened from damaged DNA by a DNA glycosylase from Escherichia coli. Nucleic Acids Res. 6, 3673-3684.
    • (1979) Nucleic Acids Res. , vol.6 , pp. 3673-3684
    • Chetsanga, C.J.1    Lindahl, T.R.2
  • 142
    • 0022500828 scopus 로고
    • Covalent binding of 1,2-dihaloalkanes to DNA and stability of the major DNA adduct S-[2-(N7-guanyl)ethyl]glutathione
    • Inskeep, P. B., Koga, N., Cmarik, J. L., and Guengerich, F. P. (1986) Covalent binding of 1,2-dihaloalkanes to DNA and stability of the major DNA adduct S-[2-(N7-guanyl)ethyl]glutathione. Carcinogenesis 46, 2839-2844.
    • (1986) Carcinogenesis , vol.46 , pp. 2839-2844
    • Inskeep, P.B.1    Koga, N.2    Cmarik, J.L.3    Guengerich, F.P.4
  • 143
    • 0017379293 scopus 로고
    • 1 causes guanine substitution in nucleic acids
    • 1 causes guanine substitution in nucleic acids. Nature 267, 863-865.
    • (1977) Nature , vol.267 , pp. 863-865
    • Martin, C.N.1    Garner, R.C.2
  • 145
    • 0021365958 scopus 로고
    • Reaction ofethyleneimine with guanosine and deoxyguanosine
    • Hemminki, K. (1984) Reaction ofethyleneimine with guanosine and deoxyguanosine. Chem.-Biol. Interact. 48, 249-260.
    • (1984) Chem.-Biol. Interact. , vol.48 , pp. 249-260
    • Hemminki, K.1
  • 146
    • 0001473891 scopus 로고    scopus 로고
    • Chemistry of glycosylases and endonucleases involved in base-excision repair
    • David, S. S., and Williams, S. D. (1998) Chemistry of glycosylases and endonucleases involved in base-excision repair. Chem. Rev. 98, 1221-1261.
    • (1998) Chem. Rev. , vol.98 , pp. 1221-1261
    • David, S.S.1    Williams, S.D.2
  • 147
    • 0030005059 scopus 로고    scopus 로고
    • Reduction of the toxicity and mutagenicity of aziridine in mammalian cells harboring the Escherichia coli fpg gene
    • Cussac, C., and Laval, F. (1996) Reduction of the toxicity and mutagenicity of aziridine in mammalian cells harboring the Escherichia coli fpg gene. Nucleic Acids Res. 24, 1742-1746.
    • (1996) Nucleic Acids Res. , vol.24 , pp. 1742-1746
    • Cussac, C.1    Laval, F.2
  • 148
    • 0027367893 scopus 로고
    • Reversibility of the duocarmycin A and SA DNA alkylation reaction
    • Boger, D. L., and Yun, W. (1993) Reversibility of the duocarmycin A and SA DNA alkylation reaction. J. Am. Chem. Soc. 115, 9872-9873.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 9872-9873
    • Boger, D.L.1    Yun, W.2
  • 149
    • 0028236007 scopus 로고
    • The reversible DNA-alkylating activity of duocarmycin and its analogues
    • Asai, A., Nagamura, S., Saito, H., Takahashi, I., and Nakano, H. (1994) The reversible DNA-alkylating activity of duocarmycin and its analogues. Nucleic Acids Res. 22, 88-93.
    • (1994) Nucleic Acids Res. , vol.22 , pp. 88-93
    • Asai, A.1    Nagamura, S.2    Saito, H.3    Takahashi, I.4    Nakano, H.5
  • 150
    • 0026511431 scopus 로고
    • Reversiblity of the covalent reaction of CC-1065 and analogues with DNA
    • Warpehoski, M. A., Harper, D. E., Mitchell, M. A., and Monroe, T. J. (1992) Reversiblity of the covalent reaction of CC-1065 and analogues with DNA. Biochemistry 31, 2502-2508.
    • (1992) Biochemistry , vol.31 , pp. 2502-2508
    • Warpehoski, M.A.1    Harper, D.E.2    Mitchell, M.A.3    Monroe, T.J.4
  • 151
    • 0034814388 scopus 로고    scopus 로고
    • Differential rates of reversibility of ecteinascidin 743-DNA covalent adducts from different sequences lead to migration to favored bonding sites
    • Zewail-Foote, M., and Hurley, L. H. (2001) Differential rates of reversibility of ecteinascidin 743-DNA covalent adducts from different sequences lead to migration to favored bonding sites. J. Am. Chem. Soc. 123, 6485-6495.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 6485-6495
    • Zewail-Foote, M.1    Hurley, L.H.2
  • 152
    • 0035861060 scopus 로고    scopus 로고
    • Thermodynamic versus kinetic products of DNA alkylation as modeled by reaction of deoxyadenosine
    • Veldhuyzen, W. F., Shallop, A. J., Jones, R. A., and Rokita, S. E. (2001) Thermodynamic versus kinetic products of DNA alkylation as modeled by reaction of deoxyadenosine. J. Am. Chem. Soc. 123, 11126-11132.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 11126-11132
    • Veldhuyzen, W.F.1    Shallop, A.J.2    Jones, R.A.3    Rokita, S.E.4
  • 153
    • 0034485898 scopus 로고    scopus 로고
    • Reactivity and mutagenicity of endogenous DNA oxopropenylating agents: Base propenals, malondialdehyde, and N-oxopropenyllysine
    • Plastaras, J. P., Riggins, J. N., Otteneder, M., and Marnett, L. J. (2000) Reactivity and mutagenicity of endogenous DNA oxopropenylating agents: base propenals, malondialdehyde, and N-oxopropenyllysine. Chem. Res. Toxicol. 13, 1235-1242.
    • (2000) Chem. Res. Toxicol. , vol.13 , pp. 1235-1242
    • Plastaras, J.P.1    Riggins, J.N.2    Otteneder, M.3    Marnett, L.J.4
  • 154
    • 0032530416 scopus 로고    scopus 로고
    • Indirect mutagenesis by oxidative DNA damage: Formation of the pyrimidopurinone adduct of deoxyguanosine by base propenal
    • Dedon, P. C., Plastaras, J. P., Rouzer, C. A., and Marnett, L. J. (1998) Indirect mutagenesis by oxidative DNA damage: formation of the pyrimidopurinone adduct of deoxyguanosine by base propenal. Proc. Natl. Acad. Sci. U.S.A. 95, 11113-11116.
    • (1998) Proc. Natl. Acad. Sci. U.S.A. , vol.95 , pp. 11113-11116
    • Dedon, P.C.1    Plastaras, J.P.2    Rouzer, C.A.3    Marnett, L.J.4
  • 156
    • 3242660375 scopus 로고
    • Demethylation of 7-methylguanosine with lithium 2-methylpropane-2- thiolate
    • Hecht, S. M., and Kozarich, J. W. (1973) Demethylation of 7-methylguanosine with lithium 2-methylpropane-2-thiolate. J. Chem. Soc. Chem. Commun. 387.
    • (1973) J. Chem. Soc. Chem. Commun. , pp. 387
    • Hecht, S.M.1    Kozarich, J.W.2
  • 157
    • 0037325167 scopus 로고    scopus 로고
    • Identification of adducts produced by the reaction of 4-(acetoxymethylnitresamino)-1-(3-pyridyl)-1-butanol with deoxyguanosine and DNA
    • Upadhyaya, P., Sturla, S. J., Tretyakova, N., Ziegel, R., Villalta, P. W., Wang, M., and Hecht, S. S. (2003) Identification of adducts produced by the reaction of 4-(acetoxymethylnitresamino)-1-(3-pyridyl)-1-butanol with deoxyguanosine and DNA. Chem. Res. Toxicol. 16, 180-190.
    • (2003) Chem. Res. Toxicol. , vol.16 , pp. 180-190
    • Upadhyaya, P.1    Sturla, S.J.2    Tretyakova, N.3    Ziegel, R.4    Villalta, P.W.5    Wang, M.6    Hecht, S.S.7
  • 158
    • 0032549593 scopus 로고    scopus 로고
    • Design of a cyclopropyl quinone methide reductive alkylating agent
    • Ouyang, A., and Skibo, E. B. (1998) Design of a cyclopropyl quinone methide reductive alkylating agent. J. Org. Chem. 63, 1893-1900.
    • (1998) J. Org. Chem. , vol.63 , pp. 1893-1900
    • Ouyang, A.1    Skibo, E.B.2
  • 159
    • 0038025295 scopus 로고    scopus 로고
    • Identification of adducts formed by pyridyloxobutylation of deoxyguanosine and DNA by 4-(acetoxymethylnitrosamino)-1-(3-pyridyl)-1-butanone, a chemically activated form of tobacco specific carcinogens
    • Wang, M., Cheng, G., Sturla, S. J., Shi, Y., McIntee, E. J., Villalta, P. W., Upadhyaya, P., and Hecht, S. S. (2003) Identification of adducts formed by pyridyloxobutylation of deoxyguanosine and DNA by 4-(acetoxymethylnitrosamino)- 1-(3-pyridyl)-1-butanone, a chemically activated form of tobacco specific carcinogens. Chem. Res. Toxicol. 16, 616-626.
    • (2003) Chem. Res. Toxicol. , vol.16 , pp. 616-626
    • Wang, M.1    Cheng, G.2    Sturla, S.J.3    Shi, Y.4    McIntee, E.J.5    Villalta, P.W.6    Upadhyaya, P.7    Hecht, S.S.8
  • 160
    • 0029860623 scopus 로고    scopus 로고
    • DNA guanine adducts from 3-methyl-1,2,3-oxadiazolinium ions
    • Loeppky, R. N., Yu, L., Gu, F., and Ye, Q. (1996) DNA guanine adducts from 3-methyl-1,2,3-oxadiazolinium ions. J. Am. Chem. Soc. 118, 10995-11005.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 10995-11005
    • Loeppky, R.N.1    Yu, L.2    Gu, F.3    Ye, Q.4
  • 162
    • 0002091013 scopus 로고
    • The mechanisms of nuclephilic subsitution in aliphatic compounds
    • Katritzky, A. R., and Brycki, B. E. (1990) The mechanisms of nuclephilic subsitution in aliphatic compounds. Chem. Soc. Rev. 19, 83-105.
    • (1990) Chem. Soc. Rev. , vol.19 , pp. 83-105
    • Katritzky, A.R.1    Brycki, B.E.2
  • 163
    • 0030929002 scopus 로고    scopus 로고
    • Reactions of ester derivatives of carcinogenic N-(4-biphenyl) hydroxylamine and the corresponding hydroxamic acid with purine nucleosides
    • Kennedy, S. A., Novak, M., and Kolb, B. A. (1997) Reactions of ester derivatives of carcinogenic N-(4-biphenyl)hydroxylamine and the corresponding hydroxamic acid with purine nucleosides. J. Am. Chem. Soc. 119, 7654-7664.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 7654-7664
    • Kennedy, S.A.1    Novak, M.2    Kolb, B.A.3
  • 165
    • 4243545125 scopus 로고    scopus 로고
    • Oxidative nucleobase modifications leading to strand scission
    • Burrows, C. J., and Muller, J. G. (1998) Oxidative nucleobase modifications leading to strand scission. Chem. Rev. 98, 1109-1151.
    • (1998) Chem. Rev. , vol.98 , pp. 1109-1151
    • Burrows, C.J.1    Muller, J.G.2
  • 166
    • 0028923064 scopus 로고
    • DNA base and deoxyribose modification by the carbon-centered radical generated from 4-(hydroxymethyl)benzene-diazonium ion salt, a carcinogen in mushroom
    • Hiramoto, K., Kaku, M., Sueyoshi, A., Fujise, M., and Kikugawa, K. (1995) DNA base and deoxyribose modification by the carbon-centered radical generated from 4-(hydroxymethyl)benzene-diazonium ion salt, a carcinogen in mushroom. Chem. Res. Toxicol. 8, 356-362.
    • (1995) Chem. Res. Toxicol. , vol.8 , pp. 356-362
    • Hiramoto, K.1    Kaku, M.2    Sueyoshi, A.3    Fujise, M.4    Kikugawa, K.5
  • 167
    • 0032587901 scopus 로고    scopus 로고
    • C8-Arylguanine and C8-aryladenine formation in calf thymus DNA from arenediazonium ions
    • Gannett, P. M., Powell, J. H., Rao, R., Shi, X., Lawson, T., Kolar, C., and and Toth, B. (1999) C8-Arylguanine and C8-aryladenine formation in calf thymus DNA from arenediazonium ions. Chem. Res. Toxicol. 12, 297-304.
    • (1999) Chem. Res. Toxicol. , vol.12 , pp. 297-304
    • Gannett, P.M.1    Powell, J.H.2    Rao, R.3    Shi, X.4    Lawson, T.5    Kolar, C.6    Toth, B.7
  • 168
    • 0035966184 scopus 로고    scopus 로고
    • Quantum chemical characterization of the reactions of guanine with the phenylnitrenium ion
    • Parks, J. M., Ford, G. P., and Cramer, C. J. (2001) Quantum chemical characterization of the reactions of guanine with the phenylnitrenium ion. J. Org. Chem. 66, 8997-9004.
    • (2001) J. Org. Chem. , vol.66 , pp. 8997-9004
    • Parks, J.M.1    Ford, G.P.2    Cramer, C.J.3
  • 169
    • 0010316447 scopus 로고
    • Methylation of deoxyribonucleic acid by diazomethane
    • Kriek, E., and Emmelot, P. (1964) Methylation of deoxyribonucleic acid by diazomethane. Biochim. Biophs. Acta 91, 59-66.
    • (1964) Biochim. Biophs. Acta , vol.91 , pp. 59-66
    • Kriek, E.1    Emmelot, P.2
  • 170
    • 0034014664 scopus 로고    scopus 로고
    • Preparation of a methylated DNA standard, and its stability on storage
    • Osborne, M. R., and Philips, D. H. (2000) Preparation of a methylated DNA standard, and its stability on storage. Chem. Res. Toxicol. 13, 257-261.
    • (2000) Chem. Res. Toxicol. , vol.13 , pp. 257-261
    • Osborne, M.R.1    Philips, D.H.2
  • 171
    • 0017257991 scopus 로고
    • Removal of minor methylation products 7-methyladenine and 3-methylguanine from DNA of Escherichia Coli treated with dimethyl sulfate
    • Lawley, P. D., and Warren, W. (1976) Removal of minor methylation products 7-methyladenine and 3-methylguanine from DNA of Escherichia Coli treated with dimethyl sulfate. Chem.-Biol. Interact. 12, 211-220.
    • (1976) Chem.-Biol. Interact. , vol.12 , pp. 211-220
    • Lawley, P.D.1    Warren, W.2
  • 172
    • 0017066620 scopus 로고
    • Methylated purines in the deoxyribonucleic acid of various Syrian-golden-hamster tissues after administration of a hepatocarcinogenic dose of dimethylnitrosamine
    • Margison, G. P., Margison, J. M., and Montesano, R. (1976) Methylated purines in the deoxyribonucleic acid of various Syrian-golden-hamster tissues after administration of a hepatocarcinogenic dose of dimethylnitrosamine. Biochem. J. 157, 627-634.
    • (1976) Biochem. J. , vol.157 , pp. 627-634
    • Margison, G.P.1    Margison, J.M.2    Montesano, R.3
  • 173
    • 0016646416 scopus 로고
    • Excision of bases from DNA methylated by carcinogens in vivo and its possible significance in mutagenesis and carcinogenesis
    • Lawley, P. D. (1975) Excision of bases from DNA methylated by carcinogens in vivo and its possible significance in mutagenesis and carcinogenesis. Basic Life Sci. (Mol. Mech. Repair DNA) 5A, 25-28.
    • (1975) Basic Life Sci. (Mol. Mech. Repair DNA) , vol.5 A , pp. 25-28
    • Lawley, P.D.1
  • 174
    • 0023035312 scopus 로고
    • Properties of 7-substituted deoxyguanosines formed by cis-diamminedichloroplatinum(II)
    • Forsti, A., Laatikainen, R., and Hemminki, K. (1986) Properties of 7-substituted deoxyguanosines formed by cis-diamminedichloroplatinum(II). Chem.-Biol. Interact. 60, 143-158.
    • (1986) Chem.-Biol. Interact. , vol.60 , pp. 143-158
    • Forsti, A.1    Laatikainen, R.2    Hemminki, K.3
  • 175
    • 0026087923 scopus 로고
    • Release of 7-alkylguanines from N-(2-Chloroethyl)-N′-cyclohexyl-N- nitrosourea modified DNA by 3′-methyladenine DNA glycosylase II
    • Habraken, Y., Carter, C. A., Kirk, M. C., and Ludlum, D. B. (1991) Release of 7-alkylguanines from N-(2-Chloroethyl)-N′-cyclohexyl-N- nitrosourea modified DNA by 3′-methyladenine DNA glycosylase II. Cancer Res. 51, 499-503.
    • (1991) Cancer Res. , vol.51 , pp. 499-503
    • Habraken, Y.1    Carter, C.A.2    Kirk, M.C.3    Ludlum, D.B.4
  • 176
    • 0023101923 scopus 로고
    • DNA-binding properties of nornitrogen mustard, a metabolite of cyclophosphamide
    • Hemminki, K. (1987) DNA-binding properties of nornitrogen mustard, a metabolite of cyclophosphamide. Chem.-Biol. Interact. 61, 75-88.
    • (1987) Chem.-Biol. Interact. , vol.61 , pp. 75-88
    • Hemminki, K.1
  • 177
    • 0015501849 scopus 로고
    • Reaction of guanosine with ethylating agents
    • Singer, B. (1972) Reaction of guanosine with ethylating agents. Biochemistry 11, 3939-3947.
    • (1972) Biochemistry , vol.11 , pp. 3939-3947
    • Singer, B.1
  • 178
    • 0028219492 scopus 로고
    • DNA damage by ptaquiloside, a potent bracken carcinogen: Detection of selective strand breaks and identification of DNA cleavage products
    • Kushida, T., Uesugi, M., Sugiura, Y., Kigoshi, H., Tanaka, H., Hirokawa, J., Ojika, M., and Yamada, K. (1994) DNA damage by ptaquiloside, a potent bracken carcinogen: Detection of selective strand breaks and identification of DNA cleavage products. J. Am. Chem. Soc. 116, 479-486.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 479-486
    • Kushida, T.1    Uesugi, M.2    Sugiura, Y.3    Kigoshi, H.4    Tanaka, H.5    Hirokawa, J.6    Ojika, M.7    Yamada, K.8
  • 179
    • 37049138901 scopus 로고
    • The preparation and properties of some benzylated nucleosides
    • Brookes, P., Dipple, A., and Lawley, P. D. (1968) The preparation and properties of some benzylated nucleosides. J. Chem. Soc. C, 2026-2028.
    • (1968) J. Chem. Soc. C , pp. 2026-2028
    • Brookes, P.1    Dipple, A.2    Lawley, P.D.3
  • 180
    • 0001253917 scopus 로고
    • The reaction of mono- and di-functional alkylating agents with nucleic acids
    • Brookes, P., and Lawley, P. D. (1961) The reaction of mono- and di-functional alkylating agents with nucleic acids. Biochem. J. 80, 496-503.
    • (1961) Biochem. J. , vol.80 , pp. 496-503
    • Brookes, P.1    Lawley, P.D.2
  • 181
    • 0023647088 scopus 로고
    • Formation of S-[2-(N7-Guanyl)ethyl] adducts by the postulated S-(2-chloroethyl)cysteinyl and S-(2-chloroethyl)glutathionyl conjugates of 1,2-dichloroethane
    • Foureman, G. L., and Reed, D. J. (1987) Formation of S-[2-(N7-Guanyl) ethyl] adducts by the postulated S-(2-chloroethyl)cysteinyl and S-(2-chloroethyl)glutathionyl conjugates of 1,2-dichloroethane. Biochemistry 26, 2028-2033.
    • (1987) Biochemistry , vol.26 , pp. 2028-2033
    • Foureman, G.L.1    Reed, D.J.2
  • 182
    • 0022500828 scopus 로고
    • Covalent binding of 1,2-dihaloalkanes to DNA and stability of the major DNA adduct, S-[2-(N7-Guanyl)ethyl]-glutathione
    • Inskeep, P. B., Koga, N., Cmarik, J. L., and Guengerich, F. P. (1986) Covalent binding of 1,2-dihaloalkanes to DNA and stability of the major DNA adduct, S-[2-(N7-Guanyl)ethyl]-glutathione. Cancer Res. 46, 2839-2844.
    • (1986) Cancer Res. , vol.46 , pp. 2839-2844
    • Inskeep, P.B.1    Koga, N.2    Cmarik, J.L.3    Guengerich, F.P.4
  • 183
    • 0022559064 scopus 로고
    • S-[2-(N7-Guanyl)ethyl]glutathione, the major DNA adduct formed from 1,2-dibromoethane
    • Koga, N., Inskeep, P. B., Harris, T. B., and Guengerich, F. P. (1986) S-[2-(N7-Guanyl)ethyl]glutathione, the major DNA adduct formed from 1,2-dibromoethane. Biochemistry 25, 2192-2198.
    • (1986) Biochemistry , vol.25 , pp. 2192-2198
    • Koga, N.1    Inskeep, P.B.2    Harris, T.B.3    Guengerich, F.P.4
  • 184
    • 0030011255 scopus 로고    scopus 로고
    • DNA adduct formation by allyl glycidyl ether
    • Plna, K., Segerback, D., and Schweda, E. K. H. (1996) DNA adduct formation by allyl glycidyl ether. Carcinogenesis 17, 1465-1471.
    • (1996) Carcinogenesis , vol.17 , pp. 1465-1471
    • Plna, K.1    Segerback, D.2    Schweda, E.K.H.3
  • 185
    • 0025099493 scopus 로고
    • Reaction products in hemoglobin and DNA after in vitro treatment with ethylene oxide and N-(2-hydroxyethyl)-N-nitrosourea
    • Segerback, D. (1990) Reaction products in hemoglobin and DNA after in vitro treatment with ethylene oxide and N-(2-hydroxyethyl)-N-nitrosourea. Carcinogenesis 11, 307-312.
    • (1990) Carcinogenesis , vol.11 , pp. 307-312
    • Segerback, D.1
  • 186
    • 0344349003 scopus 로고    scopus 로고
    • Butadiene diolepoxide-and diepoxybutane-derived DNA adducts at N7-guanine: A high occurrence of diolepoxide-derived adducts in mouse lung after 1,3-butadiene exposure
    • Koivisto, P., Kilpelainen, I., Rasanen, I., Adler, I., Pacchierotti, F., and Peltonen, K. (1999) Butadiene diolepoxide-and diepoxybutane-derived DNA adducts at N7-guanine: a high occurrence of diolepoxide-derived adducts in mouse lung after 1,3-butadiene exposure. Carcinogenesis 20, 1253-1259.
    • (1999) Carcinogenesis , vol.20 , pp. 1253-1259
    • Koivisto, P.1    Kilpelainen, I.2    Rasanen, I.3    Adler, I.4    Pacchierotti, F.5    Peltonen, K.6
  • 187
    • 0021338990 scopus 로고
    • The reaction of 3,4-epoxy-1-butene with deoxyguanosine and DNA in vitro: Synthesis and characterization of the main adducts
    • Citti, L., Gervasi, P. G., Turchi, G., Bellucci, G., and Bianchini, R. (1984) The reaction of 3,4-epoxy-1-butene with deoxyguanosine and DNA in vitro: synthesis and characterization of the main adducts. Carcinogenesis 5, 47-52.
    • (1984) Carcinogenesis , vol.5 , pp. 47-52
    • Citti, L.1    Gervasi, P.G.2    Turchi, G.3    Bellucci, G.4    Bianchini, R.5
  • 188
  • 189
    • 0019506460 scopus 로고
    • Mutagenicities of styrene oxide derivatives on bacterial test systems: Relationship between mutagenic potencies and chemical reactivity
    • Sugiura, K., and Goto, M. (1981) Mutagenicities of styrene oxide derivatives on bacterial test systems: Relationship between mutagenic potencies and chemical reactivity. Chem.-Biol. Interact. 35, 71-91.
    • (1981) Chem.-Biol. Interact. , vol.35 , pp. 71-91
    • Sugiura, K.1    Goto, M.2
  • 190
    • 0028295561 scopus 로고
    • Identification of a novel, N7-deoxyguanosine adduct as the major DNA adduct formed by a nonbay-region diol epoxide of benzo[a]pyrene with low mutagenic potential
    • Mcleod, M. C., Evans, F. E., Lay, J., Chiarelli, P., Geacintov, N. E., Powell, K. L., Daylong, A., Luna, E., and Harvey, R. G. (1994) Identification of a novel, N7-deoxyguanosine adduct as the major DNA adduct formed by a nonbay-region diol epoxide of benzo[a]pyrene with low mutagenic potential. Biochemistry 33, 2977-2987.
    • (1994) Biochemistry , vol.33 , pp. 2977-2987
    • Mcleod, M.C.1    Evans, F.E.2    Lay, J.3    Chiarelli, P.4    Geacintov, N.E.5    Powell, K.L.6    Daylong, A.7    Luna, E.8    Harvey, R.G.9
  • 191
    • 0018741678 scopus 로고
    • The in vitro and in vivo reaction at the N7-position of guanine of the ultimate carcinogen derived from benzo[a]pyrene
    • King, H. W. S., Osborne, M. R., and Brookes, P. (1979) The in vitro and in vivo reaction at the N7-position of guanine of the ultimate carcinogen derived from benzo[a]pyrene. Chem.-Biol. Interact. 24, 345-353.
    • (1979) Chem.-Biol. Interact. , vol.24 , pp. 345-353
    • King, H.W.S.1    Osborne, M.R.2    Brookes, P.3
  • 192
    • 0021871431 scopus 로고
    • Depurination of benzo[a]pyrene-diolepoxide treated DNA
    • Osborne, M., and Merrifield, K. (1985) Depurination of benzo[a]pyrene-diolepoxide treated DNA. Chem.-Biol. Interact. 53, 183-195.
    • (1985) Chem.-Biol. Interact. , vol.53 , pp. 183-195
    • Osborne, M.1    Merrifield, K.2
  • 193
    • 0022763969 scopus 로고
    • The reaction of a 3-methylcholanthrene diol epoxide with DNA in relation to the binding of 3-methylcholanthrene to the DNA of mammalian cells
    • Osborne, M., Brookes, P., Lee, H., and Harvey, R. (1986) The reaction of a 3-methylcholanthrene diol epoxide with DNA in relation to the binding of 3-methylcholanthrene to the DNA of mammalian cells. Carcinogenesis 7, 1345-1350.
    • (1986) Carcinogenesis , vol.7 , pp. 1345-1350
    • Osborne, M.1    Brookes, P.2    Lee, H.3    Harvey, R.4
  • 194
    • 0022624169 scopus 로고
    • Stabilities of 7-alkylguanosines and 7-deoxyguanosines formed by phosphoramide mustard and nitrogen mustard
    • Kallama, S., and Hemminki, K. (1986) Stabilities of 7-alkylguanosines and 7-deoxyguanosines formed by phosphoramide mustard and nitrogen mustard. Chem.-Biol. Interact. 57, 85-96.
    • (1986) Chem.-Biol. Interact. , vol.57 , pp. 85-96
    • Kallama, S.1    Hemminki, K.2
  • 195
    • 0002850997 scopus 로고    scopus 로고
    • Relative stability of 4-hydroxyestradiol-1-N7dG compared to other depurinating nucleoside adducts Proc
    • Li, K.-M., Liang, W., Devanesan, P. D., Rogan, E. G., and Cavalieri, E. L. (1999) Relative stability of 4-hydroxyestradiol-1-N7dG compared to other depurinating nucleoside adducts Proc. Am. Assoc. Cancer Res. 40, 46.
    • (1999) Am. Assoc. Cancer Res. , vol.40 , pp. 46
    • Li, K.-M.1    Liang, W.2    Devanesan, P.D.3    Rogan, E.G.4    Cavalieri, E.L.5
  • 197
    • 0032476143 scopus 로고    scopus 로고
    • Tissue distribution of DNA adducts in male Fischer rats exposed to 500 ppm of propylene oxide: Quantitative analysis of 7-(2-hydroxypropyl)-guanine by 32-P labeling
    • Segerback, D., Plna, K., Faller, T., Kreuzer, P. E., Hakansson, K., Filser, J. G., and Nilsson, R. (1998) Tissue distribution of DNA adducts in male Fischer rats exposed to 500 ppm of propylene oxide: quantitative analysis of 7-(2-hydroxypropyl)-guanine by 32-P labeling. Chem.-Biol. Interact. 115, 229-246.
    • (1998) Chem.-Biol. Interact. , vol.115 , pp. 229-246
    • Segerback, D.1    Plna, K.2    Faller, T.3    Kreuzer, P.E.4    Hakansson, K.5    Filser, J.G.6    Nilsson, R.7
  • 198
    • 0025365572 scopus 로고
    • Synthesis and stability of 2′-deoxyguanosine 3′-monophosphate adducts of dimethyl sulfate, ethylene oxide, and styrene oxide
    • Hemminki, K., Alhonen-Raatesalmi, A., Koivisto, P., and Vodicka, P. (1990) Synthesis and stability of 2′-deoxyguanosine 3′-monophosphate adducts of dimethyl sulfate, ethylene oxide, and styrene oxide. Chem.-Biol. Interact. 75, 281-292.
    • (1990) Chem.-Biol. Interact. , vol.75 , pp. 281-292
    • Hemminki, K.1    Alhonen-Raatesalmi, A.2    Koivisto, P.3    Vodicka, P.4


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