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Volumn 5, Issue 1, 2006, Pages 23-31

Alkylpurine-DNA-N-glycosylase excision of 7-(hydroxymethyl)-1,N 6-ethenoadenine, a glycidaldehyde-derived DNA adduct

Author keywords

Base excision repair; DNA glycosylases; Etheno adduct; Glycidaldehyde; Hydroxymethyl etheno adduct

Indexed keywords

7 (HYDROXYMETHYL) 1,N 6 ETHENOADENINE; ALDEHYDE DERIVATIVE; DNA GLYCOSYLTRANSFERASE; OLIGONUCLEOTIDE; UNCLASSIFIED DRUG;

EID: 29244482553     PISSN: 15687864     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dnarep.2005.07.013     Document Type: Article
Times cited : (4)

References (52)
  • 3
    • 29244460812 scopus 로고
    • IRIS, U.S. Environmental Protection Agency
    • Glycidaldehyde (CASRN 765-34-4), IRIS, U.S. Environmental Protection Agency, 1988.
    • (1988) Glycidaldehyde (CASRN 765-34-4)
  • 4
    • 0038522158 scopus 로고    scopus 로고
    • National Toxicology Program
    • U.S. Department of Health and Human Services, 10th Report on Carcinogens, National Toxicology Program, 2002.
    • (2002) 10th Report on Carcinogens
  • 5
    • 0018911059 scopus 로고
    • The biotransformation of allyl alcohol and acrolein in rat liver and lung preparations
    • J.M. Patel, J.C. Wood, and K.C. Leibman The biotransformation of allyl alcohol and acrolein in rat liver and lung preparations Drug Metab. Dispos. 8 1980 305 308
    • (1980) Drug Metab. Dispos. , vol.8 , pp. 305-308
    • Patel, J.M.1    Wood, J.C.2    Leibman, K.C.3
  • 6
    • 0028057103 scopus 로고
    • Acrolein genotoxicity in Drosophila melanogaster. III. Effects of metabolism modification
    • A.R. Barros, L.M. Sierra, and M.A. Comendador Acrolein genotoxicity in Drosophila melanogaster. III. Effects of metabolism modification Mutat. Res. 321 1994 119 126
    • (1994) Mutat. Res. , vol.321 , pp. 119-126
    • Barros, A.R.1    Sierra, L.M.2    Comendador, M.A.3
  • 7
    • 0024561048 scopus 로고
    • Hydrolysis of bisphenol a diglycidylether by epoxide hydrolases in cytosolic and microsomal fractions of mouse liver and skin: Inhibition by bis epoxycyclopentylether and the effects upon the covalent binding to mouse skin DNA
    • P. Bentley, F. Bieri, H. Kuster, S. Muakkassah-Kelly, P. Sagelsdorff, W. Staubli, and F. Waechter Hydrolysis of bisphenol A diglycidylether by epoxide hydrolases in cytosolic and microsomal fractions of mouse liver and skin: inhibition by bis epoxycyclopentylether and the effects upon the covalent binding to mouse skin DNA Carcinogenesis 10 1989 321 327
    • (1989) Carcinogenesis , vol.10 , pp. 321-327
    • Bentley, P.1    Bieri, F.2    Kuster, H.3    Muakkassah-Kelly, S.4    Sagelsdorff, P.5    Staubli, W.6    Waechter, F.7
  • 8
    • 0014250433 scopus 로고
    • The reaction of guanosine and deoxyguanosine with glycidaldehyde
    • B.M. Goldschmidt, T.P. Blazej, and B.L. Van Duuren The reaction of guanosine and deoxyguanosine with glycidaldehyde Tetrahedron Lett. 13 1968 1583 1586
    • (1968) Tetrahedron Lett. , vol.13 , pp. 1583-1586
    • Goldschmidt, B.M.1    Blazej, T.P.2    Van Duuren, B.L.3
  • 9
    • 0017687390 scopus 로고
    • Reaction of DNA with glycidaldehyde. Isolation and identification of a deoxyguanosine reaction product
    • B.L. Van Duuren, and G. Loewengart Reaction of DNA with glycidaldehyde. Isolation and identification of a deoxyguanosine reaction product J. Biol. Chem. 252 1977 5370 5371
    • (1977) J. Biol. Chem. , vol.252 , pp. 5370-5371
    • Van Duuren, B.L.1    Loewengart, G.2
  • 10
    • 0006137820 scopus 로고
    • Determination of the structure of the adduct from guanosine and glycidaldehyde
    • V. Nair, and G.A. Turner Determination of the structure of the adduct from guanosine and glycidaldehyde Tetrahedron Lett. 25 1984 247 250
    • (1984) Tetrahedron Lett. , vol.25 , pp. 247-250
    • Nair, V.1    Turner, G.A.2
  • 12
    • 0030031218 scopus 로고    scopus 로고
    • Mechanisms of formation of adducts from reactions of glycidaldehyde with 2′-deoxyguanosine and/or guanosine
    • B.T. Golding, P.K. Slaich, G. Kennedy, C. Bleasdale, and W.P. Watson Mechanisms of formation of adducts from reactions of glycidaldehyde with 2′-deoxyguanosine and/or guanosine Chem. Res. Toxicol. 9 1996 147 157
    • (1996) Chem. Res. Toxicol. , vol.9 , pp. 147-157
    • Golding, B.T.1    Slaich, P.K.2    Kennedy, G.3    Bleasdale, C.4    Watson, W.P.5
  • 13
    • 0026500617 scopus 로고
    • Molecular dosimetry of DNA adducts in C3H mice treated with glycidaldehyde
    • S. Steiner, A.E. Crane, and W.P. Watson Molecular dosimetry of DNA adducts in C3H mice treated with glycidaldehyde Carcinogenesis 13 1992 119 124
    • (1992) Carcinogenesis , vol.13 , pp. 119-124
    • Steiner, S.1    Crane, A.E.2    Watson, W.P.3
  • 14
    • 0024453997 scopus 로고
    • Non-B DNA structure: Preferential target for the chemical carcinogen glycidaldehyde
    • Y. Kohwi Non-B DNA structure: preferential target for the chemical carcinogen glycidaldehyde Carcinogenesis 10 1989 2035 2042
    • (1989) Carcinogenesis , vol.10 , pp. 2035-2042
    • Kohwi, Y.1
  • 15
    • 0020569856 scopus 로고
    • Detection of an altered DNA conformation at specific sites in chromatin and supercoiled DNA
    • T. Kohwi-Shigematsu, R. Gelinas, and H. Weintraub Detection of an altered DNA conformation at specific sites in chromatin and supercoiled DNA Proc. Natl. Acad. Sci. U.S.A. 80 1983 4389 4393
    • (1983) Proc. Natl. Acad. Sci. U.S.A. , vol.80 , pp. 4389-4393
    • Kohwi-Shigematsu, T.1    Gelinas, R.2    Weintraub, H.3
  • 16
    • 0024247168 scopus 로고
    • The chemical carcinogen, chloroacetaldehyde, modifies a specific site within the regulatory sequence of human cytomegalo virus major immediate early gene in vivo
    • T. Kohwi-Shigematsu, and J.A. Nelson The chemical carcinogen, chloroacetaldehyde, modifies a specific site within the regulatory sequence of human cytomegalo virus major immediate early gene in vivo Mol. Carcinog. 1 1988 20 25
    • (1988) Mol. Carcinog. , vol.1 , pp. 20-25
    • Kohwi-Shigematsu, T.1    Nelson, J.A.2
  • 17
    • 0026632598 scopus 로고
    • Molecular dosimetry of DNA adducts in C3H mice treated with Bis phenol a diglycidyl ether
    • S. Steiner, G. Hönger, and P. Sagelsdorff Molecular dosimetry of DNA adducts in C3H mice treated with Bis phenol A diglycidyl ether Carcinogenesis 13 1992 969 972
    • (1992) Carcinogenesis , vol.13 , pp. 969-972
    • Steiner, S.1    Hönger, G.2    Sagelsdorff, P.3
  • 18
    • 0000168477 scopus 로고
    • Etheno-bridged nucleotides in structural diagnosis and carcinogenesis
    • N.J. Leonard Etheno-bridged nucleotides in structural diagnosis and carcinogenesis Biochem. Mol. Biol. Chemtracts 3 1992 273 297
    • (1992) Biochem. Mol. Biol. Chemtracts , vol.3 , pp. 273-297
    • Leonard, N.J.1
  • 20
    • 0034031990 scopus 로고    scopus 로고
    • Etheno-adduct-forming chemicals: From mutagenicity testing to tumor mutation spectra
    • A. Barbin Etheno-adduct-forming chemicals: from mutagenicity testing to tumor mutation spectra Mutat. Res. 462 2000 55 69
    • (2000) Mutat. Res. , vol.462 , pp. 55-69
    • Barbin, A.1
  • 21
    • 8844260373 scopus 로고    scopus 로고
    • Repair of exocyclic DNA adducts: Rings of complexity
    • B. Hang Repair of exocyclic DNA adducts: rings of complexity BioEssays 26 2004 1195 1208
    • (2004) BioEssays , vol.26 , pp. 1195-1208
    • Hang, B.1
  • 22
    • 0034122752 scopus 로고    scopus 로고
    • 4-etheno-2′- deoxycytidine, a potential carcinogenic glycidaldehyde adduct and its site-specific incorporation into DNA oligonucleotides
    • 4-etheno-2′-deoxycytidine, a potential carcinogenic glycidaldehyde adduct and its site-specific incorporation into DNA oligonucleotides Chem. Res. Toxicol. 13 2000 208 213
    • (2000) Chem. Res. Toxicol. , vol.13 , pp. 208-213
    • Chenna, A.1    Perry, A.2    Singer, B.3
  • 23
    • 0037133232 scopus 로고    scopus 로고
    • 4-ethenocytosine, a potential product resulting from glycidaldehyde reaction
    • 4-ethenocytosine, a potential product resulting from glycidaldehyde reaction Biochemistry 41 2002 2158 2165
    • (2002) Biochemistry , vol.41 , pp. 2158-2165
    • Hang, B.1    Downing, G.2    Guliaev, A.B.3    Singer, B.4
  • 24
    • 0037065724 scopus 로고    scopus 로고
    • 4-etheno-dC, a potential carcinogenic glycidaldehyde product, miscodes in vitro using mammalian polymerases
    • 4-etheno-dC, a potential carcinogenic glycidaldehyde product, miscodes in vitro using mammalian polymerases Biochemistry 41 2002 1778 1785
    • (2002) Biochemistry , vol.41 , pp. 1778-1785
    • Singer, B.1    Medina, M.2    Wang, Z.3    Guliaev, A.B.4    Hang, B.5
  • 27
    • 0036715036 scopus 로고    scopus 로고
    • Structural insights by molecular dynamics simulations into differential repair efficiency for ethano-A versus etheno-A adducts by the human alkylpurine-DNA N-glycosylase
    • A.B. Guliaev, B. Hang, and B. Singer Structural insights by molecular dynamics simulations into differential repair efficiency for ethano-A versus etheno-A adducts by the human alkylpurine-DNA N-glycosylase Nucl. Acids Res. 30 2002 3778 3787
    • (2002) Nucl. Acids Res. , vol.30 , pp. 3778-3787
    • Guliaev, A.B.1    Hang, B.2    Singer, B.3
  • 28
    • 4444253104 scopus 로고    scopus 로고
    • Chloroethyl nitrosourea-derived ethano cytosine and adenine adducts are substrates for Escherichia coli glycosylases excising analogous etheno adducts
    • A.B. Guliaev, B. Singer, and B. Hang Chloroethyl nitrosourea-derived ethano cytosine and adenine adducts are substrates for Escherichia coli glycosylases excising analogous etheno adducts DNA Rep. (Amst) 3 2004 1311 1321
    • (2004) DNA Rep. (Amst) , vol.3 , pp. 1311-1321
    • Guliaev, A.B.1    Singer, B.2    Hang, B.3
  • 30
    • 0028087282 scopus 로고
    • All four known cyclic adducts formed in DNA by the vinyl chloride metabolite chloroacetaldehyde are released by a human DNA glycosylase
    • M.K. Dosanjh, A. Chenna, E. Kim, H. Fraenkel-Conrat, L. Samson, and B. Singer All four known cyclic adducts formed in DNA by the vinyl chloride metabolite chloroacetaldehyde are released by a human DNA glycosylase Proc. Natl. Acad. Sci. U.S.A. 91 1994 1024 1028
    • (1994) Proc. Natl. Acad. Sci. U.S.A. , vol.91 , pp. 1024-1028
    • Dosanjh, M.K.1    Chenna, A.2    Kim, E.3    Fraenkel-Conrat, H.4    Samson, L.5    Singer, B.6
  • 33
    • 3042524904 scopus 로고
    • A well-behaved electrostatic potential based method using charge restraints for deriving atomic charges: The RESP model
    • C. Bayly, P. Cieplak, W. Cornell, and P.A. Kolman A well-behaved electrostatic potential based method using charge restraints for deriving atomic charges: the RESP model J. Phys. Chem. 97 1993 10269 10280
    • (1993) J. Phys. Chem. , vol.97 , pp. 10269-10280
    • Bayly, C.1    Cieplak, P.2    Cornell, W.3    Kolman, P.A.4
  • 35
    • 0033851504 scopus 로고    scopus 로고
    • Sequence-dependent conformational perturbation in DNA duplexes containing an εa·T mismatch using molecular dynamics simulation
    • A.B. Guliaev, J. Sagi, and B. Singer Sequence-dependent conformational perturbation in DNA duplexes containing an εA·T mismatch using molecular dynamics simulation Carcinogenesis 21 2000 1727 1736
    • (2000) Carcinogenesis , vol.21 , pp. 1727-1736
    • Guliaev, A.B.1    Sagi, J.2    Singer, B.3
  • 36
    • 3042845812 scopus 로고    scopus 로고
    • Structural insights by molecular dynamics simulations into specificity of the major human AP endonuclease toward the benzene-derived DNA adduct, pBQ-C
    • A.B. Guliaev, B. Hang, and B. Singer Structural insights by molecular dynamics simulations into specificity of the major human AP endonuclease toward the benzene-derived DNA adduct, pBQ-C Nucl. Acids Res. 32 2004 2844 2852
    • (2004) Nucl. Acids Res. , vol.32 , pp. 2844-2852
    • Guliaev, A.B.1    Hang, B.2    Singer, B.3
  • 39
    • 0037743666 scopus 로고    scopus 로고
    • Mismatch uracil glycosylase from Eschenchia coli: A general mismatch or a specific DNA glycosylase?
    • R.J. O'Neill, O.V. Vorob'eva, H. Shahbakhti, E. Zmuda, A.S. Bhagwat, and G.S. Baldwin Mismatch uracil glycosylase from Eschenchia coli: a general mismatch or a specific DNA glycosylase? J. Biol. Chem. 278 2003 20526 20532
    • (2003) J. Biol. Chem. , vol.278 , pp. 20526-20532
    • O'Neill, R.J.1    Vorob'Eva, O.V.2    Shahbakhti, H.3    Zmuda, E.4    Bhagwat, A.S.5    Baldwin, G.S.6
  • 41
    • 0037178808 scopus 로고    scopus 로고
    • 2-ethenoguanine, a mutagenic DNA adduct, is a primary substrate of Escherichia coli mismatch-specific uracil-DNA glycosylase and human alkylpurine-DNA-N-glycosylase
    • 2-ethenoguanine, a mutagenic DNA adduct, is a primary substrate of Escherichia coli mismatch-specific uracil-DNA glycosylase and human alkylpurine-DNA-N-glycosylase J. Biol. Chem. 277 2002 26987 26993
    • (2002) J. Biol. Chem. , vol.277 , pp. 26987-26993
    • Saparbaev, M.1    Langouet, S.2    Privezentzev, C.V.3    Guengerich, F.P.4    Cai, H.5    Elder, R.H.6    Laval, J.7
  • 43
    • 0025851827 scopus 로고
    • 6-ethenodeoxyadenosine adduct (εdA) opposite thymidine in a DNA duplex. Nonplanar alignment of εdA (anti) and dT (anti) at the lesion site
    • 6-ethenodeoxyadenosine adduct (εdA) opposite thymidine in a DNA duplex. Nonplanar alignment of εdA (anti) and dT (anti) at the lesion site Biochemistry 30 1991 1820 1828
    • (1991) Biochemistry , vol.30 , pp. 1820-1828
    • Kouchakdjian, M.1    Eisenberg, M.2    Yarema, K.3    Basu, A.4    Essigmann, J.5    Patel, D.J.6
  • 45
    • 0034711946 scopus 로고    scopus 로고
    • 6-ethenocytosine adduct opposite 2′-deoxycytidine: Implications for the recognition of exocyclic lesions by DNA glycosylases
    • 6-ethenocytosine adduct opposite 2′-deoxycytidine: implications for the recognition of exocyclic lesions by DNA glycosylases J. Mol. Biol. 296 2000 851 861
    • (2000) J. Mol. Biol. , vol.296 , pp. 851-861
    • Cullinan, D.1    Johnson, F.2    De Los Santos, C.3
  • 46
    • 0034610336 scopus 로고    scopus 로고
    • Molecular basis for discriminating between normal and damaged bases by the human alkyladenine glycosylase, AAG
    • A.Y. Lau, M.D. Wyatt, B.J. Glassner, L.D. Samson, and T. Ellenberger Molecular basis for discriminating between normal and damaged bases by the human alkyladenine glycosylase, AAG Proc. Natl. Acad. Sci. U.S.A. 97 2000 13573 13578
    • (2000) Proc. Natl. Acad. Sci. U.S.A. , vol.97 , pp. 13573-13578
    • Lau, A.Y.1    Wyatt, M.D.2    Glassner, B.J.3    Samson, L.D.4    Ellenberger, T.5
  • 47
    • 12144272489 scopus 로고    scopus 로고
    • Effects of substrate specificity on initiating the base excision repair of N-methylpurines by variant human 3-methyladenine DNA glycosylases
    • E.E. Connor, J.J. Wilson, and M.D. Wyatt Effects of substrate specificity on initiating the base excision repair of N-methylpurines by variant human 3-methyladenine DNA glycosylases Chem. Res. Toxicol. 18 2005 87 94
    • (2005) Chem. Res. Toxicol. , vol.18 , pp. 87-94
    • Connor, E.E.1    Wilson, J.J.2    Wyatt, M.D.3
  • 48
    • 0036753352 scopus 로고    scopus 로고
    • Active-site clashes prevent the human 3-methyladenine DNA glycosylase from improperly removing bases
    • E.E. Connor, and M.D. Wyatt Active-site clashes prevent the human 3-methyladenine DNA glycosylase from improperly removing bases Chem. Biol. 9 2002 1033 1041
    • (2002) Chem. Biol. , vol.9 , pp. 1033-1041
    • Connor, E.E.1    Wyatt, M.D.2
  • 49
    • 0029943449 scopus 로고    scopus 로고
    • Mismatch repair in replication fidelity, genetic recombination, and cancer biology
    • P. Modrich, and R. Lahue Mismatch repair in replication fidelity, genetic recombination, and cancer biology Annu. Rev. Biochem. 65 1996 101 133
    • (1996) Annu. Rev. Biochem. , vol.65 , pp. 101-133
    • Modrich, P.1    Lahue, R.2
  • 50
    • 0020332947 scopus 로고
    • 6-methylguanine residues in E. coli DNA
    • 6- methylguanine residues in E. coli DNA Nature 296 1982 868 8699
    • (1982) Nature , vol.296 , pp. 868-8699
    • Karran, P.1    Marinus, M.G.2
  • 51
    • 0029812676 scopus 로고    scopus 로고
    • Cisplatin and adriamycin resistance are associated with MutLα and mismatch repair deficiency in an ovarian tumor cell line
    • J.T. Drummond, A. Anthoney, R. Brown, and P. Modrich Cisplatin and adriamycin resistance are associated with MutLα and mismatch repair deficiency in an ovarian tumor cell line J. Biol. Chem. 271 1996 19645 19648
    • (1996) J. Biol. Chem. , vol.271 , pp. 19645-19648
    • Drummond, J.T.1    Anthoney, A.2    Brown, R.3    Modrich, P.4
  • 52
    • 0033513097 scopus 로고    scopus 로고
    • Mismatch repair processing of carcinogen-DNA adducts triggers apoptosis
    • J. Wu, L. Gu, H. Wang, N.E. Geacintov, and G.M. Li Mismatch repair processing of carcinogen-DNA adducts triggers apoptosis Mol. Cell. Biol. 19 1999 8292 8301
    • (1999) Mol. Cell. Biol. , vol.19 , pp. 8292-8301
    • Wu, J.1    Gu, L.2    Wang, H.3    Geacintov, N.E.4    Li, G.M.5


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