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Volumn 11, Issue 1, 1998, Pages 44-53

Aralkylation of guanosine with para-substituted styrene oxides

Author keywords

[No Author keywords available]

Indexed keywords

GUANOSINE; STYRENE OXIDE;

EID: 0031885120     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx970126i     Document Type: Article
Times cited : (15)

References (35)
  • 1
    • 0028691022 scopus 로고
    • From fluorescence spectra to mutational spectra, a historical overview of DNA-reactive compounds
    • Hemminki, K., Dipple, A., Shuker, D. E. G., Kadlubar, F. F., Seger-bäck, D., and Bartsch, H., Eds., IARC Scientific Publications No. 125, IARC, Lyon, France
    • Lawley, P. D. (1994) From fluorescence spectra to mutational spectra, a historical overview of DNA-reactive compounds. In DNA Adducts: Identification and Biological Significance (Hemminki, K., Dipple, A., Shuker, D. E. G., Kadlubar, F. F., Seger-bäck, D., and Bartsch, H., Eds.) pp 3-22, IARC Scientific Publications No. 125, IARC, Lyon, France.
    • (1994) DNA Adducts: Identification and Biological Significance , pp. 3-22
    • Lawley, P.D.1
  • 2
    • 2642613365 scopus 로고    scopus 로고
    • DNA-reactive agents
    • Sipes, I. G., McQueen, C. A., and Gandolphi, A. J., Eds., Elsevier Science Ltd., Oxford
    • Dipple, A. (1997) DNA-reactive agents. In Comprehensive Toxicology (Sipes, I. G., McQueen, C. A., and Gandolphi, A. J., Eds.) pp 303-314, Elsevier Science Ltd., Oxford.
    • (1997) Comprehensive Toxicology , pp. 303-314
    • Dipple, A.1
  • 3
    • 0025099493 scopus 로고
    • Reaction products in haemoglobin and DNA after in vitro treatment with ethylene oxide and N-(2-hydroxyethyl)-N-nitrosourea
    • Segerbäck, D. (1990) Reaction products in haemoglobin 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
    • Segerbäck, D.1
  • 4
    • 0023787141 scopus 로고
    • Reactions of propylene oxide with 2′-deoxynucleosides and in vitro with calf thymus DNA
    • Solomon, J. J., Mukai, F., Fedyk, J., and Segal, A. (1988) Reactions of propylene oxide with 2′-deoxynucleosides and in vitro with calf thymus DNA. Chem.-Biol. Interact. 67, 275-294.
    • (1988) Chem.-Biol. Interact. , vol.67 , pp. 275-294
    • Solomon, J.J.1    Mukai, F.2    Fedyk, J.3    Segal, A.4
  • 5
    • 0028693095 scopus 로고
    • DNA alkylation by ethylene oxide and some monosubstituted epoxides
    • Hemminki, K., Dipple, A., Shuker, D. E. G., Kadlubar, F. F., Segerbäck, D., and Bartsch, H., Eds., IARC Scientific Publications No. 125, IARC, Lyon, France
    • Segerbäck, D. (1994) DNA alkylation by ethylene oxide and some monosubstituted epoxides. In DNA Adducts: Identification and Biological Significance (Hemminki, K., Dipple, A., Shuker, D. E. G., Kadlubar, F. F., Segerbäck, D., and Bartsch, H., Eds.) pp 37-47, IARC Scientific Publications No. 125, IARC, Lyon, France.
    • (1994) DNA Adducts: Identification and Biological Significance , pp. 37-47
    • Segerbäck, D.1
  • 7
    • 0017625473 scopus 로고
    • Benzo[a]pyrene diol epoxide covalently binds to deoxyguanosine and deoxyadenosine in DNA
    • Meehan, T., Staub, K., and Calvin, M. (1977) Benzo[a]pyrene diol epoxide covalently binds to deoxyguanosine and deoxyadenosine in DNA. Nature 269, 725-727.
    • (1977) Nature , vol.269 , pp. 725-727
    • Meehan, T.1    Staub, K.2    Calvin, M.3
  • 8
    • 0018137343 scopus 로고
    • Binding of benzo[a]pyrene 7,8-diol-9,10-epoxides to DNA, RNA and protein of mouse skin occurs with high stereoselectivity
    • Koreeda, M., Moore, P. D., Wislocki, P. G., Levin, W., Conney, A. H., Yagi, H., and Jerina, D. M. (1978) Binding of benzo[a]pyrene 7,8-diol-9,10-epoxides to DNA, RNA and protein of mouse skin occurs with high stereoselectivity. Science 199, 778-781.
    • (1978) Science , vol.199 , pp. 778-781
    • Koreeda, M.1    Moore, P.D.2    Wislocki, P.G.3    Levin, W.4    Conney, A.H.5    Yagi, H.6    Jerina, D.M.7
  • 9
    • 0021139865 scopus 로고
    • Identification of the major adducts formed by reaction with 5-methylchrysene anti-dihydrodiol-epoxides with DNA in vitro
    • Melikian, A. A., Amin, S., Hecht, S. S., Hoffmann, D., Pataki, J., and Harvey, R. G. (1984) Identification of the major adducts formed by reaction with 5-methylchrysene anti-dihydrodiol-epoxides with DNA in vitro. Cancer Res. 414, 2524-2529.
    • (1984) Cancer Res. , vol.414 , pp. 2524-2529
    • Melikian, A.A.1    Amin, S.2    Hecht, S.S.3    Hoffmann, D.4    Pataki, J.5    Harvey, R.G.6
  • 11
    • 0025857782 scopus 로고
    • Spectroscopic characterization of syn-5-methylchrysene-1,2-dihydrodiol 3,4-epoxide-deoxyribonucleoside adducts
    • Peltonen, K., Hilton, B. D., Pataki, J., Lee, H., Harvey, R. G., and Dipple, A. (1991) Spectroscopic characterization of syn-5-methylchrysene-1,2-dihydrodiol 3,4-epoxide-deoxyribonucleoside adducts. Chem. Res. Toxicol. 4, 305-310.
    • (1991) Chem. Res. Toxicol. , vol.4 , pp. 305-310
    • Peltonen, K.1    Hilton, B.D.2    Pataki, J.3    Lee, H.4    Harvey, R.G.5    Dipple, A.6
  • 12
    • 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. 2026-2028.
    • (1968) J. Chem. Soc. , pp. 2026-2028
    • Brookes, P.1    Dipple, A.2    Lawley, P.D.3
  • 13
    • 0018605735 scopus 로고
    • Selectivity in nucleoside alkylation and aralkylation in relation to chemical carcinogenesis
    • Moschel, R. C., Hudgins, W. R., and Dipple, A. (1979) Selectivity in nucleoside alkylation and aralkylation in relation to chemical carcinogenesis. J. Org. Chem. 44, 3324-3328.
    • (1979) J. Org. Chem. , vol.44 , pp. 3324-3328
    • Moschel, R.C.1    Hudgins, W.R.2    Dipple, A.3
  • 14
    • 0018900384 scopus 로고
    • Aralkylation of guanosine by the carcinogen N-nitroso-N-benzylurea
    • Moschel, R. C., Hudgins, W. R., and Dipple, A. (1980) Aralkylation of guanosine by the carcinogen N-nitroso-N-benzylurea. J. Org. Chem. 45, 533-535.
    • (1980) J. Org. Chem. , vol.45 , pp. 533-535
    • Moschel, R.C.1    Hudgins, W.R.2    Dipple, A.3
  • 15
    • 0019970186 scopus 로고
    • Selectivity of alkylation and aralkylation of nucleic acid components
    • Dipple, A., Moschel, R. C., and Hudgins, W. R. (1982) Selectivity of alkylation and aralkylation of nucleic acid components. Drug Metab. Rev. 13, 249-268.
    • (1982) Drug Metab. Rev. , vol.13 , pp. 249-268
    • Dipple, A.1    Moschel, R.C.2    Hudgins, W.R.3
  • 16
    • 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. (1979) 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.
    • (1979) J. Org. Chem. , vol.49 , pp. 363-372
    • Moschel, R.C.1    Hudgins, W.R.2    Dipple, A.3
  • 17
    • 0001670615 scopus 로고
    • Reactivity effects on site selectivity in nucleoside aralkylation: A model for the factors influencing the sites of carcinogen-nucleic acid interactions
    • Moschel, R. C., Hudgins, W. R., and Dipple, A. (1986) Reactivity effects on site selectivity in nucleoside aralkylation: A model for the factors influencing the sites of carcinogen-nucleic acid interactions. J. Org. Chem. 51, 4180-4185.
    • (1986) J. Org. Chem. , vol.51 , pp. 4180-4185
    • Moschel, R.C.1    Hudgins, W.R.2    Dipple, A.3
  • 18
    • 0024264870 scopus 로고
    • Styrene oxide as a stereochemical probe for the mechanism of aralkylation at different sites of guanosine
    • Latif, F., Moschel, R. C., Hemminki, K., and Dipple, A. (1988) Styrene oxide as a stereochemical probe for the mechanism of aralkylation at different sites of guanosine. Chem. Res. Toxicol. 1, 364-369.
    • (1988) Chem. Res. Toxicol. , vol.1 , pp. 364-369
    • Latif, F.1    Moschel, R.C.2    Hemminki, K.3    Dipple, A.4
  • 20
    • 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
  • 21
    • 0018634890 scopus 로고
    • First experimental demonstration of the carcinogenic effects of styrene oxide
    • Maltoni, C., Failla, G., and Kassapidis, G. (1979) First experimental demonstration of the carcinogenic effects of styrene oxide. Med. Lav. 5, 358-362.
    • (1979) Med. Lav. , vol.5 , pp. 358-362
    • Maltoni, C.1    Failla, G.2    Kassapidis, G.3
  • 22
    • 0022469749 scopus 로고
    • Rat and mouse forestomach tumors induced by chronic oral administration of styrene oxide
    • Lijinsky, W. (1986) Rat and mouse forestomach tumors induced by chronic oral administration of styrene oxide. J. Natl. Cancer Inst. 77, 471-476.
    • (1986) J. Natl. Cancer Inst. , vol.77 , pp. 471-476
    • Lijinsky, W.1
  • 23
    • 0021233580 scopus 로고
    • Reaction products of styrene oxide with guanosine in aqueous media
    • Hemminki, K., and Hesso, A. (1984) Reaction products of styrene oxide with guanosine in aqueous media. Carcinogenesis 5, 601-607.
    • (1984) Carcinogenesis , vol.5 , pp. 601-607
    • Hemminki, K.1    Hesso, A.2
  • 24
    • 0022971368 scopus 로고
    • Characterization of reaction products between styrene oxide and deoxynucleosides and DNA
    • Savela, K., Hesso, A., and Hemminki, K. (1986) Characterization of reaction products between styrene oxide and deoxynucleosides and DNA. Chem.-Biol. Interact. 60, 235-246.
    • (1986) Chem.-Biol. Interact. , vol.60 , pp. 235-246
    • Savela, K.1    Hesso, A.2    Hemminki, K.3
  • 27
    • 0006061776 scopus 로고
    • 6-substituted guanosine products resulting from the reaction of guanosine with styrene oxide
    • 6-substituted guanosine products resulting from the reaction of guanosine with styrene oxide. J. Org. Chem. 51, 2952-2955.
    • (1986) J. Org. Chem. , vol.51 , pp. 2952-2955
    • Moschel, R.C.1    Hemminki, K.2    Dipple, A.3
  • 28
    • 0019880773 scopus 로고
    • Mechanistic studies of epoxide hydrolase utilizing a continuous spectrophotometric assay
    • Westkaemper, R. B., and Hanzlik, R. P. (1981) Mechanistic studies of epoxide hydrolase utilizing a continuous spectrophotometric assay. Arch. Biochem. Biophys. 208, 195-204.
    • (1981) Arch. Biochem. Biophys. , vol.208 , pp. 195-204
    • Westkaemper, R.B.1    Hanzlik, R.P.2
  • 30
    • 0029937757 scopus 로고    scopus 로고
    • A practical route to enantiopure 1,2-amino alcohols
    • Chang, H.-T., and Sharpless, K. B. (1996) A practical route to enantiopure 1,2-amino alcohols Tetrahedron Lett. 37, 3219-3222.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 3219-3222
    • Chang, H.-T.1    Sharpless, K.B.2
  • 32
    • 0001245170 scopus 로고
    • The mechanism of epoxide reaction. IV. The reactions of benzylamine with a series of m-and p-substituted styrene oxides in ethanol
    • Laird, R. M., and Parker, R. E. (1961) The mechanism of epoxide reaction. IV. The reactions of benzylamine with a series of m-and p-substituted styrene oxides in ethanol. J. Am. Chem. Soc. 4277-4281.
    • (1961) J. Am. Chem. Soc. , pp. 4277-4281
    • Laird, R.M.1    Parker, R.E.2
  • 33
    • 0343090718 scopus 로고
    • An analysis of the factors contributing to the regioselectivity observed in the opening of oxiranes
    • Keiyser, M. M., and Morand, P. (1980) An analysis of the factors contributing to the regioselectivity observed in the opening of oxiranes. Can. J. Chem. 58, 302-306.
    • (1980) Can. J. Chem. , vol.58 , pp. 302-306
    • Keiyser, M.M.1    Morand, P.2
  • 34
    • 0027323384 scopus 로고
    • In vitro reactions of 2-cyanoethylene oxide with calf thymus DNA
    • Solomon, J. J., Singh, U. S., and Segal, A. (1993) In vitro reactions of 2-cyanoethylene oxide with calf thymus DNA. Chem.-Biol. Interact 88, 115-135.
    • (1993) Chem.-Biol. Interact , vol.88 , pp. 115-135
    • Solomon, J.J.1    Singh, U.S.2    Segal, A.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.