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Volumn 11, Issue 6, 1998, Pages 696-702

Effect of ionic state of 2'-deoxyguanosine and solvent on its aralkylation by benzyl bromide

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATING AGENT; BENZYL BROMIDE; DEOXYGUANOSINE; UNCLASSIFIED DRUG;

EID: 0031802890     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx980012m     Document Type: Article
Times cited : (26)

References (28)
  • 1
    • 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
  • 2
    • 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
  • 3
    • 2642704013 scopus 로고
    • A novel product from the reaction of p-methylbenzyl chloride with guanosine in neutral aqueous solution
    • Moschel, R. C., Hudgins, W. R., and Dipple A. (1981) A novel product from the reaction of p-methylbenzyl chloride with guanosine in neutral aqueous solution. Tetrahedron Lett. 22, 2427-2430.
    • (1981) Tetrahedron Lett. , vol.22 , pp. 2427-2430
    • Moschel, R.C.1    Hudgins, W.R.2    Dipple, A.3
  • 4
    • 0000594201 scopus 로고
    • 6-(p-methoxybenzyl)guanosine in aqueous solution to yield guanosine, p-methoxybenzylguanosines, and 4-(p-methoxybenzyl)-5-guanidino-1-β-D-ribofuranosylimidazole
    • 6-(p-methoxybenzyl)guanosine in aqueous solution to yield guanosine, p-methoxybenzylguanosines, and 4-(p-methoxybenzyl)-5-guanidino-1-β-D-ribofuranosylimidazole. J. Am. Chem. Soc. 103, 5489-5494.
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 5489-5494
    • Moschel, R.C.1    Hudgins, W.R.2    Dipple, A.3
  • 5
    • 0021326895 scopus 로고
    • Substituent-induced effects on the stability of benzylated guanosmes: Model systems for the factors influencing the stability of carcinogenmodified nucleic acids
    • Moschel, R. C., Hudgins, W. R., and Dipple, A (1984) Substituent-induced effects on the stability of benzylated guanosmes: model systems for the factors influencing the stability of carcinogenmodified 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
  • 6
    • 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
  • 7
    • 0023034210 scopus 로고
    • Electrophilic attack at carbon-5 of guanine nucleosides: Structure and properties of the resulting guanidinoimidazole products
    • (Singer, B., and Bartsch, H., Eds.) IARC Scientific Publication No. 70, IARC, Lyon, France
    • Moschel, R. C., Hudgins, W. R., and Dipple, A. (1986) Electrophilic attack at carbon-5 of guanine nucleosides: structure and properties of the resulting guanidinoimidazole products. In Role of Cyclic Nucleic Acid Adducts in Carcinogenesis and Mutagenesis (Singer, B., and Bartsch, H., Eds.) IARC Scientific Publication No. 70, pp 235-240, IARC, Lyon, France.
    • (1986) Role of Cyclic Nucleic Acid Adducts in Carcinogenesis and Mutagenesis , pp. 235-240
    • Moschel, R.C.1    Hudgins, W.R.2    Dipple, A.3
  • 8
    • 0025082621 scopus 로고
    • Aralkylation of 2′-deoxyguanosine: Medium effects on sites of reaction with 7-(bromomethyl)benz[a]anthracene
    • Pei, G. K., and Moschel, R. C. (1990) Aralkylation of 2′-deoxyguanosine: medium effects on sites of reaction with 7-(bromomethyl)benz[a]anthracene. Chem. Res. Toxicol. 3, 292-295.
    • (1990) Chem. Res. Toxicol. , vol.3 , pp. 292-295
    • Pei, G.K.1    Moschel, R.C.2
  • 9
    • 0028694291 scopus 로고
    • Reaction of aralkyl halides with nucleic acid components and DNA
    • (Hemminki, K., Dipple, A Shuker D. E. G., Kadlubar, F. F., Segerbäck, and Bartsch, H., Eds.) IAKC Scientific Publication No. 128, IARC, Lyon, France
    • Moschel, R. C. (1994) Reaction of aralkyl halides with nucleic acid components and DNA. In DNA Adducts: Identification and Biological Significance (Hemminki, K., Dipple, A Shuker D. E. G., Kadlubar, F. F., Segerbäck, and Bartsch, H., Eds.) IAKC Scientific Publication No. 128, pp 25-36, IARC, Lyon, France.
    • (1994) DNA Adducts: Identification and Biological Significance , pp. 25-36
    • Moschel, R.C.1
  • 10
    • 33644610627 scopus 로고
    • Medium effects on the rates and mechanisms of solvolytic reactions
    • Bentley, T. W., and Schleyer, P. v. R. (1977) Medium effects on the rates and mechanisms of solvolytic reactions. Adv. Phys. Org. Chem. 14, 1-67.
    • (1977) Adv. Phys. Org. Chem. , vol.14 , pp. 1-67
    • Bentley, T.W.1    Schleyer, P.V.R.2
  • 11
    • 0020805704 scopus 로고
    • 4-methylthymidme in place of deoxythymidine in primed Poly(dA-dT),Poly (dA-dT) synthesis
    • 4-methylthymidme in place of deoxythymidine in primed Poly(dA-dT),Poly (dA-dT) synthesis. Proc. Natl. Acad. Sci. U.S.A. 80, 4884-4888.
    • (1983) Proc. Natl. Acad. Sci. U.S.A. , vol.80 , pp. 4884-4888
    • Singer, B.1    Kusmierek, J.T.2
  • 14
    • 0024246378 scopus 로고
    • 6substituted 2′-deoxyguanosine residues at the first, second, or both positions of codon 12
    • 6substituted 2′-deoxyguanosine residues at the first, second, or both positions of codon 12. Chem. Res. Toxicol. 1, 391-397.
    • (1988) Chem. Res. Toxicol. , vol.1 , pp. 391-397
    • Pauly, G.T.1    Powers, M.2    Pei, G.K.3    Moschel, R.C.4
  • 15
    • 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
  • 16
    • 2642618370 scopus 로고
    • 7-Benzylguanine
    • (Zorbacn, W. W., and Tipson, R. S., Eds.) Wiley-Interscience, New
    • Rogers, G. T., and Ulbricht, T. L. V. (1968) 7-Benzylguanine. In Synthetic Procedures in Nucleic Acid Chemistry Vol. 1 (Zorbacn, W. W., and Tipson, R. S., Eds.) pp 15-17, Wiley-Interscience, New
    • (1968) Synthetic Procedures in Nucleic Acid Chemistry , vol.1 , pp. 15-17
    • Rogers, G.T.1    Ulbricht, T.L.V.2
  • 17
    • 0015902519 scopus 로고
    • The alkylation of 2′-deoxyguanosine and of thymidine with diazoalkanes
    • Farmer, P. B., Foster, A. B., Jarman, M., and Tisdale, M. J. (1973) The alkylation of 2′-deoxyguanosine and of thymidine with diazoalkanes. Biochem. J. 135, 203-213.
    • (1973) Biochem. J. , vol.135 , pp. 203-213
    • Farmer, P.B.1    Foster, A.B.2    Jarman, M.3    Tisdale, M.J.4
  • 18
    • 0003644543 scopus 로고
    • UV spectral characteristics and acidic dissociation constants of 280 alkyl bases, nucleosides and nucleotides
    • (Fasman, G. D., Ed.)
    • Singer, B. (1975) UV spectral characteristics and acidic dissociation constants of 280 alkyl bases, nucleosides and nucleotides. In Handbook of Biochemistry and Molecular Biology, Vol. 1, Nucleic Acids, 3rd ed. (Fasman, G. D., Ed.) pp 409-447.
    • (1975) Handbook of Biochemistry and Molecular Biology, Vol. 1, Nucleic Acids, 3rd Ed. , vol.1 , pp. 409-447
    • Singer, B.1
  • 19
    • 2642675829 scopus 로고
    • 3-methylguanine
    • (Zorbach, W. W., and Tipson, R. S., Eds.) Wiley-Interscience, New York
    • Townsend, L. B., and Robins, R. K. (1968) 3-methylguanine. In Synthetic Procedures in Nucleic Acid Chemistry, Vol. 1 (Zorbach, W. W., and Tipson, R. S., Eds.) pp 18-21, Wiley-Interscience, New York.
    • (1968) Synthetic Procedures in Nucleic Acid Chemistry , vol.1 , pp. 18-21
    • Townsend, L.B.1    Robins, R.K.2
  • 20
    • 85008284659 scopus 로고
    • N→N alkyl and glycosyl migration of purines and pyrimidines. III. N-N alkyl and glycosyl migration of purine derivatives
    • Miyaki, M., and Bunji, S. (1970) N→N alkyl and glycosyl migration of purines and pyrimidines. III. N-N alkyl and glycosyl migration of purine derivatives. Chem. Pharm. Bull. 18, 1446-1456.
    • (1970) Chem. Pharm. Bull. , vol.18 , pp. 1446-1456
    • Miyaki, M.1    Bunji, S.2
  • 21
    • 0014227479 scopus 로고
    • The chemistry of guanine and its biologically significant derivatives
    • Shapiro, R. (1968) The chemistry of guanine and its biologically significant derivatives. Prog. Nucleic Acid Res. Mol Biol. 8, 73-112.
    • (1968) Prog. Nucleic Acid Res. Mol Biol. , vol.8 , pp. 73-112
    • Shapiro, R.1
  • 24
    • 0000785768 scopus 로고
    • Carcinogenesis by alkylating agents
    • (Searle, C. E., Ed.) ACS Monograph 182, American Chemical Society, Washington, DC
    • Lawley, P. D. (1984) Carcinogenesis by alkylating agents. In Chemical Carcinogens, 2nd ed. (Searle, C. E., Ed.) ACS Monograph 182, Vol. 1, pp 325-484, American Chemical Society, Washington, DC.
    • (1984) Chemical Carcinogens, 2nd Ed. , vol.1 , pp. 325-484
    • Lawley, P.D.1
  • 25
    • 0015146551 scopus 로고
    • Reaction of 7-bromomethylbenz[a]anthracene with nucleic acids, polynucleotides, and nucleosides
    • Dipple, A., Brookes, P., Mackintosh, D. S., and Rayman, M. P. (1971) Reaction of 7-bromomethylbenz[a]anthracene with nucleic acids, polynucleotides, and nucleosides. Biochemistry 10, 4323-4330.
    • (1971) Biochemistry , vol.10 , pp. 4323-4330
    • Dipple, A.1    Brookes, P.2    Mackintosh, D.S.3    Rayman, M.P.4
  • 26
    • 0031575858 scopus 로고    scopus 로고
    • The mechanism of decomposition of N-methyl-N-nitrosourea (MNU) in water and a study of its reactions with 2′-deoxyguanosine, 2′-deoxyguanosine 5′-monophosphate and d(GTGCAC)
    • Golding, B. T., Bleasdale, C., McGinnis, J., Müller, S., Rees, H. T., Rees, N. H., Farmer, P. B., and Watson, W. P. (1997) The mechanism of decomposition of N-methyl-N-nitrosourea (MNU) in water and a study of its reactions with 2′-deoxyguanosine, 2′-deoxyguanosine 5′-monophosphate and d(GTGCAC). Tetrahedron 53, 4063-4082.
    • (1997) Tetrahedron , vol.53 , pp. 4063-4082
    • Golding, B.T.1    Bleasdale, C.2    McGinnis, J.3    Müller, S.4    Rees, H.T.5    Rees, N.H.6    Farmer, P.B.7    Watson, W.P.8
  • 27
    • 0028690473 scopus 로고
    • DNA adducts of nitrosamines
    • (Hemminki, K., Dipple, A., Shuker, D. E. G., Kadlubar, F. F., Segerbäck, and Bartsch, H., Eds.) IARC Scientific Publication No. 128, IARC, Lyon, France
    • Shuker, D. E. G., and Bartsch, H. (1994) DNA adducts of nitrosamines. In DNA Adducts: Identification and Biological Significance (Hemminki, K., Dipple, A., Shuker, D. E. G., Kadlubar, F. F., Segerbäck, and Bartsch, H., Eds.) IARC Scientific Publication No. 128, pp 73-89, IARC, Lyon, France.
    • (1994) DNA Adducts: Identification and Biological Significance , pp. 73-89
    • Shuker, D.E.G.1    Bartsch, H.2
  • 28
    • 0028707724 scopus 로고
    • Reactions of polycyclic aromatic hydrocarbons with DNA
    • (Hemminki, K., Dipple, A., Shuker, D. E. G., Kadlubar, F. F., Segerbäck, and Bartsch, H., Eds.) IARC Scientific Publication No, 128, IARC, Lyon, France
    • Dipple, A. (1994) Reactions of polycyclic aromatic hydrocarbons with DNA. In DNA Adducts: Identification and Biological Significance (Hemminki, K., Dipple, A., Shuker, D. E. G., Kadlubar, F. F., Segerbäck, and Bartsch, H., Eds.) IARC Scientific Publication No, 128, pp 107-129, IARC, Lyon, France.
    • (1994) DNA Adducts: Identification and Biological Significance , pp. 107-129
    • Dipple, A.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.