메뉴 건너뛰기




Volumn 9, Issue 1, 1996, Pages 172-178

Oxidative metabolism of 1-(2-chloroethyl)-3-alkyl-3-(methylcarbamoyl)triazenes: Formation of chloroacetaldehyde and relevance to biological activity

Author keywords

[No Author keywords available]

Indexed keywords

1 (2 CHLOROETHYL) 3 METHYL 3 (METHYLCARBAMOYL)TRIAZENE; 3 BENZYL 1 (2 CHLOROETHYL) 3 (METHYLCARBAMOYL)TRIAZENE; CHLOROACETALDEHYDE; TRIAZINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0030069798     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx9500639     Document Type: Article
Times cited : (49)

References (23)
  • 1
    • 0023023177 scopus 로고
    • 1,3-Dimethyl-3-acyltriazenes: Synthesis and chemistry of a novel class of biological methylating agents
    • Smith, R. H., Mehl, A. F., Hicks, A., Denlinger, C. L., Kratz, L., Andrews, A. W., and Michejda, C. J. (1986) 1,3-Dimethyl-3-acyltriazenes: Synthesis and chemistry of a novel class of biological methylating agents. J. Org. Chem. 51, 3751-3757.
    • (1986) J. Org. Chem. , vol.51 , pp. 3751-3757
    • Smith, R.H.1    Mehl, A.F.2    Hicks, A.3    Denlinger, C.L.4    Kratz, L.5    Andrews, A.W.6    Michejda, C.J.7
  • 2
    • 0023882250 scopus 로고
    • Novel cross-linking alkylating agents, 1-(2-chloroethyl)-3-methyl-3-acyltriazenes
    • Smith, R. H., Mehl, A. F., Shantz, D. L., Chmurny, G. N., and Michejda, C. J. (1988) Novel cross-linking alkylating agents, 1-(2-chloroethyl)-3-methyl-3-acyltriazenes. J. Org. Chem. 53, 1467-1471.
    • (1988) J. Org. Chem. , vol.53 , pp. 1467-1471
    • Smith, R.H.1    Mehl, A.F.2    Shantz, D.L.3    Chmurny, G.N.4    Michejda, C.J.5
  • 3
    • 0025122538 scopus 로고
    • 1,3-Diaikyl-3-acyltriazenes, a novel class of antineoplastic alkylating agents
    • Smith, R. H., Scudiero, D. A., and Michejda, C. J. (1990) 1,3-Diaikyl-3-acyltriazenes, a novel class of antineoplastic alkylating agents. J. Med. Chem. 33, 2579-2583.
    • (1990) J. Med. Chem. , vol.33 , pp. 2579-2583
    • Smith, R.H.1    Scudiero, D.A.2    Michejda, C.J.3
  • 6
    • 0026739566 scopus 로고
    • Alkylation of DNA by 1,3-dialkyl-3-acyltriazenes: Correlation of biological activity with chemical behavior
    • Kroeger-Koepke, M. B., Michejda, C. J., and Smith, R. H. (1992) Alkylation of DNA by 1,3-dialkyl-3-acyltriazenes: Correlation of biological activity with chemical behavior. Chem. Res. Toxicol. 5, 541-547.
    • (1992) Chem. Res. Toxicol. , vol.5 , pp. 541-547
    • Kroeger-Koepke, M.B.1    Michejda, C.J.2    Smith, R.H.3
  • 7
    • 0000556620 scopus 로고
    • Decomposition of 1,3-dialkyltriazenes in aqueous buffers: Kinetic and mechanistic studies
    • Smith, R. H., Denlinger, C. L., Kupper, R., Mehl, A. F., and Michejda, C. J. (1986) Decomposition of 1,3-dialkyltriazenes in aqueous buffers: Kinetic and mechanistic studies. J. Am. Chem. Soc. 108, 3726-3730.
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 3726-3730
    • Smith, R.H.1    Denlinger, C.L.2    Kupper, R.3    Mehl, A.F.4    Michejda, C.J.5
  • 10
    • 0017184389 scopus 로고
    • A rapid and sensitive method for the quantification of microgram quantities of protein utilizing the principle of protein-dye binding
    • Bradford, M. (1976) A rapid and sensitive method for the quantification of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72, 248-254.
    • (1976) Anal. Biochem. , vol.72 , pp. 248-254
    • Bradford, M.1
  • 11
    • 0018963344 scopus 로고
    • A new assay for the microsomal metabolism of nitrosamines
    • Farelly, J. G. (1980) A new assay for the microsomal metabolism of nitrosamines. Cancer Res. 40, 3241-3244.
    • (1980) Cancer Res. , vol.40 , pp. 3241-3244
    • Farelly, J.G.1
  • 13
    • 0016442262 scopus 로고
    • Preliminary studies of the fate of inhaled vinyl chloride monomer (VCM) in rats
    • Hefner, R. E., Watanabe, P. G., and Gehring, P. J. (1975) Preliminary studies of the fate of inhaled vinyl chloride monomer (VCM) in rats. Ann. N.Y. Acad Sci. 246, 135-149.
    • (1975) Ann. N.Y. Acad Sci. , vol.246 , pp. 135-149
    • Hefner, R.E.1    Watanabe, P.G.2    Gehring, P.J.3
  • 14
    • 0016210178 scopus 로고
    • Trapping with 3,4-dichlorobenzenethiol of reactive metabolites formed in vitro from the carcinogen vinyl chloride
    • Göthe, R., Callerman, C. J., Ehrenberg, L., and Wachmeister, C. A. (1974) Trapping with 3,4-dichlorobenzenethiol of reactive metabolites formed in vitro from the carcinogen vinyl chloride. Ambio 3, 234-236.
    • (1974) Ambio , vol.3 , pp. 234-236
    • Göthe, R.1    Callerman, C.J.2    Ehrenberg, L.3    Wachmeister, C.A.4
  • 15
    • 0017097821 scopus 로고
    • Studies on the metabolism of isophosphamide (NSC-109724) in man
    • Norpoth, K. (1976) Studies on the metabolism of isophosphamide (NSC-109724) in man. Can. Treat. Rep. 60, 437-443.
    • (1976) Can. Treat. Rep. , vol.60 , pp. 437-443
    • Norpoth, K.1
  • 16
    • 0026507888 scopus 로고
    • Roles of the vinyl chloride oxidation products 2-chlorooxirane and 2-chloroacetaldehyde in the in vitro formation of etheno adducts of nucleic acid bases
    • Guengerich, F. P. (1992) Roles of the vinyl chloride oxidation products 2-chlorooxirane and 2-chloroacetaldehyde in the in vitro formation of etheno adducts of nucleic acid bases. Chem Res. Toxicol. 5, 2-5.
    • (1992) Chem Res. Toxicol. , vol.5 , pp. 2-5
    • Guengerich, F.P.1
  • 17
    • 0011733086 scopus 로고
    • Mutagenicity of chloroacetaldehyde, a possible metabolic product of 1,2-dichloroethane (ethylene dichloride), chloroethanol (ethylene chlorohydrin), vinyl chloride, and cyclophosphamide
    • McCann, J., Simmon, V., Streitwieser, D., and Ames, B. N. (1975) Mutagenicity of chloroacetaldehyde, a possible metabolic product of 1,2-dichloroethane (ethylene dichloride), chloroethanol (ethylene chlorohydrin), vinyl chloride, and cyclophosphamide. Proc. Natl. Acad. Sci. U.S.A. 72, 3190-3193.
    • (1975) Proc. Natl. Acad. Sci. U.S.A. , vol.72 , pp. 3190-3193
    • McCann, J.1    Simmon, V.2    Streitwieser, D.3    Ames, B.N.4
  • 18
    • 0016594805 scopus 로고
    • Mutation induction in Chinese hamster V79 cells by two vinyl chloride metabolites, chloroethylene oxide and 2-chloroacetaldehyde
    • Huberman, E., Bartsch, H., and Sachs, L. (1975) Mutation induction in Chinese hamster V79 cells by two vinyl chloride metabolites, chloroethylene oxide and 2-chloroacetaldehyde. Int. J. Cancer 16, 639-644.
    • (1975) Int. J. Cancer , vol.16 , pp. 639-644
    • Huberman, E.1    Bartsch, H.2    Sachs, L.3
  • 19
    • 0018905425 scopus 로고
    • Mutagenicity of halogenated aliphatic hydrocarbons in Salmonella typhimurium, Streptomyces coelicolor and Aspergillus nidulans
    • Bignami, M., Conti, G., Crebelli, R., Misuraca, F., Puglia, A. M., Randazzo, R., Sciandrello, G., and Carere, A. (1980) Mutagenicity of halogenated aliphatic hydrocarbons in Salmonella typhimurium, Streptomyces coelicolor and Aspergillus nidulans. Chem.-Biol. Interact 30, 9-23.
    • (1980) Chem.-Biol. Interact , vol.30 , pp. 9-23
    • Bignami, M.1    Conti, G.2    Crebelli, R.3    Misuraca, F.4    Puglia, A.M.5    Randazzo, R.6    Sciandrello, G.7    Carere, A.8
  • 22
    • 0020491921 scopus 로고
    • Chloroacetaldehyde-treated ribo- and deoxyribopolynucleotides. 1. Reaction products
    • Kúsmierek, J. T., and Singer, B. (1982) Chloroacetaldehyde-treated ribo- and deoxyribopolynucleotides. 1. Reaction products. Biochemistry 21, 5717-5722.
    • (1982) Biochemistry , vol.21 , pp. 5717-5722
    • Kúsmierek, J.T.1    Singer, B.2
  • 23
    • 0023812997 scopus 로고
    • Formation of interstrand cross-links in chloroacetaldehyde-treated DNA demonstrated by ethidium bromide fluorescence
    • Spengler, S. J., and Singer, B. (1988) Formation of interstrand cross-links in chloroacetaldehyde-treated DNA demonstrated by ethidium bromide fluorescence. Cancer Res. 48, 4804-4806.
    • (1988) Cancer Res. , vol.48 , pp. 4804-4806
    • Spengler, S.J.1    Singer, B.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.