메뉴 건너뛰기




Volumn 20, Issue 2, 1999, Pages 285-292

In vitro reactions of butadiene monoxide with single- and double-stranded DNA: Characterization and quantitation of several purine and pyrimidine adducts

Author keywords

[No Author keywords available]

Indexed keywords

1,2 EPOXY 3 BUTENE; DOUBLE STRANDED DNA; PURINE; PYRIMIDINE; SINGLE STRANDED DNA;

EID: 0032907873     PISSN: 01433334     EISSN: None     Source Type: Journal    
DOI: 10.1093/carcin/20.2.285     Document Type: Article
Times cited : (52)

References (50)
  • 1
    • 0027861146 scopus 로고
    • Cancer mortality among workers at a butadiene production facility
    • Sorsa, M., Peltonen, K., Vianio, H. and Hemminki, K. (eds) IARC Scientific Publications IARC, Lyon
    • Divine, B.J., Wendt, J.K. and Hartman, C.M. (1993) Cancer mortality among workers at a butadiene production facility. In Sorsa, M., Peltonen, K., Vianio, H. and Hemminki, K. (eds) Butadiene and Styrene: Assessment of Health Hazards. IARC Scientific Publications no. 127, IARC, Lyon, pp. 345-362.
    • (1993) Butadiene and Styrene: Assessment of Health Hazards , vol.127 , pp. 345-362
    • Divine, B.J.1    Wendt, J.K.2    Hartman, C.M.3
  • 2
    • 0026540253 scopus 로고
    • Lymphohematopoietic cancer in styrene-butadiene polymerization workers
    • Santos-Burgoa, C. Matanoski, G.M., Zeger, S. and Schwartz, L. (1992) Lymphohematopoietic cancer in styrene-butadiene polymerization workers. Am. J. Epidemiol., 136, 843-854.
    • (1992) Am. J. Epidemiol. , vol.136 , pp. 843-854
    • Santos-Burgoa, C.1    Matanoski, G.M.2    Zeger, S.3    Schwartz, L.4
  • 3
    • 0025048644 scopus 로고
    • Carcinogenicity of 1,3-butadiene in C57BL/6×CH3 F1 mice at low exposure concentrations
    • Melnick, R.L., Huff, J., Chou, B.J. and Miller, R.A. (1990) Carcinogenicity of 1,3-butadiene in C57BL/6×CH3 F1 mice at low exposure concentrations. Cancer Res., 50, 6592-6599.
    • (1990) Cancer Res. , vol.50 , pp. 6592-6599
    • Melnick, R.L.1    Huff, J.2    Chou, B.J.3    Miller, R.A.4
  • 4
    • 0023262639 scopus 로고
    • Inhalation toxicity studies with 1,3-butadiene. 3. Two year toxicity/carcinogenicity study in rats
    • Owen, P.E., Glaister, J.F., Gaunt, I.F. and Pullinger, D.H. (1987) Inhalation toxicity studies with 1,3-butadiene. 3. Two year toxicity/carcinogenicity study in rats. Am. Ind. Hyg. Assoc. J., 48, 407-413.
    • (1987) Am. Ind. Hyg. Assoc. J. , vol.48 , pp. 407-413
    • Owen, P.E.1    Glaister, J.F.2    Gaunt, I.F.3    Pullinger, D.H.4
  • 5
    • 0019125048 scopus 로고
    • The mutagenicity of butadiene towards Salmonella typhimurium
    • de Meester, C., Poncelet, F. Roberfroid, M. and Mercier, M. (1980) The mutagenicity of butadiene towards Salmonella typhimurium. Toxicol. Lett., 6, 125-130.
    • (1980) Toxicol. Lett. , vol.6 , pp. 125-130
    • Meester, C.1    Poncelet, F.2    Roberfroid, M.3    Mercier, M.4
  • 6
    • 0021056672 scopus 로고
    • Biological activation of 1,3-butadiene to vinyl oxirane by rat liver microsomes and expiration of the reactive metabolite by exposed rats
    • Bolt, H.M., Schmiedel, G., Gilser, J.G., Rolzhauser, H.P., Lieser, K., Wistuba, D. and Schurig, V. (1983) Biological activation of 1,3-butadiene to vinyl oxirane by rat liver microsomes and expiration of the reactive metabolite by exposed rats. J. Cancer Res. Clin. Oncol., 106, 112-116.
    • (1983) J. Cancer Res. Clin. Oncol. , vol.106 , pp. 112-116
    • Bolt, H.M.1    Schmiedel, G.2    Gilser, J.G.3    Rolzhauser, H.P.4    Lieser, K.5    Wistuba, D.6    Schurig, V.7
  • 7
    • 0025817764 scopus 로고
    • Mechanisms of 1,3-butadiene oxidations to butadiene monoxide and crotonaldehyde by mouse liver microsomes and chloroperoxidase
    • Elfarra, A.A., Duescher, R.J. and Pasch, C.M. (1991) Mechanisms of 1,3-butadiene oxidations to butadiene monoxide and crotonaldehyde by mouse liver microsomes and chloroperoxidase. Arch. Biochem. Biophys., 286, 244-251.
    • (1991) Arch. Biochem. Biophys. , vol.286 , pp. 244-251
    • Elfarra, A.A.1    Duescher, R.J.2    Pasch, C.M.3
  • 8
    • 0026669438 scopus 로고
    • Species and tissue differences in the microsomal oxidation of 1,3-butadiene and the glutathione conjugation of butadiene monoxide in mice and rats. Possible role in 1,3-butadiene-induced toxicity
    • Sharer, J.E., Duescher, R.J. and Elfarra, A.A. (1992) Species and tissue differences in the microsomal oxidation of 1,3-butadiene and the glutathione conjugation of butadiene monoxide in mice and rats. Possible role in 1,3-butadiene-induced toxicity. Drug. Metab. Dispos., 20, 658-664.
    • (1992) Drug. Metab. Dispos. , vol.20 , pp. 658-664
    • Sharer, J.E.1    Duescher, R.J.2    Elfarra, A.A.3
  • 9
    • 0026722815 scopus 로고
    • 1,3-Butadiene oxidation by human myeloperoxidase. Role of chloride ion in catalysis of divergent pathways
    • Duescher, R.J. and Elfarra, A.A. (1992) 1,3-Butadiene oxidation by human myeloperoxidase. Role of chloride ion in catalysis of divergent pathways. J. Biol. Chem., 267, 19859-19865.
    • (1992) J. Biol. Chem. , vol.267 , pp. 19859-19865
    • Duescher, R.J.1    Elfarra, A.A.2
  • 10
    • 0028340688 scopus 로고
    • Human liver microsomes are efficient catalysts of 1,3-butadiene oxidation: Evidence for major roles by cytochromes P450 2A6 and 2E1
    • Duescher, R.J. and Elfarra, A.A. (1994) Human liver microsomes are efficient catalysts of 1,3-butadiene oxidation: evidence for major roles by cytochromes P450 2A6 and 2E1. Arch. Biochem. Biophys., 311, 342-349.
    • (1994) Arch. Biochem. Biophys. , vol.311 , pp. 342-349
    • Duescher, R.J.1    Elfarra, A.A.2
  • 12
    • 0018411986 scopus 로고
    • Mutagenic action of a series of epoxides
    • Wade, M.J., Moyer, J.W. and Hine, C.H. (1979) Mutagenic action of a series of epoxides. Mutat. Res., 66, 367-371.
    • (1979) Mutat. Res. , vol.66 , pp. 367-371
    • Wade, M.J.1    Moyer, J.W.2    Hine, C.H.3
  • 14
    • 0013978828 scopus 로고
    • Carcinogenicity of epoxides, lactones and peroxy compounds. IV. Tumor response in epithelial and connective tissue in mice and rats
    • Van Duuren, B.L., Langseth, L., Orris, L., Teebor, G., Nelson, N. and Kuschner, M. (1966) Carcinogenicity of epoxides, lactones and peroxy compounds. IV. Tumor response in epithelial and connective tissue in mice and rats. J. Natl Cancer Inst., 37, 825-838.
    • (1966) J. Natl Cancer Inst. , vol.37 , pp. 825-838
    • Van Duuren, B.L.1    Langseth, L.2    Orris, L.3    Teebor, G.4    Nelson, N.K.M.5
  • 15
    • 0027951237 scopus 로고
    • Mutagenicity of butadiene and its epoxide metabolites: I. Mutagenic potential of 1,2-epoxybutene, 1,2,3,4-diepoxybutane and 3,4-epoxy-1,2-butanediol in cultured human lymphoblasts
    • Cochrane, J.E. and Skopek, T.R. (1994) Mutagenicity of butadiene and its epoxide metabolites: I. Mutagenic potential of 1,2-epoxybutene, 1,2,3,4-diepoxybutane and 3,4-epoxy-1,2-butanediol in cultured human lymphoblasts. Carcinogenesis, 15, 713-717.
    • (1994) Carcinogenesis , vol.15 , pp. 713-717
    • Cochrane, J.E.1    Skopek, T.R.2
  • 16
    • 0028026138 scopus 로고
    • Mutagenicity of butadiene and its epoxide metabolites: II. Mutational spectra of butadiene, 1,2-epoxybutene and diepoxybutane at the hprt locus in T cells from exposed B6C3F1 mice and Sprague-Dawley rats
    • Cochrane, J.E. and Skopek, T.R. (1994) Mutagenicity of butadiene and its epoxide metabolites: II. Mutational spectra of butadiene, 1,2-epoxybutene and diepoxybutane at the hprt locus in T cells from exposed B6C3F1 mice and Sprague-Dawley rats. Carcinogenesis, 15, 719-723.
    • (1994) Carcinogenesis , vol.15 , pp. 719-723
    • Cochrane, J.E.1    Skopek, T.R.2
  • 18
    • 0025766839 scopus 로고
    • 1,3-Butadiene and its epoxides induce sister-chromatid exchanges in human lymphocytes in vitro
    • Sasidek, M., Norppa, H. and Sorsa, M. (1991) 1,3-Butadiene and its epoxides induce sister-chromatid exchanges in human lymphocytes in vitro. Mutat. Res., 261, 117-121.
    • (1991) Mutat. Res. , vol.261 , pp. 117-121
    • Sasidek, M.1    Norppa, H.2    Sorsa, M.3
  • 19
    • 0023183193 scopus 로고
    • Comparative cytogenetic analysis of bone marrow damage induced in male B6C3F1 mice by multiple exposures to gaseous 1,3-butadiene
    • Tice, R.R., Boucher, R., Luke, C.A. and Shelby, M.D. (1987) Comparative cytogenetic analysis of bone marrow damage induced in male B6C3F1 mice by multiple exposures to gaseous 1,3-butadiene. Environ. Mutagen., 9, 235-250.
    • (1987) Environ. Mutagen. , vol.9 , pp. 235-250
    • Tice, R.R.1    Boucher, R.2    Luke, C.A.3    Shelby, M.D.4
  • 20
    • 0022873586 scopus 로고
    • In vivo sister chromatid exchange and micronucleus induction studies with 1,3-butadiene in B6C3F1 mice and Sprague-Dawley rats
    • Cunningham, M.J., Choy, W.N., Arce, G.T. Rickard, L.B., Vlachos, D.A., Kinney, L.A. and Sarrif, A.M. (1986) In vivo sister chromatid exchange and micronucleus induction studies with 1,3-butadiene in B6C3F1 mice and Sprague-Dawley rats. Mutagenesis, 1, 449-452.
    • (1986) Mutagenesis , vol.1 , pp. 449-452
    • Cunningham, M.J.1    Choy, W.N.2    Arce, G.T.3    Rickard, L.B.4    Vlachos, D.A.5    Kinney, L.A.6    Sarrif, A.M.7
  • 22
    • 0029146891 scopus 로고
    • Increased frequency of mutations at A:T base pairs in the bone marrow of B6C3F1 lacI transgenic mice exposed to 1,3-butadiene
    • Recio, L. and Meyer, K.G. (1995) Increased frequency of mutations at A:T base pairs in the bone marrow of B6C3F1 lacI transgenic mice exposed to 1,3-butadiene. Environ. Mol. Mutagen., 26, 1-8.
    • (1995) Environ. Mol. Mutagen. , vol.26 , pp. 1-8
    • Recio, L.1    Meyer, K.G.2
  • 23
    • 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
  • 29
    • 0031408197 scopus 로고    scopus 로고
    • Characterization of four N-3-thymidine adducts formed in vitro by the reaction of thymidine and butadiene monoxide
    • Selzer, R.R. and Elfarra, A.A. (1997) Characterization of four N-3-thymidine adducts formed in vitro by the reaction of thymidine and butadiene monoxide. Carcinogenesis, 18, 1993-1998.
    • (1997) Carcinogenesis , vol.18 , pp. 1993-1998
    • Selzer, R.R.1    Elfarra, A.A.2
  • 30
    • 0031427595 scopus 로고    scopus 로고
    • Identification and quantitation of DNA adducts from calf thymus DNA exposed to 3,4-epoxy-1-butene
    • Tretyakova, N., Lin, Y., Sangaiah, R., Upton, P.B. and Swenberg, J.A. (1997) Identification and quantitation of DNA adducts from calf thymus DNA exposed to 3,4-epoxy-1-butene. Carcinogenesis, 18, 137-147.
    • (1997) Carcinogenesis , vol.18 , pp. 137-147
    • Tretyakova, N.1    Lin, Y.2    Sangaiah, R.3    Upton, P.B.4    Swenberg, J.A.5
  • 31
    • 0030011255 scopus 로고    scopus 로고
    • DNA adduct formation by allyl glycidyl ether
    • Plna, K., Segerbäck, 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    Segerbäck, D.2    Schweda, E.K.H.3
  • 32
    • 0019156329 scopus 로고
    • A comprehensive quantitative analysis of methylated and ethylated DNA using high pressure liquid chromatography
    • Beranek, D.T., Weis, C. and Swenson, D.H. (1980) A comprehensive quantitative analysis of methylated and ethylated DNA using high pressure liquid chromatography. Carcinogenesis, 1, 595-606.
    • (1980) Carcinogenesis , vol.1 , pp. 595-606
    • Beranek, D.T.1    Weis, C.2    Swenson, D.H.3
  • 33
    • 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
  • 34
    • 73649209034 scopus 로고
    • Determination of the base composition of deoxyribonucleic acid from its thermal denaturation temperature
    • Marmur, J. and Doty, P. (1962) Determination of the base composition of deoxyribonucleic acid from its thermal denaturation temperature. J. Mol. Biol., 5, 109-118.
    • (1962) J. Mol. Biol. , vol.5 , pp. 109-118
    • Marmur, J.1    Doty, P.2
  • 35
    • 0026773508 scopus 로고
    • In vitro reaction of ethvlene oxide with DNA and characterization of DNA adducts
    • Li, F., Segal, A. and Solomon, J.J. (1992) In vitro reaction of ethvlene oxide with DNA and characterization of DNA adducts. Chem. Biol. Interact., 83, 35-54.
    • (1992) Chem. Biol. Interact. , vol.83 , pp. 35-54
    • Li, F.1    Segal, A.2    Solomon, J.J.3
  • 36
    • 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
  • 38
    • 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
  • 39
    • 0021398955 scopus 로고
    • Mutational specificity of depurination
    • Kunkel, T.A. (1984) Mutational specificity of depurination. Proc. Natl Acad. Sci. USA, 81, 1494-1498.
    • (1984) Proc. Natl Acad. Sci. USA , vol.81 , pp. 1494-1498
    • Kunkel, T.A.1
  • 40
    • 0019203733 scopus 로고
    • Estimation of apurinic/ apyrimidinic sites and phosphotriesters in deoxyribonucleic acid treated with electrophilic carcinogens and mutagens
    • Drinkwater, N.R., Miller, E.C. and Miller, J.A. (1980) Estimation of apurinic/ apyrimidinic sites and phosphotriesters in deoxyribonucleic acid treated with electrophilic carcinogens and mutagens. Biochemistry, 19, 5087-5092.
    • (1980) Biochemistry , vol.19 , pp. 5087-5092
    • Drinkwater, N.R.1    Miller, E.C.2    Miller, J.A.3
  • 41
    • 0026727768 scopus 로고
    • Mutagenesis by apurinic sites in normal and ataxia telangiectasia human lymphoblastoid cells. Mol
    • Klinedinst, D.K. and Drinkwater, N.R. (1992) Mutagenesis by apurinic sites in normal and ataxia telangiectasia human lymphoblastoid cells. Mol. Carcinogen., 6, 32-12.
    • (1992) Carcinogen. , vol.6 , pp. 32-112
    • Klinedinst, D.K.1    Drinkwater, N.R.2
  • 42
    • 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
  • 43
    • 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, 25-246.
    • (1986) Chem. Biol. Interact. , vol.60 , pp. 25-246
    • Savela, K.1    Hesso, A.2    Hemminki, K.3
  • 44
    • 85004301991 scopus 로고
    • Purines. XXVII. Hydrolytic deamination versus Dimroth rearrangement in the 9-substituted purine ring: Effect of an omega-hydroxyalkyl group at the 1-position
    • Fujii, R., Saito, B. and Terahara, N. (1986) Purines. XXVII. Hydrolytic deamination versus Dimroth rearrangement in the 9-substituted purine ring: effect of an omega-hydroxyalkyl group at the 1-position. Chem. Pharm. Bull., 34, 1094-1107.
    • (1986) Chem. Pharm. Bull. , vol.34 , pp. 1094-1107
    • Fujii, R.1    Saito, B.2    Terahara, N.3
  • 47
    • 0028104592 scopus 로고
    • The role of 3-hydroxyethyldeoxyuridine in mutagenesis by ethvlene oxide
    • Bhanot, O.S., Singh, U.S. and Solomon, J.J. (1994) The role of 3-hydroxyethyldeoxyuridine in mutagenesis by ethvlene oxide. J. Biol. Chem., 269, 30056-30064.
    • (1994) J. Biol. Chem. , vol.269 , pp. 30056-30064
    • Bhanot, O.S.1    Singh, U.S.2    Solomon, J.J.3
  • 48
    • 0025059264 scopus 로고
    • In vitro reactions of glycidol with pyrimidine bases in calf thymus DNA
    • Segal, A., Solomon, J.J. and Mukai, F. (1990) In vitro reactions of glycidol with pyrimidine bases in calf thymus DNA. Cancer Biochem. Biophys., 11, 59-67.
    • (1990) Cancer Biochem. Biophys. , vol.11 , pp. 59-67
    • Segal, A.1    Solomon, J.J.2    Mukai, F.3
  • 49
    • 0029960063 scopus 로고    scopus 로고
    • Novel activities of human uracil DNA N-glycosylase for cytosine-derived products of oxidative DNA damage
    • Dizdaroglu, M., Karadaya, A., Jaruga, P., Slupphaug, G. and Krokan, H.E. (1996) Novel activities of human uracil DNA N-glycosylase for cytosine-derived products of oxidative DNA damage. Nucleic Acids Res., 24, 418-422.
    • (1996) Nucleic Acids Res. , vol.24 , pp. 418-422
    • Dizdaroglu, M.1    Karadaya, A.2    Jaruga, P.3    Slupphaug, G.4    Krokan, H.E.5
  • 50
    • 0020582470 scopus 로고
    • Nucleic acid adducts of chemical carcinogens and mutagens
    • Hemminki, K. (1983) Nucleic acid adducts of chemical carcinogens and mutagens. Arch. Toxicol., 52, 249-285.
    • (1983) Arch. Toxicol. , vol.52 , pp. 249-285
    • Hemminki, K.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.