메뉴 건너뛰기




Volumn 26, Issue 6, 2013, Pages 1005-1013

Replication past the butadiene diepoxide-derived DNA adduct S -[4-(N 6-deoxyadenosinyl)-2,3-dihydroxybutyl]glutathione by DNA polymerases

Author keywords

[No Author keywords available]

Indexed keywords

BUTADIENE DIEPOXIDE; DEOXYADENOSINE; DNA POLYMERASE; N 6 (2,3,4 TRIHYDROXYBUTYL)DEOXYADENOSINE; UNCLASSIFIED DRUG; [4 (N 6 DEOXYADENOSINYL) 2,3 DIHYDROXYBUTYL]GLUTATHIONE; ADENOSINE; DNA ADDUCT; DNA DIRECTED DNA POLYMERASE; EPOXIDE; GLUTATHIONE;

EID: 84879179094     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx400145e     Document Type: Article
Times cited : (12)

References (52)
  • 1
    • 0025024861 scopus 로고
    • The industrial production and use of 1,3-butadiene
    • Morrow, N. L. (1990) The industrial production and use of 1,3-butadiene Environ. Health Perspect. 86, 7-8
    • (1990) Environ. Health Perspect. , vol.86 , pp. 7-8
    • Morrow, N.L.1
  • 2
    • 0025349688 scopus 로고
    • Analysis of low molecular weight hydrocarbons including 1,3-butadiene in engine exhaust gases using an aluminum oxide porous-layer open-tubular fused-silica column
    • Pelz, N., Dempster, N. M., and Shore, P. R. (1990) Analysis of low molecular weight hydrocarbons including 1,3-butadiene in engine exhaust gases using an aluminum oxide porous-layer open-tubular fused-silica column J. Chromatogr. Sci. 28, 230-235
    • (1990) J. Chromatogr. Sci. , vol.28 , pp. 230-235
    • Pelz, N.1    Dempster, N.M.2    Shore, P.R.3
  • 3
    • 84879170471 scopus 로고
    • International Agency for Research on Cancer (); Vol. 54, IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Humans, International Agency for Research on Cancer, Lyon, France.
    • International Agency for Research on Cancer (1992) 1,3-Butadiene; Vol. 54, IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Humans, International Agency for Research on Cancer, Lyon, France.
    • (1992) 1,3-Butadiene
  • 5
    • 0030605083 scopus 로고    scopus 로고
    • Leukemia and cumulative exposure to butadiene, styrene and benzene among workers in the synthetic rubber industry
    • Macaluso, M., Larson, R., Delzell, E., Sathiakumar, N., Hovinga, M., Julian, J., Muir, D., and Cole, P. (1996) Leukemia and cumulative exposure to butadiene, styrene and benzene among workers in the synthetic rubber industry Toxicology 113, 190-202
    • (1996) Toxicology , vol.113 , pp. 190-202
    • Macaluso, M.1    Larson, R.2    Delzell, E.3    Sathiakumar, N.4    Hovinga, M.5    Julian, J.6    Muir, D.7    Cole, P.8
  • 6
    • 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
  • 8
    • 0027792055 scopus 로고
    • 1,3-Butadiene induces cancer in experimental animals at all concentrations from 6.25 to 8000 parts per million
    • Melnick, R. L. and Huff, J. E. (1993) 1,3-Butadiene induces cancer in experimental animals at all concentrations from 6.25 to 8000 parts per million IARC Sci. Publ. 127, 309-322
    • (1993) IARC Sci. Publ. , vol.127 , pp. 309-322
    • Melnick, R.L.1    Huff, J.E.2
  • 9
    • 0023262639 scopus 로고
    • Inhalation toxicity studies with 1,3-butadiene. 3. Two year toxicity/carcinogenicity study in rats
    • Owen, P. E., Glaister, J. R., 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. (1958-1999) 48, 407-413
    • (1987) Am. Ind. Hyg. Assoc. J. (1958-1999) , vol.48 , pp. 407-413
    • Owen, P.E.1    Glaister, J.R.2    Gaunt, I.F.3    Pullinger, D.H.4
  • 10
    • 0030605125 scopus 로고    scopus 로고
    • Metabolism of 1,3-butadiene: Inhalation pharmacokinetics and tissue dosimetry of butadiene epoxides in rats and mice
    • Himmelstein, M. W., Turner, M. J., Asgharian, B., and Bond, J. A. (1996) Metabolism of 1,3-butadiene: Inhalation pharmacokinetics and tissue dosimetry of butadiene epoxides in rats and mice Toxicology 113, 306-309
    • (1996) Toxicology , vol.113 , pp. 306-309
    • Himmelstein, M.W.1    Turner, M.J.2    Asgharian, B.3    Bond, J.A.4
  • 11
    • 0026741034 scopus 로고
    • Comparison of the biotransformation of 1,3-butadiene and its metabolite, butadiene monoepoxide, by hepatic and pulmonary tissues from humans, rats and mice
    • Csanady, G. A., Guengerich, F. P., and Bond, J. A. (1992) Comparison of the biotransformation of 1,3-butadiene and its metabolite, butadiene monoepoxide, by hepatic and pulmonary tissues from humans, rats and mice Carcinogenesis 13, 1143-1153
    • (1992) Carcinogenesis , vol.13 , pp. 1143-1153
    • Csanady, G.A.1    Guengerich, F.P.2    Bond, J.A.3
  • 12
    • 0033795176 scopus 로고    scopus 로고
    • A review of the genetic and related effects of 1,3-butadiene in rodents and humans
    • Jackson, M. A., Stack, H. F., Rice, J. M., and Waters, M. D. (2000) A review of the genetic and related effects of 1,3-butadiene in rodents and humans Mutat. Res. 463, 181-213
    • (2000) Mutat. Res. , vol.463 , pp. 181-213
    • Jackson, M.A.1    Stack, H.F.2    Rice, J.M.3    Waters, M.D.4
  • 13
    • 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
  • 14
    • 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 splenic T cells from exposed B6C3F1 mice
    • 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 splenic T cells from exposed B6C3F1 mice Carcinogenesis 15, 719-723
    • (1994) Carcinogenesis , vol.15 , pp. 719-723
    • Cochrane, J.E.1    Skopek, T.R.2
  • 16
    • 79959436462 scopus 로고    scopus 로고
    • Persistence and repair of bifunctional DNA adducts in tissues of laboratory animals exposed to 1,3-butadiene by inhalation
    • Goggin, M., Sangaraju, D., Walker, V. E., Wickliffe, J., Swenberg, J. A., and Tretyakova, N. (2011) Persistence and repair of bifunctional DNA adducts in tissues of laboratory animals exposed to 1,3-butadiene by inhalation Chem. Res. Toxicol. 24, 809-817
    • (2011) Chem. Res. Toxicol. , vol.24 , pp. 809-817
    • Goggin, M.1    Sangaraju, D.2    Walker, V.E.3    Wickliffe, J.4    Swenberg, J.A.5    Tretyakova, N.6
  • 17
    • 77951246489 scopus 로고    scopus 로고
    • Column switching HPLC-ESI(+)-MS/MS methods for quantitative analysis of exocyclic da adducts in the DNA of laboratory animals exposed to 1,3-butadiene
    • Goggin, M., Seneviratne, U., Swenberg, J. A., Walker, V. E., and Tretyakova, N. (2010) Column switching HPLC-ESI(+)-MS/MS methods for quantitative analysis of exocyclic dA adducts in the DNA of laboratory animals exposed to 1,3-butadiene Chem. Res. Toxicol. 23, 808-812
    • (2010) Chem. Res. Toxicol. , vol.23 , pp. 808-812
    • Goggin, M.1    Seneviratne, U.2    Swenberg, J.A.3    Walker, V.E.4    Tretyakova, N.5
  • 18
    • 26844432462 scopus 로고    scopus 로고
    • Interstrand and intrastrand DNA-DNA cross-linking by 1,2,3,4- diepoxybutane: Role of stereochemistry
    • Park, S., Anderson, C., Loeber, R., Seetharaman, M., Jones, R., and Tretyakova, N. (2005) Interstrand and intrastrand DNA-DNA cross-linking by 1,2,3,4-diepoxybutane: Role of stereochemistry J. Am. Chem. Soc. 127, 14355-14365
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 14355-14365
    • Park, S.1    Anderson, C.2    Loeber, R.3    Seetharaman, M.4    Jones, R.5    Tretyakova, N.6
  • 19
    • 10844236473 scopus 로고    scopus 로고
    • Guanine-adenine DNA cross-linking by 1,2,3,4-diepoxybutane: Potential basis for biological activity
    • Park, S., Hodge, J., Anderson, C., and Tretyakova, N. (2004) Guanine-adenine DNA cross-linking by 1,2,3,4-diepoxybutane: Potential basis for biological activity Chem. Res. Toxicol. 17, 1638-1651
    • (2004) Chem. Res. Toxicol. , vol.17 , pp. 1638-1651
    • Park, S.1    Hodge, J.2    Anderson, C.3    Tretyakova, N.4
  • 20
    • 0030754684 scopus 로고    scopus 로고
    • Adenine adducts with diepoxybutane: Isolation and analysis in exposed calf thymus DNA
    • Tretyakova, N., Sangaiah, R., Yen, T. Y., Gold, A., and Swenberg, J. A. (1997) Adenine adducts with diepoxybutane: Isolation and analysis in exposed calf thymus DNA Chem. Res. Toxicol. 10, 1171-1179
    • (1997) Chem. Res. Toxicol. , vol.10 , pp. 1171-1179
    • Tretyakova, N.1    Sangaiah, R.2    Yen, T.Y.3    Gold, A.4    Swenberg, J.A.5
  • 23
    • 0028930987 scopus 로고
    • Enhancement of bacterial mutagenicity of bifunctional alkylating agents by expression of mammalian glutathione S -transferase
    • Thier, R., Muller, M., Taylor, J. B., Pemble, S. E., Ketterer, B., and Guengerich, F. P. (1995) Enhancement of bacterial mutagenicity of bifunctional alkylating agents by expression of mammalian glutathione S -transferase Chem. Res. Toxicol. 8, 465-472
    • (1995) Chem. Res. Toxicol. , vol.8 , pp. 465-472
    • Thier, R.1    Muller, M.2    Taylor, J.B.3    Pemble, S.E.4    Ketterer, B.5    Guengerich, F.P.6
  • 24
    • 0029947171 scopus 로고    scopus 로고
    • Human glutathione S -transferase T1-1 enhances mutagenicity of 1,2-dibromoethane, dibromomethane and 1,2,3,4-diepoxybutane in Salmonella typhimurium
    • Thier, R., Pemble, S. E., Kramer, H., Taylor, J. B., Guengerich, F. P., and Ketterer, B. (1996) Human glutathione S -transferase T1-1 enhances mutagenicity of 1,2-dibromoethane, dibromomethane and 1,2,3,4-diepoxybutane in Salmonella typhimurium Carcinogenesis 17, 163-166
    • (1996) Carcinogenesis , vol.17 , pp. 163-166
    • Thier, R.1    Pemble, S.E.2    Kramer, H.3    Taylor, J.B.4    Guengerich, F.P.5    Ketterer, B.6
  • 25
    • 77958088974 scopus 로고    scopus 로고
    • Mutagenicity of a glutathione conjugate of butadiene diepoxide
    • Cho, S. H., Loecken, E. M., and Guengerich, F. P. (2010) Mutagenicity of a glutathione conjugate of butadiene diepoxide Chem. Res. Toxicol. 23, 1544-1546
    • (2010) Chem. Res. Toxicol. , vol.23 , pp. 1544-1546
    • Cho, S.H.1    Loecken, E.M.2    Guengerich, F.P.3
  • 26
    • 84863963813 scopus 로고    scopus 로고
    • Mutation spectra of S -(2-hydroxy-3,4-epoxybutyl)glutathione: Comparison with 1,3-butadiene and its metabolites in the Escherichia coli rpoB gene
    • Cho, S. H. and Guengerich, F. P. (2012) Mutation spectra of S -(2-hydroxy-3,4-epoxybutyl)glutathione: Comparison with 1,3-butadiene and its metabolites in the Escherichia coli rpoB gene Chem. Res. Toxicol. 25, 1522-1530
    • (2012) Chem. Res. Toxicol. , vol.25 , pp. 1522-1530
    • Cho, S.H.1    Guengerich, F.P.2
  • 27
    • 84858686225 scopus 로고    scopus 로고
    • Conjugation of butadiene diepoxide with glutathione yields DNA adducts in vitro and in vivo
    • Cho, S. H. and Guengerich, F. P. (2012) Conjugation of butadiene diepoxide with glutathione yields DNA adducts in vitro and in vivo Chem. Res. Toxicol. 25, 706-712
    • (2012) Chem. Res. Toxicol. , vol.25 , pp. 706-712
    • Cho, S.H.1    Guengerich, F.P.2
  • 28
    • 84949380522 scopus 로고
    • New strategy for the synthesis of oligonucleotides bearing adducts at exocyclic amino sites of purine nucleotides
    • Harris, C. M., Zhou, L., Strand, E. A., and Harris, T. M. (1991) New strategy for the synthesis of oligonucleotides bearing adducts at exocyclic amino sites of purine nucleotides J. Am. Chem. Soc. 113, 4328-4329
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 4328-4329
    • Harris, C.M.1    Zhou, L.2    Strand, E.A.3    Harris, T.M.4
  • 29
    • 0025368179 scopus 로고
    • A new synthesis of dl -5-vinyloxazolidine-2-thione, a natural antithyroid factor
    • Gardrat, C., Latxague, L., and Picard, J. P. (1990) A new synthesis of dl -5-vinyloxazolidine-2-thione, a natural antithyroid factor J. Heterocycl. Chem. 27, 811-812
    • (1990) J. Heterocycl. Chem. , vol.27 , pp. 811-812
    • Gardrat, C.1    Latxague, L.2    Picard, J.P.3
  • 31
    • 23944449018 scopus 로고    scopus 로고
    • 2-guanine DNA lesions by human DNA polymerase η
    • 2-guanine DNA lesions by human DNA polymerase η J. Mol. Biol. 352, 72-90
    • (2005) J. Mol. Biol. , vol.352 , pp. 72-90
    • Choi, J.Y.1    Guengerich, F.P.2
  • 34
    • 0030918969 scopus 로고    scopus 로고
    • - and human immunodeficiency virus-1 reverse transcriptase using steady-state and pre-steady-state kinetics
    • - and human immunodeficiency virus-1 reverse transcriptase using steady-state and pre-steady-state kinetics Biochemistry 36, 6475-6487
    • (1997) Biochemistry , vol.36 , pp. 6475-6487
    • Furge, L.L.1    Guengerich, F.P.2
  • 36
    • 0036099333 scopus 로고    scopus 로고
    • SOS: A simple interactive program for ab initio oligonucleotide sequencing by mass spectrometry
    • Rozenski, J. and McCloskey, J. A. (2002) SOS: A simple interactive program for ab initio oligonucleotide sequencing by mass spectrometry J. Am. Soc. Mass Spectrom. 13, 200-203
    • (2002) J. Am. Soc. Mass Spectrom. , vol.13 , pp. 200-203
    • Rozenski, J.1    McCloskey, J.A.2
  • 37
    • 15944429355 scopus 로고    scopus 로고
    • DNA-protein crosslinks: Their induction, repair, and biological consequences
    • Barker, S., Weinfeld, M., and Murray, D. (2005) DNA-protein crosslinks: Their induction, repair, and biological consequences Mutat. Res. 589, 111-135
    • (2005) Mutat. Res. , vol.589 , pp. 111-135
    • Barker, S.1    Weinfeld, M.2    Murray, D.3
  • 38
    • 0024306062 scopus 로고
    • Species differences in DNA damage by butadiene: Role of diepoxybutane
    • Jelitto, B., Vangala, R. R., and Laib, R. J. (1989) Species differences in DNA damage by butadiene: Role of diepoxybutane Arch. Toxicol. Suppl. 13, 246-249
    • (1989) Arch. Toxicol. Suppl. , vol.13 , pp. 246-249
    • Jelitto, B.1    Vangala, R.R.2    Laib, R.J.3
  • 40
    • 41649093578 scopus 로고    scopus 로고
    • Reactions of glyceraldehyde 3-phosphate dehydrogenase sulfhydryl groups with bis -electrophiles produce DNA-protein cross-links but not mutations
    • Loecken, E. M. and Guengerich, F. P. (2008) Reactions of glyceraldehyde 3-phosphate dehydrogenase sulfhydryl groups with bis -electrophiles produce DNA-protein cross-links but not mutations Chem. Res. Toxicol. 21, 453-458
    • (2008) Chem. Res. Toxicol. , vol.21 , pp. 453-458
    • Loecken, E.M.1    Guengerich, F.P.2
  • 41
    • 67449113183 scopus 로고    scopus 로고
    • The bis -electrophile diepoxybutane cross-links DNA to human histones but does not result in enhanced mutagenesis in recombinant systems
    • Loecken, E. M., Dasari, S., Hill, S., Tabb, D. L., and Guengerich, F. P. (2009) The bis -electrophile diepoxybutane cross-links DNA to human histones but does not result in enhanced mutagenesis in recombinant systems Chem. Res. Toxicol. 22, 1069-1076
    • (2009) Chem. Res. Toxicol. , vol.22 , pp. 1069-1076
    • Loecken, E.M.1    Dasari, S.2    Hill, S.3    Tabb, D.L.4    Guengerich, F.P.5
  • 43
    • 0344154365 scopus 로고    scopus 로고
    • 6-ethanoadenine, a DNA adduct derived from reaction with the antitumor agent 1,3-bis (2-chloroethyl)-1- nitrosourea
    • 6-ethanoadenine, a DNA adduct derived from reaction with the antitumor agent 1,3-bis (2-chloroethyl)-1-nitrosourea Mutat. Res. 531, 191-203
    • (2003) Mutat. Res. , vol.531 , pp. 191-203
    • Hang, B.1    Chenna, A.2    Guliaev, A.B.3    Singer, B.4
  • 48
    • 69249101227 scopus 로고    scopus 로고
    • Structural and functional elucidation of the mechanism promoting error-prone synthesis by human DNA polymerase κ opposite the 7,8-dihydro-8-oxo-2′-deoxyguanosine adduct
    • Irimia, A., Eoff, R. L., Guengerich, F. P., and Egli, M. (2009) Structural and functional elucidation of the mechanism promoting error-prone synthesis by human DNA polymerase κ opposite the 7,8-dihydro-8-oxo- 2′-deoxyguanosine adduct J. Biol. Chem. 284, 22467-22480
    • (2009) J. Biol. Chem. , vol.284 , pp. 22467-22480
    • Irimia, A.1    Eoff, R.L.2    Guengerich, F.P.3    Egli, M.4
  • 49
    • 0028043929 scopus 로고
    • Activation of H-ras is prevalent in 1,3-butadiene-induced and spontaneously occurring murine Harderian gland tumors
    • Goodrow, T. L., Nichols, W. W., Storer, R. D., Anderson, M. W., and Maronpot, R. R. (1994) Activation of H-ras is prevalent in 1,3-butadiene-induced and spontaneously occurring murine Harderian gland tumors Carcinogenesis 15, 2665-2667
    • (1994) Carcinogenesis , vol.15 , pp. 2665-2667
    • Goodrow, T.L.1    Nichols, W.W.2    Storer, R.D.3    Anderson, M.W.4    Maronpot, R.R.5
  • 50
    • 0033972858 scopus 로고    scopus 로고
    • Human DNA adducts of 1,3-butadiene, an important environmental carcinogen
    • Zhao, C., Vodicka, P., Srám, R. J., and Hemminki, K. (2000) Human DNA adducts of 1,3-butadiene, an important environmental carcinogen Carcinogenesis 21, 107-111
    • (2000) Carcinogenesis , vol.21 , pp. 107-111
    • Zhao, C.1    Vodicka, P.2    Srám, R.J.3    Hemminki, K.4
  • 52
    • 0021398955 scopus 로고
    • Mutational specificity of depurination
    • Kunkel, T. A. (1984) Mutational specificity of depurination Proc. Natl. Acad. Sci. U.S.A. 81, 1494-1498
    • (1984) Proc. Natl. Acad. Sci. U.S.A. , vol.81 , pp. 1494-1498
    • Kunkel, T.A.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.