메뉴 건너뛰기




Volumn 26, Issue 2, 2013, Pages 138-147

The effect of the structure of polychlorinated biphenyls on their hydroxylation, oxidation, and glutathionyl conjugation reactions

Author keywords

Cytochrome P450; Glutathione; Hydroquinone; PCB metabolism; Quinone

Indexed keywords

CYTOCHROME P450; GLUTATHIONE; HYDROQUINONE; POLYCHLORINATED BIPHENYL; QUINONE DERIVATIVE;

EID: 84878760510     PISSN: 08953988     EISSN: None     Source Type: Journal    
DOI: 10.3967/0895-3988.2013.02.008     Document Type: Article
Times cited : (5)

References (34)
  • 1
    • 0028235721 scopus 로고
    • Polychlorinated biphenyls (PCBs): Environmental impact, biochemical and toxic responses, and implications for risk assessment
    • SH Safe Polychlorinated biphenyls (PCBs): environmental impact, biochemical and toxic responses, and implications for risk assessment Crit Rev Toxicol 24 2 1994 87 149
    • (1994) Crit Rev Toxicol , vol.24 , Issue.2 , pp. 87-149
    • Safe, S.H.1
  • 2
    • 77950928205 scopus 로고    scopus 로고
    • Chiral polychlorinated biphenyl transport, metabolism, and distribution: A review
    • HJ Lehmler, SJ Harrad, H Huhnerfuss et al. Chiral polychlorinated biphenyl transport, metabolism, and distribution: a review Environ Sci Technol 44 8 2010 2757 2766
    • (2010) Environ Sci Technol , vol.44 , Issue.8 , pp. 2757-2766
    • Lehmler, H.J.1    Harrad, S.J.2    Huhnerfuss, H.3
  • 4
    • 0030051958 scopus 로고    scopus 로고
    • Identification of catechol and hydroquinone metabolites of 4-monochlorobiphenyl
    • MR McLean, U Bauer, AR Amaro et al. Identification of catechol and hydroquinone metabolites of 4-monochlorobiphenyl Chem Res Toxicol 9 1 1996 158 164
    • (1996) Chem Res Toxicol , vol.9 , Issue.1 , pp. 158-164
    • McLean, M.R.1    Bauer, U.2    Amaro, A.R.3
  • 5
    • 0020534622 scopus 로고
    • Non-arene oxide aromatic ring hydroxylation of 2,2′,5,5′- tetrachlorobiphenyl as the major metabolic pathway catalyzed by phenobarbital-induced rat liver microsomes
    • BD Preston, JA Miller, EC Miller Non-arene oxide aromatic ring hydroxylation of 2,2′,5,5′-tetrachlorobiphenyl as the major metabolic pathway catalyzed by phenobarbital-induced rat liver microsomes J Biol Chem 258 13 1983 8304 8311
    • (1983) J Biol Chem , vol.258 , Issue.13 , pp. 8304-8311
    • Preston, B.D.1    Miller, J.A.2    Miller, E.C.3
  • 6
    • 0019997002 scopus 로고
    • Metabolism of 2,4′,5-trichlorobiphenyl by the mercapturic acid pathway
    • JE Bakke, AL Bergman, GL Larsen Metabolism of 2,4′,5- trichlorobiphenyl by the mercapturic acid pathway Science 217 4560 1982 645 647
    • (1982) Science , vol.217 , Issue.4560 , pp. 645-647
    • Bakke, J.E.1    Bergman, A.L.2    Larsen, G.L.3
  • 7
    • 0018174607 scopus 로고
    • Identification of sulfur-containing metabolites of 2,4,2′,4′- tetrachlorobiphenyl in mice
    • T Mizutani Identification of sulfur-containing metabolites of 2,4,2′,4′-tetrachlorobiphenyl in mice Bull Environ Contam Toxicol 20 2 1978 219 226
    • (1978) Bull Environ Contam Toxicol , vol.20 , Issue.2 , pp. 219-226
    • Mizutani, T.1
  • 8
    • 67649836351 scopus 로고    scopus 로고
    • Nonenzymatic displacement of chlorine and formation of free radicals upon the reaction of glutathione with PCB quinones
    • Y Song, BA Wagner, JR Witmer et al. Nonenzymatic displacement of chlorine and formation of free radicals upon the reaction of glutathione with PCB quinones Proc Natl Acad Sci USA 106 24 2009 9725 9730
    • (2009) Proc Natl Acad Sci USA , vol.106 , Issue.24 , pp. 9725-9730
    • Song, Y.1    Wagner, B.A.2    Witmer, J.R.3
  • 9
    • 0021893084 scopus 로고
    • PCBs: Structure-function relationships and mechanism of action
    • S Safe, S Bandiera, T Sawyer et al. PCBs: structure-function relationships and mechanism of action Environ Health Perspect 60 1985 47 56
    • (1985) Environ Health Perspect , vol.60 , pp. 47-56
    • Safe, S.1    Bandiera, S.2    Sawyer, T.3
  • 10
    • 67749145495 scopus 로고    scopus 로고
    • Cytochrome P450-dependent metabolism of PCB52 in the nematode Caenorhabditis elegans
    • P Schafer, M Muller, A Kruger et al. Cytochrome P450-dependent metabolism of PCB52 in the nematode Caenorhabditis elegans Arch Biochem Biophys 488 1 2009 60 68
    • (2009) Arch Biochem Biophys , vol.488 , Issue.1 , pp. 60-68
    • Schafer, P.1    Muller, M.2    Kruger, A.3
  • 11
    • 0029863866 scopus 로고    scopus 로고
    • Metabolic activation of PCBs to quinones: Reactivity toward nitrogen and sulfur nucleophiles and influence of superoxide dismutase
    • AR Amaro, GG Oakley, U Bauer et al. Metabolic activation of PCBs to quinones: reactivity toward nitrogen and sulfur nucleophiles and influence of superoxide dismutase Chem Res Toxicol 9 3 1996 623 629
    • (1996) Chem Res Toxicol , vol.9 , Issue.3 , pp. 623-629
    • Amaro, A.R.1    Oakley, G.G.2    Bauer, U.3
  • 12
    • 10844278294 scopus 로고    scopus 로고
    • Metabolism of polychlorinated biphenyls by Gunn rats: Identification and serum retention of catechol metabolites
    • K Haraguchi, Y Kato, N Koga et al. Metabolism of polychlorinated biphenyls by Gunn rats: identification and serum retention of catechol metabolites Chem Res Toxicol 17 12 2004 1684 1691
    • (2004) Chem Res Toxicol , vol.17 , Issue.12 , pp. 1684-1691
    • Haraguchi, K.1    Kato, Y.2    Koga, N.3
  • 13
    • 61849125819 scopus 로고    scopus 로고
    • Chiral polychlorinated biphenyls are biotransformed enantioselectively by mammalian cytochrome P-450 isozymes to form hydroxylated metabolites
    • NA Warner, JW Martin, CS Wong Chiral polychlorinated biphenyls are biotransformed enantioselectively by mammalian cytochrome P-450 isozymes to form hydroxylated metabolites Environ Sci Technol 43 1 2009 114 121
    • (2009) Environ Sci Technol , vol.43 , Issue.1 , pp. 114-121
    • Warner, N.A.1    Martin, J.W.2    Wong, C.S.3
  • 14
    • 0034793034 scopus 로고    scopus 로고
    • Synthesis of hydroxylated PCB metabolites with the Suzuki-coupling
    • HJ Lehmler, LW Robertson Synthesis of hydroxylated PCB metabolites with the Suzuki-coupling Chemosphere 45 8 2001 1119 1127
    • (2001) Chemosphere , vol.45 , Issue.8 , pp. 1119-1127
    • Lehmler, H.J.1    Robertson, L.W.2
  • 15
    • 3042757426 scopus 로고    scopus 로고
    • Synthesis of polychlorinated biphenyls and their metabolites with a modified Suzuki-coupling
    • I Kania-Korwel, S Parkin, LW Robertson et al. Synthesis of polychlorinated biphenyls and their metabolites with a modified Suzuki-coupling Chemosphere 56 8 2004 735 744
    • (2004) Chemosphere , vol.56 , Issue.8 , pp. 735-744
    • Kania-Korwel, I.1    Parkin, S.2    Robertson, L.W.3
  • 16
    • 55249085382 scopus 로고    scopus 로고
    • Chlorination increases the persistence of semiquinone free radicals derived from polychlorinated biphenyl hydroquinones and quinones
    • Y Song, GR Buettner, S Parkin et al. Chlorination increases the persistence of semiquinone free radicals derived from polychlorinated biphenyl hydroquinones and quinones J Org Chem 73 21 2008 8296 8304
    • (2008) J Org Chem , vol.73 , Issue.21 , pp. 8296-8304
    • Song, Y.1    Buettner, G.R.2    Parkin, S.3
  • 17
    • 78651165715 scopus 로고
    • The Carbon Monoxide-Binding Pigment of Liver Microsomes. I. Evidence for Its Hemoprotein Nature
    • T Omura, R Sato The Carbon Monoxide-Binding Pigment of Liver Microsomes. I. Evidence for Its Hemoprotein Nature J Biol Chem 239 1964 2370 2378
    • (1964) J Biol Chem , vol.239 , pp. 2370-2378
    • Omura, T.1    Sato, R.2
  • 18
    • 49049111308 scopus 로고    scopus 로고
    • Semiquinone radicals from oxygenated polychlorinated biphenyls: Electron paramagnetic resonance studies
    • Y Song, BA Wagner, HJ Lehmler et al. Semiquinone radicals from oxygenated polychlorinated biphenyls: electron paramagnetic resonance studies Chem Res Toxicol 21 7 2008 1359 1367
    • (2008) Chem Res Toxicol , vol.21 , Issue.7 , pp. 1359-1367
    • Song, Y.1    Wagner, B.A.2    Lehmler, H.J.3
  • 19
    • 0028941480 scopus 로고
    • Purification and characterization of a newly identified isoform of cytochrome P450 responsible for 3-hydroxylation of 2,5,2′,5′- tetrachlorobiphenyl in hamster liver
    • N Koga, N Kikuichi-Nishimura, T Hara et al. Purification and characterization of a newly identified isoform of cytochrome P450 responsible for 3-hydroxylation of 2,5,2′,5′-tetrachlorobiphenyl in hamster liver Arch Biochem Biophys 317 2 1995 464 470
    • (1995) Arch Biochem Biophys , vol.317 , Issue.2 , pp. 464-470
    • Koga, N.1    Kikuichi-Nishimura, N.2    Hara, T.3
  • 20
    • 1642458263 scopus 로고    scopus 로고
    • Carbon-carbon bond cleavage by cytochrome p450(BioI)(CYP107H1)
    • MJ Cryle, JJ De Voss Carbon-carbon bond cleavage by cytochrome p450(BioI)(CYP107H1) Chem Commun (Camb) 1 2004 86 87
    • (2004) Chem Commun (Camb) , vol.1 , pp. 86-87
    • Cryle, M.J.1    De Voss, J.J.2
  • 21
    • 0034671777 scopus 로고    scopus 로고
    • Expression, purification, and characterization of BioI: A carbon-carbon bond cleaving cytochrome P450 involved in biotin biosynthesis in Bacillus subtilis
    • JE Stok, J De Voss Expression, purification, and characterization of BioI: a carbon-carbon bond cleaving cytochrome P450 involved in biotin biosynthesis in Bacillus subtilis Arch Biochem Biophys 384 2 2000 351 360
    • (2000) Arch Biochem Biophys , vol.384 , Issue.2 , pp. 351-360
    • Stok, J.E.1    De Voss, J.2
  • 22
    • 0021987607 scopus 로고
    • Studies on the structure-activity relationships for the metabolism of polybrominated biphenyls by rat liver microsomes
    • RA Mills, CD Millis, GA Dannan et al. Studies on the structure-activity relationships for the metabolism of polybrominated biphenyls by rat liver microsomes Toxicol Appl Pharmacol 78 1 1985 96 104
    • (1985) Toxicol Appl Pharmacol , vol.78 , Issue.1 , pp. 96-104
    • Mills, R.A.1    Millis, C.D.2    Dannan, G.A.3
  • 23
    • 70449526288 scopus 로고    scopus 로고
    • Polychlorinated-biphenyl-induced oxidative stress and cytotoxicity can be mitigated by antioxidants after exposure
    • Y Zhu, AL Kalen, L Li et al. Polychlorinated-biphenyl-induced oxidative stress and cytotoxicity can be mitigated by antioxidants after exposure Free Radic Biol Med 47 12 2009 1762 1771
    • (2009) Free Radic Biol Med , vol.47 , Issue.12 , pp. 1762-1771
    • Zhu, Y.1    Kalen, A.L.2    Li, L.3
  • 24
    • 0026009466 scopus 로고
    • Effects of superoxide dismutase on the autoxidation of 1,4-hydroquinone
    • P Eyer Effects of superoxide dismutase on the autoxidation of 1,4-hydroquinone Chem Biol Interact 80 2 1991 159 176
    • (1991) Chem Biol Interact , vol.80 , Issue.2 , pp. 159-176
    • Eyer, P.1
  • 25
    • 77955512534 scopus 로고    scopus 로고
    • Thermodynamic and kinetic considerations for the reaction of semiquinone radicals to form superoxide and hydrogen peroxide
    • Y Song, GR Buettner Thermodynamic and kinetic considerations for the reaction of semiquinone radicals to form superoxide and hydrogen peroxide Free Radic Biol Med 49 6 2010 919 962
    • (2010) Free Radic Biol Med , vol.49 , Issue.6 , pp. 919-962
    • Song, Y.1    Buettner, G.R.2
  • 28
    • 0024237151 scopus 로고
    • Sequential oxidation and glutathione addition to 1,4-benzoquinone: Correlation of toxicity with increased glutathione substitution
    • SS Lau, BA Hill, RJ Highet et al. Sequential oxidation and glutathione addition to 1,4-benzoquinone: correlation of toxicity with increased glutathione substitution Mol Pharmacol 34 6 1988 829 836
    • (1988) Mol Pharmacol , vol.34 , Issue.6 , pp. 829-836
    • Lau, S.S.1    Hill, B.A.2    Highet, R.J.3
  • 29
    • 0023204457 scopus 로고
    • Free radical mediated cell toxicity by redox cycling chemicals
    • GM Cohen, M d'Arcy Doherty Free radical mediated cell toxicity by redox cycling chemicals Br J Cancer Suppl 8 1987 46 52
    • (1987) Br J Cancer Suppl , vol.8 , pp. 46-52
    • Cohen, G.M.1    D'Arcy Doherty, M.2
  • 30
    • 0024498044 scopus 로고
    • DT-diaphorase-catalysed reduction of 1,4-naphthoquinone derivatives and glutathionyl-quinone conjugates. Effect of substituents on autoxidation rates
    • GD Buffinton, K Ollinger, A Brunmark et al. DT-diaphorase-catalysed reduction of 1,4-naphthoquinone derivatives and glutathionyl-quinone conjugates. Effect of substituents on autoxidation rates Biochem J 257 2 1989 561 571
    • (1989) Biochem J , vol.257 , Issue.2 , pp. 561-571
    • Buffinton, G.D.1    Ollinger, K.2    Brunmark, A.3
  • 31
    • 0025731332 scopus 로고
    • Irreversible inhibition of rat glutathione S-transferase 1-1 by quinones and their glutathione conjugates. Structure-activity relationship and mechanism
    • B van Ommen, JH Ploemen, JJ Bogaards et al. Irreversible inhibition of rat glutathione S-transferase 1-1 by quinones and their glutathione conjugates. Structure-activity relationship and mechanism Biochem J 276 Pt 3 1991 661 666
    • (1991) Biochem J , vol.276 , Issue.PART 3 , pp. 661-666
    • Van Ommen, B.1    Ploemen, J.H.2    Bogaards, J.J.3
  • 32
    • 0025860039 scopus 로고
    • Irreversible inhibition of human glutathione S-transferase isoenzymes by tetrachloro-1,4-benzoquinone and its glutathione conjugate
    • JH Ploemen, B van Ommen, PJ van Bladeren Irreversible inhibition of human glutathione S-transferase isoenzymes by tetrachloro-1,4-benzoquinone and its glutathione conjugate Biochem Pharmacol 41 11 1991 1665 1669
    • (1991) Biochem Pharmacol , vol.41 , Issue.11 , pp. 1665-1669
    • Ploemen, J.H.1    Van Ommen, B.2    Van Bladeren, P.J.3
  • 33
    • 0019205195 scopus 로고
    • Mechanism of glutathione-dependent dechlorination of chloramphenicol and thiamphenicol by cytosol of rat liver
    • JL Martin, BJ Gross, P Morris et al. Mechanism of glutathione-dependent dechlorination of chloramphenicol and thiamphenicol by cytosol of rat liver Drug Metab Dispos 8 6 1980 371 375
    • (1980) Drug Metab Dispos , vol.8 , Issue.6 , pp. 371-375
    • Martin, J.L.1    Gross, B.J.2    Morris, P.3
  • 34
    • 0041883698 scopus 로고    scopus 로고
    • An enzyme based dechlorination of a polychlorinated biphenyl (PCB) mixture, Aroclor 1248, using glutathione S-transferases from the northern quahog Mercenaria mercenaria
    • BN Blanchette, BR Singh An enzyme based dechlorination of a polychlorinated biphenyl (PCB) mixture, Aroclor 1248, using glutathione S-transferases from the northern quahog Mercenaria mercenaria J Protein Chem 22 4 2003 377 386
    • (2003) J Protein Chem , vol.22 , Issue.4 , pp. 377-386
    • Blanchette, B.N.1    Singh, B.R.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.