Activation of 3,4,3′,4′-tetrachlorobiphenyl to protein-bound metabolites by rat liver microsomal cytochrome P-448-containing monooxygenase system☆
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Polychlorinated biphenyls (PCBs) as initiating agents in hepatocellular carcinoma
2013, Cancer LettersCitation Excerpt :In the in vitro system with microsomal proteins PCBs bound to cytochrome P-450 reductase and cytochrome P-450, but not cytochrome b5. If cytosolic proteins were present as well, strong binding to many cytosolic proteins was observed and it was hypothesized that cysteine moieties were the major binding sites [86,89]. The question whether PCBs with 6 or more chlorines can be metabolically bioactivated to covalent binding species remains controversial.
The role of African American ethnicity and metabolism in sentinel polychlorinated biphenyl congener serum levels
2009, Environmental Toxicology and PharmacologyCitation Excerpt :Although the mechanism of PCB metabolism has not been illustrated, these results show PCB 101 is rapidly metabolized and, like other studies have shown, may exhibit significant covalent binding to CYP 450 protein. Hsu et al. (1975) showed metabolites of the closely related congener PCB 52 (2,5,2′5′) were likely formed from an arene oxide intermediate and PCB arene oxide intermediates have been known to bind CYP 450 protein and heme (Schnellmann et al., 1983; Shimada and Sawabe, 1983). Using another radiolabeled non-coplanar PCB congener with open vicinal carbons Schnellmann et al. (1983) showed significant covalent binding of PCB metabolites to microsomal protein.
Binding of polychlorinated biphenyls/metabolites to hemoglobin
2003, Toxicology LettersDistribution and macromolecular binding of benzo[a]pyrene and two polychlorinated biphenyl congeners in female mice
2001, Chemico-Biological InteractionsCitation Excerpt :3,3′,4,4′-CB is a coplanar congener that is metabolized and cleared slower than 4-CB due to its higher degree of chlorination (>72 h) [41,45,46]. The in vivo formation of hydroxylated metabolites of this compound was demonstrated in rodents [46,47] and covalent binding to total macromolecules was also reported [36,48,49]. DNA adducts formation by this PCB congener was suggested [50] and its tumor promoting activity in rats was reported [51], hence supporting its choice as a second, more chlorinated model compound for our study.
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Preliminary account of this study was presented at the Fifth International Symposium on Microsomes and Drug Oxidations, Tokyo, July 1981 (Shimada et al., 1982).