Differences in Enantioselective Hydroxylation of 2,2',3,6-Tetrachlorobiphenyl(CB45)and 2,2',3,4',6-Pentachlorobiphenyl(CB91)by Human and Rat CYP2B Subfamilies

Hideyuki Inui; Terushi Ito; Chiharu Miwa

首页> 外文期刊>Environmental Science & Technology: ES&T >Differences in Enantioselective Hydroxylation of 2,2',3,6-Tetrachlorobiphenyl(CB45)and 2,2',3,4',6-Pentachlorobiphenyl(CB91)by Human and Rat CYP2B Subfamilies

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Differences in Enantioselective Hydroxylation of 2,2',3,6-Tetrachlorobiphenyl(CB45)and 2,2',3,4',6-Pentachlorobiphenyl(CB91)by Human and Rat CYP2B Subfamilies

机译：Differences in Enantioselective Hydroxylation of 2,2',3,6-Tetrachlorobiphenyl(CB45)and 2,2',3,4',6-Pentachlorobiphenyl(CB91)by Human and Rat CYP2B Subfamilies

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Although polychlorinated biphenyls(PCBs)were commercially banned half a century ago,contamination of the environment and organisms by PCBs is still observed.PCBs show high persistence and bioaccumulation,resulting in toxicity.Among PCBs,chiral PCBs with more than three chlorine atoms at the ortho-position exhibit developmental and neurodevelopmental toxicity.Because toxicity is dependent on the atropisomer,atropisomer-specific metabolism is vital in determining toxicity.However,structural information on enantioselective metabolism remains elusive.Cytochrome P450(CYP,P450)monooxygenases,particularly human CYP2B6 and rat CYP2B1,metabolize separated atropisomers of 2,2',3,6-tetrachlorobiphenyl(CB45)and 2,2',3,4',6-pentachlor-obiphenyl(CB91)to dechlorinated and hydroxylated metabolites.Docking studies using human CYP2B6 predict 4'-hydroxy(OH)-CB45 from(aR)-CB45 as a major metabolite of CB45.Di-OH-and dechlorinated OH-metabolites from human CYP2B6 and rat CYP2B1 are also detected.Several hydroxylated metabolites are derived from CB91 by both P4S0s; 5-OH-CB91 is predicted as a major metabolite.CB91 dechlorination is also detected by identifying 3-OH-CB51.A stable conformation of PCBs in the substrate-binding cavity and close distance to P450 heme are responsible for high metabolizing activities.As hydroxylation and dechlorination change PCB toxicity,this approach helps understand the possible toxicity of chiral PCBs in mammals.

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《Environmental Science & Technology: ES&T》 |2022年第14期|10204-10215|共12页
作者
Hideyuki Inui; Terushi Ito; Chiharu Miwa;
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作者单位

Graduate School of Agricultural Science,Kobe University,Kobe,Hyogo 6S7-8S01,Japan;

Faculty of Agriculture,Kobe University,Kobe,Hyogo 6S7-8S01,Japan;

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收录信息美国《科学引文索引》(SCI);美国《工程索引》(EI);美国《生物学医学文摘》(MEDLINE);美国《化学文摘》(CA);
原文格式 PDF
正文语种英语
中图分类环境科学、安全科学;
关键词
atropisomer; chiral polychlorinated biphenyl; cytochrome P4S0 monooxygenase; docking model; enantioselectivity; hydroxylation; 2; 2'; 3; 4'; 6-pentachlorobiphenyl; 6-tetrachlorobiphenyl;

Differences in Enantioselective Hydroxylation of 2,2',3,6-Tetrachlorobiphenyl(CB45)and 2,2',3,4',6-Pentachlorobiphenyl(CB91)by Human and Rat CYP2B Subfamilies

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