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题名: Computational Toxicological Investigation on the Mechanism and Pathways of Xenobiotics Metabolized by Cytochrome P450: A Case of BDE-47
作者: Wang, Xingbao1, 2;  Wang, Yong3;  Chen, Jingwen1;  Ma, Yuqin2;  Zhou, Jing1;  Fu, Zhiqiang1
刊名: ENVIRONMENTAL SCIENCE & TECHNOLOGY
发表日期: 2012-05-01
DOI: 10.1021/es203718u
卷: 46, 期:9, 页:5126-5133
收录类别: SCI
文章类型: Article
WOS标题词: Science & Technology ;  Technology ;  Life Sciences & Biomedicine
类目[WOS]: Engineering, Environmental ;  Environmental Sciences
研究领域[WOS]: Engineering ;  Environmental Sciences & Ecology
英文摘要: Understanding the transformation mechanism and products of xenobiotics catalyzed by cytochrome P450 enzymes (CYPs) is vital to risk assessment. By density functional theory computation with the B3LYP functional, we simulated the reaction of 2,24,4'-tetrabromodiphenyl ether (BDE-47) catalyzed by the active species of CYPs (Compound I). The enzymatic and aqueous environments were simulated by the polarizable continuum model. The results reveal that the addition of Compound I to BDE-47 is the rate-determining step. The addition of Compound I to the ipso and nonsubstituted C atoms forms tetrahedral sigma-adducts that further transform into epoxides. Hydroxylation of the epoxides leads to hydroxylated polybrominated diphenyl ethers and 2,4-dibromophenol. The addition to the Br-substituted C2 and C4 atoms has a higher barrier than addition to the nonsubstituted C atoms, forming phenoxide and cyclohexadienone which subsequently undergo debromination/hydroxylation. A novel mechanism was identified in which the approach of Compound I to C2 led to formation of a phenoxide and an expelled Br- ion. The predicted products were consistent with the metabolites identified by others. As a first attempt to simulate the enzymatic transformation of a polycyclic compound, this study may enlighten a computational method to predict the biotransformation of xenobiotics catalyzed by CYPs.
关键词[WOS]: POLYBROMINATED DIPHENYL ETHERS ;  BROMINATED FLAME RETARDANTS ;  HYDROXYLATED METABOLITES ;  AROMATIC HYDROXYLATION ;  BENZENE HYDROXYLATION ;  OXIDIZED METABOLITES ;  QM/MM CALCULATIONS ;  COMPOUND-I ;  REACTIVITY ;  ENZYMES
语种: 英语
WOS记录号: WOS:000303348800060
Citation statistics: 
内容类型: 期刊论文
URI标识: http://cas-ir.dicp.ac.cn/handle/321008/143155
Appears in Collections:中国科学院大连化学物理研究所_期刊论文

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作者单位: 1.Dalian Univ Technol, Sch Environm Sci & Technol, Key Lab Ind Ecol & Environm Engn MOE, Dalian 116024, Peoples R China
2.Changchun Univ Sci & Technol, Sch Chem & Environm Engn, Changchun 130022, Peoples R China
3.Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Mol React Dynam, Dalian 116023, Peoples R China

Recommended Citation:
Wang, Xingbao,Wang, Yong,Chen, Jingwen,et al. Computational Toxicological Investigation on the Mechanism and Pathways of Xenobiotics Metabolized by Cytochrome P450: A Case of BDE-47[J]. ENVIRONMENTAL SCIENCE & TECHNOLOGY,2012,46(9):5126-5133.
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