Computational Toxicological Investigation on the Mechanism and Pathways of Xenobiotics Metabolized by Cytochrome P450: A Case of BDE-47
文献类型：期刊论文
| 作者 | Wang, Xingbao1,2; Wang, Yong3; Chen, Jingwen1; Ma, Yuqin2; Zhou, Jing1; Fu, Zhiqiang1 |
| 刊名 | environmental science & technology
 |
| 出版日期 | 2012-05-01 |
| 卷号 | 46期号:9页码:5126-5133 |
| 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. |
| 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 |
| 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 |
| 收录类别 | SCI |
| 语种 | 英语 |
| WOS记录号 | WOS:000303348800060 |
| 公开日期 | 2015-11-17 |
| 源URL | [http://159.226.238.44/handle/321008/143155]  |
| 专题 | 大连化学物理研究所_中国科学院大连化学物理研究所 |
| 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 |
| 推荐引用方式 GB/T 7714 | 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. |
| APA | Wang, Xingbao,Wang, Yong,Chen, Jingwen,Ma, Yuqin,Zhou, Jing,&Fu, Zhiqiang.(2012).Computational Toxicological Investigation on the Mechanism and Pathways of Xenobiotics Metabolized by Cytochrome P450: A Case of BDE-47.environmental science & technology,46(9),5126-5133. |
| MLA | Wang, Xingbao,et al."Computational Toxicological Investigation on the Mechanism and Pathways of Xenobiotics Metabolized by Cytochrome P450: A Case of BDE-47".environmental science & technology 46.9(2012):5126-5133. |
入库方式： OAI收割
来源：大连化学物理研究所
浏览0
下载0
收藏0
其他版本
除非特别说明，本系统中所有内容都受版权保护，并保留所有权利。