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题名: Transformation Pathways of Isomeric Perfluorooctanesulfonate Precursors Catalyzed by the Active Species of P450 Enzymes: In Silico Investigation
作者: Fu, Zhiqiang1, 2;  Wang, Yong2;  Wang, Zhongyu1;  Xie, Hongbin1;  Chen, Jingwen1
刊名: CHEMICAL RESEARCH IN TOXICOLOGY
发表日期: 2015-03-01
DOI: 10.1021/tx500470f
卷: 28, 期:3, 页:482-489
收录类别: SCI
文章类型: Article
WOS标题词: Science & Technology ;  Life Sciences & Biomedicine ;  Physical Sciences
类目[WOS]: Chemistry, Medicinal ;  Chemistry, Multidisciplinary ;  Toxicology
研究领域[WOS]: Pharmacology & Pharmacy ;  Chemistry ;  Toxicology
英文摘要: As evidenced from various in vitro and in vivo studies, metabolism of perfluorooctanesulfonate (PFOS) precursors by cytochrome P450 enzymes. (CYPs) acts as an -important indirect pathway for mammal PFOS exposure. NeVertheless, the mechanism of this transformation remains largely unclarified. In this study, in silieo investigations adopting density functional theory (DFT) were performed to reveal the biotransformation of a typical PFOS precursor, N-ethyl perfluorooctane sulfonamide (N-EtPFOSA), catalyzed by the active species, of CYPs (Compound I). Results unveil that in the enzymatic environment, N-EtPFOSA is hydroxylated feasibly (reaction energy barriers Delta E = 11.4-14.5 kcal/mol) with a H atom transfer (HAT) from the ethyl C alpha to Compound I. The HAT derived C alpha radical then barrierlessly combines With the OH radical to produce a ferric-ethanolarnine intermediate. Subsequently, the ethanolamine nonenzymatically with the assistance of water molecules. The rate-limiting O-addition (Delta E = 21.2-34.0 kcal/mol) of Compound I to PFOSA initiated a novel deamination pathway that comprises O-S bond formation and S-N bond cleavage. The resulting hydroxylamine is then hydrolyzed to PFOS. In addition, the results reveal that both the N-deallcylation and deamination pathways are isomeric-specific, which is cOnsistent with experimental observations. Accordingly, DFT calculations may help uncover possible toxicological effects by predicting the biotransformation mechanisms and products of xenobioticsi by CYPs.
关键词[WOS]: FLUORINATED ORGANIC-COMPOUNDS ;  ISOTOPE EFFECT PROFILES ;  SPRAGUE-DAWLEY RATS ;  PERFLUORINATED COMPOUNDS ;  HUMAN EXPOSURE ;  SUBSTITUTED N,N-DIMETHYLANILINES ;  SULFONATE PRECURSORS ;  INITIATED OXIDATION ;  LIVER-MICROSOMES ;  CYTOCHROME-P450
语种: 英语
WOS记录号: WOS:000351326400023
Citation statistics: 
内容类型: 期刊论文
URI标识: http://cas-ir.dicp.ac.cn/handle/321008/146092
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.Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Mol React Dynam, Dalian 116023, Peoples R China

Recommended Citation:
Fu, Zhiqiang,Wang, Yong,Wang, Zhongyu,et al. Transformation Pathways of Isomeric Perfluorooctanesulfonate Precursors Catalyzed by the Active Species of P450 Enzymes: In Silico Investigation[J]. CHEMICAL RESEARCH IN TOXICOLOGY,2015,28(3):482-489.
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