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首页> 外文期刊>Environmental Science & Technology >Microsomal Oxidation of 2,2',3,3',6,6'-Hexachlorobiphenyl (PCB 136) Results in Species-Dependent Chiral Signatures of the Hydroxylated Metabolites
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Microsomal Oxidation of 2,2',3,3',6,6'-Hexachlorobiphenyl (PCB 136) Results in Species-Dependent Chiral Signatures of the Hydroxylated Metabolites

机译：2,2'，3,3'，6,6'-六氯联苯（PCB 136）的微粒体氧化导致羟基化代谢物的物种依赖性手性签名

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摘要

Chiral polychlorinated biphenyls (PCBs) display variable atropisomeric enrichment in wildlife and animal models, especially at higher trophic levels. These differences in PCBs' chiral signatures are, at least in part, due to species-dependent oxidation of PCBs to hydroxylated PCB metabolites (OH-PCBs). Here, we investigate the hypothesis that the cytochrome P450 (P450) enzyme-mediated oxidation of chiral PCBs results in species-dependent differences in the chiral signatures of OH-PCBs (i.e., the direction and extent of OH-PCBs' atropisomeric enrichment). To investigate this hypothesis, we incubated PCB 136, a representative chiral PCB, with pooled human liver microsomes (HLMs) or liver microsomes from male guinea pig, hamster, monkey, mouse, and rabbit or female dog and determined average profiles and chiral signatures of the OH-PCBs. 2,2',3,3',6,6'-Hexachlorobiphenyl-4-ol (4-136) was the major metabolite in incubations with HLMs and monkey and rabbit microsomes. 2,2',3,3',6,6'-Hexachlorobiphenyl-5-ol (5-136) was the major metabolite formed by microsomes from all other species. Both 4-136 and 5-136 were formed atropselectively in all microsomal incubations; however, the direction and extent of the atropisomeric enrichment of both OH-PCB metabolites showed considerable differences across microsomal preparations obtained from different species. These differences in OH-PCBs' atropisomeric enrichment may not only be toxicologically relevant but may also be useful to study sources and transport of OH-PCBs in the environment.
机译：手性多氯联苯（PCBs）在野生动物和动物模型中表现出可变的阻转异构体富集，尤其是在较高营养水平下。多氯联苯的手性特征的这些差异至少部分是由于多氯联苯与物种有关的氧化成羟基化多氯联苯代谢物（OH-PCBs）所致。在这里，我们研究了一种假设，即细胞色素P450（P450）酶介导的手性PCB氧化会导致OH-PCBs的手性签名（即OH-PCBs的阻转异构体富集的方向和程度）导致物种依赖性差异。为了研究这一假设，我们将PCB 136（一种代表性的手性PCB）与人类肝微粒体（HLM）或来自豚鼠，仓鼠，猴子，小鼠，兔或母犬的肝微粒体进行了孵育，并确定了它们的平均特征和手性特征。 OH-PCBs。 2,2'，3,3'，6,6'-六氯联苯-4-醇（4-136）是与HLM，猴和兔微粒体温育的主要代谢产物。 2,2'，3,3'，6,6'-六氯联苯-5-醇（5-136）是其他所有物种的微粒体形成的主要代谢产物。在所有微粒体温育中，4-136和5-136都是选择性地形成的。然而，两种OH-PCB代谢物的阻转异构体富集的方向和程度在从不同物种获得的微粒体制剂中显示出相当大的差异。 OH-PCBs的阻转异构体富集的这些差异不仅在毒理学上相关，而且对研究环境中OH-PCBs的来源和运输也可能有用。

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  • 来源
    《Environmental Science & Technology》 |2014年第4期|2436-2444|共9页
  • 作者

    Xianai Wu; Austin Kammerer; Hans-Joachim Lehmler;

  • 作者单位

    Department of Occupational and Environmental Health, College of Public Health, The University of Iowa, Iowa City, Iowa, United States;

    Department of Occupational and Environmental Health, College of Public Health, The University of Iowa, Iowa City, Iowa, United States;

    Department of Occupational and Environmental Health, College of Public Health, The University of Iowa, Iowa City, Iowa, United States;

  • 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);
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