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首页> 外文期刊>Environmental Science & Technology >Partitioning of Substituted Phenols in Liposome-Water, Biomembrane-Water, and Octanol-Water Systems
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Partitioning of Substituted Phenols in Liposome-Water, Biomembrane-Water, and Octanol-Water Systems

机译：脂质体-水，生物膜-水和辛醇-水系统中取代苯酚的分配

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摘要

The effect of pH, ionic strength, and compound concentration on the liposome-water distribution ratio has been investigated for 20 chloro- and nitrophenols covering a wide range of acidities and hydrophobicities. A comparison with membrane vesicles from Rhodobacter sphaeroides shows that liposomes composed of zwitterionic phosphatidyl-choline are appropriate model systems for mimicking the biomembrane-water partitioning behavior of all phenol species, i.e., neutral phenol, charged phe-noxide, and ion pair. At high phenoxide concentrations, the simple partition model includes an electrostatic term for the buildup of a surface potential on the liposomes due to sorbed phenoxide. The distribution ratios of the neutral phenol species are very similar in the octanol- and the liposome-water system, but the charged phenol species partition significantly better into the anisotropic lipid bilayer than into the bulk phase octanol. The liposome-water distribution ratio is a more suitable descriptor for the uptake of a hydrophobic ionizable compound into biological membranes than the corresponding octanol-water distribution ratio. The reported data form an important base for more realistic predictions of effective phenol concentrations and phenol-to-phenoxide ratios in biological membranes, which is pivotal for assessing the toxicity, in particular, the uncoupling activity of such compounds.
机译：研究了pH，离子强度和化合物浓度对脂质体-水分配比的影响，研究了20种氯和硝基苯酚，它们涵盖了广泛的酸度和疏水性。与来自球形红球菌的膜囊泡的比较表明，由两性离子磷脂酰胆碱组成的脂质体是模拟所有酚类物质（即中性酚，带电荷的环氧乙烷和离子对）的生物膜-水分配行为的合适模型系统。在高酚盐浓度下，简单的分区模型包括一个静电项，用于表示由于吸附的酚盐而在脂质体上形成的表面电势。在辛醇-和脂质体-水系统中，中性酚种类的分布比率非常相似，但是带电荷的酚种类在各向异性脂质双层中的分配要比在本体相辛醇中的分配好得多。与相应的辛醇-水分配比相比，脂质体-水分配比更适合描述疏水性可离子化化合物吸收进入生物膜。所报道的数据为生物膜中有效苯酚浓度和苯酚与酚盐比率的更现实预测提供了重要基础，这对于评估此类化合物的毒性（尤其是解偶联活性）至关重要。

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  • 来源
    《Environmental Science & Technology》 |1996年第1期|p.260-270|共11页
  • 作者

    BEATE I. ESCHER; RENE P. SCHWARZENBACH;

  • 作者单位

    Swiss Federal Institute for Environmental Sciences and Technology (EAWAG), CH-8600 Duebendorf, Switzerland;

  • 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 eng
  • 中图分类 环境化学;
  • 关键词

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