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Nonylphenol isomers differ in estrogenic activity

机译：壬基酚异构体的雌激素活性不同

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摘要

Nonylphenol belongs to the most investigated xenohormones acting at the estrogen receptor. Technical nonylphenol contains approximately 20 para-substituted isomers. Because of limitations in testing and quantifying all 20 isomers in the mixture, the linear form, 4n-NP, is often used as a reference substance, even though it is not present in the technical mixture. Here, we report on the synthesis and estrogenic potency of six nonylphenol isomers that occur at different proportions in technical nonylphenol mixtures. The relative potency of each isomer was determined by use of the MVLN transcriptional activation cell assay. As well, a subset of isomers was tested in the E-screen assay. One isomer, p353-NP, exhibited the same relative potency as the nonylphenol mixture, whereas the other isomers were found to be less potent. Two isomers, p22-NP and p262-NP, and the linear 4n-NP were found to be weak ER agonists with responses near the detection limit in the MVLN assay. Two isomers, p262-NP and 4n-NP, exhibited measurable activity in the E-screen. Our results demonstrate that defined p-NP isomers are most suitable for reflecting the estrogenic potency of technical NP mixtures. Among other applications, they should be used in the future to explain differences in estrogenic potency due to NPs as detected by various in vitro assays.
机译：壬基酚属于研究最多的作用于雌激素受体的异种激素。工业壬基酚含有约20种对位取代的异构体。由于测试和量化混合物中所有20种异构体的局限性，即使工业混合物中不存在线性形式的4n-NP，也经常用作参考物质。在这里，我们报告了在工业壬基酚混合物中以不同比例出现的六个壬基酚异构体的合成和雌激素作用。通过使用MVLN转录激活细胞测定法确定每种异构体的相对效力。同样，在电子筛选分析中测试了异构体的子集。一种异构体，p353-NP，具有与壬基酚混合物相同的相对效价，而发现其他异构体的效价较低。发现两种异构体，p22-NP和p262-NP，以及线性4n-NP是弱ER激动剂，其响应在MVLN分析中接近检测极限。两种异构体，p262-NP和4n-NP，在E筛选中表现出可测量的活性。我们的结果表明，定义的p-NP异构体最适合反映工业NP混合物的雌激素效力。除其他应用外，将来应使用它们来解释通过各种体外测定法检测到的NPs引起的雌激素效能的差异。

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