Laboratory of Microbiology and Host Defenses, School of Food and Nutritional Sciences, University of Shizuoka, 52-1 Yada, Shizuoka 422-8526, Japan.
Environ Toxicol Pharmacol. 2005 Jan;19(1):121-30. doi: 10.1016/j.etap.2004.05.009.
Alkylphenol ethoxylates, widely used non-ionic surfactants, are biodegraded into alkylphenols such as nonylphenol (NP) and t-octylphenol (OP), short-chain ethoxylates such as NP-monoethoxylate (NP1EO) and NP-diethoxylate (NP2EO), and alkylphenoxy carboxylic acids such as 4-t-octylphenoxyacetic acid (OP1EC). Bisphenol S (BPS) is more heat-stable and photo-resistant than bisphenol A (BPA), and therefore replaces BPA. These chemicals could be chlorinated during wastewater treatment. We synthesized these compounds and their chlorinated derivatives to estimate their estrogenic activities using a GFP expression system. The EC(50) ranking of NP-related compounds was NP > ClNP > diClNP > NP1EO > ClNP1EO > NP2EO. The estrogenic activity of OP1EC was 10 times less potent than parent OP. Furthermore, BPS showed comparable estrogenic activity with BPA. The EC(50) ranking of BPS-related compounds was BPA ≥ BPS > triClBPS > diClBPS > ClBPS. Other tested BPS derivatives had no estrogenic activity. Chlorination of the tested chemicals did not enhance their estrogenic activity, in contrast to certain chlorinated BPAs. Thus, our results demonstrated that chlorinated derivatives of NP, OP, and BPS, even if artificially produced during wastewater processing, were less estrogenic than their parent chemicals, known as endocrine disruptors.
烷基酚聚氧乙烯醚，广泛使用的非离子表面活性剂，可生物降解为壬基酚（NP）和叔辛基酚（OP）、短链聚氧乙烯醚如 NP-单乙氧基化物（NP1EO）和 NP-二乙氧基化物（NP2EO）以及烷基酚氧羧酸如 4-叔辛基酚氧乙酸（OP1EC）。双酚 S（BPS）比双酚 A（BPA）更耐热和耐光，因此取代了 BPA。这些化学物质在废水处理过程中可能会被氯化。我们合成了这些化合物及其氯化衍生物，并用 GFP 表达系统来评估它们的雌激素活性。NP 相关化合物的 EC（50）排序为 NP＞ClNP＞diClNP＞NP1EO＞ClNP1EO＞NP2EO。OP1EC 的雌激素活性比母体 OP 弱 10 倍。此外，BPS 的雌激素活性与 BPA 相当。BPS 相关化合物的 EC（50）排序为 BPA≥BPS＞triClBPS＞diClBPS＞ClBPS。其他测试的 BPS 衍生物没有雌激素活性。与某些氯化 BPA 不同，测试化学物质的氯化并没有增强它们的雌激素活性。因此，我们的结果表明，NP、OP 和 BPS 的氯化衍生物，即使在废水处理过程中人为产生，其雌激素活性也低于其母体化学物质，这些化学物质被称为内分泌干扰物。
