Tollefsen Knut-Erik, Julie Nilsen Anja
Norwegian Institute for Water Research, Gaustadallèen 21, N-0349 Oslo, Norway.
Ecotoxicol Environ Saf. 2008 Feb;69(2):163-72. doi: 10.1016/j.ecoenv.2007.04.010. Epub 2007 May 18.
Alkylphenols are well-known endocrine disrupters, mediating effects through the estrogen receptor (ER). In the present work, the interaction of alkylphenols and alkylated non-phenolics with hepatic rainbow trout (Oncorhynchus mykiss) estrogen receptors (rtERs) was determined. The role of alkyl chain length and branching, substituent position, number of alkylated groups, and the requirement of a phenolic ring structure was assessed. The results showed that the rtERs bound most alkylphenols, although with 20,000 to 2 million times lower affinity than the endogenous estrogen 17beta-estradiol. Mono-substituted alkylphenols with moderate (C4-C6) and long (C8 and C12) alkyl chain length in the para position exhibited the highest affinity for the rtERs. Substitution with multiple alkyl groups, presence of substituents in the ortho- and meta-position, and lack of a hydroxyl group on the benzene ring reduced the binding affinity. The rtERs resembled the reported binding specificity of the human ER for alkylphenols, although some exceptions were identified.
烷基酚是众所周知的内分泌干扰物，通过雌激素受体（ER）介导其效应。在本研究中，测定了烷基酚和烷基化非酚类物质与虹鳟鱼肝雌激素受体（rtERs）的相互作用。评估了烷基链长度和支化、取代基位置、烷基化基团数量以及酚环结构的要求。结果表明，rtERs能结合大多数烷基酚，尽管其亲和力比内源性雌激素17β-雌二醇低2万至200万倍。在对位具有中等（C4-C6）和长（C8和C12）烷基链长度的单取代烷基酚对rtERs表现出最高的亲和力。多个烷基取代、邻位和间位存在取代基以及苯环上缺乏羟基会降低结合亲和力。rtERs类似于已报道的人ER对烷基酚的结合特异性，不过也发现了一些例外情况。
