Perez P, Pulgar R, Olea-Serrano F, Villalobos M, Rivas A, Metzler M, Pedraza V, Olea N
Laboratory of Medical Investigation, Department of Radiology, School of Medicine, HUSC-University of Granada, Granada, Spain.
Environ Health Perspect. 1998 Mar;106(3):167-74. doi: 10.1289/ehp.98106167.
The chemical structure of hydroxylated diphenylalkanes or bisphenols consists of two phenolic rings joined together through a bridging carbon. This class of endocrine disruptors that mimic estrogens is widely used in industry, particularly in plastics. Bisphenol F, bisphenol A, fluorine-containing bisphenol A (bisphenol AF), and other diphenylalkanes were found to be estrogenic in a bioassay with MCF7 human breast cancer cells in culture (E-SCREEN assay). Bisphenols promoted cell proliferation and increased the synthesis and secretion of cell type-specific proteins. When ranked by proliferative potency, the longer the alkyl substituent at the bridging carbon, the lower the concentration needed for maximal cell yield; the most active compound contained two propyl chains at the bridging carbon. Bisphenols with two hydroxyl groups in the para position and an angular configuration are suitable for appropriate hydrogen bonding to the acceptor site of the estrogen receptor. Our data suggest that estrogenicity is influenced not only by the length of the substituents at the bridging carbon but also by their nature. Because diphenylalkane derivatives are widespread and their production and use are increasing, potential exposure of humans to estrogenic bisphenols is becoming a significant issue. The hazardous effects of inadvertent exposure to bisphenol-releasing chemicals in professional workers and the general populations therefore deserve investigation.
羟基化二苯烷烃或双酚的化学结构由两个通过桥连碳连接在一起的酚环组成。这类模拟雌激素的内分泌干扰物在工业中广泛使用，尤其是在塑料行业。在对培养的MCF7人乳腺癌细胞进行的生物测定（E-SCREEN测定）中，发现双酚F、双酚A、含氟双酚A（双酚AF）和其他二苯烷烃具有雌激素活性。双酚促进细胞增殖，并增加细胞类型特异性蛋白质的合成和分泌。按增殖能力排序时，桥连碳上的烷基取代基越长，达到最大细胞产量所需的浓度越低；活性最高的化合物在桥连碳上含有两条丙基链。在对位具有两个羟基且呈角型构型的双酚适合与雌激素受体的受体位点进行适当的氢键结合。我们的数据表明，雌激素活性不仅受桥连碳上取代基长度的影响，还受其性质的影响。由于二苯烷衍生物广泛存在且其生产和使用不断增加，人类潜在接触具有雌激素活性的双酚正成为一个重大问题。因此，职业工人和普通人群无意中接触释放双酚的化学物质的有害影响值得研究。
