文章基本信息

标题：Estrogenic/Antiestrogenic Activities of Quinoid Polycyclic Aromatic Hydrocarbons
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作者：Kazuichi Hayakawa ; Kanae Bekki ; Morio Yoshita 等
期刊名称：Journal of Health Science
印刷版ISSN：1344-9702
电子版ISSN：1347-5207
出版年度：2011
卷号：57
期号：3
页码：274-280
DOI：10.1248/jhs.57.274
出版社：The Pharmaceutical Society of Japan
摘要：Estrogenic and antiestrogenic activities of 19 quinoid polycyclic aromatic hydrocarbons (PAHQs) and 9 ketone PAHs were evaluated by the yeast two-hybrid assay using yeast cells expressing estrogen receptor-α (ERα). Binding affinity of PAHQs to ERα was assayed by the polarized fluorescence method using Fluormone^TM ES2. Ten PAHQs having 3-5 rings showed antiestrogenic activities. The most strongly antiestrogenic PAHQs were 1,4-chrysenequinone and 5,6-chrysenequinone. On the other hand, benzo[ a ]pyrene-3,6-quinone showed the strongest estrogenic activity. However, the other compounds tested did not show so strong estrogenic/antiestrogenic activities. Binding affinity to ER was required but not sufficient for estrogenic/antiestrogenic activities of PAHQs. The length-to-breadth ratios of the rectangular planes surrounding the ring molecules and the distances between the oxygen atom of the carbonyl group and farthest hydrogen atom of estrogenic/antiestrogenic PAHQs were in narrow ranges, suggesting a structure-activity relationship. As interactions between active PAHQ and ER, hydrogen bonding between carbonyl groups and amino acid residues and van der Waals forces were considered.
关键词：polycyclic aromatic hydrocarbon;quinone;antiestrogenic activity;yeast two-hybrid;structure-activity relationship