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J.Health Sci., 57(3), 274-280, 2011
-Regular Article-
Estrogenic/Antiestrogenic Activities of Quinoid Polycyclic Aromatic Hydrocarbons
Kazuichi Hayakawa,*, a Kanae Bekki,a
Morio Yoshita,a Chihiro Tachikawa,a
Takayuki Kameda,a Ning Tang,a
Akira Toriba,a and Shinzo Hosoib
aInstitute of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan and
bThe Research Center for Pharmacy Education, Kyoto Pharmaceutical University, Misasagi-Nakauchicho 5, Yamashinaku, Kyoto 607-8414, Japan
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 FluormoneTM 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.
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