Estrogenic/Antiestrogenic Activities of Quinoid Polycyclic Aromatic Hydrocarbons

• Hayakawa Kazuichi

  Institute of Medical, Pharmaceutical and Health Sciences, Kanazawa University

• Bekki Kanae

  Institute of Medical, Pharmaceutical and Health Sciences, Kanazawa University

• Yoshita Morio

  Institute of Medical, Pharmaceutical and Health Sciences, Kanazawa University

• Tachikawa Chihiro

  Institute of Medical, Pharmaceutical and Health Sciences, Kanazawa University

• Kameda Takayuki

  Institute of Medical, Pharmaceutical and Health Sciences, Kanazawa University

• Tang Ning

  Institute of Medical, Pharmaceutical and Health Sciences, Kanazawa University

• Toriba Akira

  Institute of Medical, Pharmaceutical and Health Sciences, Kanazawa University

• Hosoi Shinzo

  The Research Center for Pharmacy Education, Kyoto Pharmaceutical University

Abstract

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.

Journal

• Journal of Health Science

  Journal of Health Science 57 (3), 274-280, 2011

  The Pharmaceutical Society of Japan

Keywords

• polycyclic aromatic hydrocarbon
• quinone
• antiestrogenic activity
• yeast two-hybrid
• structure-activity relationship

Details

• CRID: 1390282679473972736
• NII Article ID: 130000800088
• NII Book ID: AA11316464
• DOI: 10.1248/jhs.57.274
• ISSN: 13475207
• ISSN: 13449702
• NDL BIB ID: 11094653
• Web Site: http://hdl.handle.net/2297/45017
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I11094653
• Web Site: http://www.jstage.jst.go.jp/article/jhs/57/3/57_3_274/_pdf
• Web Site: https://search.jamas.or.jp/link/ui/2012093403
• Text Lang: en
• Data Source:
  • JaLC
  • IRDB
  • NDL
  • Crossref
  • CiNii Articles
  • KAKEN
• Abstract License Flag: Disallowed