title: Stereo structure-controlled and electronic structure-controlled estrogen-like chemicals to design and develop non-estrogenic bisphenol A analogs based on chemical hardness concept.
abstract: The aim of this study was to elucidate the structure-activity relationship of bisphenol A (BPA) analogs using absolute hardness (eta) and absolute electronegativity (chi) (chemical hardness) and to design a non-estrogen active BPA. To determine the structure-activity relationships of BPA analogs, we investigated MCF-7 cell proliferation stimulated by BPA analogs and an eta-chi diagram based on the electronic structure of the BPA analogs. The results show that the actions of the environmental hormones BPA analogs have two chemical properties; (i) 'stereo structure-controlled' and (ii) 'electronic structure-controlled' estrogen-like chemical activities. Therefore, we designed and synthesized BPA analogs which do not possess these 2 characteristics, ((i) and (ii)), and demonstrate the non-estrogen activity of the analog.
authors.affiliation: Department of Analytical Chemistry of Medicines, Showa Pharmaceutical University, Tokyo, Japan. kobayasi@ac.shoyaku.ac.jp
authors.forename: Shigeki
authors.initials: S
authors.lastname: Kobayashi
authors.forename: Hidemi
authors.initials: H
authors.lastname: Shinohara
authors.forename: Kyoko
authors.initials: K
authors.lastname: Tabata
authors.forename: Naoko
authors.initials: N
authors.lastname: Yamamoto
authors.forename: Akira
authors.initials: A
authors.lastname: Miyai
mesh_terms: D001559:Benzhydryl Compounds; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D015195:Drug Design; D004968:Estrogens, Non-Steroidal / Q000737:chemistry* / Q000494:pharmacology; D006801:Humans; D015394:Molecular Structure; D010636:Phenols / Q000737:chemistry* / Q000494:pharmacology; D013329:Structure-Activity Relationship; D013997:Time Factors; D000098826:Bisphenol A Compounds
chemical_list: D001559:Benzhydryl Compounds; D004968:Estrogens, Non-Steroidal; D010636:Phenols; C006780:bisphenol A; D000098826:Bisphenol A Compounds