Stereo Structure-Controlled and Electronic Structure-Controlled Estrogen-Like Chemicals to Design and Develop Non-estrogenic Bisphenol A Analogs Based on Chemical Hardness Concept
The aim of this study was to elucidate the structure–activity relationship of bisphenol A (BPA) analogs using absolute hardness (η) and absolute electronegativity (χ) (chemical hardness) and to design a non-estrogen active BPA. To determine the structure–activity relationships of BPA analogs, we inv...
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| Veröffentlicht in: | Chemical & Pharmaceutical Bulletin 2006, Vol.54(12), pp.1633-1638 |
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| container_title | Chemical & Pharmaceutical Bulletin |
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| creator | Kobayashi, Shigeki Shinohara, Hidemi Tabata, Kyoko Yamamoto, Naoko Miyai, Akira |
| description | The aim of this study was to elucidate the structure–activity relationship of bisphenol A (BPA) analogs using absolute hardness (η) and absolute electronegativity (χ) (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 η–χ 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. |
| doi_str_mv | 10.1248/cpb.54.1633 |
| format | Article |
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To determine the structure–activity relationships of BPA analogs, we investigated MCF-7 cell proliferation stimulated by BPA analogs and an η–χ 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. 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Pharm. Bull.</addtitle><description>The aim of this study was to elucidate the structure–activity relationship of bisphenol A (BPA) analogs using absolute hardness (η) and absolute electronegativity (χ) (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 η–χ 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.</description><subject>Benzhydryl Compounds</subject><subject>bisphenol A</subject><subject>Cell Line, Tumor</subject><subject>cell proliferation</subject><subject>Cell Proliferation - drug effects</subject><subject>chemical hardness</subject><subject>Drug Design</subject><subject>environmental hormone</subject><subject>Estrogens, Non-Steroidal - chemistry</subject><subject>Estrogens, Non-Steroidal - pharmacology</subject><subject>Humans</subject><subject>MCF-7 cell</subject><subject>Molecular Structure</subject><subject>Phenols - chemistry</subject><subject>Phenols - pharmacology</subject><subject>Structure-Activity Relationship</subject><subject>Time Factors</subject><subject>η–χ diagram</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkk2P0zAQQCMEYrsLJ-7IEtJeVin-iJ342HbLLlIFh4Wz5TqTNsW1g50g8bv4gzht1JUQF48tP78Ze5xl7wieE1pUH023nfNiTgRjL7IZYUWZc0rZy2yGMZY5ZYJdZdcxHjCmHJfsdXZFSsIklnyW_XnqIYBHT30YTD8EyFfe9cFbCzXSrkZrCyatXWv-z6xjmu3A5Zv2B6DVHo6t0Tai3qN7iO3OnSz38Aus79AX73KYTiTjso3dHpy3aIEWTlu_i2ipY9J6d3GhRx1qBzGilNZA17_JXjUpBbyd4k32_dP62-ox33x9-LxabHIjRNnnphambISo5baiVSU51wxrLbbacC541eiSSiMLQgnWTV0YhgkxoiAlJUISxm6y27O3C_7nkMpWxzYasFY78ENUoiKykpgm8MM_4MEPId0nKlIIzKqKUpKouzNlgo8xQKO60B51-K0IVmMnVeqk4oUaO5no95Nz2B6hfman1iXg4Qyk3fGZvLOtg-fMJpZmfEFFMRYKY54umgI96cehIukzMDmWvzybDrHXO7ik0qFvjYVLWXQaT4LL5l4HBY79BeJ2yOY</recordid><startdate>2006</startdate><enddate>2006</enddate><creator>Kobayashi, Shigeki</creator><creator>Shinohara, Hidemi</creator><creator>Tabata, Kyoko</creator><creator>Yamamoto, Naoko</creator><creator>Miyai, Akira</creator><general>The Pharmaceutical Society of Japan</general><general>Pharmaceutical Society of Japan</general><general>Japan Science and Technology Agency</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TK</scope><scope>7TM</scope><scope>7U9</scope><scope>H94</scope><scope>7X8</scope></search><sort><creationdate>2006</creationdate><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</title><author>Kobayashi, Shigeki ; Shinohara, Hidemi ; Tabata, Kyoko ; Yamamoto, Naoko ; Miyai, Akira</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c667t-cd6c7f66d9b8288955a30aa6bac55658fa729c941210afd4c3011c64172169133</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>Benzhydryl Compounds</topic><topic>bisphenol A</topic><topic>Cell Line, Tumor</topic><topic>cell proliferation</topic><topic>Cell Proliferation - drug effects</topic><topic>chemical hardness</topic><topic>Drug Design</topic><topic>environmental hormone</topic><topic>Estrogens, Non-Steroidal - chemistry</topic><topic>Estrogens, Non-Steroidal - pharmacology</topic><topic>Humans</topic><topic>MCF-7 cell</topic><topic>Molecular Structure</topic><topic>Phenols - chemistry</topic><topic>Phenols - pharmacology</topic><topic>Structure-Activity Relationship</topic><topic>Time Factors</topic><topic>η–χ diagram</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kobayashi, Shigeki</creatorcontrib><creatorcontrib>Shinohara, Hidemi</creatorcontrib><creatorcontrib>Tabata, Kyoko</creatorcontrib><creatorcontrib>Yamamoto, Naoko</creatorcontrib><creatorcontrib>Miyai, Akira</creatorcontrib><creatorcontrib>aDepartment of Analytical Chemistry of Medicines</creatorcontrib><creatorcontrib>bSpace Environmental Technology</creatorcontrib><creatorcontrib>Corporation</creatorcontrib><creatorcontrib>Showa Pharmaceutical University</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Neurosciences Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical & Pharmaceutical Bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kobayashi, Shigeki</au><au>Shinohara, Hidemi</au><au>Tabata, Kyoko</au><au>Yamamoto, Naoko</au><au>Miyai, Akira</au><aucorp>aDepartment of Analytical Chemistry of Medicines</aucorp><aucorp>bSpace Environmental Technology</aucorp><aucorp>Corporation</aucorp><aucorp>Showa Pharmaceutical University</aucorp><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Stereo Structure-Controlled and Electronic Structure-Controlled Estrogen-Like Chemicals to Design and Develop Non-estrogenic Bisphenol A Analogs Based on Chemical Hardness Concept</atitle><jtitle>Chemical & Pharmaceutical Bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>2006</date><risdate>2006</risdate><volume>54</volume><issue>12</issue><spage>1633</spage><epage>1638</epage><pages>1633-1638</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><abstract>The aim of this study was to elucidate the structure–activity relationship of bisphenol A (BPA) analogs using absolute hardness (η) and absolute electronegativity (χ) (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 η–χ 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. 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| subjects | Benzhydryl Compounds bisphenol A Cell Line, Tumor cell proliferation Cell Proliferation - drug effects chemical hardness Drug Design environmental hormone Estrogens, Non-Steroidal - chemistry Estrogens, Non-Steroidal - pharmacology Humans MCF-7 cell Molecular Structure Phenols - chemistry Phenols - pharmacology Structure-Activity Relationship Time Factors η–χ diagram |
| 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 |
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