Estrogenic Activity of Branched 4-Nonylphenol Isomers Examined by Yeast Two-Hybrid Assay
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概要
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Various branched isomers of 4-nonylphenol (NP) and, in addition, the other 4-alkylphenols (APs) were synthesized and their estrogenic activities were assessed using the yeast two-hybrid system. We investigated the relationships between the structure of the nonyl group of NP isomers and their estrogenic activities based on the following five factors: the length of the main alkyl chain, the degree of branching on the α-carbon, the degree of bulkiness, the position of the branch, and the cyclic structure in the nonyl group. An appropriate length of the main alkyl chain was essential for the estrogenic activity. A small effect of the branching on the α-carbon was observed. The importance of the bulkiness and position of the branch in the nonyl group was suggested from the results of the synthesized NP isomers possessing the high estrogenic activities. The bulkiness on the β-carbon was the most important factor for the high estrogenic activity. The investigation of the cyclic structure also indicated the significance of the bulkiness around the β-carbon. The bulkiness on the γ-carbon was also suggested to be an important factor. The metabolic effect of the synthesized APs on the estrogenic activity was also examined using a liver S9. The estrogenic activities of the selected APs were either reduced or lost. In addition, GC-MS analyses of the commercial NP and synthesized NP isomers revealed that the nine synthesized NP isomers were included in the commercial NP.
- 公益社団法人日本薬学会の論文
- 2006-04-01
著者
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Ike Michihiko
Department Of Environmental Engineering Graduate School Of Engineering Osaka University
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Ike Michihiko
Department Of Environmental Engineering Graduate School Of Engineering
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FUJITA Masanori
Department of Environmental Engineering, Osaka University
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MIYAJI Yoko
Analytical Center, Faculty of Engineering, Osaka University
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TSUNOI Shinji
Research Center for Environmental Preservation, Osaka University
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TANAKA Minoru
Research Center for Environmental Preservation, Osaka University
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Miyaji Yoko
Analytical Center Faculty Of Engineering Osaka University
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Shioji Hirotaka
Research Center for Environmental Preservation, Osaka University
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Kobayashi Yosuke
Research Center for Environmental Preservation, Osaka University
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Shigemori Tatsushi
Department of Environmental Engineering, Graduate School of Engineering
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Ike Michihiko
Department Of Environmental Engineering Faculty Of Engineering Osaka University
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Tsunoi Shinji
Research Center For Environment Preservation Osaka University
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Tsunoi Shinji
Research Center For Environmental Preservation Osaka University
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Fujita Masanori
Department Of Cardiology Saiseikai Izuo Hospital
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Shioji Hirotaka
Research Center For Environmental Preservation Osaka University
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Shigemori Tatsushi
Department Of Environmental Engineering Graduate School Of Engineering
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Tanaka Minoru
Research Center For Environment Preservation Osaka University
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Kobayashi Yosuke
Research Center For Environmental Preservation Osaka University
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Tanaka Minoru
Research Center For Environmental Preservation Osaka University
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Fujita Masanori
Department Of Animal Science Faculty Of Agriculture Tohoku University:(present Address) Department O
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