Activation of the Aryl Hydrocarbon Receptor by Methyl Yellow and Related Congeners: Structure-Activity Relationships in Halogenated Derivatives.
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- Kato Taka-aki
- Faculty of Pharmaceutical Sciences, Nagoya City University
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- Matsuda Tomonari
- Department of Environmental Engineering, Kyoto University
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- Matsui Saburo
- Department of Environmental Engineering, Kyoto University
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- Mizutani Takaharu
- Faculty of Pharmaceutical Sciences, Nagoya City University
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- Saeki Ken-ichi
- Faculty of Pharmaceutical Sciences, Nagoya City University
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The aryl hydrocarbon receptor (AhR) is a ligand-activated transcription factor that mediates the biological action of many environmental compounds. Methyl yellow (4-dimethylaminoazobenzene; MY) is a principal azo-dye, and structurally related compounds were subjected to analysis of structure–activity relationships as AhR ligands by using a yeast AhR signaling assay. The effects of halogen-substitution among 23 halogenated MYs on the AhR ligand activity can be summarized as follows: enhancement by halogen-substitution at the ortho-position (2′- and 6′-position), and reduction by substitution at the para-position (4′-position). The greatest enhancement of the ligand activity was observed in 2′,6′-dichlorinated MY (13.5-fold of MY), and its AhR ligand activity was very close to that of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) in the present assay system. In the study of compounds structurally related to MY, benzanilide (BA) showed almost the same AhR ligand activity as azobenzene and trans-stilbene. Furthermore, 4′-chlorobenzanilide, in which the length of the molecule is similar to that of MY, enhanced the AhR ligand activity by ortho(2′)-chlorine-substitution, and the AhR ligand activity of 2′,4′-dichlorobenzanilide was similar to that of 2′-chloro-MY. These results suggest that the amide bond is equivalent to the –N=N– or –CH=CH– double bond for recognition as the ligand by AhR in 1,2-diphenyl-1,2-ene derivatives.
収録刊行物
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- Biological & Pharmaceutical Bulletin
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Biological & Pharmaceutical Bulletin 25 (4), 466-471, 2002
公益社団法人 日本薬学会
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詳細情報 詳細情報について
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- CRID
- 1390282679604433280
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- NII論文ID
- 110003638804
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- NII書誌ID
- AA10885497
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- COI
- 1:CAS:528:DC%2BD38XkslWrs7k%3D
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- ISSN
- 13475215
- 09186158
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- NDL書誌ID
- 6120787
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- PubMed
- 11995926
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- 本文言語コード
- en
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- データソース種別
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- JaLC
- NDL
- Crossref
- PubMed
- CiNii Articles
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- 抄録ライセンスフラグ
- 使用不可