Phenylphthalimides with Tumor Necrosis Factor Alpha Production-Enhancing Activity
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概要
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Phenylphthalimides (2-phenyl-1H-isoindole-1,3-diones) were prepared and their effects on tumor necrosis factor alpha (TNF-α) production by human leukemia cell line HL-60 stimulated with 12-O-tetradecanoylphorbol-13-acetate (TPA) were examined. An analysis of the structure-activity relationships of the phenylphthalimides indicated that potent enhancing activity on TPA-induced TNF-α production by HL-60 cells requires medium-sized substituent(s) at the ortho position(s) of the phenyl group; 2-(2,6-diisopropylphenyl)-1H-isoindole-1,3-dione (PP-33) increased the TNF-α production to more than 600% at the concentration of 1×10^<-5> M. Introduction of a nitro group at the phthalimide moiety of PP-33 enhanced the activity; 2-(2,6-diisopropylphenyl)-4-nitro-1H-isoindole-1,3-dione (4NPP-33) and its 5-nitro isomer (5NPP-33) enhanced the TNF-α production to more than 800% and 700%, respectively, at the concentration of 1×10^<-5> M. Introduction of fluorines into the phthalimide moiety of PP-33 greatly lowered the concentration of the compound necessary to elicit the TNF-α production-enhancing activity;2-(2,6-diisopropylphenyl)-4,5,6,7-tetrafluoro-1H-isoindole-1,3-dione (FPP-33) showed the activity at nanomolar concentration, with the optimum concentration of 1×10^<-7> M.
- 公益社団法人日本薬学会の論文
- 1996-01-15
著者
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柴田 芳宏
Institute Of Molecular And Cellular Biosciences The University Of Tokyo
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HASHIMOTO Yuichi
Institute of Molecular & Cellular Biosciences, The University of Tokyo
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IWASAKI Shigeo
Institute of Molecular and Cellular Biosciences, The University of Tokyo
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Iwasaki S
Institute Of Molecular And Cellular Biosciences The University Of Tokyo
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SHIBATA Yoshihiro
Institute of Molecular and Cellular Biosciences, University of Tokyo
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SASAKI Keizo
Institute of Molecular and Cellular Biosciences, The University of Tokyo
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Sasaki Keizo
Institute Of Molecular And Cellular Biosciences The University Of Tokyo
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Shibata Y
Environmental Chemistry Division National Institute For Environmental Studies
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Iwasaki S
Univ. Tokyo Tokyo
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Shibata Yoshihiro
Institute Of Mathematics The University Of Tsukuba
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Iwasaki Shigeo
Institute Of Molecular And Cellular Biosciences (imcb) The University Of Tokyo
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IWASAKI Shigeo
Institute of Molecular and Cellular Bioscience, The University of Tokyo
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