Inhibition of Cytopathic Effect of Human Immunodeficiency Virus Type-1 by Various Phorbol Derivatives
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概要
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Forty-eight derivatives of phorbol (9) and isophorbol (14) were evaluated for their inhibition of human immunodeficiency virus (HIV)-1 induced cytopathic effects (CPE) on MT-4 cells, as well as their activation of protein kinase C (PKC), as indices of anti-HIV-1 and tumor promoting activities, respectively. Of these compounds, the most potent inhibition of CPE was observed in 12-O-tetradecanoylphorbol 13-acetate (8) and 12-O-acetylphorbol 13-decanonte (6). The former also showed the strongest PKC activation activity, while the latter showed no activity at 10ng/ml. Both activities were generally observed in those phorbol derivatives with an A/B trans configuration, but not in the isophorbol derivatives with an A/B cis configuration. Acetylation of 20-OH in the phorbol derivatives significantly reduced the inhibition of CPE, as shown in 12-O-, 20-O-diacetylphorbol 13-decanoate (6a) (IC_<100>= 15.6 μg/ml) vs. compound 6 (IC_<100>=0.0076 μg/ml), and 12-O-tetradecanoylphorbol 13,20-diacetate (8a) (IC_<100>= 15.6 μg/ml) vs. 12-O-tetradecanoylphorbol 13-acetate (8) (IC_<100>=0.00048 μg/ml), except in the case of 12-O-decanoylphorbol 13-(2-methylbutyrate) (4) and phorbol 12,13-diacetate (9c). The reduction of a carbonyl group at C-3 abruptly reduced the inhibition of CPE, as observed in 3β-hydroxyphorbol 12,13,20-triacetate (9f) (IC_<100>=500 μg/ml) vs. phorbol 12,13,20-triacetate (9d) (IC_<100>=62.5 μg/ml). Although 8 was equipotent in the inhibition of CPE, and activation of PKC, both activities were abruptly decreased by the acetylation of 20-OH and methylation of 4-OH [as in 8a and 4-O-methyl-12-O-tetradecanoylphorbol 13,20-diacetate (8b), respectively]. On the other hand, its positional isomer (12-O-acetylphorbol 13-tetradecanoate (8c) showed neither activities. The removal of a long acyl group in 8 led to a substantial loss of both activities, as shown in phorbol 13-acetate (9b). Of the 12-O-acetyl-13-O-acylphorbol derivatives, the highest inhibition of CPE was observed in 6, which has a dodecanoyl residue at C-13. Both an increase and decrease in the number of fatty acid carbon chains resulted in significant reduction of the inhibition of CPE.
- 社団法人日本薬学会の論文
- 2002-04-01
著者
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MESELHY Meselhy
Institute of Natural Medicine, Faculty of Pharmaceutical Sciences and Pharmaceutical University
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NAKAMURA Norio
富山医科薬科大学和漢薬研究所
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花岡 美代次
金沢大学薬学部
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Nakamura Norio
Institute Of Natural Medicine University Of Toyama
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HATTORI Masao
Institute of Natural Medicine, University of Toyama
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Otake Toru
Osaka Prefectural Institute Of Public Health
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Otake Toru
Showa Denko K.k.
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Hattori Masao
Institute Of Natural Medicine University Of Toyama
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EL-MEKKAWY Sahar
Institute of Natural Medicine, Toyama Medical and Pharmaceutical University
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ABDEL-HAFEZ Atef
Institute of Natural Medicine, Toyama Medical and Pharmaceutical University
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KAWAHATA Takuya
Osaka Prefectural Institute of Public Health
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Abdel-hafez Atef
Institute Of Natural Medicine Toyama Medical And Pharmaceutical University
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Abdel‐hafez A
Institute Of Natural Medicine Toyama Medical And Pharmaceutical Uniyersity
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Abdel-hafez Atef
Institute Of Natural Medicine Toyama Medical And Pharmaceutical University:department Of Pharmaceuti
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Nakamura N
Institute Of Natural Medicine Toyama Medical And Pharmaceutical University
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Meselhy M
Toyama Medical And Pharmaceutical Univ. Toyama Jpn
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Meselhy Meselhy
Faculty Of Pharmacy Cairo University
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Meselhy Meselhy
(present Address)faculty Of Pharmacy Cairo University
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Ohi Tetsuo
Botanical Gardens Graduate School Of Sciences The University Of Tokyo
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Meselhy Meselhy
Institute Of Natural Medicine Faculty Of Pharmaceutical Sciences And Pharmaceutical University
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Kawahata T
Division Of Virology Department Of Infectious Diseases Osaka Prefectural Institute Of Public Health
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Hattori Masao
Institute Of Natural Medicine Faculty Of Pharmaceutical Sciences
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Hattori Masao
Metabolic Engineering Institute Of Natural Medicine University Of Toyama
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Nakamura Norio
Institute Of Natural Medicine Toyama And Pharmaceutical University
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Nakamura Norio
Institute Of Natural Medicine
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花岡 美代次
Institute Of Natural Medicine University Of Toyama
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