Synthesis of Novel Fatty-Acyl Gratisin Derivatives

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概要

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• To find candidates with high antimicrobial and low hemolytic activities, many gratisin (GR) analogues have been designed and synthesized. In the present account, we synthesized novel derivatives of GR having both the polycationic and fatty acyl groups, cyclo{-Val1-Orn2-Leu3-D-Phe4-Pro5-D-Lys6(X)-Val7-Orn8-Leu9-D-Phe10-Pro11-D-Lys12-} {X=-CO(CH2)6CH3 (1), -Lys-CO(CH2)6CH3 (2), -(Lys)2-CO(CH2)6CH3 (3), and -(Lys)3-CO(CH2)6CH3 (4)}, and examined the biological activities. Among them, we found that 2–4 have differential ionic interaction against the prokaryotic membrane and eukaryotic membrane. In other words, the dissociation with high antimicrobial activity and low hemolytic activity is caused by the addition of D-Lys6-{(Lys)n-CO(CH2)6CH3} residues at position 6 of [D-Lys6,12]-GR. Our findings should be helpful in finding drug candidates with high antimicrobial activity and low hemolytic activity that are capable of combating microbial resistance.

• 公益社団法人　日本薬学会の論文

著者

• Shindo Mitsuno

  Department Of Food Science And Nutrition Osaka Shoin Women's University

• Uchida Yoshiki

  Department Of Applied Chemistry Faculty Of Engineering Osaka City University

• Harada Takuji

  Department Of Chemical Engineering Graduate School Of Engineering Tohoku University

• Tamaki Makoto

  Department Of Chemistry And Biomolecular Science Toho University

• Fujinuma Kenta

  Department Of Chemistry Toho University

• Takanashi Kazumasa

  Department Of Chemistry Toho University

• Kimura Masahiro

  Department Of Chemistry Graduate School Of Science Tokyo Metropolitan University

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