含角鲨烯氨基酸的多胺毒素的合成与麻痹活性

Synthesis and paralytic activities of squaryl amino acid-containing polyamine toxins.

作者信息

Shinada T, Nakagawa Y, Hayashi K, Corzo G, Nakajima T, Ohfune Y

机构信息

Graduate School of Science, Osaka City University, Sugimoto, Osaka 558-8585, Japan.

出版信息

Amino Acids. 2003 Apr;24(3):293-301. doi: 10.1007/s00726-002-0402-9.

DOI:10.1007/s00726-002-0402-9

PMID:12707812

Abstract

Eight analogs 4A-7A and 4B-7B of philanthotoxin (PhTX) from wasp venom and nephilatoxin-8 (NPTX-8) from spider venom whose tyrosine or asparagine linker is replaced by squaryl (sq) amino acid or 4-amino squaryl (4-asq) amino acid have been synthesized in an efficient manner via coupling of N-acyl squaryl amino acid intermediate 19 or 26 with the corresponding polyamine part. Preliminary bioassay using crickets revealed that the analogs substituted by glutamate-type squaryl amino acid-containing NPTX 7A and 7B showed more potent paralytic activities than that of NPTX-8.

摘要

已通过将N-酰基方基氨基酸中间体19或26与相应的多胺部分偶联，高效合成了黄蜂毒液中 philanthotoxin（PhTX）的八种类似物4A - 7A和4B - 7B以及蜘蛛毒液中nephilatoxin - 8（NPTX - 8）的类似物，其酪氨酸或天冬酰胺连接体被方基（sq）氨基酸或4 - 氨基方基（4 - asq）氨基酸取代。使用蟋蟀进行的初步生物测定表明，被含谷氨酸型方基氨基酸的NPTX 7A和7B取代的类似物显示出比NPTX - 8更强的麻痹活性。