Synthesis and paralytic activities of squaryl amino acid-containing polyamine toxins.
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.
Shinada
T
T
Graduate School of Science, Osaka City University, Sugimoto, Osaka 558-8585, Japan.
Nakagawa
Y
Y
Hayashi
K
K
Corzo
G
G
Nakajima
T
T
Ohfune
Y
Y
D000596:Amino Acids / Q000737:chemistry*; D000818:Animals; D006135:Gryllidae / Q000187:drug effects; D008956:Models, Chemical; D015394:Molecular Structure; D010243:Paralysis / Q000139:chemically induced*; D010636:Phenols / Q000138:chemical synthesis / Q000737:chemistry / Q000633:toxicity; D011073:Polyamines / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity*; D013111:Spider Venoms / Q000737:chemistry; D014862:Wasp Venoms / Q000737:chemistry
D000596:Amino Acids; D010636:Phenols; D011073:Polyamines; D013111:Spider Venoms; D014862:Wasp Venoms; C074003:philanthotoxin 343