Syntheses and Biological Activities of Joro Spider Toxin Analogs to Spidamine and Joramine

Autor:	Motomi Matsukawa, Nobufumi Kawai, Toshifumi Akizawa, Masanori Yoshioka, Yoshiaki Kono, Tadashige Chiba
Rok vydání:	1997
Předmět:	Nephila clavata biology medicine.drug_class Ecology Chemistry Toxin Neuromuscular transmission Carboxamide Venom General Chemistry General Medicine biology.organism_classification medicine.disease_cause Spider toxin Chemical synthesis Biochemistry Drug Discovery medicine Bioassay
Zdroj:	Chemical and Pharmaceutical Bulletin. 45:93-100
ISSN:	1347-5223 0009-2363
DOI:	10.1248/cpb.45.93
Popis:	In order to study the structure-activity relationships of spidamine and joramine found in the venom of Joro spider, Nephila clavata, we attempted to synthesize various analogs. Six analogs were convergently synthesized according to our previous method for the synthesis of spidamine, N-(3-aminopropyl-β-alanyl)-N'-(2, 4-dihydroxy-phenylacetyl-L-asparaginyl)-1, 5-pentanediamine and joramine, N-(3-aminopropyl-β-alanyl)-N'-(4-hydroxyphenyl-acetyl-L-asparaginyl)-1, 5-pentanediamine. The biological activities of the analogs and four intermediates were compared with those of synthetic spidamine and joramine in three bioassay systems, lobster neuromuscular synapse, cockroaches and mosquito larvae. The glutamate receptors in these systems were inhibited by some analogs, and the D-asparagine- or indoleacetyl-containing analogs were found to be strong inhibitors. These compounds have potential application as insecticides.
Databáze:	OpenAIRE
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