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Amino Acids

, Volume 24, Issue 3, pp 293–301 | Cite as

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

  • T. Shinada
  • Y. Nakagawa
  • K. Hayashi
  • G. Corzo
  • T. Nakajima
  • Y. Ohfune

Summary.

 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.

Keywords: Philanthotoxin Nephilatoxin-8 Polyamine toxins Paralytic activity -Glutamate receptors Squaric acid Squaryl amino acid 4-Hydroxycyclobuten-1-one 3-dioxocyclobutene N-Acyl squaryl amino acid Squaryl amino acid-containing polyamine toxins Insecticidal activity 

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Copyright information

© Springer-Verlag Wien 2002

Authors and Affiliations

  • T. Shinada
    • 1
  • Y. Nakagawa
    • 1
  • K. Hayashi
    • 1
  • G. Corzo
    • 2
  • T. Nakajima
    • 2
  • Y. Ohfune
    • 1
  1. 1. Graduate School of Science, Osaka City University, Sugimoto, Osaka, JapanJP
  2. 2. Suntory Institute for Bioorganic Research, Shimamoto-cho, Mishima-gun, Osaka, JapanJP

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