Preparation and biological properties of biotinylated PhTX derivatives

Masaru Hashimoto, Ying Liu, Kan Fang, Hong Yu Li, Giuseppe Campiani, Koji Nakanishi

Research output: Contribution to journalArticle

12 Scopus citations

Abstract

We report the synthesis of several highly functionalized biotinylated philanthotoxin (PhTX) analogues (7, 8, 10, 13-16) designed on the basis of earlier structure-activity relationship studies. Despite the extensive modifications, the binding to nicotinic acetylcholine receptor (nAChR) is in the low micromolar range according to an inhibition assay using 3H-thienylcyclohexyl-piperidine (TCP). A patch clamp functional assay gave comparable results. Compounds exemplified by 16, which consists of a biotinylated ligand linked to a bifunctional photoaffinity probe (BPP), represent a new type of probe which should find use in photo-cross-linking studies of ligand-receptor interactions. Copyright (C) 1999 Elsevier Science Ltd.

Original languageEnglish (US)
Pages (from-to)1181-1194
Number of pages14
JournalBioorganic and Medicinal Chemistry
Volume7
Issue number6
DOIs
StatePublished - Jun 1 1999

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Keywords

  • Biotin-labeling
  • Philanthotoxin
  • Photoaffinity
  • nAChR

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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