The Synthesis of Membrane Permeant Derivatives of myo-Inositol 1,4,5-Trisphosphate

Stuart John Conway, J. W. Thuring, S. Andreu, B. T. Kvinlaug, H. L. Roderick, M. D. Bootman, A. B. Holmes

Research output: Contribution to journalArticlepeer-review

14 Citations (Scopus)

Abstract

In order to enable the study of the intracellular second messenger D-myo-inositol 1,4,5-trisphosphate (InsP(3)) and its receptors (InsP(3)Rs), it has been desirable to develop protected derivatives of InsP(3) that are able to enter the cell, upon extracellular application. The subsequent removal of the lipophilic protecting groups, by intracellular enzymes, releases InsP3 and leads to the activation of InsP(3)Rs. Two syntheses of D-myo-inositol 1,4,5-trisphosphate hexakis(butyryloxymethyl) ester (D-InsP(3)/BM) and one of L-InsP(3)/BM are reported. It is demonstrated that extracellular application of the D-enantiomer results in Ca2+ release, which is thought to occur via InsP(3)Rs. Application of the L-enantiomer resulted in little Ca2+ release.

Original languageEnglish
Pages (from-to)887-893
Number of pages7
JournalAustralian Journal of Chemistry
Volume59
Issue number12
DOIs
Publication statusPublished - Dec 2006

Keywords

  • CA2+ RELEASE
  • INOSITOL 1,4,5-TRISPHOSPHATE
  • CALCIUM-RELEASE
  • RECEPTORS
  • CELLS
  • SECRETION
  • PROTEINS
  • SIGNALS
  • ESTERS
  • STORE

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