Synthesis of 1D-3-deoxy-, 1D-2,3-dideoxy-, and 1D-2,3,6-trideoxy-myo-inositol 1,4,5-trisphosphate from quebrachitol, their binding affinities, and calcium release activity

A. P. Kozikowski, V. I. Ognyanov, A. H. Fauq, S. R. Nahorski, R. A. Wilcox

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75 Citations (Scopus)

Abstract

Syntheses of three optically pure, deoxygenated myo-inositol 1,4,5-trisphosphate analogues from quebrachitol are reported together with their binding affinities and 45Ca2+ release activity. The ligand-binding affinities of the analogues were determined using membrane preparations from bovine adrenal cortex. The 45Ca2+ release activities were compared to that of Ins(1,4,5)P3, using the calcium mobilizing receptor of saponin permeabilized SH-SY5Y human neuroblastoma cells. 1d-3-deoxy-Ins(1,4,5)P3 (26) and 1d-2,3-dideoxy-Ins(1,4,5)P3 (22) exhibited very potent ligand and agonist properties, while 1d-2,3,6-trideoxy-Ins(1,4,5)P3 (19) was much less potent. These data provide solid evidence of the critical role which HO-6 of Ins(1,4,5)P3 plays in its binding affinity and its Ca2+ mobilizing activity.

Original languageEnglish
Pages (from-to)4429-4434
Number of pages6
JournalJournal of The American Chemical Society
Volume115
Issue number11
DOIs
Publication statusPublished - Jun 1993
Externally publishedYes

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