Synthesis of lD-3-deoxy-, lD-2,3-dideoxy-, and lD-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

Research output: Contribution to journalArticle

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(l,4,5)P3, using the calcium mobilizing receptor of saponin permeabilized SH-SYSY human neuroblastoma cells. 1 D-3-deoxy-Ins( 1,4,5)P3 (26) and 1 D-2,3-dideoxy-Ins( 1,4,5)P3 (22) exhibited very potent ligand and agonist properties, while 1 D-2,3,6-trideoxy-Ins( 1,4,S)P3 (19) was much less potent. These data provide solid evidence of the critical role which HO-6 of Ins(l,4,S)P3 plays in its binding affinity and its Ca2+ mobilizing activity.

Original languageEnglish (US)
Pages (from-to)4429-4434
Number of pages6
JournalJournal of the American Chemical Society
Volume115
Issue number11
StatePublished - 1993
Externally publishedYes

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Inositol 1,4,5-Trisphosphate
Calcium
Ligands
Calcium-Sensing Receptors
Adrenal Cortex
Saponins
Neuroblastoma
Membranes
quebrachitol

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Synthesis of lD-3-deoxy-, lD-2,3-dideoxy-, and lD-2,3,6-trideoxy-myo-inositol 1,4,5-trisphosphate from quebrachitol, their binding affinities, and calcium release activity. / Kozikowski, A. P.; Ognyanov, V. I.; Fauq, A. H.; Nahorski, S. R.; Wilcox, R. A.

In: Journal of the American Chemical Society, Vol. 115, No. 11, 1993, p. 4429-4434.

Research output: Contribution to journalArticle

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