Synthesis and biological properties of 2-substituted myo-inositol 1,4,5-trisphosphate analogues directed toward affinity chromatography and photoaffinity labeling

Shoichiro Ozaki, Yutaka Watanabe, Tomio Ogasawara, Masato Hirata, Takashi Kanematsu

Research output: Contribution to journalArticlepeer-review

17 Citations (Scopus)

Abstract

A series of myo-inositol 1,4,5-trisphosphate analogues with the 2-acyl substituents p-aminobenzoyl (7), p-azidobenzoyl (8), 4-{5-[2-(benzamido)ethyl]-2-hydroxyphenylazo}benzoyl (9), and cis,trans-4-aminocyclohexylcarbonyl (10) were synthesised and examined for their effects on the 5-phosphatase, the 3-kinase, the tritiated trisphosphate-binding activity, and the Ca2+-releasing activity. Each analogue inhibited the hydrolysis of d-[5-32P]Ins(1,4,5)P3 and the phosphorylation of d-[3H]Ins(1,4,5)P3, catalysed by erythrocyte ghosts and brain cytosol, respectively. The analogues acted as full agonists in releasing Ca2+ from permeabilised cells and also inhibited the binding of d-[3H]Ins(1,4,5)P3 to cerebellum microsomes. The analogues 7 and 10 were utilised for immobilisation of the trisphosphate on SepharoseTM and the subsequent affinity chromatography effected purification of the above proteins. A photoaffinity probe, the appendage of which acted as the photoaffinity probe as well as a non-radioactive molecular marker, was also derived from the analogue 7.

Original languageEnglish
Pages (from-to)189-206
Number of pages18
JournalCarbohydrate Research
Volume234
Issue numberC
DOIs
Publication statusPublished - Oct 9 1992

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Synthesis and biological properties of 2-substituted myo-inositol 1,4,5-trisphosphate analogues directed toward affinity chromatography and photoaffinity labeling'. Together they form a unique fingerprint.

Cite this