The synthesis of membrane permeant derivatives of myo-inositol 1,4,5-trisphosphate

被引：14

作者：

Conway, Stuart J.

Thuring, Jan W.

Andreu, Sylvain

Kvinlaug, Brynn T.

Roderick, H. Llewelyn

Bootman, Martin D.

Holmes, Andrew B.

机构：

[1] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England

[2] Univ St Andrews, Sch Chem, St Andrews KY16 9ST, Fife, Scotland

[3] Univ St Andrews, Ctr Biomol Sci, St Andrews KY16 9ST, Fife, Scotland

[4] Babraham Inst, Mol Signalling Lab, Cambridge CB2 4AT, England

[5] Univ Cambridge, Dept Pharmacol, Cambridge CB2 1PD, England

[6] Univ Melbourne, Sch Chem, Inst Bio21, Melbourne, Vic 3010, Australia

[7] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England

来源：

AUSTRALIAN JOURNAL OF CHEMISTRY | 2006年 / 59卷 / 12期

基金：

澳大利亚研究理事会; 英国工程与自然科学研究理事会; 英国生物技术与生命科学研究理事会;

关键词：

D O I：

10.1071/CH06357

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：887 / 893

页数：7

共 39 条

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