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

Journal article

In order to enable the study of the intracellular second messenger d-myo-inositol 1,4,5-trisphosphate (InsP3) and its receptors (InsP3Rs), it has been desirable to develop protected derivatives of InsP3 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 InsP3Rs. Two syntheses of d-myo-inositol 1,4,5-trisphosphate hexakis(butyryloxymethyl) ester (d-InsP3/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 InsP3Rs. Application of the l-enantiomer resulted in little Ca2+ release. © CSIRO 2006.

Authors: Conway, S; Thuring, J; Andreu, S; Kvinlaug, B; Roderick, H

• Publication status: Published
• Journal: AUSTRALIAN JOURNAL OF CHEMISTRY
• Volume: 59
• Issue: 12
• Pages: 887-893
• Publication date: 2006-01-01
• DOI: 10.1071/CH06357
• ISSN: 0004-9425
• Language: English