The Synthesis of Membrane Permeant Derivatives of myo-Inositol 1,4,5-Trisphosphate

Stuart John Conway; J. W. Thuring; S. Andreu; B. T. Kvinlaug; H. L. Roderick; M. D. Bootman; A. B. Holmes

doi:10.1071/CH06357

The Synthesis of Membrane Permeant Derivatives of myo-Inositol 1,4,5-Trisphosphate

Stuart John Conway, J. W. Thuring, S. Andreu, B. T. Kvinlaug, H. L. Roderick, M. D. Bootman, A. B. Holmes

School of Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

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.

Original language	English
Pages (from-to)	887-893
Number of pages	7
Journal	Australian Journal of Chemistry
Volume	59
Issue number	12
DOIs	https://doi.org/10.1071/CH06357
Publication status	Published - Dec 2006

Keywords

CA2+ RELEASE
INOSITOL 1,4,5-TRISPHOSPHATE
CALCIUM-RELEASE
RECEPTORS
CELLS
SECRETION
PROTEINS
SIGNALS
ESTERS
STORE

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title = "The Synthesis of Membrane Permeant Derivatives of myo-Inositol 1,4,5-Trisphosphate",

abstract = "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.",

keywords = "CA2+ RELEASE, INOSITOL 1,4,5-TRISPHOSPHATE, CALCIUM-RELEASE, RECEPTORS, CELLS, SECRETION, PROTEINS, SIGNALS, ESTERS, STORE",

author = "Conway, {Stuart John} and Thuring, {J. W.} and S. Andreu and Kvinlaug, {B. T.} and Roderick, {H. L.} and Bootman, {M. D.} and Holmes, {A. B.}",

year = "2006",

month = dec,

doi = "10.1071/CH06357",

language = "English",

volume = "59",

pages = "887--893",

journal = "Australian Journal of Chemistry",

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AU - Conway, Stuart John

AU - Thuring, J. W.

AU - Andreu, S.

AU - Kvinlaug, B. T.

AU - Roderick, H. L.

AU - Bootman, M. D.

AU - Holmes, A. B.

PY - 2006/12

Y1 - 2006/12

N2 - 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.

AB - 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.

KW - CA2+ RELEASE

KW - INOSITOL 1,4,5-TRISPHOSPHATE

KW - CALCIUM-RELEASE

KW - RECEPTORS

KW - CELLS

KW - SECRETION

KW - PROTEINS

KW - SIGNALS

KW - ESTERS

KW - STORE

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M3 - Article

SN - 0004-9425

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JO - Australian Journal of Chemistry

JF - Australian Journal of Chemistry

IS - 12

ER -

The Synthesis of Membrane Permeant Derivatives of myo-Inositol 1,4,5-Trisphosphate

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