Development of inositol-based antagonists for the D-myo-inositol 1,4,5-trisphosphate receptor

Neil S. Keddie; Yulin Ye; Tashfeen Aslam; Tomas Luyten; Davide Bello; Clive Garnham; Geert Bultynck; Antony Galione; Stuart J. Conway

doi:10.1039/c0cc03003a

Development of inositol-based antagonists for the D-myo-inositol 1,4,5-trisphosphate receptor

Neil S. Keddie, Yulin Ye, Tashfeen Aslam, Tomas Luyten, Davide Bello, Clive Garnham, Geert Bultynck, Antony Galione, Stuart J. Conway

School of Chemistry

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

Abstract

The syntheses of four D-myo-inositol 1,4,5-trisphosphate (InsP(3)) derivatives, incorporating phosphate bioisosteres at the 5-position, are reported. The methyl phosphate ester and sulfate derivatives retain InsP(3) receptor (InsP(3)R) agonist activity; the compounds that possess a methylphosphonate or a carboxymethyl moiety are InsP(3)R antagonists.

Original language	English
Pages (from-to)	242-244
Number of pages	3
Journal	Chemical Communications
Volume	47
Issue number	1
DOIs	https://doi.org/10.1039/c0cc03003a
Publication status	Published - 2011

Keywords

2-AMINOETHOXYDIPHENYL BORATE 2-APB
CALCIUM-RELEASE
MYOINOSITOL 1,4,5-TRISPHOSPHATE
5-PHOSPHONATE ANALOGS
PARTIAL AGONISTS
CA2+ RELEASE
DERIVATIVES
PATHWAY
BINDING
NAADP

Access to Document

10.1039/c0cc03003a

BB/C515255/1: A Reverse chemical genetics and chemical biology approach to probing 1,4,5-trisphosphate receptor function
Conway, S. J. (PI)
BBSRC
1/02/05 → 31/08/08
Project: Standard

Cite this

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title = "Development of inositol-based antagonists for the D-myo-inositol 1,4,5-trisphosphate receptor",

abstract = "The syntheses of four D-myo-inositol 1,4,5-trisphosphate (InsP(3)) derivatives, incorporating phosphate bioisosteres at the 5-position, are reported. The methyl phosphate ester and sulfate derivatives retain InsP(3) receptor (InsP(3)R) agonist activity; the compounds that possess a methylphosphonate or a carboxymethyl moiety are InsP(3)R antagonists.",

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author = "Keddie, {Neil S.} and Yulin Ye and Tashfeen Aslam and Tomas Luyten and Davide Bello and Clive Garnham and Geert Bultynck and Antony Galione and Conway, {Stuart J.}",

year = "2011",

doi = "10.1039/c0cc03003a",

language = "English",

volume = "47",

pages = "242--244",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "1",

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TY - JOUR

T1 - Development of inositol-based antagonists for the D-myo-inositol 1,4,5-trisphosphate receptor

AU - Keddie, Neil S.

AU - Ye, Yulin

AU - Aslam, Tashfeen

AU - Luyten, Tomas

AU - Bello, Davide

AU - Garnham, Clive

AU - Bultynck, Geert

AU - Galione, Antony

AU - Conway, Stuart J.

PY - 2011

Y1 - 2011

N2 - The syntheses of four D-myo-inositol 1,4,5-trisphosphate (InsP(3)) derivatives, incorporating phosphate bioisosteres at the 5-position, are reported. The methyl phosphate ester and sulfate derivatives retain InsP(3) receptor (InsP(3)R) agonist activity; the compounds that possess a methylphosphonate or a carboxymethyl moiety are InsP(3)R antagonists.

AB - The syntheses of four D-myo-inositol 1,4,5-trisphosphate (InsP(3)) derivatives, incorporating phosphate bioisosteres at the 5-position, are reported. The methyl phosphate ester and sulfate derivatives retain InsP(3) receptor (InsP(3)R) agonist activity; the compounds that possess a methylphosphonate or a carboxymethyl moiety are InsP(3)R antagonists.

KW - 2-AMINOETHOXYDIPHENYL BORATE 2-APB

KW - CALCIUM-RELEASE

KW - MYOINOSITOL 1,4,5-TRISPHOSPHATE

KW - 5-PHOSPHONATE ANALOGS

KW - PARTIAL AGONISTS

KW - CA2+ RELEASE

KW - DERIVATIVES

KW - PATHWAY

KW - BINDING

KW - NAADP

U2 - 10.1039/c0cc03003a

DO - 10.1039/c0cc03003a

M3 - Article

SN - 1359-7345

VL - 47

SP - 242

EP - 244

JO - Chemical Communications

JF - Chemical Communications

IS - 1

ER -

Development of inositol-based antagonists for the D-myo-inositol 1,4,5-trisphosphate receptor

Abstract

Keywords

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Projects

BB/C515255/1: A Reverse chemical genetics and chemical biology approach to probing 1,4,5-trisphosphate receptor function

Cite this