Simplification of adenophostin A defines a minimal structure for potent glucopyranoside-based mimics of D-myo-inositol 1,4,5-trisphosphate.
The synthesis of 1-O-[(3S,4R)-3-hydroxytetrahydrofuran-4-yl]-alpha-D-glucopyranosid e 3,4,3'-trisphosphate (7), a novel Ca2+ mobilising agonist at the Ins(1,4,5)P3 receptor, designed by excision of two motifs of adenophostin A is reported, defining a potential minimal structure for potent glucopyranoside-based agonists of Ins(1,4,5)P3 receptors.
Marwood
R D
RD
Department of Pharmacy and Pharmacology, University of Bath, UK.
Riley
A M
AM
Correa
V
V
Taylor
C W
CW
Potter
B V
BV
D000241:Adenosine / Q000031:analogs & derivatives* / Q000737:chemistry; D000818:Animals; D002118:Calcium / Q000378:metabolism; D002236:Carbohydrate Conformation; D002478:Cells, Cultured; D005663:Furans / Q000737:chemistry* / Q000494:pharmacology; D005958:Glucosephosphates / Q000737:chemistry* / Q000494:pharmacology; D006027:Glycosides / Q000737:chemistry*; D015544:Inositol 1,4,5-Trisphosphate / Q000737:chemistry*; D008099:Liver / Q000166:cytology / Q000187:drug effects / Q000378:metabolism; D018716:Molecular Mimicry; D051381:Rats
C118932:1-O-(3-hydroxytetrahydrofuran-4-yl)glucopyranoside 3,4,3'-trisphosphate; D005663:Furans; D005958:Glucosephosphates; D006027:Glycosides; C085029:adenophostin A; D015544:Inositol 1,4,5-Trisphosphate; D000241:Adenosine; D002118:Calcium