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Bicyclic analogues of D-myo-inositol 1,4,5-trisphosphate related to adenophostin A: Synthesis and biological activity


Reference:

Riley, A. M., Correa, V., Mahon, M. F., Taylor, C. W. and Potter, B. V. L., 2001. Bicyclic analogues of D-myo-inositol 1,4,5-trisphosphate related to adenophostin A: Synthesis and biological activity. Journal of Medicinal Chemistry, 44 (13), pp. 2108-2117.

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Abstract

The high affinity of adenophostin A for 1D-myo-inositol 1,4,5-trisphosphate [Ins(1,4,5)P-3] receptors may be related to an alteration in the position of its 2'-phosphate group relative to the corresponding 1-phosphate group in Ins(1,4,5)P-3. To investigate this possibility, two bicyclic trisphosphates 9 and 10, designed to explore the effect of relocating the l-phosphate group of Ins(1,4,5)P-3 using a novel fused-ring system, were synthesized from myo-inositol. Biological evaluation of 9 and 10 at the Ins(1,4,5)P-3 receptors of hepatocytes showed that both were recognized by hepatic Ins(1,4,5)P-3 receptors and both stimulated release of Ca2+ from intracellular stores, but they had lower affinity than Ins(1,4,5)P-3. This finding may be explained by considering the three-dimensional structures of 9 and 10 in light of recent studies on the conformation of adenophostin A.

Details

Item Type Articles
CreatorsRiley, A. M., Correa, V., Mahon, M. F., Taylor, C. W. and Potter, B. V. L.
DOI10.1021/jm0005499
DepartmentsFaculty of Science > Chemistry
RefereedYes
StatusPublished
ID Code5190
Additional InformationID number: ISI:000169367000008

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