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(-)-Xestospongin C

(Synonyms: XeC, Araguspongine E) 目录号 : GC14484

A membrane-permeable antagonist of the inositol-1,4,5-triphosphate receptor

(-)-Xestospongin C Chemical Structure

Cas No.:88903-69-9

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Sample solution is provided at 25 µL, 10mM.

Description

Xestospongin C is a marine natural product which was first isolated from Pacific basin sponges, and noted to have vasodilatory properties.[1] Xestospongin C antagonizes the calcium-releasing action of inositol-1,4,5-trisphosphate (IP3) at the receptor level. Inositol phosphates are important signal transduction messengers acting via IP3 receptors to promote the mobilization of Ca2+ from intracellular stores. Xestospongin C blocks the increase in intracellular calcium in vascular smooth muscle cells completely at a concentration of 25 µM.[2] Xestospongin C also inhibits the sarcoplasmic reticulum Ca2+ ATPase pump at concentrations of 700 nM.[3]

Reference:
[1]. Nakagawa, M., and Endo, M. Structures of xestospongin A, B, C and D, novel vasodilative compounds from marine sponge, Xestospongia exigua. Tetrahedron Letters 25(30), 3227-3230 (1984).
[2]. Gafni, J., Munsch, J.A., Lam, T.H., et al. Xestospongins: Potent membrane permeable blockers of the inositol 1,4,5-triphosphate receptor. Neuron 19, 723-733 (1997).
[3]. Castonguay, A., and Robitaille, R. Xestospongin C is a potent inhibitor of SERCA at a vertabrate synapse. Cell Calcium 32(1), 39-47 (2002).

化学性质

Cas No. 88903-69-9 SDF
别名 XeC, Araguspongine E
化学名 [1R-(1R,4aR,11R,12aS,13S,16aS,23R,24aS)]-eicosahydro-5H,17H-1,23:11,13-diethano-2H,14H-[1,11]dioxacycloeicosino[2,3-b:12,13-b1]dipyridine
Canonical SMILES N12[C@@H]([C@@H](CCCCCC[C@@H]3O[C@@H]4N(CC3)CCC[C@@H]4CCCCCC5)CCC2)O[C@@H]5CC1
分子式 C28H50N2O2 分子量 446.71
溶解度 Chloroform: soluble; Ethyl Acetate: soluble; Methyl Acetate: soluble 储存条件 Desiccate at -20°C,protect from light
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1 mM 2.2386 mL 11.1929 mL 22.3859 mL
5 mM 0.4477 mL 2.2386 mL 4.4772 mL
10 mM 0.2239 mL 1.1193 mL 2.2386 mL
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