| Identification | Back Directory | [Name]
XESTOSPONGIN C | [CAS]
88903-69-9 | [Synonyms]
XEC
XESTOSPONGIN
ARGUSPONGINE E
XESTOSPONGIN C
(-)-Xestospongin C
PQYOPBRFUUEHRC-HCKQMYSWSA-N
Xestospongin C 4-((1H-Indol-7-yl)carbamoyl)phenyl diethylcarbamate
(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-b']dipyridine
5H,17H-1,23:11,13-Diethano-2H,14H-[1,11]dioxacycloeicosino[2,3-b:12,13-b']dipyridine, eicosahydro-, (1R,4aR,11R,12aS,13S,16aS,23R,24aS)-
[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-B']DIPYRIDINE | [Molecular Formula]
C28H50N2O2 | [MDL Number]
MFCD01862629 | [MOL File]
88903-69-9.mol | [Molecular Weight]
446.71 |
| Chemical Properties | Back Directory | [Melting point ]
146-147 °C(Solv: acetone (67-64-1)) | [Boiling point ]
564.7±35.0 °C(Predicted) | [density ]
1.05±0.1 g/cm3(Predicted) | [storage temp. ]
-20°C | [solubility ]
DMSO: soluble | [form ]
film | [pka]
7.73±0.20(Predicted) | [color ]
off-white | [Stability:]
Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month. |
| Hazard Information | Back Directory | [Description]
Xestospongin C (88903-69-9) is a potent and reversible inhibitor of IP3-mediated Ca2+?release, IC50?= 358 nM.1?Experiments with guinea-pig ileum permeabilized with alpha toxin revealed that Xestospongin C inhibits the IP3 receptor but not the ryanodine receptor in SR membranes. In intact smooth muscle cells it inhibits voltage-dependent Ca2+?and K+?currents at a concentration range similar to that at which it inhibits the IP3 receptor. Xestospongin C is a useful tool for probing the involvement of IP3 receptors in cellular signaling.3?Cell permeable. | [Uses]
Xestospongin C is a marine natural product which was first isolated from Pacific basin sponges, and noted to have vasodilatory properties. 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. Xestospongin C also inhibits the sarcoplasmic reticulum Ca2+ ATPase pump at concentrations of 700 nM. | [Uses]
Xestospongin C is a potent, membrane-permeable IP3 receptor blocker. | [Definition]
ChEBI: An organic heteropentacyclic compound that is isolated from the marine sponge Xestospongia exigua. | [General Description]
Synthetic form of the macrocyclic bis-1-oxaquinolizidine isolated from the Okanowan marine sponge. | [Biochem/physiol Actions]
Xestospongin C is a selective, reversible and membrane-permeable inhibitor of IP3 receptor. Reversibly blocks bradykinin- and carbamylcholine- Ca2+ efflux from the endoplasmic reticulum stores. | [storage]
Desiccate at -20°C,protect from light | [References]
1) Wilcox?et al. (1998),?New developments in the molecular pharmacology of the myo-inositol 1,4,5-trisphosphate receptor;? Trends Pharmacol. Sci.,?19?467
2) Ozaki?et al. (2002),?Inhibitory mechanism of xestospongin-C on contraction and ion channels in the intestinal smooth muscle;? Br. J. Pharmacol.,?137?1207
3) Kandasamy?et al. (2013),?Lipopolysaccharide induces endoplasmic store Ca2+-dependent inflammatory responses in lung microvessels;? PLoS One,?8?e63465 |
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