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XESTOSPONGIN C

CAS No.
88903-69-9
Chemical Name:
XESTOSPONGIN C
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
CBNumber:
CB0479020
Molecular Formula:
C28H50N2O2
Molecular Weight:
446.71
MDL Number:
MFCD01862629
MOL File:
88903-69-9.mol
Last updated:2023-07-14 17:33:25

XESTOSPONGIN C Properties

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.

SAFETY

Risk and Safety Statements

WGK Germany  3

XESTOSPONGIN C price More Price(13)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich X2628 Xestospongin C film 88903-69-9 10μg $463 2024-03-01 Buy
Sigma-Aldrich X2628 Xestospongin C film 88903-69-9 50μg $1670 2024-03-01 Buy
Cayman Chemical 64950 Xestospongin C ≥90% 88903-69-9 10μg $86 2024-03-01 Buy
Cayman Chemical 64950 Xestospongin C ≥90% 88903-69-9 50μg $353 2024-03-01 Buy
Cayman Chemical 64950 Xestospongin C ≥90% 88903-69-9 100μg $629 2024-03-01 Buy
Product number Packaging Price Buy
X2628 10μg $463 Buy
X2628 50μg $1670 Buy
64950 10μg $86 Buy
64950 50μg $353 Buy
64950 100μg $629 Buy

XESTOSPONGIN C Chemical Properties,Uses,Production

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 potent, membrane-permeable IP3 receptor blocker.

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.

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

Store at -20°C

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

XESTOSPONGIN C Preparation Products And Raw materials

Raw materials

Preparation Products

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ARGUSPONGINE E [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 XESTOSPONGIN C XEC XESTOSPONGIN (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 PQYOPBRFUUEHRC-HCKQMYSWSA-N 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)- (-)-Xestospongin C Xestospongin C 4-((1H-Indol-7-yl)carbamoyl)phenyl diethylcarbamate 88903-69-9 C28H50N2O2 Cell Signaling and Neuroscience Cell Biology BioChemical Intracellular Calcium Signaling Intracellular Calcium Regulators