Xestospongin C

Names

[ Name ]:
Xestospongin C

[Synonym ]:
(1R,8S,10R,15S,22S,29R)-9,30-Dioxa-11,25-diazapentacyclo[20.6.2.2.0.0]dotriacontane
araguspongine E
XESTOSPONGIN
Xestospongine C
XEC
(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[10,9-b:20,19-b']dipyridine, eicosahydro-, (4aR,11S,12aR,16aS,23S,24aR)-
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

Biological Activity

[Description]:

Xestospongin C ((-)-Xestospongin C) is a selective, reversible inositol 1,4,5-trisphosphate receptor (IP3R) inhibitor. Xestospongin C acts as an inhibitor of the sarcoplasmic/endoplasmic reticulum Ca2+ ATPase (SERCA) pump of internal stores. Xestospongin C blocks IP3-induced Ca2+ release from cerebellar microsomes with an IC50 of 358 nM. Xestospongin C is a valuable tool for investigating the structure and function of IP3Rs and Ca2+ signaling in neuronal and nonneuronal cells[1][2][3].

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> Calcium Channel

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Neurological Disease

[Target]

IP3R

[In Vitro]

Xestospongin C (XeC; 10 μM; 1 h before Aβ) pretreatment before Aβ1-42 (20 μM; 24 hours) application displays a significant decrease in the early apoptotic rate (9.87%) compared to the Aβ alone treated group (18.38%)[1]. Xestospongin C (10 μM; 1 h before Aβ) and Aβ1-42 (20 μM; 100 s) has significant main effects on the peak value and average values of Ca2+ changes, as well as a significant interaction in primary cultured hippocampal neurons[1].

[In Vivo]

Xestospongin C (3 μM; intracerebroventrical injection by a pump for four weeks) ameliorates the disinhibition-like behavior and long term spatial memory deficits of 8-month-old male APP/PS1 mice of Alzheimer's disease[1].

[References]

[1]. Wang ZJ, et al. Xestospongin C, a Reversible IP3 Receptor Antagonist, Alleviates the Cognitive and Pathological Impairments in APP/PS1 Mice of Alzheimer's Disease. J Alzheimers Dis. 2019;72(4):1217-1231.

[2]. Gafni J, Munsch JA, Lam TH, Catlin MC, Costa LG, Molinski TF, Pessah IN. Xestospongins: potent membrane permeable blockers of the inositol 1,4,5-trisphosphate receptor. Neuron. 1997 Sep;19(3):723-33. doi: 10.1016/s0896-6273(00)80384-0. PMID: 9331361.

[3]. Castonguay A, et al. Xestospongin C is a potent inhibitor of SERCA at a vertebrate synapse. Cell Calcium. 2002;32(1):39-47.

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
564.7±35.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₈H₅₀N₂O₂

[ Molecular Weight ]:
446.709

[ Flash Point ]:
145.6±23.2 °C

[ Exact Mass ]:
446.387238

[ PSA ]:
24.94000

[ LogP ]:
9.02

[ Vapour Pressure ]:
0.0±1.5 mmHg at 25°C

[ Index of Refraction ]:
1.542

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ RIDADR ]:
NONH for all modes of transport

Articles

mGluR5 in the nucleus accumbens shell regulates morphine-associated contextual memory through reactive oxygen species signaling.

Addict. Biol. 20 , 927-40, (2015)

Emerging evidence indicates that metabotropic glutamate receptor 5 (mGluR5) critically modulates drug and drug-related behaviors. However, the role of mGluR5 in the opiate-induced contextual memory re...

Aβ and NMDAR activation cause mitochondrial dysfunction involving ER calcium release.

Neurobiol. Aging 36(2) , 680-92, (2015)

Early cognitive deficits in Alzheimer's disease (AD) seem to be correlated to dysregulation of glutamate receptors evoked by amyloid-beta (Aβ) peptide. Aβ interference with the activity of N-methyl-d-...

Intracellular Ca(2+) release from endoplasmic reticulum regulates slow wave currents and pacemaker activity of interstitial cells of Cajal.

Am. J. Physiol. Cell Physiol. 308 , C608-20, (2015)

Interstitial cells of Cajal (ICC) provide pacemaker activity in gastrointestinal muscles that underlies segmental and peristaltic contractions. ICC generate electrical slow waves that are due to large...