(-)-Xestospongin C

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Cat.No. 1280 - (-)-Xestospongin C | C28H50N2O2 | CAS No. 88903-69-9
Description: Reported inhibitor of IP3-dependent Ca2+ release
Alternative Names: XeC
Chemical Name: (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
Datasheet
Citations (14)
Reviews (1)

Biological Activity

Reported inhibitor of IP3-dependent Ca2+ release. Inhibits bradykinin-induced Ca2+ release in PC12 cells and attenuates PHP-induced IL-2 production in Jurkat T cells. Exhibits no effect on ryanodine receptor-mediated Ca2+ release in PC12 cells. Does not interact with the IP3 binding site. Recently shown to be an ineffective antagonist of IP3-evoked Ca2+ release in IP3 receptor expressing DT40 cells. Cell permeable.

Technical Data

M. Wt 446.71
Formula C28H50N2O2
Storage Desiccate at -20°C
CAS Number 88903-69-9
PubChem ID 9846431
InChI Key PQYOPBRFUUEHRC-HCKQMYSWSA-N
Smiles [H][C@]12[C@@H](CCCCCC[C@@H]3CCN(CCC[C@H]4CCCCCC5)[C@@]4([H])O3)CCCN1CC[C@@H]5O2

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

Tocris products are intended for laboratory research use only, unless stated otherwise.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 0.89 2
ethanol 0.89 2

Preparing Stock Solutions

The following data is based on the product molecular weight 446.71. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
0.02 mM 111.93 mL 559.65 mL 1119.29 mL
0.1 mM 22.39 mL 111.93 mL 223.86 mL
0.2 mM 11.19 mL 55.96 mL 111.93 mL
1 mM 2.24 mL 11.19 mL 22.39 mL

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Product Datasheets

Certificate of Analysis / Product Datasheet
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References

References are publications that support the biological activity of the product.

Gafni et al (1997) Xestospongins: potent membrane permeable blockers of the inositol 1,4,5-trisphosphate receptor. Neuron 19 723 PMID: 9331361

Ozaki et al (2002) Inhibitory mechanism of xestospongin-C on contraction and ion channels in the intestinal smooth muscle. Br.J.Pharmacol. 137 1207 PMID: 12466229

Dadsetan et al (2008) Store-operated Ca2+ influx causes Ca2+ release from the intracellular Ca2+ channels that is required for T cell activation. J.Biol.Chem. 283 12512 PMID: 18316371

Saleem et al (2014) Interactions of antagonists with subtypes of inositol 1,4,5-trisphosphate (IP3) receptor. Br.J.Pharmacol. 171 3298 PMID: 24628114


If you know of a relevant reference for (-)-Xestospongin C, please let us know.

Keywords: (-)-Xestospongin C, (-)-Xestospongin C supplier, inhibitors, inhibits, IP3-mediated, Ca2+, release, blocks, endoplasmic-reticulum, pump, calcium, channels, XeC, General, Calcium, Signaling, Agents, IP3, Receptors, 1280, Tocris Bioscience

14 Citations for (-)-Xestospongin C

Citations are publications that use Tocris products. Selected citations for (-)-Xestospongin C include:

Tabatadze et al (2015) Sex Differences in Molecular Signaling at Inhibitory Synapses in the Hippocampus. J Neurosci 35 11252 PMID: 26269634

Xu et al (2011) The human immunodeficiency virus coat protein gp120 promotes forward trafficking and surface clustering of NMDA receptors in membrane microdomains. Am J Physiol Renal Physiol 31 17074 PMID: 22114277

Nordman and Kabbani (2014) Microtubule dynamics at the growth cone are mediated by α7 nicotinic receptor activation of a Gαq and IP3 receptor pathway. J Neurosci 28 2995 PMID: 24687992

Azab et al (2015) Binding of αherpesvirus Glycoprotein H to Surface α4β1-Integrins Activates Calcium-Signaling Pathways and Induces Phosphatidylserine Exposure on the Plasma Membrane. Endocrinology 6 PMID: 26489864

Oh et al (2015) Heterosynaptic structural plasticity on local dendritic segments of hippocampal CA1 neurons. FASEB J 10 162 PMID: 25558061

Bellono et al (2014) UV light activates a Gαq/11-coupled phototransduction pathway in human melanocytes. J Gen Physiol 143 203 PMID: 24470488

Grafe et al (2014) The role of the hypothalamic paraventricular nucleus and the organum vasculosum lateral terminalis in the control of sodium appetite in male rats. J Neurosci 34 9249 PMID: 25009258

Hellmer et al (2018) A group I metabotropic glutamate receptor controls synaptic gain between rods and rod bipolar cells in the mouse retina. Physiol Rep 6 e13885 PMID: 30338673

Lim et al (2018) Neuronal Activity-Dependent Activation of Astroglial Calcineurin in Mouse Primary Hippocampal Cultures. Int J Mol Sci 19 PMID: 30274399

Chen et al (2018) A Type IIb, but Not Type IIa, GnRH Receptor Mediates GnRH-Induced Release of Growth Hormone in the Ricefield Eel. Front Endocrinol (Lausanne) 9 721 PMID: 30555419

Abedini et al (2016) WNT5a is required for normal ovarian follicle development and antagonizes g.tropin responsiveness in granulosa cells by suppressing canonical WNT signaling. FASEB J 30 1534 PMID: 26667040

Oh et al (2013) Synapse-specific and size-dependent mechanisms of spine structural plasticity accompanying synaptic weakening. Proc Natl Acad Sci U S A 110 E305 PMID: 23269840

Belal et al (2012) The homocysteine-inducible endoplasmic reticulum (ER) stress protein Herp counteracts mutant α-synuclein-induced ER stress via the homeostatic regulation of ER-resident calcium release channel proteins. Hum Mol Genet 21 963 PMID: 22045699

Glanowska and Moenter (2015) Differential regulation of GnRH secretion in the preoptic area (POA) and the median eminence (ME) in male mice. Cell Rep 156 231 PMID: 25314270


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Reviews for (-)-Xestospongin C

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Blocker of IP3 channels.
By Sergiy Sylantyev on 05/19/2019
Assay Type: In Vitro
Species: Rat
Cell Line/Tissue: Hippocampus

We used (-)-Xestospongin C (XeC) to block calcium release from endoplasmic reticulum via IP3 channels in presynaptic neurons. As a result, LPI, agonist of GPR55 receptor, failed to induce an increase of neurotransmitter release, since this process is calcium-dependent. As a sequence, after application of XeC there was no augmentation of the amplitude of evoked post-synaptic response in postsynaptic neuron: see image.

PMID: 23472002
review image