MRS 2500 tetraammonium salt

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Cat.No. 2159 - MRS 2500 tetraammonium salt | C13H18N5O8P2I.4NH3 | CAS No. 630103-23-0
Description: Extremely potent and selective P2Y1 antagonist
Chemical Name: (1R*,2S*)-4-[2-Iodo-6-(methylamino)-9H-purin-9-yl]-2-(phosphonooxy)bicyclo[3.1.0]hexane-1-methanol dihydrogen phosphate ester tetraammonium salt
Purity: ≥96% (HPLC)
Datasheet
Citations (15)
Literature

Biological Activity

Highly potent and selective antagonist of the platelet P2Y1 receptor (Ki = 0.78 nM). Inhibits ADP-induced aggregation of human platelets with an IC50 value of 0.95 nM. Inhibits the upregulation of NTPDase1 by ATPγS. Prevents thrombus formation in vivo.

Licensing Information

Sold under license from the NIH, US Patent 10/169975

Technical Data

M. Wt 629.29
Formula C13H18N5O8P2I.4NH3
Storage Store at -20°C
Purity ≥96% (HPLC)
CAS Number 630103-23-0
PubChem ID 90488745
InChI Key FVTFHHDVLNQSME-AVAGOIHISA-N
Smiles IC4=NC1=C(C(NC)=N4)N=CN1[C@H]2C[C@H](OP(O)(O)=O)[C@@]3(COP(O)(O)=O)[C@@H]2C3.N.N.N.N

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

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
water 56.12 100

Preparing Stock Solutions

The following data is based on the product molecular weight 629.29. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.59 mL 7.95 mL 15.89 mL
5 mM 0.32 mL 1.59 mL 3.18 mL
10 mM 0.16 mL 0.79 mL 1.59 mL
50 mM 0.03 mL 0.16 mL 0.32 mL

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Product Datasheets

Certificate of Analysis / Product Datasheet
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Safety Datasheet

References

References are publications that support the products' biological activity.

Kim et al (2003) 2-Substitution of adenine nucleotide analogues containing a bicyclo[3.1.0]hexane ring system locked in a northern conformation: enhanced potency as P2Y1 receptor antagonists. J.Med.Chem 46 4974 PMID: 14584948

Cattaneo et al (2004) Antiaggregatory activity in human platelets of potent antagonists of the P2Y1 receptor. Biochem.Pharmacol. 68 1995 PMID: 15476670

Hechler et al (2006) MRS2500 [2-iodo-N6-methyl-(N)-methanocarba-2'-deoxyadenosine-3', 5'-bisphosphate], a potent, selective, and stable antagonist of the platelet P2Y1 receptor with strong antithrombotic activity in mice. J.Pharmacol.Exp.Ther. 316 556 PMID: 16236815

Lu et al (2007) Stimulation of the P2Y1 receptor up-regulates nucleoside-triphosphate diphosphohydrolase-1 in human retinal pigment epithelial cells. J.Pharmacol.Exp.Ther. 323 157 PMID: 17626796


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Keywords: potent selective P2Y1 antagonists Receptors Purinergic purinoceptors MRS2500 prevents thrombus formation Purinergic P2Y Receptors

15 Citations for MRS 2500 tetraammonium salt

Citations are publications that use Tocris products. Selected citations for MRS 2500 tetraammonium salt include:

Baron et al (2015) The NLRP3 inflammasome is activated by nanoparticles through ATP, ADP and adenosine. Thromb J 6 e1629 PMID: 25654762

Erdélyi et al (2014) Analyzing receptor assemblies in the cell membrane using fluorescence anisotropy imaging with TIRF microscopy. PLoS One 9 e100526 PMID: 24945870

Kurahashi et al (2014) Platelet-derived growth factor receptor-α-positive cells and not smooth muscle cells mediate purinergic hyperpolarization in murine colonic muscles. Am J Physiol Cell Physiol 307 C561 PMID: 25055825

Ilatovskaya et al (2013) Pharmacological characterization of the P2 receptors profile in the podocytes of the freshly isolated rat glomeruli. Am J Physiol Cell Physiol 305 C1050 PMID: 24048730

Alefishat et al (2013) Antagonism of P2Y1-induced vasorelaxation by acyl CoA: a critical role for palmitate and 3'-phosphate. Br J Pharmacol 168 1911 PMID: 23215951

Fei et al (2013) Neurogenic mucosal bicarbonate secretion in guinea pig duodenum. Br J Pharmacol 168 880 PMID: 22994306

Helms et al (2013) Mechanisms of hemolysis-associated platelet activation. J Thromb Haemost 11 2148 PMID: 24119131

Gao et al (2013) The role of P2Y(14) and other P2Y receptors in degranulation of human LAD2 mast cells. J Pharmacol Exp Ther 9 31 PMID: 22825617

Duffy et al (2012) Changes in neuromuscular transmission in the W/W(v) mouse internal anal sphincter. Neurogastroenterol Motil 24 e41 PMID: 22074497

Hwang et al (2011) β-nicotinamide adenine dinucleotide is an enteric inhibitory neurotransmitter in human and nonhuman primate colons. Gastroenterology 140 608 PMID: 20875415

Gorman et al (2010) Adenine nucleotide control of coronary blood flow during exercise. Am J Physiol Heart Circ Physiol 299 H1981 PMID: 20852039

Ham et al (2010) Endogenous luminal surface adenosine signaling regulates duodenal bicarbonate secretion in rats. J Cell Biochem 335 607 PMID: 20805305

Konopatskaya et al (2009) PKCalpha regulates platelet granule secretion and thrombus formation in mice. J Clin Invest 119 399 PMID: 19147982

Högberg et al (2009) Mild hypothermia does not attenuate platelet aggregation and may even increase ADP-stimulated platelet aggregation after clopidogrel treatment. Purinergic Signal 7 2 PMID: 19236702

Ohtani et al (2008) Evidence for the possible involvement of the P2Y(6) receptor in Ca (2+) mobilization and insulin secretion in mouse pancreatic islets. Purinergic Signal 4 365 PMID: 18784987


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