8-(3-Chlorostyryl)caffeine

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Cat.No. 3306 - 8-(3-Chlorostyryl)caffeine | C16H15ClN4O2 | CAS No. 147700-11-6
Description: Selective A2A antagonist. Also MAO-B inhibitor
Alternative Names: CSC
Chemical Name: (E)-8-[2-(3-Chlorophenyl)ethenyl]-3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
Purity: ≥99% (HPLC)
Datasheet
Citations (3)
Reviews
Literature

Biological Activity

Selective adenosine A2A receptor antagonist and monoamine oxidase B (MAO-B) inhibitor (Ki values are 54 and 28200 nM at rat A2A and A1 receptors respectively and Ki ~ 100 nM at MAO-B). Potently protects against quinolinic acid-induced (Cat. No. 0225) neuronal damage and is neuroprotective in the MPTP model of Parkinson's disease.

Technical Data

M. Wt 330.77
Formula C16H15ClN4O2
Storage Store at -20°C
Purity ≥99% (HPLC)
CAS Number 147700-11-6
PubChem ID 5353365
InChI Key WBWFIUAVMCNYPG-BQYQJAHWSA-N
Smiles ClC1=CC(/C=C/C(N3C)=NC2=C3C(N(C)C(N2C)=O)=O)=CC=C1

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
DMSO 8.27 25

Preparing Stock Solutions

The following data is based on the product molecular weight 330.77. 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.

Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 3.02 mL 15.12 mL 30.23 mL
5 mM 0.6 mL 3.02 mL 6.05 mL
10 mM 0.3 mL 1.51 mL 3.02 mL
50 mM 0.06 mL 0.3 mL 0.6 mL

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Product Datasheets

Safety Datasheet

References

References are publications that support the products' biological activity.

Chen et al (2002) 8-(3-Chlorostyryl)caffeine may attenuate MPTP neurotoxicity through dual actions on monoamine oxidase inhibition and A2A receptor antagonism. J.Biol.Chem. 277 36040 PMID: 12130655

Behan and Stone (2002) Enhanced neuronal damage by co-administration of quinolinic acid and free radicals, and protection by adenosine A2A receptor antagonists. Br.J.Pharmacol. 135 1435 PMID: 11906956

Vlok et al (2006) Inhibition of monoamine oxidase B by analogues of the adenosine A2A receptor antagonist (E)-8-(3-chlorostyryl)caffeine (CSC). Bioorg.Med.Chem. 14 3512 PMID: 16442801


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View all Adenosine A2A Receptor Antagonists

Keywords: 8-(3-Chlorostyryl)caffeine, supplier, Selective, A2A, antagonists, MAO-B, inhibitors, inhibits, Receptors, adenosines, Monoamine, Oxygenases, Oxidases, CSC, Adenosine, A2A, Receptors, Monoamine, Oxidase, 5-HT-Related, Adrenergic, Related, Compounds, Dopaminergic-Related, 5-HT3, Receptors, Adenosine, A2A, Receptors, Tocris Bioscience

3 Citations for 8-(3-Chlorostyryl)caffeine

Citations are publications that use Tocris products. Selected citations for 8-(3-Chlorostyryl)caffeine include:

Benada et al (2015) Polo-like kinase 1 inhibits DNA damage response during mitosis. Oncotarget 14 219 PMID: 25607646

Factor et al (2007) Adenosine regulation of alveolar fluid clearance. Cell Cycle 104 4083 PMID: 17360481

Li et al (2014) Regulation of photoreceptor gap junction phosphorylation by adenosine in zebrafish retina. Vis Neurosci 31 237 PMID: 24844306


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