8-(3-Chlorostyryl)caffeineA selective Adenosine A2A-R and MAO-B inhibitor

8-(3-Chlorostyryl)caffeine (CAS 147700-11-6)

8-(3-Chlorostyryl)caffeine | CAS 147700-11-6 is rated 5.0 out of 5 by 1.
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Synonym: CSC
Application: A selective Adenosine A2A-R and MAO-B inhibitor
CAS Number: 147700-11-6
Purity: >99%
Molecular Weight: 330.77
Molecular Formula: C16H15CIN4O2
* Refer to Certificate of Analysis for lot specific data (including water content).
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8-(3-Chlorostyryl)caffeine is a selective Adenosine A2A-R antagonist and monoamine oxidase B (MAO-B) inhibitor (Ki values are 54 and 28200 at Adenosine A2A-R and Adenosine A1-R, respectively and Ki ~ 100 nM at MAO-B). 8-(3-Chlorostyryl)caffeine potently protects against quinolinic acid-induced neuronal damage and is neuroprotective in the MPTP model of Parkinson's disease.

Physical State :
Solid
Solubility :
Soluble in DMSO (25 mM).
Storage :
Store at -20° C
Melting Point :
209-211° C
Boiling Point :
~559.4° C at 760 mmHg (Predicted)
Density :
~1.4 g/cm3 (Predicted)
Refractive Index :
n20D 1.66 (Predicted)
IC50 :
Ah Receptor: EC5050 = 3.34 µM; Plasmodium falciparum : IC50 = 10 µM; PXR: EC5050 ≥115.94 µM
Ki Data :
Adenosine A2a receptor: Ki= 9.08 nM (rat); Adenosine A2A-R: Ki= 36 nM (human); Adenosine A2 receptor: Ki= 54 nM (rat); MAO-B: Ki= 70 nM (human); SINGLE PROTEIN: Ki= 100 nM (mouse)
pK Values :
pKb: 0.12 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
PubChem CID :
5353365
MDL Number :
MFCD00934671
SMILES :
CN1C(=NC2=C1C(=O)N(C(=O)N2C)C)/C=C/C3=CC(=CC=C3)Cl

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Certificate of Analysis

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8-(3-Chlorostyryl)caffeine  Product Citations

See how others have used 8-(3-Chlorostyryl)caffeine. Click on the entry to view the PubMed entry .

Citations 1 to 7 of 7 total

PMID: # 19463706  Kalda, A. et al. 2009. Behav. Brain Res. 202: 232-237.

PMID: # 19234224  Rajakariar, R. et al. 2009. J. Immunol. 182: 3262-3269.

PMID: # 18368531  Klaasse, EC. et al. 2008. Purinergic Signal. 4: 21-37.

PMID: # 15452191  Gan, XT. et al. 2005. J. Pharmacol. Exp. Ther. 312: 27-34.

PMID: # 15235914  Guerra, L. et al. 2004. Pflugers Arch. 449: 66-75.

PMID: # 14720203  Fink, JS. et al. 2004. J. Neurochem. 88: 538-544.

PMID: # 8702522  Liang, BT. et al. 1996. J. Biol. Chem. 271: 18678-18685.

Citations 1 to 7 of 7 total
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Rated 5 out of 5 by from Rajakariar Rajakariar, R. et al. (PubMed 19234224) used 8-(3-Chlorostyryl)caffeine, a selective A2A receptor antagonist, to show that adenosine signaling through its A2A receptor (causing an elevation in cAMP) is anti-inflammatory and does not impair pro-resolution pathways. Introduction of 8-(3-Chlorostyryl)caffeine significantly reduced A2A receptor activation and led to an increased and prolonged inflammatory response. -SCBT Publication Review
Date published: 2015-04-28
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