Chemistry:3-Chlorostyrylcaffeine

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3-Chlorostyrylcaffeine (CSC), or 8-(3-chlorostyryl)caffeine (8-CSC), is a potent and selective adenosine A2A receptor antagonist which is used in scientific research.[1][2]

It has 520-fold selectivity for the adenosine A2A receptor over the adenosine A1 receptor (Ki = 54 nM and 28,000 nM for the rat receptors, respectively).[1][2] Its affinities for the adenosine A2B and A3 receptors are similarly low (Ki = 8,200 nM and >10,000 nM, respectively).[3]

CSC has been found to reverse the catalepsy induced by the dopamine D1 receptor antagonist SCH-23390 and the dopamine D2 receptor antagonists raclopride and sulpiride in animals.[4][5][6]

The drug was one of the first selective adenosine A2A receptor antagonists to be developed.[1] However, in addition to its adenosine receptor antagonism, CSC was subsequently found to be a potent monoamine oxidase B (MAO-B) inhibitor (Ki = 80.6 nM for baboon MAO-B).[2][1][3][7][8] CSC was first described in the scientific literature by 1993.[9]

See also

References

  1. ↑ 1.0 1.1 1.2 1.3 "Recent Developments in Adenosine A2A Receptor Ligands". Adenosine Receptors in Health and Disease. Handbook of Experimental Pharmacology. 193. 2009. 59–98. doi:10.1007/978-3-540-89615-9_3. ISBN 978-3-540-89614-2. 
  2. ↑ 2.0 2.1 2.2 "Xanthines as Adenosine Receptor Antagonists". Methylxanthines. Handbook of Experimental Pharmacology. 200. 2011. 151–199. doi:10.1007/978-3-642-13443-2_6. ISBN 978-3-642-13442-5. 
  3. ↑ 3.0 3.1 "Recent developments in adenosine receptor ligands and their potential as novel drugs". Biochim Biophys Acta 1808 (5): 1290–1308. May 2011. doi:10.1016/j.bbamem.2010.12.017. PMID 21185259. 
  4. ↑ "A2A antagonists as novel non-dopaminergic therapy for motor dysfunction in PD". Neurology 61 (11 Suppl 6): S32–S38. December 2003. doi:10.1212/01.wnl.0000095209.59347.79. PMID 14663007. 
  5. ↑ "The adenosine A2A antagonist MSX-3 reverses the effort-related effects of dopamine blockade: differential interaction with D1 and D2 family antagonists". Psychopharmacology (Berl) 203 (3): 489–499. April 2009. doi:10.1007/s00213-008-1396-0. PMID 19048234. 
  6. ↑ "Catalepsy induced by a blockade of dopamine D1 or D2 receptors was reversed by a concomitant blockade of adenosine A(2A) receptors in the caudate-putamen of rats". Eur J Neurosci 14 (8): 1287–1293. October 2001. doi:10.1046/j.0953-816x.2001.01759.x. PMID 11703457. 
  7. ↑ "8-(3-Chlorostyryl)caffeine may attenuate MPTP neurotoxicity through dual actions of monoamine oxidase inhibition and A2A receptor antagonism". J Biol Chem 277 (39): 36040–36044. September 2002. doi:10.1074/jbc.M206830200. PMID 12130655. 
  8. ↑ "Dual inhibition of monoamine oxidase B and antagonism of the adenosine A(2A) receptor by (E,E)-8-(4-phenylbutadien-1-yl)caffeine analogues". Bioorg Med Chem 16 (18): 8676–8684. September 2008. doi:10.1016/j.bmc.2008.07.088. PMID 18723354. 
  9. ↑ "Structure-activity relationships of 8-styrylxanthines as A2-selective adenosine antagonists". J Med Chem 36 (10): 1333–1342. May 1993. doi:10.1021/jm00062a005. PMID 8496902. 



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