3-Chlorostyrylcaffeine
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| Other names | CSC; 8-CSC; 8-(3-Chlorostyryl)caffeine; 8-(3-Chlorostyryl)-1,3,7-trimethylxanthine |
| Drug class | Adenosine A2A receptor antagonist |
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| Chemical and physical data | |
| Formula | C16H15ClN4O2 |
| Molar mass | 330.77 g·mol−1 |
| 3D model (JSmol) | |
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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
[edit]References
[edit]- ^ a b c d Cristalli G, Müller CE, Volpini R (2009). "Recent developments in adenosine A2A receptor ligands". Handb Exp Pharmacol (193): 59–98. doi:10.1007/978-3-540-89615-9_3. PMID 19639279.
- ^ a b c Müller CE, Jacobson KA (2011). "Xanthines as adenosine receptor antagonists". Handb Exp Pharmacol (200): 151–199. doi:10.1007/978-3-642-13443-2_6. PMC 3882893. PMID 20859796.
- ^ a b Müller CE, Jacobson KA (May 2011). "Recent developments in adenosine receptor ligands and their potential as novel drugs". Biochim Biophys Acta. 1808 (5): 1290–1308. doi:10.1016/j.bbamem.2010.12.017. PMC 3437328. PMID 21185259.
- ^ Jenner P (December 2003). "A2A antagonists as novel non-dopaminergic therapy for motor dysfunction in PD". Neurology. 61 (11 Suppl 6): S32–S38. doi:10.1212/01.wnl.0000095209.59347.79. PMID 14663007.
- ^ Worden LT, Shahriari M, Farrar AM, Sink KS, Hockemeyer J, Müller CE, Salamone JD (April 2009). "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. doi:10.1007/s00213-008-1396-0. PMC 2875246. PMID 19048234.
- ^ Hauber W, Neuscheler P, Nagel J, Müller CE (October 2001). "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. doi:10.1046/j.0953-816x.2001.01759.x. PMID 11703457.
- ^ Chen JF, Steyn S, Staal R, Petzer JP, Xu K, Van Der Schyf CJ, Castagnoli K, Sonsalla PK, Castagnoli N, Schwarzschild MA (September 2002). "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. doi:10.1074/jbc.M206830200. PMID 12130655.
{{cite journal}}: CS1 maint: unflagged free DOI (link) - ^ Pretorius J, Malan SF, Castagnoli N, Bergh JJ, Petzer JP (September 2008). "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. doi:10.1016/j.bmc.2008.07.088. PMID 18723354.
- ^ Jacobson KA, Gallo-Rodriguez C, Melman N, Fischer B, Maillard M, van Bergen A, van Galen PJ, Karton Y (May 1993). "Structure-activity relationships of 8-styrylxanthines as A2-selective adenosine antagonists". J Med Chem. 36 (10): 1333–1342. doi:10.1021/jm00062a005. PMC 5975975. PMID 8496902.
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