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MSX-2

From Wikipedia, the free encyclopedia
Not to be confused withMSX2.
A selective adenosine A2A receptor antagonist
Pharmaceutical compound
MSX-2
Clinical data
Other names3-(3-Hydroxypropyl)-7-methyl-8-(3-methoxystyryl)-1-propargylxanthine
Drug classAdenosineA2A receptorantagonist
Identifiers
  • 3-(3-hydroxypropyl)-8-[(E)-2-(3-methoxyphenyl)ethenyl]-7-methyl-1-prop-2-ynylpurine-2,6-dione
CAS Number
PubChemCID
IUPHAR/BPS
ChemSpider
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC21H22N4O4
Molar mass394.431 g·mol−1
3D model (JSmol)
  • CN1C(=NC2=C1C(=O)N(C(=O)N2CCCO)CC#C)/C=C/C3=CC(=CC=C3)OC
  • InChI=1S/C21H22N4O4/c1-4-11-25-20(27)18-19(24(21(25)28)12-6-13-26)22-17(23(18)2)10-9-15-7-5-8-16(14-15)29-3/h1,5,7-10,14,26H,6,11-13H2,2-3H3/b10-9+
  • Key:FWLDDFYHEQMIGG-MDZDMXLPSA-N

MSX-2 is aselectiveadenosineA2A receptorantagonist used inscientific research.[1] It is axanthine and aderivative of thenon-selectiveadenosine receptor antagonistcaffeine.[1][2]

Theaffinities (Ki) of MSX-2 for the humanadenosine receptors are 5.38 to 14.5 nM for the adenosine A2A receptor, 2,500 nM for the adenosineA1 receptor (172- to 465-fold lower than for the A2A receptor), and >10,000 nM for the adenosineA2B andA3 receptors (>690-fold lower than for the A2A receptor).[3][4]

MSX-2 has poorwater solubility, which has limited the use of MSX-2 itself.[1][5] Water-solubleesterprodrugs of MSX-2, includingMSX-3 (aphosphate ester prodrug) andMSX-4 (anamino acid ester prodrug), have been developed and used in place of MSX-2.[1][5] MSX-3 is best-suited for use byintravenous administration, whereas MSX-4 can be administered byoral administration.[5][6]

MSX-3 and MSX-4 reversemotivational deficits in animals and hence have the capacity to producepro-motivational effects.[7][8][9]

MSX-2 and MSX-3 were first described in thescientific literature by 1998.[10][11] Subsequently, MSX-4 was developed and described by 2008.[5][6]

See also

[edit]

References

[edit]
  1. ^abcdde Lera Ruiz M, Lim YH, Zheng J (May 2014). "Adenosine A2A receptor as a drug discovery target".Journal of Medicinal Chemistry.57 (9):3623–3650.doi:10.1021/jm4011669.PMID 24164628.
  2. ^Yuzlenko O, Kieć-Kononowicz K (2006). "Potent adenosine A1 and A2A receptors antagonists: recent developments".Current Medicinal Chemistry.13 (30):3609–3625.doi:10.2174/092986706779026093.PMID 17168726.
  3. ^Khayat MT, Hanif A, Geldenhuys WJ, Nayeem MA (2019)."Adenosine Receptors and Drug Discovery in the Cardiovascular System". In Choudhary MI (ed.).Frontiers in Cardiovascular Drug Discovery: Volume 4. Amazon Digital Services LLC - Kdp. pp. 16–64.ISBN 978-1-68108-400-8. Retrieved23 September 2024.
  4. ^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.
  5. ^abcdMüller CE (November 2009). "Prodrug approaches for enhancing the bioavailability of drugs with low solubility".Chemistry & Biodiversity.6 (11):2071–2083.doi:10.1002/cbdv.200900114.PMID 19937841.
  6. ^abVollmann K, Qurishi R, Hockemeyer J, Müller CE (February 2008)."Synthesis and properties of a new water-soluble prodrug of the adenosine A 2A receptor antagonist MSX-2".Molecules.13 (2):348–359.doi:10.3390/molecules13020348.PMC 6244838.PMID 18305423.
  7. ^Salamone JD, Correa M, Ferrigno S, Yang JH, Rotolo RA, Presby RE (October 2018)."The Psychopharmacology of Effort-Related Decision Making: Dopamine, Adenosine, and Insights into the Neurochemistry of Motivation".Pharmacological Reviews.70 (4):747–762.doi:10.1124/pr.117.015107.PMC 6169368.PMID 30209181.
  8. ^López-Cruz L, Salamone JD, Correa M (2018)."Caffeine and Selective Adenosine Receptor Antagonists as New Therapeutic Tools for the Motivational Symptoms of Depression".Frontiers in Pharmacology.9: 526.doi:10.3389/fphar.2018.00526.PMC 5992708.PMID 29910727.
  9. ^Salamone JD, Correa M, Farrar AM, Nunes EJ, Collins LE (5 May 2010). "Role of dopamine–adenosine interactions in the brain circuitry regulating effort-related decision making: insights into pathological aspects of motivation".Future Neurology.5 (3):377–392.doi:10.2217/fnl.10.19.hdl:10234/35900.ISSN 1479-6708.
  10. ^Müller CE, Sauer R, Maurinsh Y, Huertas R, Fülle F, Klotz KN, Nagel J, Hauber W (1998). "A2A-selective adenosine receptor antagonists: Development of water-soluble prodrugs and a new tritiated radioligand".Drug Development Research.45 (3–4):190–197.doi:10.1002/(SICI)1098-2299(199811/12)45:3/4<190::AID-DDR16>3.0.CO;2-A.ISSN 0272-4391.
  11. ^Hauber W, Nagel J, Sauer R, Müller CE (June 1998). "Motor effects induced by a blockade of adenosine A2A receptors in the caudate-putamen".NeuroReport.9 (8):1803–1806.doi:10.1097/00001756-199806010-00024.PMID 9665604.
Receptor
(ligands)
P0 (adenine)
P1
(adenosine)
P2
(nucleotide)
P2X
(ATPTooltip Adenosine triphosphate)
P2Y
Transporter
(blockers)
CNTsTooltip Concentrative nucleoside transporters
ENTsTooltip Equilibrative nucleoside transporters
PMATTooltip Plasma membrane monoamine transporter
Enzyme
(inhibitors)
XOTooltip Xanthine oxidase
Others
Others


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