SCH 58261

Cat. No. 2270

SCH 58261 C18H15N7O [160098-96-4]

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Chemical Name: 2-(2-Furanyl)-7-(2-phenylethyl)-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine

Biological Activity

Potent and selective A2A adenosine receptor competitive antagonist (Ki = 1.3 nM). Displays 323-, 53- and 100-fold selectivity over A1, A2B and A3 receptors, respectively.

Technical Data

M.Wt:
345.36
Formula:
C18H15N7O
Solubility:
Soluble to 100 mM in DMSO
Purity:
>99 %
Storage:
Store at RT
CAS No:
160098-96-4

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.

Certificate of Analysis / Product Datasheet / Safety Data Sheet

Certificate of Analysis / Product Datasheet
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Bastia et al (2002) Effects of A1 and A2A adenosine receptor ligands in mouse acute models of pain. Neurosci.Lett. 328 241. PMID: 12147316.

Belardinelli et al (1997) The A2A adenosine receptor mediates coronary vasodilation. J.Pharmacol.Exp.Ther. 284 1066.

Zocchi et al (1996) Binding of the radioligand [3H]-SCH 58261, a new non-xanthine A2A adenosine receptor antagonist, to rat striatal membranes. J.Pharmacol.Exp.Ther. 276 398. PMID: 8632302.

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Citations are publications that use Tocris products. Selected citations for SCH 58261 include:

Nadal et al (2016) Presynaptic muscarinic acetylcholine autoreceptors (M1, M2 and M4 subtypes), adenosine receptors (A1 and A2A) and tropomyosin-related kinase B receptor (TrkB) modulate the developmental synapse elimination process at the neuromuscular junction. Cancer Biol Ther 9 67. PMID: 27339059.

Kermanian et al (2015) Effects of adenosine A2a receptor agonist and antagonist on cerebellar nuclear factor-kB expression preceded by MDMA toxicity. J Neuroinflammation 28 120. PMID: 25678999.

Madeira et al (2015) Adenosine A2AR blockade prevents neuroinflammation-induced death of retinal ganglion cells caused by elevated pressure. J Neurosci 12 115. PMID: 26054642.

Perez-Aso et al (2015) Apremilast, a novel phosphodiesterase 4 (PDE4) inhibitor, regulates inflammation through multiple cAMP downstream effectors. Arthritis Res Ther 17 249. PMID: 26370839.

Stoddart et al (2015) Application of BRET to monitor ligand binding to GPCRs. Nat Methods 12 661. PMID: 26030448.

Wydra et al (2015) On the role of A2A and D2 receptors in control of cocaine and food-seeking behaviors in rats. Mol Brain 232 1767. PMID: 25420611.

Zhu et al (2015) Different patterns of electrical activity lead to long-term potentiation by activating different intracellular pathways. Psychopharmacology (Berl) 35 621. PMID: 25589756.

Häusler et al (2014) Anti-CD39 and anti-CD73 antibodies A1 and 7G2 improve targeted therapy in ovarian cancer by blocking adenosine-dependent immune evasion. Neuroscience 6 129. PMID: 24489992.

Haanes and Edvinsson (2014) Expression and characterization of purinergic receptors in rat middle meningeal artery-potential role in migraine. Med J Islam Repub Iran 9 e108782. PMID: 25265286.

Augusto et al (2013) Ecto-5'-nucleotidase (CD73)-mediated formation of adenosine is critical for the striatal adenosine A2A receptor functions. Proc Natl Acad Sci U S A 33 11390. PMID: 23843511.

Hikida et al (2013) Pathway-specific modulation of nucleus accumbens in reward and aversive behavior via selective transmitter receptors. Nat Neurosci 110 342. PMID: 23248274.

Mediavilla-Varela et al (2013) Antagonism of adenosine A2A receptor expressed by lung adenocarcinoma tumor cells and cancer associated fibroblasts inhibits their growth. Am J Transl Res 14 860. PMID: 23917542.

Wu et al (2013) Opiate-induced changes in brain adenosine levels and narcotic drug responses. J Neuroinflammation 228 235. PMID: 23098802.

Kan et al (2012) Imiquimod suppresses propagation of herpes simplex virus 1 by upregulation of cystatin A via the adenosine receptor A1 pathway. J Virol 86 10338. PMID: 22787201.

Lee et al (2012) When cytokinin, a plant hormone, meets the adenosine A2A receptor: a novel neuroprotectant and lead for treating neurodegenerative disorders? PLoS One 7 e38865. PMID: 22719969.

Mills et al (2012) Extracellular adenosine signaling induces CX3CL1 expression in the brain to promote experimental autoimmune encephalomyelitis. J Neurosci 9 193. PMID: 22883932.

Teng and Mustafa (2011) A(2A) adenosine receptor-mediated increase in coronary flow in hyperlipidemic APOE-knockout mice. J Exp Pharmacol 2011 59. PMID: 21847356.

Garavaglia et al (2010) Adaptation of NS cells growth and differentiation to high-throughput screening-compatible plates. BMC Neurosci 11 7. PMID: 20085655.

Higley and Sabatini (2010) Competitive regulation of synaptic Ca2+ influx by D2 dopamine and A2A adenosine receptors. Nat Neurosci 13 958. PMID: 20601948.

Alam et al (2009) A2A adenosine receptor (AR) activation inhibits pro-inflammatory cytokine production by human CD4+ helper T cells and regulates Helicobacter-induced gastritis and bacterial persistence. Mucosal Immunol 2 232. PMID: 19262506.

Wilson et al (2009) The A2B adenosine receptor impairs the maturation and immunogenicity of dendritic cells. J Immunol 182 4616. PMID: 19342636.

Xi et al (2009) Adenosine A2A and A2B receptors work in concert to induce a strong protection against reperfusion injury in rat hearts. J Mol Cell Cardiol 47 684. PMID: 19695259.

Guerreiro et al (2008) Paraxanthine, the primary metabolite of caffeine, provides protection against dopaminergic cell death via stimulation of ryanodine receptor channels. Mol Pharmacol 74 980. PMID: 18621927.

Shen et al (2008) Dichotomous dopaminergic control of striatal synaptic plasticity. Science 321 848. PMID: 18687967.

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