SCH 58261

Pricing Availability   Qty
Cat.No. 2270 - SCH 58261 | C18H15N7O | CAS No. 160098-96-4
Description: Potent, highly selective A2A antagonist
Chemical Name: 2-(2-Furanyl)-7-(2-phenylethyl)-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine
Purity: ≥99% (HPLC)
Datasheet
Citations (40)
Reviews
Literature (6)

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.

Compound Libraries

SCH 58261 is also offered as part of the Tocriscreen 2.0 Max. Find out more about compound libraries available from Tocris.

Technical Data

M. Wt 345.36
Formula C18H15N7O
Storage Store at RT
Purity ≥99% (HPLC)
CAS Number 160098-96-4
PubChem ID 176408
InChI Key UTLPKQYUXOEJIL-UHFFFAOYSA-N
Smiles NC1=NC2=C(C=NN2CCC2=CC=CC=C2)C2=NC(=NN12)C1=CC=CO1

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

Tocris products are intended for laboratory research use only, unless stated otherwise.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 34.54 100

Preparing Stock Solutions

The following data is based on the product molecular weight 345.36. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 2.9 mL 14.48 mL 28.96 mL
5 mM 0.58 mL 2.9 mL 5.79 mL
10 mM 0.29 mL 1.45 mL 2.9 mL
50 mM 0.06 mL 0.29 mL 0.58 mL

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Product Datasheets

Certificate of Analysis / Product Datasheet
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References

References are publications that support the biological activity of the product.

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

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


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Keywords: SCH 58261, SCH 58261 supplier, Potent, selective, A2A, antagonists, Receptors, adenosines, SCH58261, Adenosine, 2270, Tocris Bioscience

40 Citations for SCH 58261

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

Lin et al (2019) Functional roles of ST8SIA3-mediated sialylation of striatal DA D2 and adenosine A2A receptors. Transl Psychiatry 9 209 PMID: 31455764

Bao et al (2013) Pannexin 1 channels link chemoattractant receptor signaling to local excitation and global inhibition responses at the front and back of polarized neutrophils. J Biol Chem 288 22650 PMID: 23798685

Xiong et al (2017) Osteoblastic Lrp4 promotes osteoclastogenesis by regulating ATP release and adenosine-A2AR signaling. J Cell Biol 216 761 PMID: 28193701

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

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

Aires et al (2019) Blockade of microglial adenosine A2A receptor suppresses elevated pressure-induced inflammation, oxidative stress, and cell death in retinal cells. Glia 67 896 PMID: 30667095

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

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

Napolitano et al (2010) Role of aberrant striatal DA D1 receptor/cAMP/protein kinase A/DARPP32 signaling in the paradoxical calming effect of amphetamine. J Neurosci 30 11043 PMID: 20720111

Leffa et al (2019) Adenosine A2A Receptors in the Rat Prelimbic Medial Prefrontal Cortex Control Delay-Based Cost-Benefit Decision Making. Front Mol Neurosci 11 475 PMID: 30618621

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

Carman et al (2011) Adenosine receptor signaling modulates permeability of the blood-brain barrier. J Neurosci 31 13272 PMID: 21917810

Pugliese et al (2009) The adenosine A2A receptor antagonist ZM241385 enhances neuronal survival after oxygen-glucose deprivation in rat CA1 hippocampal slices. Br J Pharmacol 157 818 PMID: 19422385

Kinoshita et al (2018) Anti-Depressant Flu Reveals its Therapeutic Effect Via Astrocytes. EBioMedicine 32 72 PMID: 29887330

Cheng et al (2017) Structures of Human A1 and A2A Adenosine Receptors with Xanthines Reveal Determinants of Selectivity. Structure 25 1275 PMID: 28712806

Salimu et al (2017) Dominant immunosuppression of dendritic cell function by prostate-cancer-derived exosomes. J Extracell Vesicles 6 1368823 PMID: 28959385

Al-Taei et al (2017) Prostaglandin E2-mediated adenosinergic effects on CD14+ cells: Self-amplifying immunosuppression in cancer. Oncoimmunology 6 e1268308 PMID: 28344879

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

Zhan et al (2011) Adenosine A2A and A2B receptors are both required for adenosine A1 receptor-mediated cardioprotection. Am J Physiol Heart Circ Physiol 301 H1183 PMID: 21743001

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

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

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

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

Chen et al (2014) Prolonged adenosine A1 receptor activation in hypoxia and pial vessel disruption focal cortical ischemia facilitates clathrin-mediated AMPA receptor endocytosis and long-lasting synaptic inhibition in rat hippocampal CA3-CA1 synapses: differential regulat J Neurosci 34 9621 PMID: 25031403

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

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

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

Liu et al (2018) Adenosine binds predominantly to adenosine receptor A1 subtype in astrocytes and mediates an immunosuppressive effect. Brain Res 1700 47 PMID: 29935155

Diógenes et al (2014) Homeostatic control of synaptic activity by endogenous adenosine is mediated by adenosine kinase. Cereb Cortex 24 67 PMID: 22997174

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

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

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

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


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Literature in this Area

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