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Submit ReviewBAY 60-6583
Description: Potent partial A2B agonist; cardioprotective
Chemical Name: 2-[[6-Amino-3,5-dicyano-4-[4-(cyclopropylmethoxy)phenyl]-2-pyridinyl]thio]-acetamide
Purity: ≥98% (HPLC)
Biological Activity for BAY 60-6583
BAY 60-6583 is a partial agonist at adenosine A2B receptors (EC50 = 2.83 nM for murine A2B receptor). Displays selectivity for A2B over A1, A2A and A3 receptors. BAY 60-6583 antagonizes the effect of NECA (Cat. No. 1691) and adenosine (Cat. No. 3624) in cAMP accumulation assays. Decreases fMLP-induced superoxide production in neutrophils at low concentrations (1-10 nM). Cardioprotective; attenuates infarct size in a mouse model of myocardial ischemia. Exhibits ERK1/2-biased agonism.
Compound Libraries for BAY 60-6583
BAY 60-6583 is also offered as part of the Tocriscreen 2.0 Max. Find out more about compound libraries available from Tocris.
Technical Data for BAY 60-6583
| M. Wt | 379.44 |
| Formula | C19H17N5O2S |
| Storage | Store at +4°C |
| Purity | ≥98% (HPLC) |
| CAS Number | 910487-58-0 |
| PubChem ID | 11717831 |
| InChI Key | ZTYHZMAZUWOXNC-UHFFFAOYSA-N |
| Smiles | NC1=NC(SCC(N)=O)=C(C#N)C(C2=CC=C(OCC3CC3)C=C2)=C1C#N |
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 for BAY 60-6583
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 37.94 | 100 |
Preparing Stock Solutions for BAY 60-6583
The following data is based on the product molecular weight 379.44. 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.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 2.64 mL | 13.18 mL | 26.35 mL |
| 5 mM | 0.53 mL | 2.64 mL | 5.27 mL |
| 10 mM | 0.26 mL | 1.32 mL | 2.64 mL |
| 50 mM | 0.05 mL | 0.26 mL | 0.53 mL |
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Product Datasheets for BAY 60-6583
References for BAY 60-6583
References are publications that support the biological activity of the product.
Eckle et al (2007) Cardioprotection by ecto-5'-nucleotidase (CD73) and A2B adenosine receptors. Circulation 115 1581 PMID: 17353435
van der Hoeven et al (2011) A role for the low-affinity A2B adenosine receptor in regulating superoxide generation by murine neutrophils. J.Pharmacol.Exp.Ther. 338 1004 PMID: 21693629
Auchampach et al (2009) Characterization of the A2B adenosine receptor from mouse, rabbit, and dog. J.Pharmacol.Exp.Ther. 329 2 PMID: 19141710
Gao et al (2014) Probing biased/partial agonism at the G protein-coupled A2B adenosine receptor. Biochem. Pharmacol. 90 297 PMID: 24853985
Hinz et al (2014) BAY60-6583 acts as a partial agonist at adenosine A2B receptors. J.Pharmacol.Exp.Ther. 349 427 PMID: 24633424
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Keywords: BAY 60-6583, BAY 60-6583 supplier, BAY60-6583, adenosine, A2B, receptor, partial, agonists, agonism, potent, cAMP, cardioprotective, ischemia, superoxide, neutrophils, ERK1/2, biased, Adenosine, Receptors, 4472, Tocris Bioscience
19 Citations for BAY 60-6583
Citations are publications that use Tocris products. Selected citations for BAY 60-6583 include:
Wilson et al (2016) Differences in the Phosphorylation-Dependent Regulation of Prenylation of Rap1A and Rap1B. J Mol Biol 428 4929 PMID: 27760305
Merighi (2016) A2B adenosine receptors stimulate IL-6 production in primary murine microglia through p38 MAPKkinase pathway. Pharmacological Res 117 9 PMID: 27974241
Stefano et al (2021) Pharmacological Insights Into Safety and Efficacy Determinants for the Development of Adenosine Receptor Biased Agonists in the Treatment of Heart Failure. Front Pharmacol 12 628060 PMID: 33776771
Mairena et al (2021) Antitumoral Action of Resveratrol Through Adenosinergic Signaling in C6 Glioma Cells. Front Neurosci 15 702817 PMID: 34539333
Shih et al (2019) Dysregulation of ectonucleotidase-mediated extracellular adenosine during postmenopausal bone loss. Sci Adv 5 eaax1387 PMID: 31457100
Nuccio et al (2019) Adenosine A2A receptor stimulation restores cell functions and differentiation in Niemann-Pick type C-like oligodendrocytes. Sci Rep 9 9782 PMID: 31278313
Asano (2017) Aminophylline suppresses stress-induced visceral hypersensitivity and defecation in irritable bowel syndrome. Scientific Reports 7 40214 PMID: 28054654
Song (2017) Erythrocytes retain hypoxic adenosine response for faster acclimatization upon re-ascent. Nat Commun 8 14108 PMID: 28169986
Iannone et al (2013) Blockade of A2b adenosine receptor reduces tumor growth and immune suppression mediated by myeloid-derived suppressor cells in a mouse model of melanoma. Neoplasia 15 1400 PMID: 24403862
Fei et al (2022) Adenosine metabolized from extracellular ATP promotes type 2 immunity through triggering A2BAR signaling in intestinal epithelial cells. Cell Rep 40 111150 PMID: 35926464
Mark et al (2022) Regionally selective cardiovascular responses to adenosine A2A and A2B receptor activation. FASEB J 36 e22214 PMID: 35230706
Tomoaki et al (2019) Adenosine Attenuates Aortic Smooth Muscle Cell Calcification through A3 Adenosine Receptor. Tohoku J Exp Med 249 275-283 PMID: 31875581
Caglar et al (2019) Adenosine Receptor Signaling Targets Both PKA and Epac Pathways to Polarize Dendritic Cells to a Suppressive Phenotype. J Immunol 203 3247-3255 PMID: 31722989
Jain et al (2018) Melanotan II causes hypothermia in mice by activation of mast cells and stimulation of histamine 1 receptors. Am J Physiol Endocrinol Metab 315 E357 PMID: 29812984
Aherne et al (2015) Epithelial-specific A2B adenosine receptor signaling protects the colonic epithelial barrier during acute colitis. Autophagy 8 1324 PMID: 25850656
Gemma et al (2020) Adenosine/A2B Receptor Signaling Ameliorates the Effects of Aging and Counteracts Obesity. Cell Metab 32 56-70.e7 PMID: 32589947
Stephanie et al (2020) CD73+ extracellular vesicles inhibit angiogenesis through adenosine A2B receptor signalling. J Extracell Vesicles 9 1757900 PMID: 32489531
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
Mertens et al (2018) Switching-Off Adora2b in Vascular Smooth Muscle Cells Halts the Development of Pulmonary Hypertension. Front Physiol 9 555 PMID: 29910735
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