Evodenoson

    WARNING: This product is for research use only, not for human or veterinary use.

Hodoodo CAT#: H319696

CAS#: 844873-47-8

Description: Evodenoson, also known as ATL313 and DE-112, is a potent and selective A(2A)AR agonist (A2A adenosine receptor agonist) in development for novel treatment for sepsis. ATL313 significantly reduced infarct size and improved LV contractility at the end of reperfusion assessed by LV dp/dt at a dose of 900 ng/Kg. ATL313, reduces inflammation and improves survival in murine sepsis models.


Chemical Structure

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Evodenoson
CAS# 844873-47-8

Theoretical Analysis

Hodoodo Cat#: H319696
Name: Evodenoson
CAS#: 844873-47-8
Chemical Formula: C23H29N7O6
Exact Mass: 499.22
Molecular Weight: 499.528
Elemental Analysis: C, 55.30; H, 5.85; N, 19.63; O, 19.22

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @hodoodo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: ATL313; ATL313; ATL313; DE-112; DE112; DE 112; Evodenoson.

IUPAC/Chemical Name: methyl 4-[3-[6-amino-9-[(2R,3R,4S,5S)-5-(cyclopropylcarbamoyl)-3,4-dihydroxyoxolan-2-yl]purin-2-yl]prop-2-ynyl]piperidine-1-carboxylate

InChi Key: SQJXTUJMBYVDBB-RQXXJAGISA-N

InChi Code: InChI=1S/C23H29N7O6/c1-35-23(34)29-9-7-12(8-10-29)3-2-4-14-27-19(24)15-20(28-14)30(11-25-15)22-17(32)16(31)18(36-22)21(33)26-13-5-6-13/h11-13,16-18,22,31-32H,3,5-10H2,1H3,(H,26,33)(H2,24,27,28)/t16-,17+,18-,22+/m0/s1

SMILES Code: O=C(N1CCC(CC#CC2=NC(N)=C3N=CN([C@@H]4O[C@H](C(NC5CC5)=O)[C@@H](O)[C@H]4O)C3=N2)CC1)OC

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 499.53 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.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Yago T, Tsukamoto H, Liu Z, Wang Y, Thompson LF, McEver RP. Multi-Inhibitory Effects of A2A Adenosine Receptor Signaling on Neutrophil Adhesion Under Flow. J Immunol. 2015 Oct 15;195(8):3880-9. doi: 10.4049/jimmunol.1500775. Epub 2015 Sep 9. PubMed PMID: 26355151; PubMed Central PMCID: PMC4592819.

2: Loram LC, Strand KA, Taylor FR, Sloane E, Van Dam AM, Rieger J, Maier SF, Watkins LR. Adenosine 2A receptor agonism: A single intrathecal administration attenuates motor paralysis in experimental autoimmune encephalopathy in rats. Brain Behav Immun. 2015 May;46:50-4. doi: 10.1016/j.bbi.2015.01.014. Epub 2015 Jan 31. PubMed PMID: 25653191; PubMed Central PMCID: PMC4447711.

3: Naresh NK, Chen X, Roy RJ, Antkowiak PF, Annex BH, Epstein FH. Accelerated dual-contrast first-pass perfusion MRI of the mouse heart: development and application to diet-induced obese mice. Magn Reson Med. 2015 Mar;73(3):1237-45. doi: 10.1002/mrm.25238. Epub 2014 Apr 23. PubMed PMID: 24760707; PubMed Central PMCID: PMC4207851.

4: Loram LC, Taylor FR, Strand KA, Harrison JA, Rzasalynn R, Sholar P, Rieger J, Maier SF, Watkins LR. Intrathecal injection of adenosine 2A receptor agonists reversed neuropathic allodynia through protein kinase (PK)A/PKC signaling. Brain Behav Immun. 2013 Oct;33:112-22. doi: 10.1016/j.bbi.2013.06.004. Epub 2013 Jun 28. PubMed PMID: 23811314; PubMed Central PMCID: PMC4447865.

5: Voloshyna I, Carsons S, Littlefield MJ, Rieger JM, Figler R, Reiss AB. Adenosine A(2A) receptor activation supports an atheroprotective cholesterol balance in human macrophages and endothelial cells. Biochim Biophys Acta. 2013 Feb;1831(2):407-16. doi: 10.1016/j.bbalip.2012.11.005. Epub 2012 Nov 17. PubMed PMID: 23168167.

6: de Araújo Junqueira AF, Dias AA, Vale ML, Spilborghs GM, Bossa AS, Lima BB, Carvalho AF, Guerrant RL, Ribeiro RA, Brito GA. Adenosine deaminase inhibition prevents Clostridium difficile toxin A-induced enteritis in mice. Infect Immun. 2011 Feb;79(2):653-62. doi: 10.1128/IAI.01159-10. Epub 2010 Nov 29. PubMed PMID: 21115723; PubMed Central PMCID: PMC3028843.

7: Gazoni LM, Walters DM, Unger EB, Linden J, Kron IL, Laubach VE. Activation of A1, A2A, or A3 adenosine receptors attenuates lung ischemia-reperfusion injury. J Thorac Cardiovasc Surg. 2010 Aug;140(2):440-6. doi: 10.1016/j.jtcvs.2010.03.002. Epub 2010 Apr 15. PubMed PMID: 20398911; PubMed Central PMCID: PMC2906677.

8: Genovese T, Melani A, Esposito E, Paterniti I, Mazzon E, Di Paola R, Bramanti P, Linden J, Pedata F, Cuzzocrea S. Selective adenosine A(2a) receptor agonists reduce the apoptosis in an experimental model of spinal cord trauma. J Biol Regul Homeost Agents. 2010 Jan-Mar;24(1):73-86. Erratum in: J Biol Regul Homeost Agents. 2010 Apr-Jun;24(2):228. PubMed PMID: 20385073.

9: Chhabra P, Wang K, Zeng Q, Jecmenica M, Langman L, Linden J, Ketchum RJ, Brayman KL. Adenosine A(2A) agonist administration improves islet transplant outcome: Evidence for the role of innate immunity in islet graft rejection. Cell Transplant. 2010;19(5):597-612. doi: 10.3727/096368910X491806. Epub 2010 Mar 26. PubMed PMID: 20350347.

10: Dai W, Hale SL, Nayak R, Kloner RA. ATL 313, A Selective A(2A) Adenosine Receptor Agonist, Reduces Myocardial Infarct Size in a Rat Ischemia/Reperfusion Model. Open Cardiovasc Med J. 2009 Nov 25;3:166-72. doi: 10.2174/1874192400903010166. PubMed PMID: 20111666; PubMed Central PMCID: PMC2811859.

11: Sun WC, Berghaus LJ, Moore JN, Hurley DJ, Vandenplas ML, Thompson R, Linden J. Lipopolysaccharide and TNF-alpha modify adenosine A(2A) receptor expression and function in equine monocytes. Vet Immunol Immunopathol. 2010 Jun 15;135(3-4):289-95. doi: 10.1016/j.vetimm.2009.12.001. Epub 2009 Dec 11. PubMed PMID: 20056284.

12: Sharma AK, Laubach VE, Ramos SI, Zhao Y, Stukenborg G, Linden J, Kron IL, Yang Z. Adenosine A2A receptor activation on CD4+ T lymphocytes and neutrophils attenuates lung ischemia-reperfusion injury. J Thorac Cardiovasc Surg. 2010 Feb;139(2):474-82. doi: 10.1016/j.jtcvs.2009.08.033. Epub 2009 Nov 11. PubMed PMID: 19909990; PubMed Central PMCID: PMC2813368.

13: Loram LC, Harrison JA, Sloane EM, Hutchinson MR, Sholar P, Taylor FR, Berkelhammer D, Coats BD, Poole S, Milligan ED, Maier SF, Rieger J, Watkins LR. Enduring reversal of neuropathic pain by a single intrathecal injection of adenosine 2A receptor agonists: a novel therapy for neuropathic pain. J Neurosci. 2009 Nov 4;29(44):14015-25. doi: 10.1523/JNEUROSCI.3447-09.2009. PubMed PMID: 19890011; PubMed Central PMCID: PMC2799253.

14: Sun WC, Moore JN, Hurley DJ, Vandenplas ML, Fortes B, Thompson R, Linden J. Differential modulation of lipopolysaccharide-induced expression of inflammatory genes in equine monocytes through activation of adenosine A2A receptors. Vet Immunol Immunopathol. 2010 Apr 15;134(3-4):169-77. doi: 10.1016/j.vetimm.2009.08.018. Epub 2009 Sep 2. PubMed PMID: 19766323.

15: Sharma AK, Linden J, Kron IL, Laubach VE. Protection from pulmonary ischemia-reperfusion injury by adenosine A2A receptor activation. Respir Res. 2009 Jun 26;10:58. doi: 10.1186/1465-9921-10-58. PubMed PMID: 19558673; PubMed Central PMCID: PMC2711962.

16: Koizumi S, Odashima M, Otaka M, Jin M, Linden J, Watanabe S, Ohnishi H. Attenuation of gastric mucosal inflammation induced by indomethacin through activation of the A2A adenosine receptor in rats. J Gastroenterol. 2009;44(5):419-25. doi: 10.1007/s00535-009-0028-8. Epub 2009 Apr 1. PubMed PMID: 19333545; PubMed Central PMCID: PMC3328190.

17: Alam MS, Kurtz CC, Wilson JM, Burnette BR, Wiznerowicz EB, Ross WG, Rieger JM, Figler RA, Linden J, Crowe SE, Ernst PB. 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. 2009 May;2(3):232-42. doi: 10.1038/mi.2009.4. Epub 2009 Mar 4. PubMed PMID: 19262506; PubMed Central PMCID: PMC3036970.

18: Lisle TC, Gazoni LM, Fernandez LG, Sharma AK, Bellizzi AM, Shifflett GD, Laubach VE, Kron IL. Inflammatory lung injury after cardiopulmonary bypass is attenuated by adenosine A(2A) receptor activation. J Thorac Cardiovasc Surg. 2008 Nov;136(5):1280-7; discussion 1287-8. doi: 10.1016/j.jtcvs.2008.07.010. Epub 2008 Aug 30. Erratum in: J Thorac Cardiovasc Surg. 2014 Aug;148(2):756. Schifflett GD[corrected to Shifflett, Grant D]. PubMed PMID: 19026816; PubMed Central PMCID: PMC2652167.

19: Moore CC, Martin EN, Lee GH, Obrig T, Linden J, Scheld WM. An A2A adenosine receptor agonist, ATL313, reduces inflammation and improves survival in murine sepsis models. BMC Infect Dis. 2008 Oct 20;8:141. doi: 10.1186/1471-2334-8-141. PubMed PMID: 18937852; PubMed Central PMCID: PMC2588444.

20: Gazoni LM, Laubach VE, Mulloy DP, Bellizzi A, Unger EB, Linden J, Ellman PI, Lisle TC, Kron IL. Additive protection against lung ischemia-reperfusion injury by adenosine A2A receptor activation before procurement and during reperfusion. J Thorac Cardiovasc Surg. 2008 Jan;135(1):156-65. doi: 10.1016/j.jtcvs.2007.08.041. Epub 2007 Nov 26. PubMed PMID: 18179933.