2-Chloroadenosine

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

MedKoo CAT#: 540070

CAS#: 146-77-0

Description: 2-Chloroadenosine is an adenosine analog and receptor agonist that terminates DNA chain elongation. It induces double-standed DNA breaks and apoptosis in lung cancer cells. It also stimulates arterial dilation and decreases expression of TNF-α.


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2-Chloroadenosine is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 540070
Name: 2-Chloroadenosine
CAS#: 146-77-0
Chemical Formula: C10H12ClN5O4
Exact Mass: 301.0578
Molecular Weight: 301.687
Elemental Analysis: C, 39.81; H, 4.01; Cl, 11.75; N, 23.21; O, 21.21


Synonym: BRN 0043957; BRN0043957; BRN-0043957; NSC 36896; NSC36896; NSC-36896

IUPAC/Chemical Name: (2R,3R,4S,5R)-2-(6-amino-2-chloro-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

InChi Key: BIXYYZIIJIXVFW-UUOKFMHZSA-N

InChi Code: InChI=1S/C10H12ClN5O4/c11-10-14-7(12)4-8(15-10)16(2-13-4)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1H2,(H2,12,14,15)/t3-,5-,6-,9-/m1/s1

SMILES Code: O[C@H]1[C@H](N2C=NC3=C(N)N=C(Cl)N=C23)O[C@H](CO)[C@H]1O


Technical Data

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

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).

Harmonized System Code:
293490


References

1: Mareš P. Anticonvulsant action of 2-chloroadenosine against pentetrazol-induced seizures in immature rats is due to activation of A1 adenosine receptors. J Neural Transm (Vienna). 2010 Nov;117(11):1269-77. doi: 10.1007/s00702-010-0465-9. Epub 2010 Aug 31. PubMed PMID: 20809069.

2: Kumar V, Harjai K, Chhibber S. 2-Chloroadenosine (2-CADO) treatment modulates the pro-inflammatory immune response to prevent acute lung inflammation in BALB/c mice suffering from Klebsiella pneumoniae B5055-induced pneumonia. Int J Antimicrob Agents. 2010 Jun;35(6):599-602. doi: 10.1016/j.ijantimicag.2010.01.014. Epub 2010 Mar 1. PubMed PMID: 20189776.

3: Pometlová M, Kubová H, Mares P. Effects of 2-chloroadenosine on cortical epileptic afterdischarges in immature rats. Pharmacol Rep. 2010 Jan-Feb;62(1):62-7. PubMed PMID: 20360616.

4: Kumar V, Chhibber S. Intravenous 2-chloroadenosine protects BALB/c mice from Klebsiella pneumoniae B5055-induced sepsis by modulating the pro-inflammatory immune response. J Chemother. 2009 Dec;21(6):639-45. PubMed PMID: 20071287.

5: Bellezza I, Tucci A, Minelli A. 2-Chloroadenosine and human prostate cancer cells. Anticancer Agents Med Chem. 2008 Oct;8(7):783-9. Review. PubMed PMID: 18855579.

6: Bastin-Coyette L, Smal C, Cardoen S, Saussoy P, Van den Neste E, Bontemps F. Mechanisms of cell death induced by 2-chloroadenosine in leukemic B-cells. Biochem Pharmacol. 2008 Apr 1;75(7):1451-60. doi: 10.1016/j.bcp.2007.12.007. Epub 2007 Dec 27. PubMed PMID: 18242582.

7: Minelli A, Bellezza I, Tucci A, Conte C, Bracarda S, Culig Z. 2-chloroadenosine modulates PAR-1 and IL-23 expression and enhances docetaxel effects on PC3 cells. Prostate. 2008 Mar 1;68(4):360-72. doi: 10.1002/pros.20703. PubMed PMID: 18189232.

8: Minelli A, Bellezza I, Agostini M, Bracarda S, Culig Z. Mechanism of 2-chloroadenosine toxicity to PC3 cell line. Prostate. 2006 Sep 15;66(13):1425-36. PubMed PMID: 16741921.

9: Ates N, Ilbay G, Sahin D. Suppression of generalized seizures activity by intrathalamic 2-chloroadenosine application. Exp Biol Med (Maywood). 2005 Jul;230(7):501-5. PubMed PMID: 15985626.

10: Sakamaki F, Ishizaka A, Urano T, Sayama K, Nakamura H, Terashima T, Waki Y, Soejima K, Tasaka S, Sawafuji M, Kobayashi K, Yamaguchi K, Kanazawa M. Attenuation by intravenous 2-chloroadenosine of acute lung injury induced by live escherichia coli or latex particles added to endotoxin in the neutropenic state. J Lab Clin Med. 2003 Aug;142(2):128-35. PubMed PMID: 12960960.

11: Kearney AY, Fan YH, Giri U, Saigal B, Gandhi V, Heymach JV, Zurita AJ. 8-Chloroadenosine Sensitivity in Renal Cell Carcinoma Is Associated with AMPK Activation and mTOR Pathway Inhibition. PLoS One. 2015 Aug 27;10(8):e0135962. doi: 10.1371/journal.pone.0135962. eCollection 2015. PubMed PMID: 26313261; PubMed Central PMCID: PMC4552467.

12: Hirsh JK, Silinsky EM. Inhibition of spontaneous acetylcholine secretion by 2-chloroadenosine as revealed by a protein kinase inhibitor at the mouse neuromuscular junction. Br J Pharmacol. 2002 Apr;135(8):1897-902. PubMed PMID: 11959792; PubMed Central PMCID: PMC1573317.

13: Borowicz KK, Łuszczki J, Czuczwar SJ. 2-Chloroadenosine, a preferential agonist of adenosine A1 receptors, enhances the anticonvulsant activity of carbamazepine and clonazepam in mice. Eur Neuropsychopharmacol. 2002 Apr;12(2):173-9. PubMed PMID: 11872335.

14: Koshiba M, Kosaka H, Nakazawa T, Hayashi N, Saura R, Kitamura N, Kumagai S. 2-Chloroadenosine but not adenosine induces apoptosis in rheumatoid fibroblasts independently of cell surface adenosine receptor signalling. Br J Pharmacol. 2002 Mar;135(6):1477-86. PubMed PMID: 11906961; PubMed Central PMCID: PMC1573274.

15: Zhao C, Qi J, Tao W, He L, Xu W, Chan J, Deng Z. Characterization of biosynthetic genes of ascamycin/dealanylascamycin featuring a 5'-O-sulfonamide moiety in Streptomyces sp. JCM9888. PLoS One. 2014 Dec 5;9(12):e114722. doi: 10.1371/journal.pone.0114722. eCollection 2014. PubMed PMID: 25479601; PubMed Central PMCID: PMC4257720.

16: Dubey RK, Fingerle J, Gillespie DG, Mi Z, Rosselli M, Imthurn B, Jackson EK. Adenosine Attenuates Human Coronary Artery Smooth Muscle Cell Proliferation by Inhibiting Multiple Signaling Pathways That Converge on Cyclin D. Hypertension. 2015 Dec;66(6):1207-19. doi: 10.1161/HYPERTENSIONAHA.115.05912. Epub 2015 Sep 28. PubMed PMID: 26416848; PubMed Central PMCID: PMC4644125.

17: Stellrecht CM, Vangapandu HV, Le XF, Mao W, Shentu S. ATP directed agent, 8-chloro-adenosine, induces AMP activated protein kinase activity, leading to autophagic cell death in breast cancer cells. J Hematol Oncol. 2014 Mar 14;7:23. doi: 10.1186/1756-8722-7-23. PubMed PMID: 24628795; PubMed Central PMCID: PMC4007639.

18: Santafe MM, Priego M, Obis T, Garcia N, Tomàs M, Lanuza MA, Tomàs J. Adenosine receptors and muscarinic receptors cooperate in acetylcholine release modulation in the neuromuscular synapse. Eur J Neurosci. 2015 Jul;42(2):1775-87. doi: 10.1111/ejn.12922. Epub 2015 May 18. PubMed PMID: 25892551.

19: Gonçalves FQ, Pires J, Pliassova A, Beleza R, Lemos C, Marques JM, Rodrigues RJ, Canas PM, Köfalvi A, Cunha RA, Rial D. Adenosine A2b receptors control A1 receptor-mediated inhibition of synaptic transmission in the mouse hippocampus. Eur J Neurosci. 2015 Apr;41(7):878-88. doi: 10.1111/ejn.12851. Epub 2015 Feb 19. PubMed PMID: 25704806.

20: Han YY, Zhou Z, Cao JX, Jin YQ, Li SY, Ni JH, An GS, Zhang YX, Jia HT. E2F1-mediated DNA damage is implicated in 8-Cl-adenosine-induced chromosome missegregation and apoptosis in human lung cancer H1299 cells. Mol Cell Biochem. 2013 Dec;384(1-2):187-96. doi: 10.1007/s11010-013-1797-1. Epub 2013 Sep 15. PubMed PMID: 24037421.