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Cordycepin

Cordycepin is originally found in a variety of species of the fungus Cordyceps and displays anticancer, neuromodulatory, anti-inflammatory, anti-parasitic, and antiviral activities. Cordycepin induces double-stranded DNA breaks in cancer cells with incorporated into nucleic acid chains as it is a 3-deoxy analog of adenosine. Additionally, cordycepin increases generation of reactive oxygen species (ROS), increases caspase activity and PARP cleavage, and activates AMPK, inducing caspase-mediated apoptosis in cells. Cordycepin decreases the amplitude of excitatory presynaptic membrane potentials and indirectly inhibits AMPA receptor- and NMDA receptor-mediated responses through inhibition of presynaptic excitatory neurotransmitter release. In vitro, cordycepin decreases production of NO, activation of NF-κB, and expression of iNOS, COX-2, and TNF-α. This compound displays antimicrobial activity against Leishmania and also terminates RNA chains in cells infected with picornavirus.

References PubMed ID::http://www.ncbi.nlm.nih.gov/pubmed/18853302

Cas No.

73-03-0

Purity

≥98%

Formula

C10H13N5O3

Formula Wt.

251.24

Chemical Name

3-deoxyadenosine

IUPAC Name

(2R,3R,5S)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolan-3-ol

Solubility

Water

Appearance

White Crystal Powder

Yao LH, Huang JN, Li CH, et al. Cordycepin suppresses excitatory synaptic transmission in rat hippocampal slices via a presynaptic mechanism. CNS Neurosci Ther. 2013 Apr;19(4):216-21. PMID: 23419191.

Lee HJ, Burger P, Vogel M, et al. The nucleoside antagonist cordycepin causes DNA double strand breaks in breast cancer cells. Invest New Drugs. 2012 Oct;30(5):1917-25. PMID: 22821173.

Jeong JW, Jin CY, Park C, et al. Induction of apoptosis by cordycepin via reactive oxygen species generation in human leukemia cells. Toxicol In Vitro. 2011 Jun;25(4):817-24. PMID: 21310227.

Wang Z, Wang X, Qu K, et al. Binding of cordycepin monophosphate to AMP-activated protein kinase and its effect on AMP-activated protein kinase activation. Chem Biol Drug Des. 2010 Oct;76(4):340-4. PMID: 20738312.

Kim HG, Shrestha B, Lim SY, et al. Cordycepin inhibits lipopolysaccharide-induced inflammation by the suppression of NF-kappaB through Akt and p38 inhibition in RAW 264.7 macrophage cells. Eur J Pharmacol. 2006 Sep 18;545(2-3):192-9. PMID: 16899239.

Wataya Y, Hiraoka O. 3-Deoxyinosine as an anti-leishmanial agent: the metabolism and cytotoxic effects of 3-deoxyinosine in Leishmania tropica promastigotes. Biochem Biophys Res Commun. 1984 Sep 17;123(2):677-83. PMID: 6487305.

Panicali DL, Nair CN. Effect of cordycepin triphosphate on in vitro RNA synthesis by picornavirus polymerase complexes. J Virol. 1978 Jan;25(1):124-8. PMID: 202731.

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