Cordycepin

• CAT Number: R008436
• CAS Number: 73-03-0
• Molecular Formula: C10H13N5O3
• Molecular Weight: 251.246
• Purity: ≥95%
• Storage: -20°C
• IUPAC Name: (2R,3R,5S)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolan-3-ol
• InChI: InChI=1S/C10H13N5O3/c11-8-7-9(13-3-12-8)15(4-14-7)10-6(17)1-5(2-16)18-10/h3-6,10,16-17H,1-2H2,(H2,11,12,13)/t5-,6+,10+/m0/s1
• InChIKey: OFEZSBMBBKLLBJ-BAJZRUMYSA-N
• SMILES: C1C(OC(C1O)N2C=NC3=C2N=CN=C3N)CO

Cordycepin, also known as 3/'-Deoxyadenosine, is a purine nucleoside antimetabolite and antibiotic isolated from the fungus Cordyceps militaris with potential antineoplastic activity. Cordycepin is an adenosine analogue, which is readily phosphorylated to its mono-, di-, and triphosphate intracellularly. Triphosphate cordycepin can be incorporated into RNA, and inhibits transcription elongation and RNA synthesis due to the absence of a hydroxyl moiety at the 3/' position. Because it can be converted to an inactive metabolite by adenosine deaminase, this agent must be administered with an adenosine deaminase inhibitor in order to be effective. Cordycepin has displayed cytotoxicity against some leukemic cell lines in vitro.

Reference

1:The Protective Effect of Cordycepin on D-Galactosamine/Lipopolysaccharide-Induced Acute Liver Injury. Li J, Zhong L, Zhu H, Wang F.Mediators Inflamm. 2017;2017:3946706. doi: 10.1155/2017/3946706. Epub 2017 Mar 28. PMID: 28522898
2:Characterization of Newly Bred Cordyceps militaris Strains for Higher Production of Cordycepin through HPLC and URP-PCR Analysis. Lee HH, Kang N, Park I, Park J, Kim I, Kim J, Kim N, Lee JY, Seo YS.J Microbiol Biotechnol. 2017 Apr 25. doi: 10.4014/jmb.1701.01043. [Epub ahead of print] PMID: 28438013 Free Article
3:Development of High Cordycepin-Producing Cordyceps militaris Strains. Kang N, Lee HH, Park I, Seo YS.Mycobiology. 2017 Mar;45(1):31-38. doi: 10.5941/MYCO.2017.45.1.31. Epub 2017 Mar 31. PMID: 28435352 Free PMC Article
4:Metronomic Cordycepin Therapy Prolongs Survival of Oral Cancer-Bearing Mice and Inhibits Epithelial-Mesenchymal Transition. Su NW, Wu SH, Chi CW, Liu CJ, Tsai TH, Chen YJ.Molecules. 2017 Apr 13;22(4). pii: E629. doi: 10.3390/molecules22040629. PMID: 28406456 Free Article
5:Protective Effect of Cordycepin on Experimental Testicular Ischemia/Reperfusion Injury in Rats. Okur MH, Arslan S, Aydogdu B, Zeytun H, Basuguy E, Arslan MS, Ibiloglu I, Kaplan I.J Invest Surg. 2017 Apr 12:1-8. doi: 10.1080/08941939.2016.1246629. [Epub ahead of print] PMID: 28402715
6:Cordycepin confers neuroprotection in mice models of intracerebral hemorrhage via suppressing NLRP3 inflammasome activation. Cheng Y, Wei Y, Yang W, Song Y, Shang H, Cai Y, Wu Z, Zhao W.Metab Brain Dis. 2017 Apr 11. doi: 10.1007/s11011-017-0003-7. [Epub ahead of print] PMID: 28401330
7:Cordycepin induces human lung cancer cell apoptosis by inhibiting nitric oxide mediated ERK/Slug signaling pathway. Hwang JH, Park SJ, Ko WG, Kang SM, Lee DB, Bang J, Park BJ, Wee CB, Kim DJ, Jang IS, Ko JH.Am J Cancer Res. 2017 Mar 1;7(3):417-432. eCollection 2017. PMID: 28401001 Free PMC Article
8:Cordycepin-enriched WIB-801C from Cordyceps militaris improves functional recovery by attenuating blood-spinal cord barrier disruption after spinal cord injury. Lee JY, Choi HY, Baik HH, Ju BG, Kim WK, Yune TY.J Ethnopharmacol. 2017 May 5;203:90-100. doi: 10.1016/j.jep.2017.03.047. Epub 2017 Mar 30. PMID: 28363523
9:Cordycepin negatively modulates lipopolysaccharide-induced cytokine production by up-regulation of heme oxygenase-1. Qing R, Huang Z, Tang Y, Xiang Q, Yang F.Int Immunopharmacol. 2017 Mar 25;47:20-27. doi: 10.1016/j.intimp.2017.03.002. [Epub ahead of print] PMID: 28351780
10:Cordycepin disrupts leukemia association with mesenchymal stromal cells and eliminates leukemia stem cell activity. Liang SM, Lu YJ, Ko BS, Jan YJ, Shyue SK, Yet SF, Liou JY.Sci Rep. 2017 Mar 7;7:43930. doi: 10.1038/srep43930. PMID: 28266575 Free PMC Article