Description
Cordycepin (73-03-0) is an adenosine analog lacking the hydroxyl at the 3’ position. Inhibits PARP1?and polyadenylation2. Displays anti-inflammatory effects1,3?and neuroprotective effects by inhibiting Aβ-induced apoptosis in hippocampal neurons4. Induces apoptosis in a variety of cancer cell lines5. Displays antiobesity effects.6?Inhibits cell senescence via activation of AMPK.7?Maintains stem cell pluripotency and increases iPS cell generation efficiency.8
Chemical Properties
Crystalline Solid
Definition
ChEBI: Cordycepin is a 3'-deoxyribonucleoside and a member of adenosines. It has a role as an antimetabolite and a nucleoside antibiotic.
General Description
Chemical structure: nucleoside
Biological Activity
Nucleoside analog that acts as an anticancer and antifungal agent. Can be converted to 3'-deoxyadenosine triphosphate (3'-dATP), which inhibits ATP-dependent DNA synthesis. Inhibits growth of various tumor cells in vitro .
Biochem/physiol Actions
Cordycepin is an adenosine analogue that is readily converted to cordycepin 5′-triphosphate; can be used for 3′-end labeling of RNA.
Purification Methods
3'-Deoxyadenosine forms needles from EtOH, n-BuOH and n-PrOH, and a monohydrate from H2O. It has max 260nm ( 14,600) in EtOH. The picrate has m 195o(dec, yellow crystals from H2O). [Kaczka et al. Biochim Biophys Acta 14 456 1964, Todd & Ulbricht J Chem Soc 3275 1960, Lee et al. J Am Chem Soc 83 1906 1961, Walton et al. J Am Chem Soc 86 2952 1964, Beilstein 26 III/IV 3594.]
References
1) Kim?et al. (2011),?Cordycepin blocks lung injury-associated inflammation and promotes BRCA1-deficient breast cancer cell killing by effectively inhibiting PARP; Mol. Med.?17?893
2) Kondrashov?et al.?(2012),?Inhibition of polyadenylation reduces inflammatory gene induction; RNA?18?2236
3)Yang?et al.?(2017),?Cordycepin inhibits LPS-induced inflammatory response by modulating NOD-Like Receptor Protein 3 inflammasome activation; Biomed. Pharmacother.?95?1777
4) Song?et al.?(2018),?Neuroprotective effects of cordycepin inhibit Aβ-induced apoptosis in hippocampal neurons; Neurotoxicology?68?73
5) Zhang?et al.?(2018),?Cordycepin induces apoptosis in human pancreatic cancer cells via the mitochondrial-mediated intrinsic pathway and suppresses tumor growth in vivo; OncoTargets Ther.?11?4479
6) Li?et al.?(2018),?Cordycepin modulates body weight by reducing prolactin via an adenosine A1 receptor; Curr. Pharm. Des.,?24?3240
7) Wang?et al?(2019)?Cordycepin prevents radiation ulcer by inhibiting cell senescence via NRF2 and SMPK in rodents;?Nat. Commun.?10?2538
8) Wang?et al.?(2020)?The novel application of cordycepin in maintaining stem cell pluripotency and increasing iPS cell generation efficiency; Sci. Rep.?10?2187
