Cordycepin

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

The Uses of Cordycepin

First reported nucleoside antibiotic.

What are the applications of Application

Cordycepin is an anticancer, antifungal nucleoside analog

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.

storage

Store at +4°C

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