Cordycepin

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Cordycepin
Cordycepin.svg
Names
IUPAC name
9-(3-Deoxy-β-D-ribofuranosyl)adenine
Other names
Cordycepine
3'-Deoxyadenosine
Identifiers
73-03-0 N
ChEMBL ChEMBL305686 N
ChemSpider 6064 N
4630
Jmol 3D model Interactive image
Interactive image
PubChem 6303
Properties
C10H13N5O3
Molar mass 251.25 g·mol−1
Melting point 225.5 °C (437.9 °F; 498.6 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Cordycepin, or 3'-deoxyadenosine, is a derivative of the nucleoside adenosine, differing from the latter by the absence of the hydroxy group in the 3' position of its ribose part. It was initially extracted from the fungus Cordyceps militaris,[1] but is now produced synthetically.

Because cordycepin is similar to adenosine, some enzymes cannot discriminate between the two. Therefore, it can participate in certain biochemical reactions (for example, be incorporated into an RNA molecule, thus causing the premature termination of its synthesis).[2][3]

Cordycepin has displayed cytotoxicity against some leukemic cell lines in vitro, and at least one clinical trial of cordycepin as a leukemia treatment is in progress.[4]

Cordycepin has been found to produce rapid, robust ketamine-like antidepressant effects in animal models of depression, and these effects, similarly to those of ketamine, are dependent on enhancement of AMPA receptor signaling.[5]

See also[edit]

References[edit]

  1. ^ Cunningham, K. G.; Manson, W.; Spring, F. S. & Hutchinson, S. A. (1950). "Cordycepin, a Metabolic Product isolated from Cultures of Cordyceps militaris (Linn.) Link.". Nature 166: 949. doi:10.1038/166949a0. PMID 14796634. 
  2. ^ Siev, M.; Weinberg, R. & Penman, S. (1969). "The selective interruption of nucleolar RNA synthesis in HeLa cells by cordycepin". J. Cell Biol. 41 (2): 510–520. doi:10.1083/jcb.41.2.510. PMC 2107749. PMID 5783871. 
  3. ^ Kondrashov A, Meijer HA, Barthet-Barateig A, Parker HN, Khurshid A, Tessier S, et al. (2012). "Inhibition of polyadenylation reduces inflammatory gene induction". RNA 18 (12): 2236–50. doi:10.1261/rna.032391.112. PMC 3504674. PMID 23118416. 
  4. ^ National Cancer Institute. "Definition of cordycepin". NCI Drug Dictionary. Retrieved 21 December 2015. 
  5. ^ Li, Bai; Hou, Yangyang; Zhu, Ming; Bao, Hongkun; Nie, Jun; Zhang, Grace Y.; Shan, Liping; Yao, Yao; Du, Kai; Yang, Hongju; Li, Meizhang; Zheng, Bingrong; Xu, Xiufeng; Xiao, Chunjie; Du, Jing (2016). "3’-Deoxyadenosine (Cordycepin) Produces a Rapid and Robust Antidepressant Effect via Enhancing Prefrontal AMPA Receptor Signaling Pathway". International Journal of Neuropsychopharmacology 19 (4): pyv112. doi:10.1093/ijnp/pyv112. ISSN 1461-1457.