Cordycepin

From Wikipedia, the free encyclopedia
Jump to navigation Jump to search
Cordycepin
Cordycepin.svg
Names
IUPAC name
3′-Deoxyadenosine
Preferred IUPAC name
(2S,3R,5S)-2-(6-Amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolan-3-ol
Other names
Cordycepine
9-(3-Deoxy-β-D-ribofuranosyl)adenine
3-dA
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.000.720 Edit this at Wikidata
UNII
  • 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 ☒N
    Key: OFEZSBMBBKLLBJ-BAJZRUMYSA-N ☒N
  • O[C@@H]1C[C@@H](CO)O[C@H]1N2C(N=CN=C3N)=C3N=C2
  • n2c1c(ncnc1n(c2)[C@@H]3O[C@@H](C[C@H]3O)CO)N
Properties
C10H13N5O3
Molar mass 251.246 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).
☒N verify (what is checkY☒N ?)

Cordycepin, or 3'-deoxyadenosine, is a derivative of the nucleoside adenosine, differing from the latter by the replacement of the hydroxy group in the 3' position with a hydrogen. It was initially extracted from the fungus Cordyceps militaris,[1] but can now be produced synthetically. It is also found in other Cordyceps species as well as Ophiocordyceps sinensis.[2]

Because cordycepin is similar to adenosine, some enzymes cannot discriminate between the two. It can therefore participate in certain biochemical reactions (for example, 3-dA can trigger the premature termination of mRNA synthesis).[3][4] By acting as an adenosine analog, cordycepin was found to be the most potent molecular circadian clock resetter out of several screened compounds.[5]

Cordycepin has displayed cytotoxicity against some leukemic cell lines in vitro.[6]

Cordycepin has been found to produce rapid, robust imipramine-like antidepressant effects in animal models of depression, and these effects, similarly to those of imipramine, are dependent on enhancement of AMPA receptor signaling.[7]

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 (4231): 949. Bibcode:1950Natur.166..949C. doi:10.1038/166949a0. PMID 14796634.
  2. ^ Zhou, X; Luo, L; Dressel, W; Shadier, G; Krumbiegel, D; Schmidtke, P; Zepp, F; Meyer, CU (2008). "Cordycepin is an immunoregulatory active ingredient of Cordyceps sinensis". The American Journal of Chinese Medicine. 36 (5): 967–80. doi:10.1142/S0192415X08006387. PMID 19051361.
  3. ^ 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.
  4. ^ 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.
  5. ^ Ju, Dapeng; Zhang, Wei; Yan, Jiawei; Zhao, Haijiao; Li, Wei; Wang, Jiawen; Liao, Meimei; Xu, Zhancong; Wang, Zhiqiang; Zhou, Guanshen; Mei, Long; Hou, Nannan; Ying, Shuhua; Cai, Tao; Chen, She; Xie, Xiaowen; Lai, Luhua; Tang, Chao; Park, Noheon; Takahashi, Joseph S.; Huang, Niu; Qi, Xiangbing; Zhang, Eric Erquan (6 May 2020). "Chemical perturbations reveal that RUVBL2 regulates the circadian phase in mammals". Science Translational Medicine. 12 (542): eaba0769. doi:10.1126/scitranslmed.aba0769. PMID 32376767. S2CID 218533423.
  6. ^ National Cancer Institute (2011-02-02). "Definition of cordycepin". NCI Drug Dictionary. Retrieved 21 December 2015.
  7. ^ 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. PMC 4851261. PMID 26443809.