Cordycepin

Source: Wikipedia, the free encyclopedia.
Cordycepin
Names
IUPAC name
3′-Deoxyadenosine
Systematic 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
IUPHAR/BPS
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

3' position with a hydrogen. It was initially extracted from the fungus Cordyceps militaris,[1] but can now be produced synthetically.[2] It is also found in other Cordyceps species as well as Ophiocordyceps sinensis.[3]

Cordycepin is produced in cordyceps as a means of infecting insect populations, due to cordycepin's biological activity[4]

Because cordycepin is similar to adenosine, some enzymes cannot discriminate between the two.[citation needed] It can therefore participate in certain biochemical reactions (for example, 3-dA can trigger the premature termination of mRNA synthesis).[5][6] By acting as an adenosine analog, cordycepin was found to be the most potent molecular circadian clock resetter out of several screened compounds.[7]

Cordycepin has displayed cytotoxicity against some leukemic cell lines in vitro.[8][9][10] Additionally, cordycepin has been shown to display an effect in some types of other cancers, such as lung,[11] renal,[12] colon,[13] and breast cancer.[14] Cordycepin has been shown to reduce viable A549 lung cancer cell populations by 50%.[11]

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.[15]

Cordycepin has been shown to have anti-inflammatory qualities,[16] as well as the ability to defend against injury from cerebral ischemia in mice.[17]

See also

References

  1. PMID 14796634
    .
  2. S2CID 90915876
    .
  3. PMID 19051361
    .
  4. PMID 31890138
    .
  5. PMID 5783871
    .
  6. PMID 23118416
    .
  7. S2CID 218533423
    .
  8. ^ National Cancer Institute (2011-02-02). "Definition of cordycepin". NCI Drug Dictionary. Retrieved 21 December 2015.
  9. PMID 10609556
    .
  10. PMID 25442260
    .
  11. ^
    doi:10.3906/biy-1408-14
    .
  12. PMID 29045468
    .
  13. PMID 23941773
    .
  14. PMID 31454995
    .
  15. PMID 26443809
    .
  16. S2CID 224828245
    .
  17. PMID 21554870
    .
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