Cordycepin

Cordycepin
Names
	IUPAC name 9-(3-Deoxy-β-D-ribofuranosyl)adenine
	Other names Cordycepine; 3'-Deoxyadenosine
Identifiers
CAS Number	73-03-0 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEMBL	ChEMBL305686 ;
ChemSpider	6064 ;
ECHA InfoCard	100.000.720
IUPHAR/BPS	4630;
PubChem CID	6303;
CompTox Dashboard (EPA)	DTXSID1041007 ;
	InChI 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 Key: OFEZSBMBBKLLBJ-BAJZRUMYSA-N ;
	SMILES 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
Chemical formula	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). verify (what is ?) 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]

References

^ 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. {{cite journal}}: Unknown parameter |last-author-amp= ignored (|name-list-style= suggested) (help)
^ 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. {{cite journal}}: Unknown parameter |last-author-amp= ignored (|name-list-style= suggested) (help)
^ Kondrashov A, Meijer HA, Barthet-Barateig A, Parker HN, Khurshid A, Tessier S (2012). "Inhibition of polyadenylation reduces inflammatory gene induction". RNA. 18 (12): 2236–50. doi:10.1261/rna.032391.112. PMC 3504674. PMID 23118416. {{cite journal}}: Unknown parameter |displayauthors= ignored (|display-authors= suggested) (help)
^ National Cancer Institute. "Definition of cordycepin". NCI Drug Dictionary. Retrieved 21 December 2015.
^ 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.

[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. {{cite journal}}: Unknown parameter |last-author-amp= ignored (|name-list-style= suggested) (help)

[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. {{cite journal}}: Unknown parameter |last-author-amp= ignored (|name-list-style= suggested) (help)

[pmid23118416-3] Kondrashov A, Meijer HA, Barthet-Barateig A, Parker HN, Khurshid A, Tessier S (2012). "Inhibition of polyadenylation reduces inflammatory gene induction". RNA. 18 (12): 2236–50. doi:10.1261/rna.032391.112. PMC 3504674. PMID 23118416. {{cite journal}}: Unknown parameter |displayauthors= ignored (|display-authors= suggested) (help)

[4] National Cancer Institute. "Definition of cordycepin". NCI Drug Dictionary. Retrieved 21 December 2015.

[LiHou2016-5] 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.

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See also

References