Cytidine

Cytidine
Names
	IUPAC name 4-amino-1-[3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2-one
Identifiers
CAS Number	65-46-3 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:17562 ;
ChEMBL	ChEMBL95606 ;
ChemSpider	5940 ;
ECHA InfoCard	100.000.555
IUPHAR/BPS	4728;
KEGG	D07769 ;
MeSH	Cytidine
PubChem CID	6175;
UNII	5CSZ8459RP ;
	InChI InChI=1S/C9H13N3O5/c10-5-1-2-12(9(16)11-5)8-7(15)6(14)4(3-13)17-8/h1-2,4,6-8,13-15H,3H2,(H2,10,11,16)/t4-,6-,7-,8-/m1/s1 Key: UHDGCWIWMRVCDJ-XVFCMESISA-N ; InChI=1/C9H13N3O5/c10-5-1-2-12(9(16)11-5)8-7(15)6(14)4(3-13)17-8/h1-2,4,6-8,13-15H,3H2,(H2,10,11,16)/t4-,6-,7-,8-/m1/s1 Key: UHDGCWIWMRVCDJ-XVFCMESIBD;
	SMILES O=C1/N=C(/N)\C=C/N1[C@@H]2O[C@@H]([C@@H](O)[C@H]2O)CO;
Properties
Chemical formula	C9H13N3O5
Molar mass	243.217
Magnetic susceptibility (χ)	-123.7·10−6 cm3/mol
	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

Cytidine is a nucleoside molecule that is formed when cytosine is attached to a ribose ring (also known as a ribofuranose) via a β-N₁-glycosidic bond. Cytidine is a component of RNA.

If cytosine is attached to a deoxyribose ring, it is known as a deoxycytidine.

Dietary sources

Dietary sources of cytidine include foods with high RNA (ribonucleic acid) content,^[1] such as organ meats, Brewer's yeast, as well as pyrimidine-rich foods such as beer. During digestion, RNA-rich foods are broken-down into ribosyl pyrimidines (cytidine and uridine), which are absorbed intact.^[1] In humans, dietary cytidine is converted into uridine,^[2] which is probably the compound behind cytidine's metabolic effects.

Cytidine analogues

There are a variety of cytidine analogues with potentially useful pharmacology. For example, KP-1461 is an anti-HIV agent that works as a viral mutagen,^[3] and zebularine exists in E. coli and is being examined for chemotherapy. Low doses of azacitidine and its analog decitabine have shown results against cancer through epigenetic demethylation.^[4]

Biological actions

In addition to its role as a pyrimidine component of RNA, cytidine has been found to control neuronal-glial glutamate cycling, with supplementation decreasing midfrontal/cerebral glutamate/glutamine levels.^[5] As such, cytidine has generated interest as a potential glutamatergic antidepressant drug.^[5]

References

1 2 Jonas DA; Elmadfa I; Engel KH; et al. (2001). "Safety considerations of DNA in food". Ann Nutr Metab. 45 (6): 235–54. doi:10.1159/000046734. PMID 11786646.
↑ Wurtman RJ, Regan M, Ulus I, Yu L (Oct 2000). "Effect of oral CDP-choline on plasma choline and uridine levels in humans". Biochem. Pharmacol. 60 (7): 989–92. doi:10.1016/S0006-2952(00)00436-6. PMID 10974208.
↑ John S. James. "New Kind of Antiretroviral, KP-1461". AIDS Treatment News.
↑ "Scientists reprogram cancer cells with low doses of epigenetic drugs". Medical XPress. March 22, 2012.
1 2 Machado-Vieira, Rodrigo; Salvadore, Giacomo; DiazGranados, Nancy; Ibrahim, Lobna; Latov, David; Wheeler-Castillo, Cristina; Baumann, Jacqueline; Henter, Ioline D.; Zarate, Carlos A. (2010). "New Therapeutic Targets for Mood Disorders". The Scientific World Journal. 10: 713–726. doi:10.1100/tsw.2010.65. ISSN 1537-744X.

External links

Cytidine MS Spectrum

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[Jonas-1] 1 2 Jonas DA; Elmadfa I; Engel KH; et al. (2001). "Safety considerations of DNA in food". Ann Nutr Metab. 45 (6): 235–54. doi:10.1159/000046734. PMID 11786646.

[2] Wurtman RJ, Regan M, Ulus I, Yu L (Oct 2000). "Effect of oral CDP-choline on plasma choline and uridine levels in humans". Biochem. Pharmacol. 60 (7): 989–92. doi:10.1016/S0006-2952(00)00436-6. PMID 10974208.

[3] John S. James. "New Kind of Antiretroviral, KP-1461". AIDS Treatment News.

[4] "Scientists reprogram cancer cells with low doses of epigenetic drugs". Medical XPress. March 22, 2012.

[Machado-VieiraSalvadore2010-5] 1 2 Machado-Vieira, Rodrigo; Salvadore, Giacomo; DiazGranados, Nancy; Ibrahim, Lobna; Latov, David; Wheeler-Castillo, Cristina; Baumann, Jacqueline; Henter, Ioline D.; Zarate, Carlos A. (2010). "New Therapeutic Targets for Mood Disorders". The Scientific World Journal. 10: 713–726. doi:10.1100/tsw.2010.65. ISSN 1537-744X.