Cytidine

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Cytidine
Skeletal formula of cytidine
Ball-and-stick model of the cytidine molecule
Names
IUPAC name
4-​amino-​1-​[3,​4-​dihydroxy-​5-​(hydroxymethyl)​tetrahydrofuran-​2-​yl]​pyrimidin-​2-​one
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.000.555
KEGG
MeSH Cytidine
UNII
Properties
C9H13N3O5
Molar mass 243.217
-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[edit]

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[edit]

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[edit]

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[edit]

  1. ^ a b Jonas DA; Elmadfa I; Engel KH; et al. (2001). "Safety considerations of DNA in food". Ann Nutr Metab. 45 (6): 235–54. PMID 11786646. doi:10.1159/000046734. 
  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. PMID 10974208. doi:10.1016/S0006-2952(00)00436-6. 
  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. 
  5. ^ a b 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. ISSN 1537-744X. doi:10.1100/tsw.2010.65. 

External links[edit]