cytidine

{{chembox

| Watchedfields = changed

| verifiedrevid = 443554948

| ImageFile = Cytidin.svg

| ImageSize = 150px

| ImageAlt = Skeletal formula of cytidine

| ImageFile1 = Cytidine 3D ball.png

| ImageAlt1 = Ball-and-stick model of the cytidine molecule

| IUPACName = Cytidine

| SystematicName = 4-Amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2(1H)-one

| OtherNames = 4-Amino-1-β-D-ribofuranosyl-2(1H)-pyrimidinone{{cite book | author=William M. Haynes | title=CRC Handbook of Chemistry and Physics | edition=97th | year=2016 | publisher=CRC Press | location=Boca Raton | isbn=978-1-4987-5429-3 | pages=3–140 | url=https://books.google.com/books?id=VVezDAAAQBAJ}}
4-Amino-1-[3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2-one

|Section1={{Chembox Identifiers

| IUPHAR_ligand = 4728

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 5940

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D07769

| 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

| InChIKey = UHDGCWIWMRVCDJ-XVFCMESIBD

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 95606

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = UHDGCWIWMRVCDJ-XVFCMESISA-N

| CASNo=65-46-3

| CASNo_Ref = {{cascite|correct|CAS}}

| PubChem=6175

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 5CSZ8459RP

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 17562

| SMILES = O=C1/N=C(/N)\C=C/N1[C@@H]2O[C@@H]([C@@H](O)[C@H]2O)CO

| MeSHName=Cytidine

}}

|Section2={{Chembox Properties

| C=9 | H=13 | N=3 | O=5

| MolarMass=243.217

| Appearance= white, crystalline powder{{cite book | author=Robert A. Lewis, Michael D. Larrañaga, Richard J. Lewis Sr. | title=Hawley's Condensed Chemical Dictionary | edition=16th | year=2016 | publisher=John Wiley & Sons, Inc. | location=Hoboken, New Jersey | isbn=978-1-118-13515-0 | page=688}}

| Density=

| MeltingPt=230 °C (decomposes)

| BoilingPt=

| Solubility=

| MagSus = −123.7·10⁻⁶ cm³/mol

}}

|Section3={{Chembox Hazards

| MainHazards=

| FlashPt=

| AutoignitionPt =

}}

Cytidine (symbol C or Cyd) 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. It is a white water-soluble solid that is only slightly soluble in ethanol.

Dietary sources

Dietary sources of cytidine include foods with high RNA (ribonucleic acid) content,{{cite journal |author=Jonas DA |title=Safety considerations of DNA in food |journal=Ann Nutr Metab |volume=45 |issue=6 |pages=235–54 |year=2001 |pmid=11786646 |url=http://content.karger.com/produktedb/produkte.asp?typ=fulltext&file=anm45235 |doi=10.1159/000046734 |author2=Elmadfa I |author3=Engel KH |display-authors=3 |last4=Heller |first4=K.J. |last5=Kozianowski |first5=G. |last6=kÖNig |first6=A. |last7=mÜLler |first7=D. |last8=Narbonne |first8=J.F. |last9=Wackernagel |first9=W.|doi-access=free }} 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. In humans, dietary cytidine is converted into uridine,{{cite journal |vauthors=Wurtman RJ, Regan M, Ulus I, Yu L |title=Effect of oral CDP-choline on plasma choline and uridine levels in humans |journal=Biochem. Pharmacol. |volume=60 |issue=7 |pages=989–92 |date=Oct 2000 |pmid=10974208 |doi=10.1016/S0006-2952(00)00436-6|s2cid=18687483 }} which is probably the compound behind cytidine's metabolic effects.

Cytidine analogues

A variety of cytidine analogues are known, some with potentially useful pharmacology. For example, KP-1461 is an anti-HIV agent that works as a viral mutagen,{{cite web | url = http://www.aidsnews.org/2007/10/kp-1461.html | title = New Kind of Antiretroviral, KP-1461 | author = John S. James | publisher = AIDS Treatment News | access-date = 2012-03-23 | archive-url = https://web.archive.org/web/20190330230051/http://www.aidsnews.org/2007/10/kp-1461.html | archive-date = 2019-03-30 | url-status = dead }} 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.{{cite web | url = http://medicalxpress.com/news/2012-03-scientists-reprogram-cancer-cells-doses.html | title = Scientists reprogram cancer cells with low doses of epigenetic drugs | date = March 22, 2012 | publisher = Medical XPress}}

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.{{cite journal|last1=Machado-Vieira|first1=Rodrigo|last2=Salvadore|first2=Giacomo|last3=DiazGranados|first3=Nancy|last4=Ibrahim|first4=Lobna|last5=Latov|first5=David|last6=Wheeler-Castillo|first6=Cristina|last7=Baumann|first7=Jacqueline|last8=Henter|first8=Ioline D.|last9=Zarate|first9=Carlos A.|title=New Therapeutic Targets for Mood Disorders|journal=The Scientific World Journal|volume=10|year=2010|pages=713–726|issn=1537-744X|doi=10.1100/tsw.2010.65|pmid=20419280|pmc=3035047 |doi-access=free }} As such, cytidine has generated interest as a potential glutamatergic antidepressant drug.

Related compounds

Deoxycytidine is cytosine attached to a deoxyribose.

Properties

References

External links

[https://web.archive.org/web/20160303223452/http://gmd.mpimp-golm.mpg.de/Spectrums/2af6fe93-60d8-48bf-95c0-9b1dde66da88.aspx Cytidine MS Spectrum]

Category:Nucleosides

Category:Pyrimidones

Category:Hydroxymethyl compounds