Editing Deoxycytidine

{{Chembox
| verifiedrevid = 460776018
| ImageFile = Desoxycytidin.svg
| ImageSize = 150px
| ImageAlt = Skeletal formula of deoxycytidine
| ImageFile1 = Deoxycytidine 3D ball.png
| ImageAlt1 = Ball-and-stick model of the deoxycytidine molecule
| IUPACName = 2′-Deoxycytidine
| SystematicName = 4-Amino-1-[(2''R'',4''S'',5''R'')-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2(1''H'')-one
| OtherNames = 
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 13117
| InChI = 1/C9H13N3O4/c10-7-1-2-12(9(15)11-7)8-3-5(14)6(4-13)16-8/h1-2,5-6,8,13-14H,3-4H2,(H2,10,11,15)/t5-,6+,8+/m0/s1
| InChIKey = CKTSBUTUHBMZGZ-SHYZEUOFBO
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C9H13N3O4/c10-7-1-2-12(9(15)11-7)8-3-5(14)6(4-13)16-8/h1-2,5-6,8,13-14H,3-4H2,(H2,10,11,15)/t5-,6+,8+/m0/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = CKTSBUTUHBMZGZ-SHYZEUOFSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo=951-77-9
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 0W860991D6
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 66115
| PubChem=13711
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 15698
| SMILES = c1cn(c(=O)nc1N)[C@H]2C[C@@H]([C@H](O2)CO)O
| MeSHName=Deoxycytidine
  }}
|Section2={{Chembox Properties
| Formula=C<sub>9</sub>H<sub>13</sub>N<sub>3</sub>O<sub>4</sub>
| MolarMass=227.217
| Appearance=
| Density=
| MeltingPt=
| BoilingPt=
| Solubility=
  }}
|Section3={{Chembox Hazards
| MainHazards=
| FlashPt=
| AutoignitionPt =
  }}
}}
'''Deoxycytidine''' is a [[deoxyribonucleoside]], a component of [[deoxyribonucleic acid]].  It is similar to the [[ribonucleoside]] [[cytidine]], but with one [[hydroxyl]] group removed from the C2' position.

Deoxycytidine can be phosphorylated at C5' of the [[deoxyribose]] by [[deoxycytidine kinase]], converting it to [[deoxycytidine monophosphate]] (dCMP), a DNA precursor.<ref>{{cite book | vauthors = Staub M, Eriksson S | chapter = The Role of Deoxycytidine Kinase in DNA Synthesis and Nucleoside Analog Activation|date=2006 | title = Deoxynucleoside Analogs In Cancer Therapy|pages=29–52 | veditors = Peters GJ |series=Cancer Drug Discovery and Development|publisher=Humana Press|language=en|doi=10.1007/978-1-59745-148-2_2|isbn=978-1-59745-148-2 }}</ref> dCMP can be converted to dUMP and dTMP.

It can also be used as a precursor for [[5-aza-2′-deoxycytidine]], a treatment for [[Myelodysplastic_syndrome|MDS]] patients. This compound slows the cell cycle by interfering with the [[DNA methylation|methylation]] of the P15/INK4B gene, increasing the expression of P15/INK4B protein which subdues the transformation of MDS to [[leukemia]].<ref>{{cite book | vauthors = Kim KW, Roh JK, Wee HJ, Kim C | chapter =Molecular Targeted Anticancer Drugs|date=2016 | title =Cancer Drug Discovery: Science and History |pages=175–238 | veditors = Kim KW, Roh JK, Wee HJ, Kim C |publisher=Springer Netherlands |language=en |doi=10.1007/978-94-024-0844-7_9|isbn=978-94-024-0844-7 }}</ref>

Deoxycytidine can also serve as a biomarker for tumor diagnosis. Deoxycytidine can be used as a biomarker for breast cancer patients and healthy individuals. 5-(Hydroxymethyl)-2′-deoxycytidine (5-hmdC), 5-(formyl)-2′-deoxycytidine (5-fodC), and 5-(carboxyl)-2′-deoxycytidine (5-cadC) are intermediates in the DNA demethylation pathway and can act as biomarkers. 5-hmdC levels were significantly reduced in urine samples of breast cancer patients, while 5-fodC and 5-cadC levels were elevated.<ref>{{Cite journal |last1=Guo |first1=Mengzhe |last2=Zhang |first2=Liyan |last3=Du |first3=Yan |last4=Du |first4=Wencheng |last5=Liu |first5=Dantong |last6=Guo |first6=Cheng |last7=Pan |first7=Yuanjiang |last8=Tang |first8=Daoquan |date=2018-03-20 |title=Enrichment and Quantitative Determination of 5-(Hydroxymethyl)-2′-deoxycytidine, 5-(Formyl)-2′-deoxycytidine, and 5-(Carboxyl)-2′-deoxycytidine in Human Urine of Breast Cancer Patients by Magnetic Hyper-Cross-Linked Microporous Polymers Based on Polyionic Liquid |url=https://pubs.acs.org/doi/10.1021/acs.analchem.7b04755 |journal=Analytical Chemistry |language=en |volume=90 |issue=6 |pages=3906–3913 |doi=10.1021/acs.analchem.7b04755 |pmid=29316399 |issn=0003-2700}}</ref>
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== References ==
{{Reflist}}

{{Nucleobases, nucleosides, and nucleotides}}

[[Category:Nucleosides]]
[[Category:Pyrimidones]]
[[Category:Hydroxymethyl compounds]]