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.
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IUPAC name
2′-Deoxycytidine
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Systematic IUPAC name
4-Amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2(1H)-one | |
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3D model (JSmol)
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ECHA InfoCard | 100.012.231 |
MeSH | Deoxycytidine |
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Properties | |
C9H13N3O4 | |
Molar mass | 227.217 |
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
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Deoxycytidine can be phosphorylated at C5' of the deoxyribose by deoxycytidine kinase, converting it to deoxycytidine monophosphate (dCMP), a DNA precursor.[1] dCMP can be converted to dUMP and dTMP.
It can also be used as a precursor for 5-aza-2′-deoxycytidine, a treatment for MDS patients. This compound slows the cell cycle by interfering with the methylation of the P15/INK4B gene, increasing the expression of P15/INK4B protein which subdues the transformation of MDS to leukemia.[2]
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.[3]