951-77-9 Usage
Description
2'-Deoxycytidine is a deoxyribonucleotide that is used in the synthesis of DNA. 2'-Deoxycytidine has been shown to inhibit the kinase activity of IL-2 receptor and Toll-like receptor, which are proteins that regulate the immune response. 2'-Deoxycytidine also inhibits DNA polymerase activity and thermal expansion, which may make it a good candidate as an anticancer drug.
Chemical Properties
White crystalline powder
Uses
2?-Deoxycytidine (deoxyC) is one of the deoxynucleosides which after phosphorylation to dCTP is used to synthesis DNA via various DNA polymerases or reverse transcriptases. 2?-Deoxycytidine (deoxyC) is the substrate for deoxycytidine deaminase (EC 3.5.4.14) which converts it into 2?-deoxyuridine. 2?-Deoxycytidine is phosphorylated to the nucleotide dCMP by the enzyme deoxycytidine kinase (DCK).
Definition
ChEBI: A pyrimidine 2'-deoxyribonucleoside having cytosine as the nucleobase.
General Description
2′-Deoxycytidine (deoxyC) is one of the deoxynucleosides containing cytosine as the nucleobase. It is found in the blood, feces, and urine.
Biological Activity
2-deoxycytidine is a cytidine analog [1].2-deoxycytidine prevents dna methylation by incorporating itself into newly synthesizing dna strand. 2-deoxycytidine also binds to dna methyltransferase irreversibly and hinders its activity. thus, 2-deoxycytidine was approved as the most efective demethylating agent for the treatment of cancer [1].2-deoxycytidine at clinically achievable and nontoxic concentrations (≥ 100 μmol/l) protected normal bone marrow progenitor cells against the inhibitory effects of co-administered, high concentrations of 3’-azido-3’-deoxythymidine (azt) (≥ 10 μmol/l). in normal bone marrow mononuclear cells (bmmc), 2-deoxycytidine also significantly corrected azt-mediated depletion of intracellular thymidine triphosphate and 2-deoxycytidine triphosphate levels. furthermore, 2-deoxycytidine reduced the intracellular accumulation of azt triphosphate and its dna incorporation in bmmc [2].in a rat model of myocardial infarction induced by ligating left anterior descending coronary artery, human umbilical cord mesenchymal stem cells treated with 2-deoxycytidine (5, 10, 20 and 40 μm) before transplantation to the left ventricular wall immediately after ligation significantly improved the cardiac systolic and diastolic functions, and pumping ability. fibrotic area and left ventricular wall thickness were also significantly improved [1].[1]. ali s r, ahmad w, naeem n, et al. small molecule 2'-deoxycytidine differentiates human umbilical cord-derived mscs into cardiac progenitors in vitro and their in vivo xeno-transplantation improves cardiac function. molecular and cellular biochemistry, 2020, 470(1-2): 99-113.[2]. bhalla k, birkhofer m, li g r, et al. 2'-deoxycytidine protects normal human bone marrow progenitor cells in vitro against the cytotoxicity of 3'-azido-3'-deoxythymidine with preservation of antiretroviral activity. blood, 1989, 74(6): 1923-1928.
Biochem/physiol Actions
2′-Deoxycytidine (deoxyC) forms dCTP upon phosphorylation which is used to synthesis DNA via various DNA polymerases or reverse transcriptases. DeoxyC is the substrate for deoxycytidine deaminase (EC 3.5.4.14) which converts it into 2′-deoxyuridine. DeoxyC is phosphorylated to the nucleotide dCMP by the enzyme deoxycytidine kinase (DCK). DeoxyC serves as a potential head and neck cancer marker.
Safety Profile
Experimental
reproductive effects. Mutation data
reported. When heated to decomposition it
emits toxic fumes of NOx.
Check Digit Verification of cas no
The CAS Registry Mumber 951-77-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 9,5 and 1 respectively; the second part has 2 digits, 7 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 951-77:
(5*9)+(4*5)+(3*1)+(2*7)+(1*7)=89
89 % 10 = 9
So 951-77-9 is a valid CAS Registry Number.
951-77-9Relevant articles and documents
Synthesis of novel pyrimidine nucleoside analogues
De Napoli,Mayol,Piccialli,et al.
, p. 1401 - 1403 (1986)
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Solid-phase synthesis and structural characterisation of phosphoroselenolate-modified DNA: A backbone analogue which does not impose conformational bias and facilitates SAD X-ray crystallography
Conlon, Patrick F.,Eguaogie, Olga,Wilson, Jordan J.,Sweet, Jamie S. T.,Steinhoegl, Julian,Englert, Klaudia,Hancox, Oliver G. A.,Law, Christopher J.,Allman, Sarah A.,Tucker, James H. R.,Hall, James P.,Vyle, Joseph S.
, p. 10948 - 10957 (2019/12/23)
Oligodeoxynucleotides incorporating internucleotide phosphoroselenolate linkages have been prepared under solid-phase synthesis conditions using dimer phosphoramidites. These dimers were constructed following the high yielding Michaelis-Arbuzov (M-A) reaction of nucleoside H-phosphonate derivatives with 5′-deoxythymidine-5′-selenocyanate and subsequent phosphitylation. Efficient coupling of the dimer phosphoramidites to solid-supported substrates was observed under both manual and automated conditions and required only minor modifications to the standard DNA synthesis cycle. In a further demonstration of the utility of M-A chemistry, the support-bound selenonucleoside was reacted with an H-phosphonate and then chain extended using phosphoramidite chemistry. Following initial unmasking of methyl-protected phosphoroselenolate diesters, pure oligodeoxynucleotides were isolated using standard deprotection and purification procedures and subsequently characterised by mass spectrometry and circular dichroism. The CD spectra of both modified and native duplexes derived from self-complementary sequences with A-form, B-form or mixed conformational preferences were essentially superimposable. These sequences were also used to study the effect of the modification upon duplex stability which showed context-dependent destabilisation (-0.4 to-3.1 °C per phosphoroselenolate) when introduced at the 5′-Termini of A-form or mixed duplexes or at juxtaposed central loci within a B-form duplex (-1.0 °C per modification). As found with other nucleic acids incorporating selenium, expeditious crystallisation of a modified decanucleotide A-form duplex was observed and the structure solved to a resolution of 1.45 ?. The DNA structure adjacent to the modification was not significantly perturbed. The phosphoroselenolate linkage was found to impart resistance to nuclease activity.
Dehalogenation of Halogenated Nucleobases and Nucleosides by Organoselenium Compounds
Mondal, Santanu,Mugesh, Govindasamy
, p. 1773 - 1780 (2019/01/10)
Halogenated nucleosides, such as 5-iodo-2′-deoxyuridine and 5-iodo-2′-deoxycytidine, are incorporated into the DNA of replicating cells to facilitate DNA single-strand breaks and intra- or interstrand crosslinks upon UV irradiation. In this work, it is shown that the naphthyl-based organoselenium compounds can mediate the dehalogenation of halogenated pyrimidine-based nucleosides, such as 5-X-2′-deoxyuridine and 5-X-2′-deoxycytidine (X=Br or I). The rate of deiodination was found to be significantly higher than that of the debromination for both nucleosides. Furthermore, the deiodination of iodo-cytidines was found to be faster than that of iodo-uridines. The initial rates of the deiodinations of 5-iodocytosine and 5-iodouracil indicated that the nature of the sugar moiety influences the kinetics of the deiodination. For both the nucleobases and nucleosides, the deiodination and debromination reactions follow a halogen-bond-mediated and addition/elimination pathway, respectively.
