F5307
5−Fluoro−2′−deoxycytidine
≥98% (HPLC), powder
Synonym(s):
2′-deoxy-5-fluoro-Cytidine, FCDR, FdCyd
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About This Item
Empirical Formula (Hill Notation):
C9H12FN3O4
CAS Number:
Molecular Weight:
245.21
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352200
MDL number:
InChI key
IDYKCXHJJGMAEV-RRKCRQDMSA-N
SMILES string
NC1=NC(=O)N(C=C1F)[C@H]2C[C@H](O)[C@@H](CO)O2
InChI
1S/C9H12FN3O4/c10-4-2-13(9(16)12-8(4)11)7-1-5(15)6(3-14)17-7/h2,5-7,14-15H,1,3H2,(H2,11,12,16)/t5-,6+,7+/m0/s1
assay
≥98% (HPLC)
form
powder
color
white to off-white
solubility
DMSO: >20 mg/mL
storage temp.
room temp
Quality Level
Related Categories
Biochem/physiol Actions
5-Fluoro-2′-deoxycytidine is a mechanism based DNMT (DNA cytosine-5 methyltransferase) inhibitor, that forms a covalent link with the cysteine residue in the active site of DNMT.
Features and Benefits
This compound is a featured product for Gene Regulation research. Click here to discover more featured Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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D A Boothman et al.
Cancer research, 47(9), 2344-2353 (1987-05-01)
Treatment of C57BL X DBA/2 F (hereafter called BD2F) mice bearing ascitic mammary adenocarcinoma-755 (ADC-755) with [3H]-5-fluoro-2'-deoxycytidine ([3H]FdCyd) plus tetrahydrouridine (H4Urd) resulted in antimetabolite pool sizes indicative of a tumor-selective, dual pathway metabolism of FdCyd via both cytidine deaminase and
Duoli Guo et al.
AAPS PharmSciTech, 11(1), 247-252 (2010-02-13)
In vivo, the DNA methyltransferase inhibitor, 5-fluoro-2'-deoxycytidine (FdCyd, NSC-48006), is rapidly converted to its unwanted metabolites. Tetrahydrouridine (THU, NSC-112907), a cytidine deaminase inhibitor can block the first metabolic step in FdCyd catabolism. Clinical studies have shown that co-administration with THU
G Ia Sheflian et al.
Biokhimiia (Moscow, Russia), 58(11), 1806-1811 (1993-11-01)
Cleavage by restriction endonucleases MvaI kappa EcoRII of DNA duplexes, in which the internal deoxycytidine in one of the strands of the recognition site is substituted for 5-fluorodeoxycytidine, has been studied. It has been found that the modified strands of
Theodore C Jessop et al.
Bioorganic & medicinal chemistry letters, 19(23), 6784-6787 (2009-10-20)
A series of deoxycytidine kinase inhibitors was simultaneously optimized for potency and PK properties. A co-crystal structure then allowed merging this series with a high throughput screening hit to afford a highly potent, selective and orally bioavailable inhibitor, compound 10.
J A Yoder et al.
Journal of molecular biology, 270(3), 385-395 (1997-07-18)
The mechanisms that establish and maintain methylation patterns in the mammalian genome are very poorly understood, even though perturbations of methylation patterns lead to a loss of genomic imprinting, ectopic X chromosome inactivation, and death of mammalian embryos. A family
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