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F5307

Sigma-Aldrich

5−Fluoro−2′−deoxycytidine

≥98% (HPLC), powder

Sinónimos:

2′-deoxy-5-fluoro-Cytidine, FCDR, FdCyd

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About This Item

Fórmula empírica (notación de Hill):
C9H12FN3O4
Número de CAS:
10356-76-0
Peso molecular:
245.21
MDL number:
MFCD00077348
UNSPSC Code:
12352200
PubChem Substance ID:
329799711
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to off-white

solubility

DMSO: >20 mg/mL

storage temp.

room temp

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

InChI key

IDYKCXHJJGMAEV-RRKCRQDMSA-N

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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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
E De Clercq et al.
Molecular pharmacology, 32(1), 286-292 (1987-08-01)
5-Fluorouracil, 5-fluorouridine (FUrd), 5-fluoro-2'-deoxyuridine (FdUrd), 5-fluorocytidine (FCyd), 5-fluoro-2'-deoxycytidine (FdCyd), 5-trifluoro-2'-deoxythymidine (F3dThd), and the 5'-monophosphates and 3',5'-cyclic monophosphates thereof were found to inhibit thymidine kinase-deficient (TK-) mutant strains of herpes simplex virus (HSV) at a much lower concentration than the wild-type
M Iigo et al.
Cancer chemotherapy and pharmacology, 20(1), 1-4 (1987-01-01)
The plasma concentration of 5-fluorouracil (FUra) following the i.v. administration of FUra and guanosine 5'-monophosphate (GMP) or guanosine 5'-triphosphate (GTP) was markedly elevated. These values were more than 5-fold higher than those obtained with FUra alone over 60 min after
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.
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
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We offer a variety of small molecule research tools, such as transcription factor modulators, inhibitors of chromatin modifying enzymes, and agonists/antagonists for target identification and validation in gene regulation research; a selection of these research tools is shown below.

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