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F5307

Sigma-Aldrich

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:
10356-76-0
Molecular Weight:
245.21
MDL number:
MFCD00077348
UNSPSC Code:
12352200
PubChem Substance ID:
329799711
NACRES:
NA.77

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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D A Boothman et al.
Cancer research, 47(9), 2354-2362 (1987-05-01)
The metabolic products formed and incorporated into the nucleic acids (RNA and DNA) of mice bearing Lewis lung carcinoma (LLC) following optimal doses of 5-fluorouracil (FUra), 5-fluoro-2'-deoxyuridine (FdUrd), and 5-fluoro-2'-deoxycytidine (FdCyd) coadministered with tetrahydrouridine (H4Urd), a potent inhibitor of cytidine
D J Baker et al.
Biochemical and biophysical research communications, 196(2), 864-871 (1993-10-29)
A new class of affinity labels has been developed for human DNA (cytosine-5) methyltransferases. These oligodeoxynucleotides contain 5-fluorodeoxycytidine at a mispair within the recognition motif of the human enzyme. They were not effectively recognized by bacterial methyltransferases. They can be
Avik K Ghosh et al.
Journal of the American Chemical Society, 128(13), 4172-4173 (2006-03-30)
Oxidation of a guanine nucleobase to its radical cation in DNA oligomers causes an increase in the acidity of the N1 imino proton that may lead to its spontaneous transfer to N3 of the paired cytosine. This proton transfer is
B Vandamme et al.
Human genetics, 79(4), 341-346 (1988-08-01)
The modes of action of 5-fluoro-2'-deoxyuridine (FdUrd) and 5-fluoro-2'-deoxycytidine (FdCyd) were studied in PHA-stimulated lymphocytes from normal volunteer donors and a fragile X patient. In both cell types, FdUrd and FdCyd inhibited cell proliferation at concentrations of 3 x 10(-8)
S Greer et al.
International journal of radiation oncology, biology, physics, 32(4), 1059-1069 (1995-07-15)
To extend our findings in previous radiation and biochemical studies with five rodent tumors, in which we used one and occasionally two or three irradiations. The extent of control of the EMT-6 mammary adenocarcinoma was determined using fractionated radiation (12
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