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F5130

Sigma-Aldrich

5-Fluorouridine

proapoptotic anitproliferative plant growth regulator

Synonyme(s) :

5-Fluorouracil 1β-D-ribofuranoside, FUrd

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About This Item

Formule empirique (notation de Hill):
C9H11FN2O6
Numéro CAS:
316-46-1
Poids moléculaire :
262.19
Numéro Beilstein :
33662
Numéro CE :
206-260-3
Numéro MDL:
MFCD00036832
Code UNSPSC :
41106305
ID de substance PubChem :
24894883
Nomenclature NACRES :
NA.51

Source biologique

synthetic (organic)

Niveau de qualité

100

Pureté

≥99% (HPLC)

Forme

powder

Solubilité

water: 50 mg/mL, clear to slightly hazy, colorless to faintly yellow

Chaîne SMILES 

OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N2C=C(F)C(=O)NC2=O

InChI

1S/C9H11FN2O6/c10-3-1-12(9(17)11-7(3)16)8-6(15)5(14)4(2-13)18-8/h1,4-6,8,13-15H,2H2,(H,11,16,17)/t4-,5-,6-,8-/m1/s1

Clé InChI

FHIDNBAQOFJWCA-UAKXSSHOSA-N

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Description générale

5-Fluorouridine (FUrd) is a fluoropyrimidine nucleoside analog and a cell-permeable modified RNA precursor.

Application

5-Fluorouridine has been used for labeling active transcription sites in the porcine fetal fibroblasts and human cell lines for immunocytochemistry analysis. It has also been used to monitor apoptosis during drug sensitivity assay in esophageal squamous cell carcinoma (ESCC) cells.

Actions biochimiques/physiologiques

5-Fluorouridine (FUrd) is cytotoxic towards cancer cells. FUrd is often used in chemical and biochemical comparison studies with fluorouracil and thymine analogs.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves

Certificats d'analyse (COA)

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Inhibition of RNA synthesis by 5-fluorouridine accounts for its cyto toxicity on colorectal cancer cells in vitro
Subbarayan PR, et al.
Cancer research, 65(9) (2005)
P V Sahasrabudhe et al.
Nucleic acids research, 23(19), 3916-3921 (1995-10-11)
The effects of 5-fluorouridine (FUrd) and 5-fluorodeoxyuridine (FdUrd) substitution on the stabilities of duplex RNA and DNA have been studied to determine how FUrd substitution in nucleic acids may alter the efficiency of biochemical processes that require complementary base pairing
Angelica M Bello et al.
Journal of medicinal chemistry, 52(6), 1648-1658 (2009-03-06)
A series of 6-substituted and 5-fluoro-6-substituted uridine derivatives were synthesized and evaluated for their potential as anticancer agents. The designed molecules were synthesized from either fully protected uridine or the corresponding 5-fluorouridine derivatives. The mononucleotide derivatives were used for enzyme
P M Ellery et al.
Placenta, 30(4), 329-334 (2009-02-14)
The aim was to test for evidence of transcriptional activity within the nuclei of the syncytiotrophoblast of the human placenta. The syncytiotrophoblast forms the epithelial covering of the villous tree, and is a multinucleated, terminally-differentiated syncytium generated through fusion of
Nikolaos Tsesmetzis et al.
Cancers, 10(7) (2018-07-26)
Antimetabolites, in particular nucleobase and nucleoside analogues, are cytotoxic drugs that, starting from the small field of paediatric oncology, in combination with other chemotherapeutics, have revolutionised clinical oncology and transformed cancer into a curable disease. However, even though combination chemotherapy
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