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Merck

F5130

Sigma-Aldrich

5-Fluorouridine

proapoptotic anitproliferative plant growth regulator

Sinónimos:

5-Fluorouracil 1β-D-ribofuranoside, FUrd

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About This Item

Fórmula empírica (notación de Hill):
C9H11FN2O6
Número de CAS:
Peso molecular:
262.19
Beilstein:
33662
Número CE:
Número MDL:
Código UNSPSC:
41106305
ID de la sustancia en PubChem:
NACRES:
NA.51

origen biológico

synthetic (organic)

Nivel de calidad

Ensayo

≥99% (HPLC)

Formulario

powder

solubilidad

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

cadena 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

Clave InChI

FHIDNBAQOFJWCA-UAKXSSHOSA-N

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Descripción general

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

Aplicación

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.

Acciones bioquímicas o fisiológicas

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

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

Eyeshields, Gloves


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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
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
Mingjie Chen et al.
The Plant cell, 23(8), 2991-3006 (2011-08-11)
Nucleotides are synthesized from de novo and salvage pathways. To characterize the uridine salvage pathway, two genes, UKL1 and UKL2, that tentatively encode uridine kinase (UK) and uracil phosphoribosyltransferase (UPRT) bifunctional enzymes were studied in Arabidopsis thaliana. T-DNA insertions in
Ales Obrdlik et al.
Nucleus (Austin, Tex.), 2(1), 72-79 (2011-06-08)
In mammals actin contributes to transcription elongation by facilitating establishment of permissive chromatin. Here we report that the F-actin severing protein cofilin-1 is part of the same complex with actin and phosphorylated RNA polymerase (pol) II. In chromatin immunoprecipitation assays

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