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F5130

Sigma-Aldrich

5-Fluoruridin

proapoptotic anitproliferative plant growth regulator

Synonym(e):

5-Fluor-uracil-1β-D-ribofuranosid, FUrd

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About This Item

Empirische Formel (Hill-System):
C9H11FN2O6
CAS-Nummer:
316-46-1
Molekulargewicht:
262.19
Beilstein:
33662
EG-Nummer:
206-260-3
MDL-Nummer:
MFCD00036832
UNSPSC-Code:
41106305
PubChem Substanz-ID:
24894883
NACRES:
NA.51

Biologische Quelle

synthetic (organic)

Qualitätsniveau

100

Assay

≥99% (HPLC)

Form

powder

Löslichkeit

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

SMILES String

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

InChIKey

FHIDNBAQOFJWCA-UAKXSSHOSA-N

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Allgemeine Beschreibung

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

Anwendung

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.

Biochem./physiol. Wirkung

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

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves

Analysenzertifikate (COA)

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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
Olaf H Temmink et al.
The international journal of biochemistry & cell biology, 39(3), 565-575 (2006-11-14)
Thymidine phosphorylase (TP) and uridine phosphorylase (UP) are often upregulated in solid tumors and catalyze the phosphorolysis of natural (deoxy)nucleosides and a wide variety of fluorinated pyrimidine nucleosides. Because the relative contribution of each of the two enzymes to these
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