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Merck

F5130

5-Fluorouridine

≥99% (HPLC), synthetic (organic), powder

Synonyme(s) :

5-Fluorouracil 1β-D-ribofuranoside, FUrd

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A propos de cet article

Formule empirique (notation de Hill) :
C9H11FN2O6
Numéro CAS:
Poids moléculaire :
262.19
NACRES:
NA.51
PubChem Substance ID:
UNSPSC Code:
41106305
EC Number:
206-260-3
MDL number:
Beilstein/REAXYS Number:
33662
Assay:
≥99% (HPLC)
Biological source:
synthetic (organic)
Form:
powder
Solubility:
water: 50 mg/mL, clear to slightly hazy, colorless to faintly yellow
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Nom du produit

5-Fluorouridine, proapoptotic anitproliferative plant growth regulator

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

InChI key

FHIDNBAQOFJWCA-UAKXSSHOSA-N

biological source

synthetic (organic)

assay

≥99% (HPLC)

form

powder

solubility

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

Quality Level

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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.

Biochem/physiol Actions

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

General description

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

Classe de stockage

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves


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Consulter la Bibliothèque de documents

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)
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
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

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