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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)

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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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
Edward J Miracco et al.
Journal of the American Chemical Society, 133(31), 11826-11829 (2011-07-13)
The pseudouridine synthase TruB handles 5-fluorouridine in RNA as a substrate, converting it into two isomeric hydrated products. Unexpectedly, the two products differ not in the hydrated pyrimidine ring but in the pentose ring, which is epimerized to arabinose in
Iñigo Casafont et al.
Neurotoxicity research, 17(2), 167-178 (2009-07-18)
The ubiquitin-dependent proteasome system (UPS) is the major pathway responsible for selective nuclear and cytoplasmic protein degradation. Bortezomib, a boronic acid dipeptide, is a reversible 20S proteasome inhibitor used as novel anticancer drug, particularly in the treatment of multiple myeloma
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