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U5377

Sigma-Aldrich

Uracil 1-β-D-arabinofuranosid

lymphoma antiproliferative

Synonym(e):

Arauridine, Spongouridin, 1-β-D-Arabinofuranosyluracil

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About This Item

Empirische Formel (Hill-System):
C9H12N2O6
CAS-Nummer:
3083-77-0
Molekulargewicht:
244.20
Beilstein:
28749
EG-Nummer:
221-386-9
MDL-Nummer:
MFCD00065998
UNSPSC-Code:
41106305
PubChem Substanz-ID:
24900655
NACRES:
NA.51

Biologische Quelle

synthetic (organic)

Qualitätsniveau

200

Assay

≥98% (HPLC)

Form

powder

Löslichkeit

water: 50 mg/mL, clear, colorless

Lagertemp.

−20°C

SMILES String

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

InChI

1S/C9H12N2O6/c12-3-4-6(14)7(15)8(17-4)11-2-1-5(13)10-9(11)16/h1-2,4,6-8,12,14-15H,3H2,(H,10,13,16)/t4-,6-,7+,8-/m1/s1

InChIKey

DRTQHJPVMGBUCF-CCXZUQQUSA-N

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Allgemeine Beschreibung

1-β-d-arabinofuranosyluracil (Ara-U) is the detoxification product or metabolite of 1-β-d-arabinofuranosylcytosine (Ara-C). Uracil 1-β-D-arabinofuranoside is the human metabolite of a cytostatic agent called cytarabine (CYT).

Anwendung

Uracil 1-β-D-arabinofuranoside may be used as a reference compound in the analysis of cytostatics and metabolites in hospital wastewater by hydrophilic interaction chromatography/tandem mass spectrometry to demonstrate its analytical possibilities and limitations. It may also be used as a standard for chemical analysis to investigate the ecotoxicity and genotoxicity of cytotoxic antineoplastic drugs, like cytarabine (CYT) and their metabolites, like uracil-1-β-d-arabinofuranoside (AraU).

Biochem./physiol. Wirkung

1-β-D-Arabinofuranosyluracil (ara-U) is capable of inhibiting proliferation of L5178Y mouse lymphoma cells at 17 μM concentration.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)

Analysenzertifikate (COA)

Suchen Sie nach Analysenzertifikate (COA), indem Sie die Lot-/Chargennummer des Produkts eingeben. Lot- und Chargennummern sind auf dem Produktetikett hinter den Wörtern ‘Lot’ oder ‘Batch’ (Lot oder Charge) zu finden.

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Uracil ≥99.0%

Sigma-Aldrich

U0750

Uracil

Methylsulfoxid ≥99%, FG

Sigma-Aldrich

W387520

Methylsulfoxid

Metabolism of 1-beta-D-arabinofuranosyluracil in mouse L5178Y cells.
W E Müller et al.
Cancer research, 39(3), 1102-1107 (1979-03-01)
Radka Zounkova et al.
Chemosphere, 81(2), 253-260 (2010-07-14)
In spite of growing scientific concern about pharmaceuticals in the environment, there is still a lack of information especially with regard to their metabolites. The present study investigated ecotoxicity and genotoxicity of three widely used cytostatic agents 5-fluorouracil (5-FU), cytarabine
Melissa N McCracken et al.
Proceedings of the National Academy of Sciences of the United States of America, 110(5), 1857-1862 (2013-01-16)
Positron emission tomography (PET) reporter genes allow noninvasive whole-body imaging of transplanted cells by detection with radiolabeled probes. We used a human deoxycytidine kinase containing three amino acid substitutions within the active site (hdCK3mut) as a reporter gene in combination
Kai Chen et al.
Nuclear medicine and biology, 39(7), 1019-1025 (2012-04-17)
[(18)F]-FMAU is a PET tracer being evaluated for imaging cell proliferation. Current multi-step procedures of [(18)F]-FMAU synthesis are time-consuming, resulting in low radiochemical yield and inconvenient applications for the clinic. We have previously reported the use of Friedel-Crafts catalysts for
Richard Wiegand et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 891-892, 64-70 (2012-03-14)
A liquid chromatography coupled with tandem mass spectrometry (LC-MS/MS) assay was developed and validated for simultaneous determination of 1-(2'-deoxy-2'-fluoro-β-D-arabinofuranosyl) uracil (FAU) and its active metabolite 1-(2'-deoxy-2'-fluoro-β-D-arabinofuranosyl) 5-methyluracil (FMAU) in human plasma. FAU and FMAU were extracted from plasma samples using
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