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U5377

Sigma-Aldrich

Uracil 1-β-D-arabinofuranoside

lymphoma antiproliferative

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Synonym(s):
Arauridine, Spongouridin, 1-β-D-Arabinofuranosyluracil
Empirical Formula (Hill Notation):
C9H12N2O6
CAS Number:
Molecular Weight:
244.20
Beilstein/REAXYS Number:
28749
EC Number:
MDL number:
UNSPSC Code:
41106305
PubChem Substance ID:
NACRES:
NA.51

biological source

synthetic (organic)

Quality Level

assay

≥98% (HPLC)

form

powder

solubility

water: 50 mg/mL, clear, colorless

storage temp.

−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

InChI key

DRTQHJPVMGBUCF-CCXZUQQUSA-N

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General description

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).

Application

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 Actions

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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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
P Linssen et al.
Journal of chromatography, 223(2), 371-378 (1981-05-08)
A method is described for the determination of 1-beta-D-arabinofuranosylcytosine (Ara-C) and its metabolite 1-beta-D-arabinofuranosyluracil (Ara-U) in human plasma. After deproteinization of the plasma sample, separation is performed by reversed-phase liquid chromatography. For Ara-C concentrations exceeding 0.05 mg/l and for Ara-U
Lubomira Kovalova et al.
Journal of chromatography. A, 1216(7), 1100-1108 (2009-01-13)
A method for solid phase extraction and HPLC-MS/MS of the cytostatics 5-fluorouracil, cytarabine, and gemcitabine and human metabolites uracil 1-beta-d-arabinofuranoside and 2',2'-difluorodeoxyuridine in wastewater was established. Wastewater samples from a Swiss hospital were analyzed for 5-fluorouracil, gemcitabine and 2',2'-difluorodeoxyuridine. The
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

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