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A1882

Sigma-Aldrich

6-Azauridine

Synonyma:

2-β-D-Ribofuranosyl-1,2,4-triazine-3,5(2H,4H)-dione, 6-Azauracil riboside

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About This Item

Empirický vzorec (Hillův zápis):
C8H11N3O6
Číslo CAS:
54-25-1
Molekulová hmotnost:
245.19
EC Number:
200-199-6
MDL number:
MFCD00006472
UNSPSC Code:
41106305
PubChem Substance ID:
24890597
NACRES:
NA.51

assay

≥99% (TLC)

form

powder

mp

157-159 °C (lit.)

solubility

water: 50 mg/mL, clear, colorless

storage temp.

2-8°C

SMILES string

OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N2N=CC(=O)NC2=O

InChI

1S/C8H11N3O6/c12-2-3-5(14)6(15)7(17-3)11-8(16)10-4(13)1-9-11/h1,3,5-7,12,14-15H,2H2,(H,10,13,16)/t3-,5-,6-,7-/m1/s1

InChI key

WYXSYVWAUAUWLD-SHUUEZRQSA-N

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General description

6-Azauridine is a pyrimidine nucleoside analog.

Application

6-Azauridine (AzUrd) blocks the conversion of orotic acid into UMP and it is used in antiviral studies.
6-Azauridine has been used:
  • in uridine monophosphate synthase (UMPS) activity assay
  • as an antiviral agent to study its inhibition effect and cytotoxic potential on foot and mouth disease virus
  • to screen for anticryptosporidial activity
  • in the pretreatment of HeLa cells to study its effect on inhibition of cellular uridine synthesis before and during chase with 5-bromouridine 5′-triphosphate (BrUTP)
  • as a reference compound for comparing the antiviral activity and cytotoxic activity against viral host cell lines

Biochem/physiol Actions

6-azauridine is a prodrug, upon conversion to 6-aza-UMP, inhibits uridine monophosphate synthase (UMPS). It is a broad spectrum anti-metabolite. It interferes with pyrimidine biosynthesis and affects the cellular nucleic acid levels. It is considered as a antineoplastic metabolite. It inhibits RNA viruses like chikungunya virus, semliki forest virus, and human coronavirus. It significantly inhibits the growth of Cryptosporidium parasites.

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Osvědčení o analýze (COA)

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Enhanced inhibition of foot-and-mouth disease virus by combinations of porcine interferon-alpha and antiviral agents
Kim SM, et al.
Antiviral research, 96(2), 213-220 (2012)
Krzysztof Pyrc et al.
Antimicrobial agents and chemotherapy, 50(6), 2000-2008 (2006-05-26)
Human coronavirus NL63 (HCoV-NL63), a recently discovered member of the Coronaviridae family, has spread worldwide and is associated with acute respiratory illness in young children and elderly and immunocompromised persons. Further analysis of HCoV-NL63 pathogenicity seems warranted, in particular because
Jean Marc Crance et al.
Antiviral research, 58(1), 73-79 (2003-04-30)
Ribavirin, interferon-alpha (IFN-alpha), 6-azauridine and glycyrrhizin were tested in vitro for their antiviral activities against 11 pathogenic flaviviruses belonging to principal antigenic complexes or individual serogroups of medical importance: dengue, Japanese encephalitis, mammalian tick-borne and yellow fever virus (YFV) groups.
Donald F Smee et al.
Journal of virological methods, 246, 51-57 (2017-04-01)
Studies were conducted to determine the performance of four dyes in assessing antiviral activities of compounds against three RNA viruses with differing cytopathogenic properties. Dyes included alamarBlue
Takashi Kobayashi et al.
Physical chemistry chemical physics : PCCP, 12(19), 5140-5148 (2010-05-07)
Excited state characteristics of 6-azauridine (6AUd), which is known as a medicine against psoriasis and neoplastic, were investigated with laser plash photolysis, time-resolved thermal lensing, and near IR single photon counting method. The triplet-triplet absorption spectrum of 6AUd was observed
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