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A1882

Sigma-Aldrich

6-Azauridine

Sinônimo(s):

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

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About This Item

Fórmula empírica (Notação de Hill):
C8H11N3O6
Número CAS:
54-25-1
Peso molecular:
245.19
Número CE:
200-199-6
Número MDL:
MFCD00006472
Código UNSPSC:
41106305
ID de substância PubChem:
24890597
NACRES:
NA.51

Ensaio

≥99% (TLC)

Nível de qualidade

200

forma

powder

pf

157-159 °C (lit.)

solubilidade

water: 50 mg/mL, clear, colorless

temperatura de armazenamento

2-8°C

cadeia de caracteres SMILES

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

chave InChI

WYXSYVWAUAUWLD-SHUUEZRQSA-N

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Descrição geral

6-Azauridine is a pyrimidine nucleoside analog.

Aplicação

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

Ações bioquímicas/fisiológicas

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.

Pictogramas

Health hazardExclamation mark
GHS08,GHS07

Palavra indicadora

Warning

Frases de perigo

H302 + H312 + H332,H351

Classificações de perigo

Acute Tox. 4 Oral - Carc. 2

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

dust mask type N95 (US), Eyeshields, Gloves

Certificados de análise (COA)

Busque Certificados de análise (COA) digitando o Número do Lote do produto. Os números de lote e remessa podem ser encontrados no rótulo de um produto após a palavra “Lot” ou “Batch”.

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Sigma-Aldrich

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Drug repurposing screen reveals FDA-approved inhibitors of human HMG-CoA reductase and isoprenoid synthesis that block Cryptosporidium parvum growth
Bessoff K, et al.
Antimicrobial agents and chemotherapy, 57(4), 1804-1814 (2013)
Physiologic medium rewires cellular metabolism and reveals uric acid as an endogenous inhibitor of UMP synthase
Cantor JR, et al.
Cell, 169(2), 258-272 (2017)
Jason Paragas et al.
Antiviral research, 62(1), 21-25 (2004-03-18)
Crimean-Congo hemorrhagic fever virus (CCHFV) is a tick-borne virus that is emerging as a significant human pathogen in many regions of the world, including Africa, Asia, and Europe. In this report, we describe a simple screening method for discovering new
S Briolant et al.
Antiviral research, 61(2), 111-117 (2003-12-13)
Chikungunya virus (CHIKV) and Semliki Forest virus (SFV) were used in our laboratory to screen active antiviral compounds against viruses of the Alphavirus genus. Antiviral activity was estimated by the reduction of the cytopathic effect of each alphavirus on infected
Joo-Hyung Choi et al.
Journal of veterinary science, 19(6), 788-797 (2018-10-12)
In many countries, vaccines are used for the prevention of foot-and-mouth disease (FMD). However, because there is no protection against FMD immediately after vaccination, research and development on antiviral agents is being conducted to induce protection until immunological competence is
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