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A1882

6-Azauridine

Name: 6-Azauridine
Brand: SIGMA
Price: 75.8 EUR

Sinónimos:

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

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Tamaño de envase	SKU	Disponibilidad	Precio
1 g		Póngase en contacto con nuestro Servicio de Atención al Cliente para disponibilidad	75,80 €
5 g		Póngase en contacto con nuestro Servicio de Atención al Cliente para disponibilidad	351,00 €

Acerca de este artículo

Fórmula empírica (notación de Hill):

C₈H₁₁N₃O₆

Número CAS:

54-25-1

Peso molecular:

245.19

NACRES:

NA.51

PubChem Substance ID:

24890597

UNSPSC Code:

41106305

EC Number:

200-199-6

MDL number:

MFCD00006472

Assay:

≥99% (TLC)

Form:

powder

Solubility:

water: 50 mg/mL, clear, colorless

Storage temp.:

2-8°C

75,80 €

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Propiedades

assay

≥99% (TLC)

Quality Segment

200

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

Descripción

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.[1] It inhibits RNA viruses like chikungunya virus, semliki forest virus, and human coronavirus. It significantly inhibits the growth of Cryptosporidium parasites.

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Este artículo	A1757	A4036	C4654
Sigma-Aldrich A1882 6-Azauridine	Sigma-Aldrich A1757 6-Azauracil	Sigma-Aldrich A4036 Adenosine	Sigma-Aldrich C4654 Cytidine
Quality Level 200	Quality Level 100	Quality Level 300	Quality Level 300
assay ≥99% (TLC)	assay ≥98%	assay ≥99% (HPLC)	assay ≥99%
form powder	form powder	form powder	form powder
storage temp. 2-8°C	storage temp. -	storage temp. 2-8°C	storage temp. -
solubility water: 50 mg/mL, clear, colorless	solubility 1 M NH4OH: 50 mg/mL, clear to slightly hazy, colorless to light yellow-green	solubility 1 M NH4OH: 50 mg/mL, clear, colorless	solubility H₂O: 50 mg/mL
mp 157-159 °C (lit.)	mp 274-275 °C (lit.)	mp 234-236 °C (lit.)	mp 210-220 °C (dec.) (lit.)