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Documenti

A1882

Sigma-Aldrich

6-Azauridine

Sinonimo/i:

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

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About This Item

Formula empirica (notazione di Hill):
C8H11N3O6
Numero CAS:
54-25-1
Peso molecolare:
245.19
Numero CE:
200-199-6
Numero MDL:
MFCD00006472
Codice UNSPSC:
41106305
ID PubChem:
24890597
NACRES:
NA.51

Saggio

≥99% (TLC)

Forma fisica

powder

Punto di fusione

157-159 °C (lit.)

Solubilità

water: 50 mg/mL, clear, colorless

Temperatura di conservazione

2-8°C

Stringa SMILE

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
WYXSYVWAUAUWLD-SHUUEZRQSA-N

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Descrizione generale

6-Azauridine is a pyrimidine nucleoside analog.

Applicazioni

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

Azioni biochim/fisiol

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.

Pittogrammi

Health hazardExclamation mark
GHS08,GHS07

Avvertenze

Warning

Indicazioni di pericolo

H302 + H312 + H332,H351

Classi di pericolo

Acute Tox. 4 Oral - Carc. 2

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

dust mask type N95 (US), Eyeshields, Gloves

Certificati d'analisi (COA)

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The American journal of physiology, 243(3), E234-E239 (1982-09-01)
Ketonemic states complicating late pregnancy are accompanied by lower brain weights in the newborn. Potential mechanisms whereby ketone bodies might inhibit cell proliferation were therefore examined in the fetal rat brain slice by measuring their impact on the de novo
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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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Kim SM, et al.
Antiviral research, 96(2), 213-220 (2012)
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Antimicrobial agents and chemotherapy, 50(6), 2000-2008 (2006-05-26)
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Donald F Smee et al.
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