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Documentos Principais

A4142

Sigma-Aldrich

Azaserine

≥98% (TLC)

Sinônimo(s):

O-Diazoacetyl-L-serine

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About This Item

Fórmula empírica (Notação de Hill):
C5H7N3O4
Número CAS:
Peso molecular:
173.13
Beilstein:
1726602
Número CE:
Número MDL:
Código UNSPSC:
12352209
ID de substância PubChem:
NACRES:
NA.26

Nível de qualidade

Ensaio

≥98% (TLC)

Formulário

powder

cor

off-white to yellow-green

espectro de atividade do antibiótico

fungi

Modo de ação

enzyme | inhibits

temperatura de armazenamento

−20°C

cadeia de caracteres SMILES

N[C@@H](COC(=O)C=[N+]=[N-])C(O)=O

InChI

1S/C5H7N3O4/c6-3(5(10)11)2-12-4(9)1-8-7/h1,3H,2,6H2,(H,10,11)/t3-/m0/s1

chave InChI

MZZGOOYMKKIOOX-VKHMYHEASA-N

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Descrição geral

Chemical structure: amino acid derivatives

Aplicação

Used in cell culture for the selection of HGPRT revertants.

Ações bioquímicas/fisiológicas

Azaserine is an antibiotic and antifungal; it may also act as a tumor inducer. It is a structural analog of glutamine and competes with glutamine in binding to enzymes involved in purine biosynthesis. Azaserine inhibits purine biosynthesis by covalently reacting with cysteine residues in the enzyme active sites, such as in formylglycinamide ribonucleotide amidotransferase and PRPP amidotransferase. Azaserine can induce DNA damage via the formation of carboxymethylated bases and O6-methylguanine. Secretion of exo-1,3-β-glucanase and germ-tube formation of Candida albicans were inhibited by azaserine.

Pictogramas

Skull and crossbonesHealth hazard

Palavra indicadora

Danger

Frases de perigo

Declarações de precaução

Classificações de perigo

Acute Tox. 3 Oral - Carc. 2

Código de classe de armazenamento

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges


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Sigma-Aldrich

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Sigma-Aldrich

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Formaldeído

Timea Beleznai et al.
Vascular pharmacology, 56(3-4), 115-121 (2011-12-14)
We hypothesized that under high glucose conditions, activation of the hexosamine pathway leads to impaired nitric oxide (NO)-dependent arteriolar dilation. Skeletal muscle arterioles (diameter: ~160μm) isolated from male Wistar rats were exposed to normal glucose (NG, 5.5mmol/L) or high glucose
S P Ram et al.
Journal of general microbiology, 130(5), 1227-1236 (1984-05-01)
Exo-(1----3)-beta-glucanase, beta-glucosidase, autolysin and trehalase were assayed in situ in Candida albicans during yeast growth, starvation and germ-tube formation. Cell viability, germ-tube formation, intracellular glucose-6-phosphate dehydrogenase and beta-glucosidase were unaffected in cells incubated in 0.1 M-HC1 for 15 min at
Kornberg, A., and Baker, T.
DNA Replication, 57-60 (1992)
Tusty-Jiuan Hsieh et al.
The Journal of endocrinology, 183(3), 535-550 (2004-12-14)
We reported previously that insulin inhibits the stimulatory effect of high glucose on the expression of angiotensinogen (ANG) gene in both rat immortalized renal proximal tubular cells (IRPTCs) and non-diabetic rat renal proximal tubular cells (RPTCs), but has no effect
Angana Gupta Rajapakse et al.
American journal of physiology. Heart and circulatory physiology, 296(3), H815-H822 (2009-01-13)
Hexosamine biosynthetic pathway (HBP) accounts for some cardiovascular adverse effects of hyperglycemia. We investigated whether the HBP inhibitor azaserine protects against hyperglycemia-induced endothelial damage dependently of HBP. Human endothelial cells isolated from umbilical veins were exposed either to a high

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