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Merck
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Documenti

A4142

Sigma-Aldrich

Azaserine

≥98% (TLC)

Sinonimo/i:

O-Diazoacetyl-L-serine

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About This Item

Formula empirica (notazione di Hill):
C5H7N3O4
Numero CAS:
115-02-6
Peso molecolare:
173.13
Beilstein:
1726602
Numero CE:
204-061-6
Numero MDL:
MFCD00036802
Codice UNSPSC:
12352209
ID PubChem:
24890830
NACRES:
NA.26

Livello qualitativo

100

Saggio

≥98% (TLC)

Forma fisica

powder

Colore

off-white to yellow-green

Spettro attività antibiotica

fungi

Modalità d’azione

enzyme | inhibits

Temperatura di conservazione

−20°C

Stringa SMILE

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
MZZGOOYMKKIOOX-VKHMYHEASA-N

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Categorie correlate

Descrizione generale

Chemical structure: amino acid derivatives

Applicazioni

Used in cell culture for the selection of HGPRT revertants.

Azioni biochim/fisiol

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.

Pittogrammi

Skull and crossbonesHealth hazard
GHS06,GHS08

Avvertenze

Danger

Indicazioni di pericolo

H301,H351

Consigli di prudenza

P201 - P301 + P310 + P330

Classi di pericolo

Acute Tox. 3 Oral - Carc. 2

Codice della classe di stoccaggio

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

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

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

Certificati d'analisi (COA)

Cerca il Certificati d'analisi (COA) digitando il numero di lotto/batch corrispondente. I numeri di lotto o di batch sono stampati sull'etichetta dei prodotti dopo la parola ‘Lotto’ o ‘Batch’.

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Sigma-Aldrich

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Sigma-Aldrich

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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
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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
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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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