Azaserine

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Azaserine
Azaserine.svg
Clinical data
ATC code
  • none
Identifiers
  • O-(2-Diazoacetyl)-L-serine
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.003.692 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C5H7N3O4
Molar mass 173.128 g·mol−1
3D model (JSmol)
  • O=C(OC[C@H](N)C(O)=O)/C=[N+]=[N-]
  • 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 Yes check.svgY
  • Key:MZZGOOYMKKIOOX-VKHMYHEASA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Azaserine is a naturally occurring serine derivative diazo compound with antineoplastic and antibiotic properties deriving from its action as a purinergic antagonist and structural similarity to glutamine. Azaserine acts by competitively inhibiting glutamine amidotransferase, a key enzyme responsible for glutamine metabolism.

Contents

Mechanism of Action

Azaserine inhibits the rate limiting step of the metabolic hexosamine pathway and irreversibly inhibits γ-glutamyltransferase by acting directly at the substrate-binding pocket. Independent of hexosamine pathway inhibition, azaserine has been demonstrated to protect against hyperglycemic endothelial damage by elevating serum concentrations of manganese-superoxide dismutase, directly reducing the concentration of reactive oxygen species.

Azaserine also downregulates the expression of VCAM-1 and ICAM-1 in response to TNF-α, and research indicates that it may have potential in identifying the L-leucine-favoring system transporter in human T-lymphocytes.

Properties

Azaserine has a solubility of 50 mg/mL in water, a melting point of 146-162 °C, a vapor pressure of 1.53x10−10mmHg at 25 °C, and decomposes before melting.[ citation needed ]

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References