|Chemical and physical data|
|Molar mass||173.127 g/mol|
|3D model (JSmol)|
|(what is this?)|
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. Azazerine acts by competitively inhibiting glutamine amidotransferase, a key enzyme responsible for glutamine metabolism.
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.
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.
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- Angana Gupta Rajapakse, Xiu-Fen Ming, João M. Carvas, and Zhihong Yang. The hexosamine biosynthesis inhibitor azaserine prevents endothelial inflammation and dysfunction under hyperglycemic condition through antioxidant effects. http://ajpheart.physiology.org/content/296/3/H815.full
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