| 词条 | Azaserine |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 456079677 | IUPAC_name = O-(2-Diazoacetyl)-L-serine | image = azaserine.png | tradename = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration = | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion = | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 115-02-6 | ATC_prefix = none | ATC_suffix = | PubChem = 5284344 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 87299V3Q9W | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = D03032 | ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI = 74846 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 1095699 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 16735688 | smiles = O=C(OC[C@H](N)C(O)=O)/C=[N+]=[N-] | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C5H7N3O4/c6-3(5(10)11)2-12-4(9)1-8-7/h1,3H,2,6H2,(H,10,11)/t3-/m0/s1 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = MZZGOOYMKKIOOX-VKHMYHEASA-N | C=5 | H=7 | N=3 | O=4 | molecular_weight = 173.127 g/mol }} 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 ActionAzaserine 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. PropertiesAzaserine 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.{{cn|date=April 2014}} References
2 : Antineoplastic drugs|Diazo compounds |
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