Azaserine, serine derivative diazo compound  (ab145895)

Overview

  • Product name

    Azaserine, serine derivative diazo compound 
  • Description

    Serine derivative diazo compound with antibiotic, antifungal and antineoplastic properties. Structural analog of glutamine.
  • Alternative names

    • AZS
    • CI-337
    • CN 15757
    • L-azaserine
    • NSC-742
    • O-(2-Diazoacetyl)-L-serine
    • O-diazoacetyl-L-serine
    see all
  • Biological description

    Serine derivative diazo compound with antibiotic, antifungal and antineoplastic properties. Structural analog of glutamine which competes with glutamine in binding to enzymes involved in purine biosynthesis. Inhibits the glutamine-dependent amidotransferases FGAM synthetase and glucosamine-6-phosphate isomerase. Inhibits the rate-limiting step of the hexosamine biosynthesis pathway (HBP) and irreversibly inhibits GGT1 (gamma-Glutamyltranspeptidase). Downregulates the expression of VCAM-1 and ICAM-1 in response to TNF-α. Protects against hyperglycemic endothelial damage through its antioxidant effect independently of inhibiting HBP pathway.

  • Purity

    > 98%
  • CAS Number

    115-02-6
  • Chemical structure

    Chemical Structure

Properties

  • Molecular weight

    173.13
  • Molecular formula

    C5H7N3O4
  • Storage instructions

    Store at +4°C. The product can be stored for up to 12 months.
  • Solubility overview

    Soluble in water

  • Handling

    Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour.

    Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

  • Source

    Synthetic

References

This product has been referenced in:

  • Rajapakse AG  et al. The hexosamine biosynthesis inhibitor azaserine prevents endothelial inflammation and dysfunction under hyperglycemic condition through antioxidant effects. Am J Physiol Heart Circ Physiol 296:H815-22 (2009). Read more (PubMed: 19136606) »
  • Wada K  et al. Crystal structures of Escherichia coli gamma-glutamyltranspeptidase in complex with azaserine and acivicin: novel mechanistic implication for inhibition by glutamine antagonists. J Mol Biol 380:361-72 (2008). Read more (PubMed: 18555071) »
  • Lyons SD  et al. Cytotoxic mechanisms of glutamine antagonists in mouse L1210 leukemia. J Biol Chem 265:11377-81 (1990). Read more (PubMed: 2358467) »

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