Azaserine

Title: Azaserine
CAS Registry Number: 115-02-6
CAS Name: L-Serine diazoacetate (ester)
Additional Names: O-diazoacetyl-L-serine
Manufacturers' Codes: CL-337; CN-15757; P-165
Molecular Formula: C5H7N3O4
Molecular Weight: 173.13
Percent Composition: C 34.69%, H 4.08%, N 24.27%, O 36.97%
Literature References: Antitumor antibiotic produced by Streptomyces sp. Isoln, characterization, and antitumor activity: C. C. Stock et al., Nature 173, 71 (1954); J. Ehrlich et al., ibid. 72; Q. R. Bartz et al., ibid. 72; S. A. Fusari et al., J. Am. Chem. Soc. 76, 2878 (1954). Structural studies: idem et al., ibid. 2881. Synthetic studies: J. A. Moore et al., ibid., 2884; E. D. Nicolaides et al., ibid., 2887; T. J. Curphey, D. S. Daniel, J. Org. Chem. 43, 4666 (1978). Pathology and pharmacology studies: S. S. Sternberg, F. S. Philips, Cancer 10, 889 (1957). Crystal and molecular structure: A. Fitzgerald, L. H. Jensen, Acta Crystallogr. B34, 828 (1978). Review of carcinogenicity studies: IARC Monographs 10, 73-77 (1976). Review: Pettillo, Hunt, Antibiotics vol. 1, D. Gottlieb, P. Shaw, Eds. (Springer-Verlag, New York, 1967) pp 481-493. Use in study of the progression of pancreatic adenocarcinoma in rat models: K. Nagy et al., Histochem. Cell Biol. 119, 405 (2003).
Properties: Light yellow-green needles from aq ethanol, mp 146-162° (dec). [a]D27.5 -0.5° (c = 8.46% in H2O at pH 5.18). uv max (pH 7): 250.5 nm (E1%1cm 1140); in 0.1N NaOH: 252 nm (E1%1cm 1230). Very sol in water; slightly sol in abs methanol, abs ethanol, acetone, but sol in warm aq solns of these solvents. pKa 8.55. LD50 in mice, rats (mg/kg/day): 150, 170 orally (Sternberg, Philips).
Melting point: mp 146-162° (dec)
pKa: pKa 8.55
Optical Rotation: [a]D27.5 -0.5° (c = 8.46% in H2O at pH 5.18)
Absorption maximum: uv max (pH 7): 250.5 nm (E1%1cm 1140)
Toxicity data: LD50 in mice, rats (mg/kg/day): 150, 170 orally (Sternberg, Philips)
Use: Reagent used to induce pancreatic cancer in experimental animal models.
Azasetron Azatadine Azelaic Acid Azelastine Azelnidipine

Azaserine
Azaserine.png
Systematic (IUPAC) name
O-(2-Diazoacetyl)-L-serine
Clinical data
Legal status  ?
Identifiers
CAS number 115-02-6 YesY
ATC code None
PubChem CID 5284344
ChemSpider 16735688 YesY
UNII 87299V3Q9W YesY
KEGG D03032 YesY
ChEBI CHEBI:74846 N
ChEMBL CHEMBL1095699 YesY
Chemical data
Formula C5H7N3O4 
Mol. mass 173.127 g/mol
 N (what is this?)  (verify)

Azaserine is a naturally occurring serine derivative diazo compound with antineoplastic properties, Azaserine functions as a purine antagonist and glutamine analogue (glutamine amidotransferase inhibitor) that competitively inhibits pathways in which glutamine is metabolized. An antibiotic and antitumor agent, Azaserine is used in clinical studies as a potential antineoplastic agent

•Description Azaserine is an inhibitor of the rate limiting step of the hexosamine biosynthethic pathway (HBP) and an irreversible inhibitor of GGT1 (gamma-Glutamyltranspeptidase). Independent of inhibiting the HBP pathway, azarine studies have demonstrated that it can protect against hyperglycemic endothelial damage through its antioxidant effect. Azarine and acivicin (sc-200498), another GGT inhibitor, bind to GGT at its substrate-binding pocket. The compound has been shown to elevate the SOD-2 (manganese-superoxide dismutase (MnSOD)) protein level as well as inhibit the oxidative stress and the expression of VCAM-1 and ICAM-1 in response to TNFα. Research indicates that azaserine has the potential to be used as a probe for identifying the L-(leucine-favoring) system transporter in human T-lymphocytes

•Specifications Purity: ≥98%Physical Appearance: White to yellow to powder•Properties Molecular Weight: 173.127Molecular Formula: C5H7N3O4Form: SolidSolubility: Soluble in water (50 mg/ml), Slightly soluble in methanol, and absolute alcohol.Melting Point: 146-162 °C (dec.)Boling Point: 589.73 °C (Predicted)Vapor Pressure: 1.53 x 10-10 mmHg at 25 °C

References

1. Segel, G.B., et al. 1989. J. Biol. Chem. 264: 16399-16402. PMID 2789219 2. Hull, R.L., et al. 2007. Am. J. Physiol., Cell Physiol. 293: C1586-C1593. PMID 17804609 3. Wada, K., et al. 2008. J. Mol. Biol. 380: 361-372. PMID 18555071 4. Rajapakse, A.G., et al. 2009. Am. J. Physiol. Heart Circ. Physiol. 296: H815-H822. PMID 19136606 5. 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 6. Lebedeva ZI, Kabanova EA, Berezov TT. 1986 Mar;12(3):413-20. 6-diazo-5-oxo-L-norleucine and azaserine as affinity inhibitors of glutamin(asparagin)ase.

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