Azaserine | CAS#115-02-6 | glutamine amidotransferase inhibitor

MedKoo Cat#: 206059 | Name: Azaserine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

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.

Chemical Structure

Azaserine

CAS#115-02-6

Theoretical Analysis

MedKoo Cat#: 206059

Name: Azaserine

CAS#: 115-02-6

Chemical Formula: C5H7N3O4

Exact Mass: 173.0437

Molecular Weight: 173.13

Elemental Analysis: C, 34.69; H, 4.08; N, 24.27; O, 36.97

Price and Availability

Size	Price	Availability
50mg	USD 550.00	2 Weeks
100mg	USD 950.00	2 Weeks
200mg	USD 1,650.00	2 Weeks
500mg	USD 2,550.00	2 Weeks
1g	USD 3,250.00	2 Weeks
2g	USD 5,850.00	2 Weeks

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Synonym

Azaserine; diazoacetate (ester) LSerine; diazoacetylserine; serine diazoacetate. Abbreviations: AZAS; AZS. Code names: CI337; CI 337; CI-337; CN15757; CN 15757; CN-15757; NSC 742; NSC742; NSC-742; O-Diazoacetyl-L-serine

IUPAC/Chemical Name

(S)-2-amino-3-(2-diazoacetoxy)propanoic acid

InChi Key

MZZGOOYMKKIOOX-VKHMYHEASA-N

InChi Code

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

SMILES Code

O=C(O)[C@@H](N)COC(C=[N+]=[N-])=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>5 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 173.13 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Protivinsky R. Azaserine. Antibiot Chemother (1971). 1971;17:95-100. doi: 10.1159/000392366. PMID: 4951003. 2: Azaserine. IARC Monogr Eval Carcinog Risk Chem Man. 1976;10:73-7. PMID: 791808. 3: Catane R, Von Hoff DD, Glaubiger DL, Muggia FM. Azaserine, DON, and azotomycin: three diazo analogs of L-glutamine with clinical antitumor activity. Cancer Treat Rep. 1979 Jun;63(6):1033-8. PMID: 380801. 4: Geisen SM, Aloisi CMN, Huber SM, Sandell ES, Escher NA, Sturla SJ. Direct Alkylation of Deoxyguanosine by Azaserine Leads to O6-Carboxymethyldeoxyguanosine. Chem Res Toxicol. 2021 Jun 21;34(6):1518-1529. doi: 10.1021/acs.chemrestox.0c00471. Epub 2021 Jun 1. PMID: 34061515. 5: COFFEY GL, HILLEGAS AB, KNUDSEN MP, KOEPSELL HJ, OYAAS JE, EHRLICH J. Azaserine: microbiological studies. Antibiot Chemother (Northfield). 1954 Jul;4(7):775-91. PMID: 24543177. 6: Williams-Hill DM, Olesen J, Zucker C, Kubitschek HE. Azaserine: further evidence for DNA damage in Escherichia coli. Mutat Res. 1984 Nov;129(2):153-64. doi: 10.1016/0027-5107(84)90148-9. PMID: 6390189. 7: STERNBERG SS, PHILIPS FS. Azaserine: pathological and pharmacological studies. Cancer. 1957 Sep-Oct;10(5):889-901. doi: 10.1002/1097-0142(195709/10)10:5<889::aid-cncr2820100506>3.0.co;2-t. PMID: 13472634. 8: Morgan RG, Papadimitriou JM, Crass RA. Potentiation of azaserine by cholestyramine in the rat. Int J Exp Pathol. 1990 Aug;71(4):485-91. PMID: 2400737; PMCID: PMC2002277. 9: Wei ZW, Niikura H, Wang M, Ryan KS. Identification of the Azaserine Biosynthetic Gene Cluster Implicates Hydrazine as an Intermediate to the Diazo Moiety. Org Lett. 2023 Jun 9;25(22):4061-4065. doi: 10.1021/acs.orglett.3c01229. Epub 2023 May 26. PMID: 37235858. 10: EHRLICH J, ANDERSON LE, COFFEY GL, HILLEGAS AB, KNUDSEN MP, KOEPSELL HJ, KOHBERGER DL, OYAAS JE. Antibiotic studies of azaserine. Nature. 1954 Jan 9;173(4393):72. doi: 10.1038/173072a0. PMID: 13132876. 11: Mandyam D V, Muthangi S. Survival of silk worm, Bombyx mori in azaserine induced oxidative stress. Comp Biochem Physiol C Toxicol Pharmacol. 2020 Feb;228:108637. doi: 10.1016/j.cbpc.2019.108637. Epub 2019 Oct 23. PMID: 31655299. 12: Kubitschek HE, Sepanski RJ. Azaserine: survival and mutation in Escherichia coli. Mutat Res. 1982 May;94(1):31-8. doi: 10.1016/0027-5107(82)90166-x. PMID: 7048085. 13: Williams MV, Kerr TJ, Lemmon RD, Tritz GJ. Azaserine resistance in Escherichia coli: chromosomal location of multiple genes. J Bacteriol. 1980 Jul;143(1):383-8. doi: 10.1128/jb.143.1.383-388.1980. PMID: 6995438; PMCID: PMC294251. 14: STOCK CC, REILLY HC, BUCKLEY SM, CLARKE DA, RHOADS CP. Azaserine, a new tumour-inhibitory substance; studies with Crocker mouse sarcoma 180. Nature. 1954 Jan 9;173(4393):71-2. doi: 10.1038/173071a0. PMID: 13132875. 15: KAPLAN L, REILLY HC, STOCK CC. Action of azaserine on Escherichia coli. J Bacteriol. 1959 Oct;78(4):511-9. doi: 10.1128/jb.78.4.511-519.1959. PMID: 14404400; PMCID: PMC290578. 16: BARTZ QR, ELDER CC, FROHARDT RP, FUSARI SA, HASKELL TH, JOHANNESSEN DW, RYDER A. Isolation and characterization of azaserine. Nature. 1954 Jan 9;173(4393):72-3. doi: 10.1038/173072b0. PMID: 13132877. 17: Wyngaarden JB. Glutamine phosphoribosylpyrophosphate amidotransferase. Curr Top Cell Regul. 1972;5:135-76. doi: 10.1016/b978-0-12-152805-8.50011-3. PMID: 4358203. 18: Yildiz H, Kalipci E, Oztas H, Yildiz D. Effects of acetylsalicylic acid on rats: An in vivo experimental study in azaserine-rat model. J Cancer Res Ther. 2019 Jan-Mar;15(1):231-236. doi: 10.4103/jcrt.JCRT_1319_16. PMID: 30880783. 19: Fleischman RW, Baker JR, Schaeppi U, Thompson GR, Rosenkrantz H, Cooney DA, Davis RD. Azaserine-induced pathology in dogs. Toxicol Appl Pharmacol. 1972 Aug;22(4):595-606. doi: 10.1016/0041-008x(72)90287-6. PMID: 5045764. 20: Yager JD Jr, Roebuck BD, Zurlo J, Longnecker DS, Weselcouch EO, Wilpone SA. A single-dose protocol for azaserine initiation of pancreatic carcinogenesis in the rat. Int J Cancer. 1981 Nov 15;28(5):601-6. doi: 10.1002/ijc.2910280511. PMID: 6975760.