Azaserine (Synonyms: CI-337,CN 15757,O-Diazoacetyl-L-serine,NSC 742) |
Catalog No.GC14874
One-Click Copy Product Info
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Azaserine is a glutamine antagonist.
Products are for research use only. Not for human use. We do not sell to patients.
Cas No.: 115-02-6
Sample solution is provided at 25 µL, 10mM.
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Azaserine is a glutamine antagonist [1]. Azaserine inhibits glutamine amidotransferase, interfering with the production of purine nucleotides and thereby inhibiting DNA and RNA synthesis [2]. Azaserine inhibits the hexamine biosynthesis pathway, reducing the production of UDP-N-acetylglucosamine and protein O-glycosylation, thereby affecting cellular glucose metabolism and protein post-translational modification [3]. Azaserine is primarily used to treat pancreatic tumors [4].
In R28 cells, Azaserine (0.1μM; 24h) blocks the entry of glucose into the hexosamine biosynthesis pathway (HBP), thereby reversing the inhibition of high glucose on the anti-apoptotic effect of insulin [5]. In Raji cells, Azaserine (5μM; 24h) inhibits cell growth [6].
References:
[1]. Livingston R B, Venditti J M, Cooney D A, et al. Glutamine antagonists in chemotherapy[J]. Advances in Pharmacology, 1971, 8: 57-120.
[2]. SARTORELLI A C, BOOTH B A. Inhibition of the synthesis of thymine nucleotides by azaserine[J]. Molecular Pharmacology, 1967, 3(1): 71-80.
[3]. Rajapakse A G, Ming X F, Carvas J M, et al. The hexosamine biosynthesis inhibitor azaserine prevents endothelial inflammation and dysfunction under hyperglycemic condition through antioxidant effects[J]. American Journal of Physiology-Heart and Circulatory Physiology, 2009, 296(3): H815-H822.
[4]. Longnecker D S, Curphey T J. Adenocarcinoma of the pancreas in azaserine-treated rats[J]. Cancer research, 1975, 35(8): 2249-2257.
[5]. Nakamura M, Barber A J, Antonetti D A, et al. Excessive hexosamines block the neuroprotective effect of insulin and induce apoptosis in retinal neurons[J]. Journal of Biological Chemistry, 2001, 276(47): 43748-43755.
[6]. O'Driscoll M, Macpherson P, Xu Y Z, et al. The cytotoxicity of DNA carboxymethylation and methylation by the model carboxymethylating agent azaserine in human cells[J]. Carcinogenesis, 1999, 20(9): 1855-1862.
| Cell experiment [1]: | |
Cell lines | R28 cells |
Preparation Method | After incubation for 24 hours in 5mM glucose, 20mM glucose, or 5mM glucose plus 1.5mM glucosamine (with or without 10nM insulin or 0.1μM Azaserine), 100mm plates of R28 cells were washed once with ice-cold phosphate buffer and homogenized in 0.5mL of 0.3mM perchloric acid. Cells were pelleted by centrifugation, and the perchloric acid was extracted from the supernatant with two volumes of 1:4 trioctylamine:1,1,2-trichlorofluoroethane. The aqueous phase was stored at −80℃ and analyzed within 5 days. Nucleotide-linked hexoses and hexosamines were separated and determined by anion-exchange high-pressure liquid chromatography. UDP-HexNAc and UDP-hexose were quantified by UV absorption and compared to external standards. |
Reaction Conditions | 0.1μM; 24h |
Applications | Azaserine blocks the entry of glucose into the hexosamine biosynthesis pathway (HBP), thereby reversing the inhibition of high glucose on the anti-apoptotic effect of insulin. |
References: | |
| Cas No. | 115-02-6 | SDF | |
| Synonyms | CI-337,CN 15757,O-Diazoacetyl-L-serine,NSC 742 | ||
| Chemical Name | O-(2-diazoacetyl)-L-serine | ||
| Canonical SMILES | O=C(C=[N+]=[N-])OC[C@H](N)C(O)=O | ||
| Formula | C5H7N3O4 | M.Wt | 173.1 |
| Solubility | ≥ 21.4 mg/mL in Water | Storage | Store at -20°C |
| General tips | Please select the appropriate solvent to prepare the stock solution according to the
solubility of the product in different solvents; once the solution is prepared, please store it in
separate packages to avoid product failure caused by repeated freezing and thawing.Storage method
and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored
at -20°C, please use it within 1 month. To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time. |
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| Shipping Condition | Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request. | ||
| Prepare stock solution | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 5.777 mL | 28.885 mL | 57.7701 mL |
| 5 mM | 1.1554 mL | 5.777 mL | 11.554 mL |
| 10 mM | 577.7 μL | 2.8885 mL | 5.777 mL |
Step 1: Enter information below (Recommended: An additional animal making an allowance for loss during the experiment)
g
μL
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Calculation results:
Working concentration: mg/ml;
Method for preparing DMSO master liquid: mg drug pre-dissolved in μL DMSO ( Master liquid concentration mg/mL, Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug. )
Method for preparing in vivo formulation: Take μL DMSO master liquid, next addμL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL saline, mix and clarify.
Method for preparing in vivo formulation: Take μL DMSO master liquid, next add μL Corn oil, mix and clarify.
Note: 1. Please make sure the liquid is clear before adding the next solvent.
2. Be sure to add the solvent(s) in order. You must ensure that the solution obtained, in the previous addition, is a clear solution before proceeding to add the next solvent. Physical methods such as vortex, ultrasound or hot water bath can be used to aid dissolving.
3. All of the above co-solvents are available for purchase on the GlpBio website.
Quality Control & SDS
- View current batch:
- Purity: >98.00% Appearance: A solid
- COA (Certificate of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Average Rating: 5 (Based on Reviews and 16 reference(s) in Google Scholar.)