| Size | Price | Stock | Qty |
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| 10mg |
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| Targets |
L-Albizziin primarily targets two key enzymes in glutamine metabolism: glutaminase and glutaminyl-tRNA synthetase . The compound acts as a glutamase inhibitor, interfering with the utilization of L-glutamine by the enzyme, likely in a competitive and reversible manner since L-albizziin itself can also serve as a substrate of the enzyme . Importantly, studies indicate that the glutamine-binding site involved in the regulation of glutamine synthetase activity is not the active site of the enzyme, as albizziin inhibited neither the transferase nor the synthetase activity of glutamine synthetase in cell-free extracts . This suggests the compound's biological effects are mediated through a distinct regulatory binding site.
Glutaminase (from Debaryomyces spp. CECT 11815). It acts as both a substrate and a reversible competitive inhibitor of the enzyme. [1] |
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| ln Vitro |
L-albizziin is a starch-based reagent that functions as an enzyme glutaminase [1]. L-Albizziin has demonstrated multiple in vitro biological activities. As a glutaminase inhibitor, it suppresses the activity of 4-methyleneglutaminase with an IC50 of 20 mM for the peanut enzyme . The compound exhibits phytotoxic effects, decreasing frond production of duckweed (Lemna minor) with an LD50 value between 25 and 50 µM . Additionally, L-albizziin has shown antiviral activity against Newcastle disease virus and herpes infections . In hepatoma tissue culture cells, albizziin functions as an antagonist that prevents the effect of glutamine on glutamine synthetase activity, with effects that are reversible and have little impact on glutamine transport or protein synthesis .
L-Albizziin is hydrolysed by the purified glutaminase from Debaryomyces spp. at a relative activity of 9.2% compared to L-glutamine (100%), when tested at 10 mM concentration in the standard assay medium (50 mM Tris-HCl, pH 8.5, 37°C). [1] The compound inhibits glutaminase activity in a concentration-dependent manner. At 2 mM, the enzyme retains 86.8% of its relative activity; at 5 mM, relative activity is 73.3%; and at 10 mM, relative activity decreases to 57.9% (corresponding to approximately 42% inhibition). Inhibition is likely competitive and reversible because L-Albizziin is also a substrate of the enzyme. [1] |
| ln Vivo |
The compound is primarily utilized for cancer research applications as a glutaminase inhibitor, given the role of glutamine metabolism in tumor cell proliferation . The compound's natural occurrence in higher plants suggests it may play a role in plant defense or metabolic regulation, though detailed in vivo animal efficacy studies are not extensively documented in the provided references.
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| Enzyme Assay |
Glutaminase inhibition assays can be performed using purified glutaminase enzyme preparations. A representative protocol based on related studies: Prepare reaction buffer containing L-glutamine as substrate (typically 10-50 mM) in an appropriate buffer system (e.g., 50 mM Tris-HCl, pH 8.0-8.5). Add varying concentrations of L-albizziin (0-20 mM) to the reaction mixture. Initiate the reaction by adding purified glutaminase enzyme. Incubate at 37°C for 15-60 minutes. Terminate the reaction by adding trichloroacetic acid or heat inactivation. Quantify the product (L-glutamate or ammonia) using colorimetric assays (e.g., Nessler's reagent for ammonia) or HPLC. Calculate the IC50 value from dose-response curves. Control reactions without inhibitor and without enzyme should be included for background correction .
To determine the substrate activity of L-Albizziin, the purified glutaminase was incubated at 37°C in a standard assay medium containing 50 mM Tris-HCl buffer (pH 8.5) and 10 mM L-Albizziin. The reaction was stopped by adding acetic acid to a final concentration of 0.2 M. The ammonia generated from the hydrolysis was measured via a coupled reaction using glutamate dehydrogenase and NADH oxidation, following the change in absorbance at 340 nm. One unit of enzyme activity was defined as the amount that generates 1 nmol of product per minute at 37°C. [1] For inhibition studies, the glutaminase activity was assayed under the same standard conditions (50 mM Tris-HCl, pH 8.5, 10 mM L-glutamine, 37°C) in the presence of varying concentrations of L-Albizziin (2, 5, and 10 mM). The L-glutamate produced was quantified using a colorimetric method coupled with glutamate dehydrogenase, phenazine methosulphate, and iodonitrotetrazolium chloride (INT); the amount of INT-formazan was measured at 490 nm. Controls without the inhibitor were run simultaneously. The relative activity was calculated as a percentage of the control activity. [1] |
| Cell Assay |
Cellular assays for L-albizziin have been described using hepatoma tissue culture cells . A representative protocol: Culture hepatoma cells in appropriate medium containing glutamine. Treat cells with L-albizziin at varying concentrations (typically 0-20 mM) for defined periods (e.g., 4-24 hours). Assess glutamine synthetase activity in cell lysates or measure glutamine transport using radiolabeled [³H]-glutamine. The effects of albizziin on glutamine synthetase activity can be evaluated by pre-incubating cells with glutamine (10-20 mM) in the presence or absence of albizziin, then measuring enzyme activity in cell-free extracts. Since albizziin's effects are reversible, washout experiments can be performed to confirm the reversibility of inhibition .
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| Animal Protocol |
Based on its mechanism of action as a glutaminase inhibitor for cancer research , a standard xenograft model protocol can be adapted: Establish subcutaneous tumors in immunocompromised mice (e.g., using hepatoma or other glutamine-dependent cancer cell lines). When tumors reach approximately 100-150 mm³, randomize animals into treatment groups. Administer L-albizziin via intraperitoneal or intravenous routes at doses determined from preliminary toxicity studies (typical starting range: 10-100 mg/kg). Monitor tumor volume every 2-3 days using calipers, body weight as a toxicity indicator, and collect plasma/tissue samples for pharmacokinetic and pharmacodynamic analysis. Compare tumor growth inhibition rates between treatment and control groups.
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| ADME/Pharmacokinetics |
Specific pharmacokinetic parameters (e.g., half-life, Cmax, AUC, bioavailability, clearance) for L-albizziin are not available in the provided search results. However, the compound's solubility characteristics have been documented: it is soluble in water at 50 mg/mL and also soluble in DMSO . Storage recommendations include -20°C for powder form (stable for up to 3 years) and -80°C for solutions (stable for up to 6 months) . As a polar amino acid derivative, L-albizziin likely exhibits limited passive diffusion across biological membranes and may require active transport mechanisms for cellular uptake.
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| Toxicity/Toxicokinetics |
L-Albizziin is classified as a research-use-only compound not for human therapeutic or diagnostic applications . The compound exhibits phytotoxic effects with an LD50 of 25-50 µM in duckweed (Lemna minor), indicating its biological activity at relatively low concentrations in plant systems . In mammalian cell culture studies, albizziin demonstrates reversible effects with little impact on glutamine transport or protein synthesis at tested concentrations, suggesting manageable toxicity profiles in vitro . No specific data on acute toxicity (LD50), chronic toxicity, genotoxicity, or reproductive toxicity is available from the provided references. Standard safety precautions include handling in well-ventilated areas, wearing appropriate personal protective equipment (gloves, lab coat, safety glasses), and avoiding inhalation, ingestion, or skin contact.
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| References | |
| Additional Infomation |
L-Albizziine is a non-protein L-α-amino acid. It has been reported to exist in Acacia paradoxa, Mariosousa millefolia, and other organisms with relevant data.
L-Albizziin is an L-glutamine analogue that interferes with the utilisation of L-glutamine by the Debaryomyces spp. glutaminase. Unlike DON (6-diazo-5-oxo-L-norleucine), which is an irreversible inhibitor, L-Albizziin acts in a competitive and reversible manner, as it is also a substrate of the enzyme. The compound is included as a reference inhibitor for glutamine-requiring enzymes. [1] |
| Molecular Formula |
C4H9N3O3
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|---|---|
| Molecular Weight |
147.13
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| Exact Mass |
147.064
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| Elemental Analysis |
C, 32.65; H, 6.17; N, 28.56; O, 32.62
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| CAS # |
1483-07-4
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| PubChem CID |
92891
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| Appearance |
White to off-white solid powder
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| Density |
1.43 g/cm3
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| Boiling Point |
359.1ºC at 760 mmHg
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| Melting Point |
217°C (dec.)
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| Flash Point |
171ºC
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| Vapour Pressure |
3.95E-06mmHg at 25°C
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| Index of Refraction |
1.55
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| LogP |
-4.6
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
10
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| Complexity |
147
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| Defined Atom Stereocenter Count |
1
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| SMILES |
C([C@@H](C(=O)O)N)NC(=O)N
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| InChi Key |
GZYFIMLSHBLMKF-REOHCLBHSA-N
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| InChi Code |
InChI=1S/C4H9N3O3/c5-2(3(8)9)1-7-4(6)10/h2H,1,5H2,(H,8,9)(H3,6,7,10)/t2-/m0/s1
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| Chemical Name |
(S)-2-amino-3-ureidopropanoic acid
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| Synonyms |
Albizziin; L-Albizziin; L-Albizziine; L-beta-Ureidoalanine; Albizzine; NSC-132089; NSC132089; 1483-07-4; Albizzine; L-2-Amino-3-ureidopropionic acid; (2S)-2-amino-3-(carbamoylamino)propanoic acid; NSC 132089
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
H2O : ~50 mg/mL (~339.84 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: 33.33 mg/mL (226.53 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.
(Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 6.7967 mL | 33.9836 mL | 67.9671 mL | |
| 5 mM | 1.3593 mL | 6.7967 mL | 13.5934 mL | |
| 10 mM | 0.6797 mL | 3.3984 mL | 6.7967 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution 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 stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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