| Size | Price | Stock | Qty |
|---|---|---|---|
| 5g |
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| Other Sizes |
| Targets |
Proline-binding sites in protein synthesis [1][2][3]
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|---|---|
| ln Vitro |
Azetidine-2-carboxylic acid (375-5oo μg/day) was integrated into collagen produced in vitro from chick embryo cartilage [3].
In cultured chick embryo skin fibroblasts, Azetidine-2-carboxylic acid competitively substituted proline in newly synthesized collagen. At equimolar concentration (5 mM) with proline, its incorporation rate reached 32% of proline uptake, resulting in collagen with reduced thermal stability (melting point decreased by 8°C) and disrupted tertiary structure [3] In neuronal cell cultures, Azetidine-2-carboxylic acid (1-10 mM) inhibited proline incorporation into proteins in a concentration-dependent manner. At 10 mM, proline incorporation was reduced by 58%, leading to misfolded protein accumulation in the endoplasmic reticulum and increased expression of ER stress markers (GRP78 upregulated by 2.3-fold, CHOP upregulated by 1.8-fold) [2] |
| ln Vivo |
In 3-day-old chick embryos, Azetidine-2-carboxylic acid (10 mg/egg via yolk sac injection) arrested collagen accumulation in skin, bone, and connective tissues. By day 7, embryonic growth was retarded by 40%, with skin collagen content reduced by 62% compared to controls. Surviving embryos showed skeletal deformities (shortened limbs, abnormal rib cages) due to defective extracellular matrix [3]
In rats fed a diet containing 0.5% w/w Azetidine-2-carboxylic acid for 4 weeks, the compound was detected in liver (12.3 μg/g tissue), kidney (8.7 μg/g tissue), brain (4.2 μg/g tissue), and muscle (2.1 μg/g tissue), indicating systemic distribution [1] A hypothesis suggests dietary intake of Azetidine-2-carboxylic acid leads to misincorporation into human myelin proteins. This causes myelin instability and demyelination, a key pathological feature of multiple sclerosis [2] |
| Cell Assay |
Chick embryo skin fibroblasts were cultured in DMEM supplemented with essential amino acids. Azetidine-2-carboxylic acid (1-10 mM) and [3H]-proline were added to the medium. After 24-hour incubation, collagen was extracted via salt precipitation, and radioactivity was measured to calculate incorporation efficiency. Thermal stability of collagen was analyzed by monitoring absorbance at 230 nm during temperature elevation (25-60°C) [3]
Neuronal cells were cultured in neurobasal medium. Azetidine-2-carboxylic acid (1-10 mM) was added, and cells were incubated for 48 hours. Proteins were extracted, and misfolded proteins were detected by SDS-PAGE and western blot. ER stress markers (GRP78, CHOP) were quantified using sandwich ELISA, and apoptotic cells were identified by Annexin V-FITC/PI staining [2] |
| Animal Protocol |
3-day-old chick embryos were randomly divided into control and treatment groups. Azetidine-2-carboxylic acid was dissolved in physiological saline (10 mg/mL), and 1 mL (10 mg/egg) was injected into the yolk sac of treatment embryos. Control embryos received 1 mL of saline. All embryos were incubated at 37°C with 50% relative humidity and harvested on day 7 to measure collagen content, tissue morphology, and embryonic growth parameters [3]
Adult Sprague-Dawley rats (200-250 g) were assigned to control and treatment groups (n=6 per group). Treatment rats were fed a diet containing 0.5% w/w Azetidine-2-carboxylic acid for 4 weeks, while control rats received a standard diet. Rats were euthanized, and liver, kidney, brain, and muscle tissues were collected to quantify the compound via HPLC [1] |
| ADME/Pharmacokinetics |
In rats, oral administration of aziridine-2-carboxylic acid (0.5% of diet) showed good oral bioavailability, with peak plasma concentration (1.8 μg/mL) reached 2 hours after feeding [1]. The compound is widely distributed in various tissues, with the highest concentration in the liver, followed by the kidneys, brain, and muscles. It is metabolized very little, with 65% of the administered dose excreted unchanged in the urine within 24 hours [1].
|
| Toxicity/Toxicokinetics |
In chicken embryos, aziridine-2-carboxylic acid (10 mg/embryo) caused 25% embryonic death. Surviving embryos exhibited skeletal deformities and impaired connective tissue formation due to collagen defects [3]. In rats treated with aziridine-2-carboxylic acid (0.5% diet for 4 weeks), no significant changes were observed in body weight, hematological or hepatic and renal function indicators (ALT, AST, creatinine, BUN). Histological examination revealed mild vacuolation of renal tubular cells [1]. In neuronal cell culture, aziridine-2-carboxylic acid (10 mM, 72 h treatment) induced apoptosis, with an apoptosis rate 35% higher than that of control cells [2].
|
| References | |
| Additional Infomation |
Azacyclobutane-2-carboxylic acid is a azacyclobutane carboxylic acid with a structure in which azacyclobutane is replaced by a carboxyl group at the 2 position. It is a plant non-protein amino acid, both a plant metabolite and a teratogen. It is both a azacyclobutane carboxylic acid and an amino acid.
Azacyclobutane-2-carboxylic acid has been reported in lily of the valley (Convallaria majalis), Corynebacterium miyabeana, and other organisms with relevant data. It is a proline analog that can replace proline in stoichiometric proportions. It can lead to the production of abnormal proteins with impaired biological activity. Azacyclobutane-2-carboxylic acid is a non-protein amino acid and a natural proline analog, mainly found in plants of the Liliaceae family (e.g., lily, tulip, onion) and some fungi[1]. Its core mechanism of action is to competitively replace proline in protein synthesis by utilizing its structural similarity to proline. This leads to the synthesis of misfolded, defective proteins [2][3]. The compound enters the food chain through human consumption of contaminated plant products, constituting a potential dietary exposure pathway [1]. Some studies have suggested that long-term dietary exposure to aziridine-2-carboxylic acid may be involved in the pathogenesis of multiple sclerosis through misincorporation of myelin proteins, but this remains a hypothesis that requires further verification [2]. |
| Molecular Formula |
C4H7NO2
|
|---|---|
| Molecular Weight |
101.1039
|
| Exact Mass |
101.047
|
| CAS # |
2517-04-6
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| PubChem CID |
17288
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| Appearance |
White to off-white solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
242.0±33.0 °C at 760 mmHg
|
| Melting Point |
217°C (rough estimate)
|
| Flash Point |
100.1±25.4 °C
|
| Vapour Pressure |
0.0±1.0 mmHg at 25°C
|
| Index of Refraction |
1.499
|
| LogP |
-0.83
|
| Hydrogen Bond Donor Count |
2
|
| Hydrogen Bond Acceptor Count |
3
|
| Rotatable Bond Count |
1
|
| Heavy Atom Count |
7
|
| Complexity |
91.7
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| Defined Atom Stereocenter Count |
0
|
| InChi Key |
IADUEWIQBXOCDZ-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C4H7NO2/c6-4(7)3-1-2-5-3/h3,5H,1-2H2,(H,6,7)
|
| Chemical Name |
azetidine-2-carboxylic acid
|
| 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 Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
H2O : ~50 mg/mL (~494.56 mM)
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: 50 mg/mL (494.56 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication (<60°C).
(Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 9.8912 mL | 49.4560 mL | 98.9120 mL | |
| 5 mM | 1.9782 mL | 9.8912 mL | 19.7824 mL | |
| 10 mM | 0.9891 mL | 4.9456 mL | 9.8912 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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