L-Azetidine-2-carboxylic acid
Based on 1 publication(s) in Google Scholar
L-Azetidine-2-carboxylic acid is a proline analog. L-Azetidine-2-carboxylic acid upregulates the lipid autophagy marker LC3-II via activation of the PERK pathway. L-Azetidine-2-carboxylic acid increases pro-apoptotic BAX protein. L-Azetidine-2-carboxylic acid induces ATF6 cleavage and upregulates phosphorylated eIF2α levels. L-Azetidine-2-carboxylic acid induces ER stress, inducing protein misfolding and aggregation. L-Azetidine-2-carboxylic acid shows teratogenic, pro-inflammatory and pro-apoptotic effects.
For research use only. We do not sell to patients.
- Purity: 99.97%
- CAS No.: 2133-34-8
- Formula: C4H7NO2
- Molecular Weight:101.10
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Storage:
4°C, protect from light, stored under nitrogen
* In solvent : -80°C, 6 months; -20°C, 1 month (protect from light, stored under nitrogen)
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Biological Activity
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Chemical Information
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Solvent & Solubility
- Purity & Documentation
- References
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Help & FAQs
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L-Azetidine-2-carboxylic acid (Standard)
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Publications Citing Use of MedChemExpress (MCE) L-Azetidine-2-carboxylic acid
MoreAll Endogenous Metabolite Isoforms
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Biological Activity
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Human Endogenous Metabolite |
L-azetidine-2-carboxylic acid increases glycosylations of collagen in chick-embryo tendon cells[1].
L-azetidine-2-carboxylic acid (5 mM, 9 h) induces ATF6 cleavage and upregulates BiP expression and phosphorylated eIF2α levels in HeLa cells[2].
L-azetidine-2-carboxylic acid (1-10 mM) reduces L-[U-14-C]proline incorporation into hemoglobin (25, 58, and 72% for 1, 5, and 10 mM, , respectively) in rabbit reticulocytes[3].
L-azetidine-2-carboxylic acid (350 μg/egg, daily, 9 days) prevents expression of the chondrogenic phenotype in embryonated eggs of Gallus domesticus[4].
L-azetidine-2-carboxylic acid (0-2000 µM, 6-24 h) shows pro-inflammatory and pro-apoptotic effects in BV2 microglial cells[5].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Cell Line:BV2 cells
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Concentration:1000 µM
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Incubation Time:6, 24 h
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Result:Did not affect Bcl2 protein expression.
Increased pro-apoptotic BAX protein both at 6 and 24 h.
Increased BAX/Bcl2 ratio after 6 h.
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Cell Line:BV2 cells
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Concentration:1000 µM
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Incubation Time:6, 24 h
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Result:Induced CD68 after 6 h.
Up-regulated MMP-9, but only at 24 h.
L-azetidine-2-carboxylic acid (300 mg/kg, i.p., on day 8 of pregnancy) exhibits teratogenic effects on the skeletal system in rats[7].
L-azetidine-2-carboxylic acid (300 mg/kg, i.p., single) causes disrupted dentinogenesis in rats and mice[8].
L-azetidine-2-carboxylic acid (200 mg/kg, twice daily for 2 days) retards lung growth and surfactant synthesis in fetal rats[9].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:Eight-week-old pregnant virgin Wistar rats[7]
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Dosage:300 mg/kg
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Administration:Intraperitoneal injection (i.p.), on day 8,9, 10,11, 12 or 13 of pregnancy
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Result:Showed skeletal malformations, skeletal variations, delayed ossification and growth retardation.
Showed a higher mortality.
Chemical Information
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CAS No. 2133-34-8
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Appearance Solid
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Molecular Weight 101.10
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Formula C4H7NO2
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Color White to off-white
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SMILES
O=C([C@H]1NCC1)O
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Structure Classification
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Initial Source
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
4°C, protect from light, stored under nitrogen
* In solvent : -80°C, 6 months; -20°C, 1 month (protect from light, stored under nitrogen)
Publications (1)
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Journal Impact Factor
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Most Recent
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Mol Cell
Global profiling of nascent chain interactors reveals TRIM25 as a co-translational E3 ubiquitin ligase. [Abstract]2026 Mar 3:S1097-2765(26)00102-4. PMID: 41780531
Solvent & Solubility
H2O : 100 mg/mL (989.12 mM; Need ultrasonic)
DMSO : < 1 mg/mL (insoluble or slightly soluble)
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (protect from light, stored under nitrogen). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
* Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (protect from light, stored under nitrogen). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
* Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
For the following dissolution methods, please prepare the working solution directly:
It is recommended to prepare fresh solutions and use them promptly within a short period of time.
The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.
Add each solvent one by one: PBS
Solubility: 100 mg/mL (989.12 mM); Clear solution; Need ultrasonic
Purity & Documentation
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Data Sheet (281 KB)
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SDS (394 KB)
- English - EN (394 KB)
- Français - FR (394 KB)
- Deutsch - DE (394 KB)
- Norwegian - NO (394 KB)
- Español - ES (394 KB)
- Swedish - SV (394 KB)
- Italian - IT (394 KB)
- Korean - KR (394 KB)
- Portuguese - PT (394 KB)
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Handling Instructions (2659 KB)
References
[1]. Oikarinen A, et al. Effect of L-azetidine-2-carboxylic acid on glycosylations of collagen in chick-embryo tendon cells. Biochem J. 1976 Dec 15;160(3):639-45. [Content Brief]
[2]. Roest G, et al. The ER Stress Inducer l-Azetidine-2-Carboxylic Acid Elevates the Levels of Phospho-eIF2α and of LC3-II in a Ca2+-Dependent Manner. Cells. 2018 Nov 30;7(12):239. [Content Brief]
[3]. Baum BJ, et al. Incorporation of L-azetidine-2-carboxylic acid into hemoglobin in rabbit reticulocytes in vitro. J Biol Chem. 1975 Feb 25;250(4):1464-71. [Content Brief]
[4]. Hall BK. Use of the L-proline analog, L-azetidine-2-carboxylic acid (LACA) to analyse embryonic growth and determination and expression of the chondrogenic phenotype in vivo and in vitro. Anat Rec. 1978 Feb;190(2):243-55. [Content Brief]
[5]. Piper JA, et al. Pro-Inflammatory and Pro-Apoptotic Effects of the Non-Protein Amino Acid L-Azetidine-2-Carboxylic Acid in BV2 Microglial Cells. Curr Issues Mol Biol. 2022 Sep 28;44(10):4500-4516. [Content Brief]
[6]. Joneja MG. Teratogenic effects of proline analogue L-azetidine-2-carboxylic acid in hamster fetuses. Teratology. 1981 Jun;23(3):365-72. [Content Brief]
[9]. Adamson IY, et al. L-azetidine-2-carboxylic acid retards lung growth and surfactant synthesis in fetal rats. Lab Invest. [Content Brief]
Complete Stock Solution Preparation Table
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (protect from light, stored under nitrogen). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
| Optional Solvent | Concentration Solvent Mass | 1 mg | 5 mg | 10 mg | 25 mg |
|---|---|---|---|---|---|
| H2O | 1 mM | 9.8912 mL | 49.4560 mL | 98.9120 mL | 247.2799 mL |
| 5 mM | 1.9782 mL | 9.8912 mL | 19.7824 mL | 49.4560 mL | |
| 10 mM | 0.9891 mL | 4.9456 mL | 9.8912 mL | 24.7280 mL | |
| 15 mM | 0.6594 mL | 3.2971 mL | 6.5941 mL | 16.4853 mL | |
| 20 mM | 0.4946 mL | 2.4728 mL | 4.9456 mL | 12.3640 mL | |
| 25 mM | 0.3956 mL | 1.9782 mL | 3.9565 mL | 9.8912 mL | |
| 30 mM | 0.3297 mL | 1.6485 mL | 3.2971 mL | 8.2427 mL | |
| 40 mM | 0.2473 mL | 1.2364 mL | 2.4728 mL | 6.1820 mL | |
| 50 mM | 0.1978 mL | 0.9891 mL | 1.9782 mL | 4.9456 mL | |
| 60 mM | 0.1649 mL | 0.8243 mL | 1.6485 mL | 4.1213 mL | |
| 80 mM | 0.1236 mL | 0.6182 mL | 1.2364 mL | 3.0910 mL | |
| 100 mM | 0.0989 mL | 0.4946 mL | 0.9891 mL | 2.4728 mL |
* Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.
L-Azetidine-2-carboxylic acid Related Classifications
HY-W050044 Related Classifications
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