2. Metabolic Enzyme/Protease Cell Cycle/DNA Damage Autophagy Apoptosis
  3. Endogenous Metabolite PERK Atg8/LC3 Autophagy Bcl-2 Family Apoptosis Eukaryotic Initiation Factor (eIF) ATF6
  4. L-Azetidine-2-carboxylic acid

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.

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L-Azetidine-2-carboxylic acid Chemical Structure

L-Azetidine-2-carboxylic acid Chemical Structure

CAS No. : 2133-34-8

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Solid + Solvent (Highly Recommended)
10 mM * 1 mL in Water
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Based on 1 publication(s) in Google Scholar

L-Azetidine-2-carboxylic acid Related Antibodies

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Description

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[1][2][3][4][5][6][7][8][9].

IC50 & Target

Human Endogenous Metabolite

 

In Vitro

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.

L-Azetidine-2-carboxylic acid Related Antibodies

Apoptosis Analysis[5]

Cell Line: BV2 cells
Concentration: 1000 µM
Incubation Time: 6, 24 h
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.

Real Time qPCR[5]

Cell Line: BV2 cells
Concentration: 1000 µM
Incubation Time: 6, 24 h
Result: Induced CD68 after 6 h.
Up-regulated MMP-9, but only at 24 h.
In Vivo

L-azetidine-2-carboxylic acid (200-600 mg/kg, i.p., given on gestational days 7-12) exhibits teratogenic effects in hamster fetuses[6].
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.

Animal Model: Eight-week-old pregnant virgin Wistar rats[7]
Dosage: 300 mg/kg
Administration: Intraperitoneal injection (i.p.), on day 8,9, 10,11, 12 or 13 of pregnancy
Result: Showed skeletal malformations, skeletal variations, delayed ossification and growth retardation.
Showed a higher mortality.
Molecular Weight

101.10

Formula

C4H7NO2
CAS No.
Appearance

Solid

Color

White to off-white

SMILES

O=C([C@H]1NCC1)O
Structure Classification
Initial Source
Shipping

Room temperature in continental US; may vary elsewhere.
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)

Solvent & Solubility
In Vitro: 

H2O : 100 mg/mL (989.12 mM; Need ultrasonic)

DMSO : < 1 mg/mL (insoluble or slightly soluble)

Preparing
Stock Solutions
Concentration Solvent Mass 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
View the 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.

* 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.

  • Molarity Calculator

  • Dilution Calculator

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass
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Concentration
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Volume
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Molecular Weight *

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

Concentration (start)

C1

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Volume (start)

V1

=
Concentration (final)

C2

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Volume (final)

V2

In Vivo:

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.

  • Protocol 1

    Add each solvent one by one:  PBS

    Solubility: 100 mg/mL (989.12 mM); Clear solution; Need ultrasonic

In Vivo Dissolution Calculator
Please enter the basic information of animal experiments:

Dosage

mg/kg

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(per animal)

g

Dosing volume
(per animal)

μL

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Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.
Calculation results:
Working solution concentration: mg/mL
This product has good water solubility, please refer to the measured solubility data in water/PBS/Saline for details.
The concentration of the stock solution you require exceeds the measured solubility. The following solution is for reference only.If necessary, please contact MedChemExpress (MCE).
Purity & Documentation

Purity: 99.78%

SDS (393 KB)

COA (249 KB) HNMR (162 KB) LCMS (158 KB)

Handling Instructions (2659 KB)
References

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.

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L-Azetidine-2-carboxylic acid Related Classifications

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  • Do most proteins show cross-species activity?

    Species cross-reactivity must be investigated individually for each product. Many human cytokines will produce a nice response in mouse cell lines, and many mouse proteins will show activity on human cells. Other proteins may have a lower specific activity when used in the opposite species.

Keywords:

L-Azetidine-2-carboxylic acid2133-34-8Endogenous MetabolitePERKAtg8/LC3AutophagyBcl-2 FamilyApoptosisEukaryotic Initiation Factor (eIF)ATF6Protein kinase R-like endoplasmic reticulum kinasePKR-like endoplasmic reticulum kinaseAutophagy-related 8Activating transcription factor 6HeLahamsterratsBV2teratogenic pro-inflammatory and pro-apoptoticInhibitorinhibitorinhibit

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