L-AZC
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MedKoo CAT#: 463782

CAS#: 2133-34-8

Description: L-Azetidine-2-carboxylic acid is a non-proteinogenic amino acid derivative of L-proline that has been found in C. majalis and has diverse biological activities. It is toxic to a variety of bacteria, but the bacteria E. agglomerans and E. amnigenus metabolize it for use as a source of nitrogen. L-Azetidine-2-carboxylic acid induces misfolding of proteins when incorporated into the nascent polypeptide chain. It destabilizes the collagen triple helix and reduces the extracellular localization of collagen.2 L-Azetidine-2-carboxylic acid inhibits growth of type IV collagen-producing 450. murine mammary cancer cells in vitro but is inactive in a 450.1 murine model of mammary cancer when administered at doses ranging from 12.5 to 200 mg/kg twice per day and induces liver toxicity at the highest dose. It is teratogenic to, and disrupts skeletal development in, hamster fetuses when administered to pregnant hamsters at a dose of 300 mg/kg on gestational day 11.

Chemical Structure

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L-AZC
CAS# 2133-34-8
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 463782
Name: L-AZC
CAS#: 2133-34-8
Chemical Formula: C4H7NO2
Exact Mass: 101.05
Molecular Weight: 101.105
Elemental Analysis: C, 47.52; H, 6.98; N, 13.85; O, 31.65

Price and Availability

Size Price Availability Quantity
1g USD 250 2 Weeks
2g USD 350 2 Weeks
5g USD 650 2 Weeks
10g USD 950 2 Weeks
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Synonym: L-AZC; L AZC; LAZC; L-Azetidine-2-carboxylic Acid; A2C; Aze; LACA; (S)-(–)-Azetidine-2-carboxylic Acid;

IUPAC/Chemical Name: (S)-azetidine-2-carboxylic acid

InChi Key: IADUEWIQBXOCDZ-VKHMYHEASA-N

InChi Code: InChI=1S/C4H7NO2/c6-4(7)3-1-2-5-3/h3,5H,1-2H2,(H,6,7)/t3-/m0/s1

SMILES Code: OC([C@@H]1CCN1)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Product Data
Instruction:
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Biological target: L-Azetidine-2-carboxylic acid is an endogenous metabolite.
In vitro activity: AZE (L-Azetidine-2-carboxylic acid) (at concentrations > 1000 µM) significantly reduced cell viability, increased BAX/Bcl2 ratio and caused cell death. Collectively, these data indicate that AZE-induced toxicity is associated with increased pro-inflammatory activity and reduced survival in BV2 microglia. Reference: Curr Issues Mol Biol. 2022 Sep 28;44(10):4500-4516. https://pubmed.ncbi.nlm.nih.gov/36286023/
In vivo activity: The teratogenic effects of L-azetidine-2-carboxylic acid (LACA) were evaluated in hamsters. Subcutaneous hemorrhage and cleft palate were the most frequently occurring externally visible defects. Skeletal anomalies such as retarded ossification, synchronous vertebral ossification and shortening of bones were found in a high percentage of LACA-treated fetuses. The major teratological effect of LACA appeared to be the retardation of skeletal development. Reference: Teratology. 1981 Jun;23(3):365-72. https://pubmed.ncbi.nlm.nih.gov/7256659/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
PBS (pH 7.2) 1.0 9.89
Water 100.0 989.07

Preparing Stock Solutions

The following data is based on the product molecular weight 101.11 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Piper JA, Jansen MI, Thomas Broome S, Rodgers KJ, Musumeci G, Castorina A. 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. doi: 10.3390/cimb44100308. PMID: 36286023; PMCID: PMC9600089. 2. Han L, Zhao W, Li A, Zhou B, Zhang J, Wu W. Antifungal activity of l-azetidine-2-carboxylic acid isolated from Disporopsis aspera rhizomes against Podosphaera xanthii. Pest Manag Sci. 2022 May;78(5):1946-1952. doi: 10.1002/ps.6812. Epub 2022 Feb 10. PMID: 35085420. 3. Klohs WD, Steinkampf RW, Wicha MS, Mertus AE, Tunac JB, Leopold WR. Collagen-production inhibitors evaluated as antitumor agents. J Natl Cancer Inst. 1985 Aug;75(2):353-9. PMID: 3860688. 4. Joneja MG. Teratogenic effects of proline analogue L-azetidine-2-carboxylic acid in hamster fetuses. Teratology. 1981 Jun;23(3):365-72. doi: 10.1002/tera.1420230311. PMID: 7256659.
In vitro protocol: 1. Piper JA, Jansen MI, Thomas Broome S, Rodgers KJ, Musumeci G, Castorina A. 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. doi: 10.3390/cimb44100308. PMID: 36286023; PMCID: PMC9600089. 2. Han L, Zhao W, Li A, Zhou B, Zhang J, Wu W. Antifungal activity of l-azetidine-2-carboxylic acid isolated from Disporopsis aspera rhizomes against Podosphaera xanthii. Pest Manag Sci. 2022 May;78(5):1946-1952. doi: 10.1002/ps.6812. Epub 2022 Feb 10. PMID: 35085420.
In vivo protocol: 1. Klohs WD, Steinkampf RW, Wicha MS, Mertus AE, Tunac JB, Leopold WR. Collagen-production inhibitors evaluated as antitumor agents. J Natl Cancer Inst. 1985 Aug;75(2):353-9. PMID: 3860688. 2. Joneja MG. Teratogenic effects of proline analogue L-azetidine-2-carboxylic acid in hamster fetuses. Teratology. 1981 Jun;23(3):365-72. doi: 10.1002/tera.1420230311. PMID: 7256659.

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1: Sato T, Hoshida H, Akada R. Inhibition of Distinct Proline- or N-Acetylglucosamine-Induced Hyphal Formation Pathways by Proline Analogs in Candida albicans. Biomed Res Int. 2020 Nov 17;2020:7245782. doi: 10.1155/2020/7245782. PMID: 33274221; PMCID: PMC7695494.

2: Berg MD, Zhu Y, Isaacson J, Genereaux J, Loll-Krippleber R, Brown GW, Brandl CJ. Chemical-Genetic Interactions with the Proline Analog L-Azetidine-2-Carboxylic Acid in Saccharomyces cerevisiae. G3 (Bethesda). 2020 Dec 3;10(12):4335-4345. doi: 10.1534/g3.120.401876. PMID: 33082270; PMCID: PMC7718759.

3: Mat Nanyan NSB, Watanabe D, Sugimoto Y, Takagi H. Involvement of the stress- responsive transcription factor gene MSN2 in the control of amino acid uptake in Saccharomyces cerevisiae. FEMS Yeast Res. 2019 Aug 1;19(5):foz052. doi: 10.1093/femsyr/foz052. PMID: 31328231.

4: Samardzic K, Rodgers KJ. Cell death and mitochondrial dysfunction induced by the dietary non-proteinogenic amino acid L-azetidine-2-carboxylic acid (Aze). Amino Acids. 2019 Aug;51(8):1221-1232. doi: 10.1007/s00726-019-02763-w. Epub 2019 Jul 13. PMID: 31302779.

5: Roest G, Hesemans E, Welkenhuyzen K, Luyten T, Engedal N, Bultynck G, Parys JB. 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. doi: 10.3390/cells7120239. PMID: 30513588; PMCID: PMC6316609.

6: Tabara K, Iwata Y, Koizumi N. The Unfolded Protein Response. Methods Mol Biol. 2018;1691:223-230. doi: 10.1007/978-1-4939-7389-7_17. PMID: 29043681.

7: Ma ZX, Leng YJ, Chen GX, Zhou PM, Ye D, Chen LQ. The THERMOSENSITIVE MALE STERILE 1 Interacts with the BiPs via DnaJ Domain and Stimulates Their ATPase Enzyme Activities in Arabidopsis. PLoS One. 2015 Jul 17;10(7):e0132500. doi: 10.1371/journal.pone.0132500. PMID: 26186593; PMCID: PMC4505944.

8: Gournas C, Evangelidis T, Athanasopoulos A, Mikros E, Sophianopoulou V. The Aspergillus nidulans proline permease as a model for understanding the factors determining substrate binding and specificity of fungal amino acid transporters. J Biol Chem. 2015 Mar 6;290(10):6141-55. doi: 10.1074/jbc.M114.612069. Epub 2015 Jan 8. PMID: 25572393; PMCID: PMC4358254.

9: Hara R, Uchiumi N, Okamoto N, Kino K. Regio- and stereoselective oxygenation of proline derivatives by using microbial 2-oxoglutarate-dependent dioxygenases. Biosci Biotechnol Biochem. 2014;78(8):1384-8. doi: 10.1080/09168451.2014.918490. Epub 2014 Jun 26. PMID: 25130741.

10: Rivera-Ordaz A, Bracher S, Sarrach S, Li Z, Shi L, Quick M, Hilger D, Haas R, Jung H. The sodium/proline transporter PutP of Helicobacter pylori. PLoS One. 2013 Dec 17;8(12):e83576. doi: 10.1371/journal.pone.0083576. PMID: 24358297; PMCID: PMC3866251.

11: Karpov DS, Spasskaya DS, Tutyaeva VV, Mironov AS, Karpov VL. Proteasome inhibition enhances resistance to DNA damage via upregulation of Rpn4-dependent DNA repair genes. FEBS Lett. 2013 Sep 17;587(18):3108-14. doi: 10.1016/j.febslet.2013.08.007. Epub 2013 Aug 13. PMID: 23954292.

12: Bach TM, Takagi H. Properties, metabolisms, and applications of (L)-proline analogues. Appl Microbiol Biotechnol. 2013 Aug;97(15):6623-34. doi: 10.1007/s00253-013-5022-7. Epub 2013 Jun 19. PMID: 23780584.

13: Revilla-López G, Warren JG, Torras J, Jiménez AI, Cativiela C, Alemán C. Effects of ring contraction on the conformational preferences of α-substituted proline analogs. Biopolymers. 2012;98(2):98-110. doi: 10.1002/bip.21716. Epub 2011 Sep 6. PMID: 21898364.

14: Łęgowska A, Dębowski D, Łukajtis R, Sztabkowska E, Mizeria A, Brzozowski K, Wysocka M, Lesner A, Rolka K. Introduction of Pro and its analogues in the conserved P1' position of trypsin inhibitor SFTI-1 retains its inhibitory activity. Protein Pept Lett. 2011 Nov;18(11):1158-67. doi: 10.2174/092986611797201002. PMID: 21605056.

15: Guan JC, Yeh CH, Lin YP, Ke YT, Chen MT, You JW, Liu YH, Lu CA, Wu SJ, Lin CY. A 9 bp cis-element in the promoters of class I small heat shock protein genes on chromosome 3 in rice mediates L-azetidine-2-carboxylic acid and heat shock responses. J Exp Bot. 2010 Oct;61(15):4249-61. doi: 10.1093/jxb/erq230. Epub 2010 Jul 19. PMID: 20643810; PMCID: PMC2955743.

16: Tsai FY, Zhang XH, Ulanov A, Widholm JM. The application of the yeast N-acetyltransferase MPR1 gene and the proline analogue L-azetidine-2-carboxylic acid as a selectable marker system for plant transformation. J Exp Bot. 2010 Jun;61(10):2561-73. doi: 10.1093/jxb/erq086. Epub 2010 Apr 28. PMID: 20430752; PMCID: PMC2882255.

17: Ishchuk OP, Abbas CA, Sibirny AA. Heterologous expression of Saccharomyces cerevisiae MPR1 gene confers tolerance to ethanol and L: -azetidine-2-carboxylic acid in Hansenula polymorpha. J Ind Microbiol Biotechnol. 2010 Feb;37(2):213-8. doi: 10.1007/s10295-009-0674-0. Epub 2009 Dec 5. PMID: 19967446.

18: Cameron PH, Chevet E, Pluquet O, Thomas DY, Bergeron JJ. Calnexin phosphorylation attenuates the release of partially misfolded alpha1-antitrypsin to the secretory pathway. J Biol Chem. 2009 Dec 11;284(50):34570-9. doi: 10.1074/jbc.M109.053165. Epub 2009 Oct 8. PMID: 19815548; PMCID: PMC2787319.

19: Ogawa-Mitsuhashi K, Sagane K, Kuromitsu J, Takagi H, Tsukahara K. MPR1 as a novel selection marker in Saccharomyces cerevisiae. Yeast. 2009 Nov;26(11):587-93. doi: 10.1002/yea.1708. PMID: 19750564.

20: Hibi T, Yamamoto H, Nakamura G, Takagi H. Crystallization and preliminary crystallographic analysis of N-acetyltransferase Mpr1 from Saccharomyces cerevisiae. Acta Crystallogr Sect F Struct Biol Cryst Commun. 2009 Feb 1;65(Pt 2):169-72. doi: 10.1107/S1744309109000153. Epub 2009 Jan 31. PMID: 19194013; PMCID: PMC2635863.