EVALUATION AND COMPARISON OF THE ANTIMICROBIAL AND CYTOTOXIC ACTIVITIES OF SOME AMINO ACID METHYL ESTERS

Year 2023, Volume: 51 Issue: 2, 133 - 140, 01.04.2023

Tuğçe Deniz Karaca , Hüseyin Balcı , Arzu Aysan

https://doi.org/10.15671/hjbc.1183477

Cited By: 1

Abstract

In this study, the antibacterial and cytotoxic activities of some amino acid methyl esters (L-methionine, L-phenylalanine, L-histidine, L-lysine, L-tryptophan, and L-tyrosine) were investigated. The effect of amino acid methyl ester compounds on antibacterial performance was determinated against Gram-negative and Gram-positive bacteria. The effect of amino acid esters on cell viability was investigated against cancerous and non-cancerous cell lines using the MTS assay. The results showed the substances had low antimicrobial effect on both Gram-negative and Gram-positive bacteria. In addition, it was found that the studied substances did not have a toxic effect on cell growth in non-cancerous cells. For this reason, it is thought that the results obtained will contribute to research on new synthesizable compounds based on amino acid esters and studies on drug development.

Keywords

Amino Acid Esters, Antibacterial Activity, Antiproliferative Activity, Cytotoxicity

References

• Reference1 Nanayakkara, A. K., Boucher, H. W., Fowler Jr, V. G., Jezek, A., Outterson, K., & Greenberg, D. E., Antibiotic resistance in the patient with cancer: Escalating challenges and paths forward, CA: A Cancer Journal for Clinicians, 71(6) (2021) 488-504.
• Reference2 Mancuso, G., Midiri, A., Gerace, E., & Biondo, C., Bacterial antibiotic resistance: The most critical pathogens, Pathogens,10 (10) (2021) 1310.
• Reference3 Fair, R.J., Tor, Y., Antibiotics and bacterial resistance in the 21st century, Perspect. Med. Chem., (2014) 6 25-64.
• Reference4 Song, J., What’s new on the antimicrobial horizon?, Int J Antimicrob Agents, 32 (2008) 207-13.
• Reference5 Chen, S., Li, L., Zhao, C., Zheng, J., Surface hydration: Principles and applications toward low-fouling/nonfouling biomaterials, Polymer, 51 (2010) 5283−5293.
• Reference6 Sanchez. L., Martinez, V., Infante, M.R., Mitjans, M., Vinardell, M.P., Haemolysis and antihaemolysis induced by amino acid-based surfactants, Toxicol Lett, 169 (2007) 177-84.
• Reference7 Sarma, R., Alva, K.S., Marx, K.A., Tripathy, S.K., Akkara, J.A., Kaplan, D.L., Enzymatic polymer-ization of amphiphillic alkyl tyrosine derivatives from emulsions, Mater Sci Eng C, 4 (1996) 189–92.
• Reference8 Perez, L., Pinazo, A., Garcia, M.T., Moran, M.C., Infante, M.R., Monoglyceride surfactants from arginine: synthesis and biological properties, New J Chem, 28 (2004) 1326-34.
• Reference9 Perez, L., Pinazo, A., Tereza, Garcia M., Lozano, M., Manresa, A., Angelet, M., et al. Cationic surfactants from lysine: synthesis, micellisation and biological evaluation, Eur J Med Chem, 44 (2009) 1884-1892.
• Reference10 Balouiri, M., Sadiki, M., Ibnsouda, S.K., Methods for in vitro evaluating antimicrobial activity, A review. Journal of Pharmaceutical Analysis, 6 (2) (2016) 71-79.
• Reference11 Joondan, N., Jhaumeer-Laulloo, S., Caumul, P., A study of the antibacterial activity of l-Phenylalanine and l-Tyrosineesters in relation to their CMCs and their interactions with1,2-dipalmitoyl-sn-glycerol-3-phosphocholine, DPPC as model membrane, Microbiological Research, 169 (2014) 675-685.
• Reference12 Malanovic, N., Lohner, K., Gram-positive bacterial cell envelopes: The impact on the activity of antimicrobial peptides, Biochimica et Biophysica Acta (BBA)– Biomembranes, 1858 (5) (2016) 936-946.
• Reference13 Silhavy, T.J., Kahne, D., Walker, S., The bacterial cell envelope, Cold Spring Harbor Perspectives in Biology, 2 (5) (2010) 414.
• Reference14 Pinazo, A., Manresa, M.A., Marques, A.M., Bustelo, M., Espuny, M.J., Pérez, L., Amino acid–based surfactants: New antimicrobial agents, Advances in Colloid and Interface Science 228 (2016)17-39.
• Reference15 Hameurlaine, A., El-Sayed, W.A., Abdel-Rahman, A.H., Amino acid derivatives, IX [1]: synthesis and antimicrobial evaluation of α-amino acid esters bearing a tryptophane side chain, Monatshefte für Chemie-Chemical Monthly, 139 (2008) 1507–1511.
• Reference16 Siebert, A., Wysocka, M., Krawczyk, B., Cholewiński, G., Rachoń, J., Synthesis and antimicrobial activity of amino acid and peptide derivatives of mycophenolic acid, European Journal of Medicinal Chemistry, 143 (2018) 646-655.
• Reference17 Wanders, D., Hobson, K., Ji, X., Methionine restriction and cancer biology, Nutrients, 12(3) (2020) 684.
• Reference18 Hung, M.H., Lee, J.S., Ma, C. et al., Tumor methionine metabolism drives T-cell exhaustion in hepatocellular carcinoma, Nature Communications, (2021) 1455.
• Reference19 Chau, W.K., Law, P., Effect of L-Phenylalanine methyl ester on the colony formation of hematopoietic progenitor cells from human bone marrow, The International Journal Of Cell Cloning, 9 ( 3) (1991) 211–219.
• Reference20 Escobar-Resendiz, R., Reyes-Esparza, J., Ortega,Lourdes I., Rodriguez-Fragoso, L., evaluation of cytotoxic effect of l-histidine methyl ester hydrochloride of amphotericin-B (A21) on tumoral cells, The FASEB Journal, 33 (2019) 515.
• Reference21 Kandekar, U., Pujari, R., Chaudhari, P., et al, Nanocarriers for breast cancer: Advanced perspective, Hacettepe University Journal of the Faculty of Pharmacy, 41(3) (2021) 179-195.
• Reference22 Jonas, A.J., Butler, I.J., Circumvention of defective neutral amino acid transport in Hartnup disease using tryptophan ethyl ester, J Clin Invest, 84 (1) (1989) 200-4.
• Reference23 Jadhav, A., Liang, W., Balsevich, J., Bastin, G., Kroetsch, J., Heximer, S., Backx, P.H., Gopalakrishnan, V., L-tryptophan ethyl ester dilates small mesenteric arteries by inhibition of voltage-operated calcium channels in smooth muscle, Br J Pharmacol, 166 (1) (2012) 232-42.
• Reference24 Oliyai, R., Stella, V.J., Prodrugs of peptides and proteins for improved formulation and delivery, Annu Rev Pharmacol Toxicol 32 (1993) 521–544.
• Reference25 Carlsson, P.A.E., Corrodi, H.R., Aktiebolaget Hassle, Treatment of Parkinson’s disease. US Patent, (1975) 19730820.
• Reference26 Sztanke, K., Maziarka, A., Osinka, A., Sztanke, M., An insight into synthetic Schiff bases revealing antiproliferative activities in vitro, Bioorganic & Medicinal Chemistry, Volume 21, Issue 13 (1975) 3648-3666.