Research Article
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Antimicrobial activity screening of a series of taurine derivatives

Year 2021, Volume: 42 Issue: 4, 781 - 788, 29.12.2021

Özlem Akgül , Çağlar Akgünlü , Hatice Biler , Ayşegül Ateş , Şafak Ermertcan

Abstract

In this study, a series of taurinamide derivatives 1–18 were assessed for their in vitro antimicrobial activity. Enterococcus faecalis, which is the third most commonly isolated nosocomial pathogen among hospital infections, was found to be more susceptible to the tested compounds than other pathogens. Two of the tested compounds, 1 and 18, showed promising activity against E. faecalis, with minimal inhibitory concentrations (MICs) of 128 and 64 µg/mL, respectively. On the other hand, compound 3 was distinguished from other compounds by its better activity against G(−) Escherichia coli bacteria, with a MIC of 512 μg/mL. None of the compounds displayed better activity than the standard drugs Ciprofloxacin and Fluconazole.

Keywords

Taurine derivatives Antimicrobial activity Broth microdilution method.

Supporting Institution

The Scientific and Technological Research Council of Turkey

Project Number

SBAG-118S667

Thanks

The authors gratefully acknowledge The Scientific and Technological Research Council of Turkey [TÜBİTAK; Project number: SBAG-118S667] for financial assistance.

References

  • [1] Grygorenko O. O., Biitseva A. V., Zhersh S., Amino Sulfonic Acids, Peptidosulfonamides and Other Related Compounds, Tetrahedron, 74(13) (2018) 1355–1421.
  • [2] Chung M., Malatesta P., Bosquesi P., Yamasaki P., Santos J. L. dos, Vizioli E., Advances in Drug Design Based on the Amino Acid Approach: Taurine Analogues for the Treatment of CNS Diseases, Pharmaceuticals, 5(10) (2012) 1128–1146.
  • [3] Gupta R. C., Taurine Analogues and Taurine Transport: Therapeutic Advantages, in: Oja, S.S., Saransaari, P., (Eds.), Taurine 6. Springer US, New York, NY (2006) 449–467.
  • [4] Ripps H., Shen W., Review: Taurine: A ‘Very Essential’ Amino Acid, Mol. Vis., 18 (November) (2012) 2673–2686.
  • [5] Chen K., Zhang Q., Wang J., Liu F., Mi M., Xu H., Chen F., Zeng K., Taurine Protects Transformed Rat Retinal Ganglion Cells from Hypoxia-Induced Apoptosis by Preventing Mitochondrial Dysfunction, Brain Res., 1279 (2009) 131–138.
  • [6] Vanitha M. K., Baskaran K., Periyasamy K., Saravanan D., Ilakkia A., Selvaraj S., Venkateswari R., Mani B. R., Anandakumar P., Sakthisekaran D., A Review on the Biomedical Importance of Taurine, Int. J. Pharma Res. Heal. Sci., 3(3) (2015) 680–686.
  • [7] Gottardi W., Nagl M., N-Chlorotaurine, a Natural Antiseptic with Outstanding Tolerability, J. Antimicrob. Chemother., 65(3) (2010) 399–409.
  • [8] Nagl M., Hess M. W., Pfaller K., Hengster P., Gottardi W., Bactericidal Activity of MicromolarN-Chlorotaurine: Evidence for Its Antimicrobial Function in the Human Defense System, Antimicrob. Agents Chemother., 44(9) (2000) 2507–2513.
  • [9] Gottardi W., Debabov D., Nagl M., N-Chloramines, A Promising Class of Well-Tolerated Topical Anti-Infectives, Antimicrob. Agents Chemother., 57(3) (2013) 1107–1114.
  • [10] Jekle A., Yoon J., Zuck M., Najafi R., Wang L., Shiau T., Francavilla C., Rani S. A., Eitzinger C., Nagl M., Anderson M., Debabov D., NVC-422 Inactivates Staphylococcus Aureus Toxins, Antimicrob. Agents Chemother., 57(2) (2013) 924–929.
  • [11] Winterbottom R., Clapp J. W., Miller W. H., English J. P., Roblin R. O., Studies in Chemotherapy. XV. Amides of Pantoyltaurine 1,. J. Am. Chem. Soc., 69(6) (1947) 1393–1401.
  • [12] de Kraker M. E. A., Stewardson A. J., Harbarth S., Will 10 Million People Die a Year Due to Antimicrobial Resistance by 2050?, PLOS Med., 13(11) (2016) e1002184.
  • [13] Akgül Ö., Öztürk İ., Aygül A., Ermertcan Ş., Synthesis and Antimicrobial Activity of Some Taurinamide Derivatives, Marmara Pharm. J., 21(2) (2017) 361–361.
  • [14] Sun H., Tawa G., Wallqvist A., Scaffold-Hopping Provides Both a Conceptual and Practical Route for Generating New Lead Series and Chemistries with Improved Efficacy and Pharmacokinetic Properties Based on Known Drugs and Drug-Target Interactions Classification of Scaffold-Hopping Approaches, Drug Discov. Today, 17(7-8) (2012) 310-324.
  • [15] Akgül Ö., Erdoğan M. A., Birim D., Kayabaşı Ç., Gündüz C., Armağan G., Design, Synthesis, Cytotoxic Activity, and Apoptosis Inducing Effects of 4- and N-Substituted Benzoyltaurinamide Derivatives, Turkısh J. Chem., 44(6) (2020) 1674–1693.
  • [16] European Committee on Antimicrobial Susceptibility Testing, Routine and Extended Internal Quality Control for MIC Determination and Disk Diffusion as Recommended by EUCAST, Eucast, Version 10 (2020) 1–20.
  • [17] Akgül Ö., Kilic F. S., Erol K., Pabuccuoglu V., Synthesis and Anticonvulsant Activity of Some N-Phenyl-2- Phtalimidoethanesulfonamide Derivatives, Arch. Pharm. (Weinheim)., 340 (12) (2007) 656–660.
  • [18] Akgül Ö., Angeli A., Vullo D., Carta F., Supuran C. T., Unconventional Amino Acids in Medicinal Chemistry: First Report on Taurine Merged within Carbonic Anhydrase Inhibitors, Bioorg. Chem., 103 (2020) 104236.
  • [19] Akgül Ö., Ateş, Ayşegül, Ermertcan Ş., Antimicrobial Activity Evaluation of Newly Synthesized N,N-Disubstituted Taurinamidobenzenesulfonamide Derivatives, J. Turkish Chem. Soc. Sect. A Chem., 8(1) (2021) 323–330.
  • [20] López-Rojas P., Janeczko M., Kubiński K., Amesty Á., Masłyk M., Estévez-Braun A., Synthesis and Antimicrobial Activity of 4-Substituted 1,2,3-Triazole-Coumarin Derivatives, Molecules, 23(1) (2018) 199.

Year 2021, Volume: 42 Issue: 4, 781 - 788, 29.12.2021

Özlem Akgül , Çağlar Akgünlü , Hatice Biler , Ayşegül Ateş , Şafak Ermertcan

Abstract

Project Number

SBAG-118S667

References

  • [1] Grygorenko O. O., Biitseva A. V., Zhersh S., Amino Sulfonic Acids, Peptidosulfonamides and Other Related Compounds, Tetrahedron, 74(13) (2018) 1355–1421.
  • [2] Chung M., Malatesta P., Bosquesi P., Yamasaki P., Santos J. L. dos, Vizioli E., Advances in Drug Design Based on the Amino Acid Approach: Taurine Analogues for the Treatment of CNS Diseases, Pharmaceuticals, 5(10) (2012) 1128–1146.
  • [3] Gupta R. C., Taurine Analogues and Taurine Transport: Therapeutic Advantages, in: Oja, S.S., Saransaari, P., (Eds.), Taurine 6. Springer US, New York, NY (2006) 449–467.
  • [4] Ripps H., Shen W., Review: Taurine: A ‘Very Essential’ Amino Acid, Mol. Vis., 18 (November) (2012) 2673–2686.
  • [5] Chen K., Zhang Q., Wang J., Liu F., Mi M., Xu H., Chen F., Zeng K., Taurine Protects Transformed Rat Retinal Ganglion Cells from Hypoxia-Induced Apoptosis by Preventing Mitochondrial Dysfunction, Brain Res., 1279 (2009) 131–138.
  • [6] Vanitha M. K., Baskaran K., Periyasamy K., Saravanan D., Ilakkia A., Selvaraj S., Venkateswari R., Mani B. R., Anandakumar P., Sakthisekaran D., A Review on the Biomedical Importance of Taurine, Int. J. Pharma Res. Heal. Sci., 3(3) (2015) 680–686.
  • [7] Gottardi W., Nagl M., N-Chlorotaurine, a Natural Antiseptic with Outstanding Tolerability, J. Antimicrob. Chemother., 65(3) (2010) 399–409.
  • [8] Nagl M., Hess M. W., Pfaller K., Hengster P., Gottardi W., Bactericidal Activity of MicromolarN-Chlorotaurine: Evidence for Its Antimicrobial Function in the Human Defense System, Antimicrob. Agents Chemother., 44(9) (2000) 2507–2513.
  • [9] Gottardi W., Debabov D., Nagl M., N-Chloramines, A Promising Class of Well-Tolerated Topical Anti-Infectives, Antimicrob. Agents Chemother., 57(3) (2013) 1107–1114.
  • [10] Jekle A., Yoon J., Zuck M., Najafi R., Wang L., Shiau T., Francavilla C., Rani S. A., Eitzinger C., Nagl M., Anderson M., Debabov D., NVC-422 Inactivates Staphylococcus Aureus Toxins, Antimicrob. Agents Chemother., 57(2) (2013) 924–929.
  • [11] Winterbottom R., Clapp J. W., Miller W. H., English J. P., Roblin R. O., Studies in Chemotherapy. XV. Amides of Pantoyltaurine 1,. J. Am. Chem. Soc., 69(6) (1947) 1393–1401.
  • [12] de Kraker M. E. A., Stewardson A. J., Harbarth S., Will 10 Million People Die a Year Due to Antimicrobial Resistance by 2050?, PLOS Med., 13(11) (2016) e1002184.
  • [13] Akgül Ö., Öztürk İ., Aygül A., Ermertcan Ş., Synthesis and Antimicrobial Activity of Some Taurinamide Derivatives, Marmara Pharm. J., 21(2) (2017) 361–361.
  • [14] Sun H., Tawa G., Wallqvist A., Scaffold-Hopping Provides Both a Conceptual and Practical Route for Generating New Lead Series and Chemistries with Improved Efficacy and Pharmacokinetic Properties Based on Known Drugs and Drug-Target Interactions Classification of Scaffold-Hopping Approaches, Drug Discov. Today, 17(7-8) (2012) 310-324.
  • [15] Akgül Ö., Erdoğan M. A., Birim D., Kayabaşı Ç., Gündüz C., Armağan G., Design, Synthesis, Cytotoxic Activity, and Apoptosis Inducing Effects of 4- and N-Substituted Benzoyltaurinamide Derivatives, Turkısh J. Chem., 44(6) (2020) 1674–1693.
  • [16] European Committee on Antimicrobial Susceptibility Testing, Routine and Extended Internal Quality Control for MIC Determination and Disk Diffusion as Recommended by EUCAST, Eucast, Version 10 (2020) 1–20.
  • [17] Akgül Ö., Kilic F. S., Erol K., Pabuccuoglu V., Synthesis and Anticonvulsant Activity of Some N-Phenyl-2- Phtalimidoethanesulfonamide Derivatives, Arch. Pharm. (Weinheim)., 340 (12) (2007) 656–660.
  • [18] Akgül Ö., Angeli A., Vullo D., Carta F., Supuran C. T., Unconventional Amino Acids in Medicinal Chemistry: First Report on Taurine Merged within Carbonic Anhydrase Inhibitors, Bioorg. Chem., 103 (2020) 104236.
  • [19] Akgül Ö., Ateş, Ayşegül, Ermertcan Ş., Antimicrobial Activity Evaluation of Newly Synthesized N,N-Disubstituted Taurinamidobenzenesulfonamide Derivatives, J. Turkish Chem. Soc. Sect. A Chem., 8(1) (2021) 323–330.
  • [20] López-Rojas P., Janeczko M., Kubiński K., Amesty Á., Masłyk M., Estévez-Braun A., Synthesis and Antimicrobial Activity of 4-Substituted 1,2,3-Triazole-Coumarin Derivatives, Molecules, 23(1) (2018) 199.
There are 20 citations in total.

Details

Primary Language English
Subjects Pharmacology and Pharmaceutical Sciences
Journal Section Natural Sciences
Authors

Özlem Akgül 0000-0002-0011-7888

Çağlar Akgünlü 0000-0003-1195-6676

Hatice Biler 0000-0001-8629-5919

Ayşegül Ateş 0000-0001-6891-6662

Şafak Ermertcan 0000-0001-6686-6892

Project Number SBAG-118S667
Publication Date December 29, 2021
Submission Date September 1, 2021
Acceptance Date November 30, 2021
Published in Issue Year 2021Volume: 42 Issue: 4

Cite

APA Akgül, Ö., Akgünlü, Ç., Biler, H., Ateş, A., et al. (2021). Antimicrobial activity screening of a series of taurine derivatives. Cumhuriyet Science Journal, 42(4), 781-788.