Research Article
BibTex RIS Cite

Antibiofilm and Antimicrobial Properties of 1-allyl-3-(2-diisopropylaminoethyl) Benzimidazolium Chloride and its Silver(I)-NHC Complex

Year 2022, Volume: 43 Issue: 3, 432 - 436, 30.09.2022

Uğur Tutar , Cem Çelik

https://doi.org/10.17776/csj.1121787
Cited By: 1

Abstract

Today, the number of antimicrobials used in treatment has decreased, especially due to drug resistance. We need new antimicrobials. Biofilms are an important cause of antimicrobial resistance. In this study, the antimicrobial and antibiofilm properties of the salt and silver complex of benzimidazolium-based NHC compound, which were previously synthesized and characterized, were evaluated. The antimicrobial properties were tested using the broth microdilution method, while their antibiofilm potential was determined by microtiter plate assay. Salt of the NHC compound (1a) showed antimicrobial activity on microorganisms at concentrations between 31.25-125 µg/mL. The silver complex (2a) of the NHC compound showed higher antimicrobial and antibiofilm activity than the salt compound. This activity was highest on Candida albicans yeast (MIC 3.9 µg/mL). Compound 2a reduced the biofilm structure of C. albicans yeast by 86.1% compared to the control. In addition, compound 2a showed 76.4-80.6% antibiofilm activity on gram-negative bacteria. NHC compounds are seen as a promising resource for the development of new generation antimicrobials. The NHC compound evaluated in this study was found to have significant antimicrobial and antibiofilm activity. These compounds could be an important resource for the discovery of future biofilm-acting antimicrobials.

Keywords

N-heterocyclic carbene Silver Antimicrobial activity Antibiofilm activity.

Thanks

The authors would like to thank Neslihan Şahin for providing us with the compounds.

References

  • [1] Stark L.A., Beneficial Microorganisms: Countering Microbephobia, CBE Life Sci. Educ., 9 (4) (2010) 387-389.
  • [2] Institute of Medicine (US) Committee on Emerging Microbial Threats to Health in the 21st Century. Microbial Threats to Health: Emergence, Detection, and Response. Smolinski M.S., Hamburg M.A., Lederberg J., editors. Washington (DC): National Academies Press (US); 2003.
  • [3] Hutchings M.I., Truman A.W., Wilkinson B., Antibiotics: Past, Present and Future, Curr. Opin. Microbiol., 51 (2019) 72-80.
  • [4] McEwen S.A., Collignon P.J., Antimicrobial Resistance: a One Health Perspective, Microbiol. Spectr., 6 (2) (2018) 1-26.
  • [5] Frieri M., Kumar K., Boutin A., Antibiotic Resistance, J. Infect. Public. Health., 10 (4) (2017) 369-378.
  • [6] Conly J., Johnston B., Where Are All the New Antibiotics? The New Antibiotic Paradox, Can. J. Infect. Dis. Med. Microbiol., 16 (3) (2005) 159-60.
  • [7] Rabin N., Zheng Y., Opoku-Temeng C., Du Y., Bonsu E., Sintim H.O., Biofilm Formation Mechanisms and Targets for Developing Antibiofilm Agents, Future Med. Chem., 7 (4) (2015) 493-512.
  • [8] Liang J., Sun D., Yang Y., Li M., Li H., Chen L., Discovery of Metal-Based Complexes as Promising Antimicrobial Agents, Eur. J. Med. Chem., 224 (2021) 113696.
  • [9] Şahin-Yıldırım E., Şahin N., Synthesis and Structural Characterization of Chloro [1-allyl-3-(2-diisopropylaminoethyl ) benzimidazol-2-ylidene] silver(I), Ordu Univ. J. Sci. Tech., 10 (2) (2020) 66-75.
  • [10] Clinical and Laboratory Standards Institute (CLSI), Performance Standards for Antimicrobial Susceptibility Testing, Twenty-Fourth Informational Supplement, CLSI document M100-S24, Wayne, PA, 2014.
  • [11] Üstün E., Şahin N., Çelik C., Tutar U., Özdemir N., Gürbüz N., Özdemir İ., Synthesis, Characterization, Antimicrobial and Antibiofilm Activity, and Molecular Docking Analysis of NHC Precursors and Their Ag-NHC Complexes, Dalton. Trans., 50 (42) (2021) 15400-15412.
  • [12] Waglechner N., Culp E.J., Wright G.D., Ancient Antibiotics, Ancient Resistance, EcoSal Plus., 9 (2) (2021) ESP-0027-2020.
  • [13] A.Patil S., P.Hoagland A., A.Patil S., Bugarin A., N-Heterocyclic Carbene-Metal Complexes as Bio-Organometallic Antimicrobial and Anticancer Drugs, an Update (2015-2020), Future Med. Chem., 12 (24) (2020) 2239-2275.
  • [14] Kaloğlu M., Kaloğlu N., Günal S., Özdemir İ., Synthesis of N-Heterocyclic Carbene-Based Silver Complexes and Their Antimicrobial Properties Against Bacteria and Fungi, J. Coord. Chem., 74 (17-20) (2021) 3031-3047.
  • [15] Mnasri A., Mejri A., Al-Hazmy S.M., Arfaoui Y., Özdemir İ., Gürbüz N., Hamdi N., Silver-N-Heterocyclic Carbene Complexes-Catalyzed Multicomponent Reactions: Synthesis, Spectroscopic Characterization, Density Functional Theory Calculations, and Antibacterial Study, Arch. Pharm. (Weinheim)., 354 (9) (2021) e2100111.
  • [16] Sarı Y., Akkoç S., Gök Y., Sifniotis V., Özdemir İ., Günal S., Kayser V., Benzimidazolium-Based Novel Silver N-Heterocyclic Carbene Complexes: Synthesis, Characterisation and In vitro Antimicrobial Activity, J. Enzyme Inhib. Med. Chem., 31 (6) (2016) 1527-1530.
  • [17] Asekunowo P.O., Haque R.A., Razali M.R., Avicor S.W., Wajidi M.F.F., Synthesis and Characterization of Nitrile Functionalized Silver(I)-N-Heterocyclic Carbene Complexes: DNA Binding, Cleavage Studies, Antibacterial Properties and Mosquitocidal Activity Against the Dengue Vector, Aedes Albopictus, Eur. J. Med. Chem., 150 (2018) 601-615.
  • [18] Nadar S., Khan T., Patching S.G., Omri A., Development of Antibiofilm Therapeutics Strategies to Overcome Antimicrobial Drug Resistance, Microorganisms, 10 (2) (2022) 303.
  • [19] Celik C., Tutar U., Sahin N., Ozturk A., Antimicrobial, Anti-biofilm and Cytotoxic Properties of Methallyl Functionalized Benzimidazolium-Derived Ag(I)-N-Heterocyclic Carbene Complexes, Trop. J. Pharm. Res., 21

Year 2022, Volume: 43 Issue: 3, 432 - 436, 30.09.2022

Uğur Tutar , Cem Çelik

https://doi.org/10.17776/csj.1121787
Cited By: 1

Abstract

References

  • [1] Stark L.A., Beneficial Microorganisms: Countering Microbephobia, CBE Life Sci. Educ., 9 (4) (2010) 387-389.
  • [2] Institute of Medicine (US) Committee on Emerging Microbial Threats to Health in the 21st Century. Microbial Threats to Health: Emergence, Detection, and Response. Smolinski M.S., Hamburg M.A., Lederberg J., editors. Washington (DC): National Academies Press (US); 2003.
  • [3] Hutchings M.I., Truman A.W., Wilkinson B., Antibiotics: Past, Present and Future, Curr. Opin. Microbiol., 51 (2019) 72-80.
  • [4] McEwen S.A., Collignon P.J., Antimicrobial Resistance: a One Health Perspective, Microbiol. Spectr., 6 (2) (2018) 1-26.
  • [5] Frieri M., Kumar K., Boutin A., Antibiotic Resistance, J. Infect. Public. Health., 10 (4) (2017) 369-378.
  • [6] Conly J., Johnston B., Where Are All the New Antibiotics? The New Antibiotic Paradox, Can. J. Infect. Dis. Med. Microbiol., 16 (3) (2005) 159-60.
  • [7] Rabin N., Zheng Y., Opoku-Temeng C., Du Y., Bonsu E., Sintim H.O., Biofilm Formation Mechanisms and Targets for Developing Antibiofilm Agents, Future Med. Chem., 7 (4) (2015) 493-512.
  • [8] Liang J., Sun D., Yang Y., Li M., Li H., Chen L., Discovery of Metal-Based Complexes as Promising Antimicrobial Agents, Eur. J. Med. Chem., 224 (2021) 113696.
  • [9] Şahin-Yıldırım E., Şahin N., Synthesis and Structural Characterization of Chloro [1-allyl-3-(2-diisopropylaminoethyl ) benzimidazol-2-ylidene] silver(I), Ordu Univ. J. Sci. Tech., 10 (2) (2020) 66-75.
  • [10] Clinical and Laboratory Standards Institute (CLSI), Performance Standards for Antimicrobial Susceptibility Testing, Twenty-Fourth Informational Supplement, CLSI document M100-S24, Wayne, PA, 2014.
  • [11] Üstün E., Şahin N., Çelik C., Tutar U., Özdemir N., Gürbüz N., Özdemir İ., Synthesis, Characterization, Antimicrobial and Antibiofilm Activity, and Molecular Docking Analysis of NHC Precursors and Their Ag-NHC Complexes, Dalton. Trans., 50 (42) (2021) 15400-15412.
  • [12] Waglechner N., Culp E.J., Wright G.D., Ancient Antibiotics, Ancient Resistance, EcoSal Plus., 9 (2) (2021) ESP-0027-2020.
  • [13] A.Patil S., P.Hoagland A., A.Patil S., Bugarin A., N-Heterocyclic Carbene-Metal Complexes as Bio-Organometallic Antimicrobial and Anticancer Drugs, an Update (2015-2020), Future Med. Chem., 12 (24) (2020) 2239-2275.
  • [14] Kaloğlu M., Kaloğlu N., Günal S., Özdemir İ., Synthesis of N-Heterocyclic Carbene-Based Silver Complexes and Their Antimicrobial Properties Against Bacteria and Fungi, J. Coord. Chem., 74 (17-20) (2021) 3031-3047.
  • [15] Mnasri A., Mejri A., Al-Hazmy S.M., Arfaoui Y., Özdemir İ., Gürbüz N., Hamdi N., Silver-N-Heterocyclic Carbene Complexes-Catalyzed Multicomponent Reactions: Synthesis, Spectroscopic Characterization, Density Functional Theory Calculations, and Antibacterial Study, Arch. Pharm. (Weinheim)., 354 (9) (2021) e2100111.
  • [16] Sarı Y., Akkoç S., Gök Y., Sifniotis V., Özdemir İ., Günal S., Kayser V., Benzimidazolium-Based Novel Silver N-Heterocyclic Carbene Complexes: Synthesis, Characterisation and In vitro Antimicrobial Activity, J. Enzyme Inhib. Med. Chem., 31 (6) (2016) 1527-1530.
  • [17] Asekunowo P.O., Haque R.A., Razali M.R., Avicor S.W., Wajidi M.F.F., Synthesis and Characterization of Nitrile Functionalized Silver(I)-N-Heterocyclic Carbene Complexes: DNA Binding, Cleavage Studies, Antibacterial Properties and Mosquitocidal Activity Against the Dengue Vector, Aedes Albopictus, Eur. J. Med. Chem., 150 (2018) 601-615.
  • [18] Nadar S., Khan T., Patching S.G., Omri A., Development of Antibiofilm Therapeutics Strategies to Overcome Antimicrobial Drug Resistance, Microorganisms, 10 (2) (2022) 303.
  • [19] Celik C., Tutar U., Sahin N., Ozturk A., Antimicrobial, Anti-biofilm and Cytotoxic Properties of Methallyl Functionalized Benzimidazolium-Derived Ag(I)-N-Heterocyclic Carbene Complexes, Trop. J. Pharm. Res., 21
There are 19 citations in total.

Details

Primary Language English
Journal Section Natural Sciences
Authors

Uğur Tutar 0000-0002-8058-0994

Cem Çelik 0000-0002-7141-5874

Publication Date September 30, 2022
Submission Date May 26, 2022
Acceptance Date September 6, 2022
Published in Issue Year 2022Volume: 43 Issue: 3

Cite

APA Tutar, U., & Çelik, C. (2022). Antibiofilm and Antimicrobial Properties of 1-allyl-3-(2-diisopropylaminoethyl) Benzimidazolium Chloride and its Silver(I)-NHC Complex. Cumhuriyet Science Journal, 43(3), 432-436. https://doi.org/10.17776/csj.1121787

Cited By

Evaluation of Antibiofilm and Antimicrobial Activities of N-heterocyclic Carbene Complexes
Cumhuriyet Science Journal
https://doi.org/10.17776/csj.1390256
 Download Cover Image