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Evaluation of Antibiofilm and Antimicrobial Activities of N-heterocyclic Carbene Complexes

Year 2024, , 29 - 34, 28.03.2024

Uğur Tutar , Cem Çelik , Mehmet Ataş

https://doi.org/10.17776/csj.1390256

Abstract

In recent years, resistance to antimicrobials has become a global problem. Despite the need for new antibiotics with the increase of resistant bacteria, developing new antimicrobials is problematic. Biofilms formed by microorganisms play an essential role in the development of resistance. We aimed to investigate the antimicrobial and antibiofilm activities of N-heterocyclic carbene (NHC) complexes. In this study, previously synthesized and characterized NHC complexes on standard bacterial and fungal strains were investigated. The minimal inhibition concentration (MIC) test was used to determine the antimicrobial activities of the compounds, and the biofilm inhibition concentration test was used to determine the anti-biofilm activities. Compounds 2b and 2c showed potent antimicrobial activity on microorganisms between <=1.9 and 7.8µg/mL. Antimicrobial activity in salts of compounds (1a-1c) was weaker than silver compounds (2a-2c). The antibiofilm activity was between 27 and 79%, especially in silver-bound compounds (2a-2c). Benzimidazole derivative NHC compounds that we evaluated in our study were found to have significant antimicrobial and antibiofilm effects on pathogenic microorganisms. These compounds, which we assessed in our study, may be antimicrobial drug candidates that can be used in different areas. It will be essential to conduct further in vitro and in vivo studies on this subject.

Keywords

N heterocyclic carbene Benzimidazole Antimicrobial activity Antibiofilm activity

Thanks

Çalışmada kullanılan bileşiklerin temini konusunda destek veren Doç Dr Neslihan Şahine teşekkür ederiz

References

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  • [6] Ventola CL., The Antibiotic Resistance Crisis: Part 1: Causes and Threats, P T., 40 (4) (2015) 277-283.
  • [7] Conly J., Johnston B., Where Are All the New Antibiotics? The New Antibiotic Paradox, Can J Infect Dis Med Microbiol., 16 (3) (2005) 159-160.
  • [8] Chen CH., Lu TK., Development and Challenges of Antimicrobial Peptides for Therapeutic Applications, Antibiotics (Basel)., 9 (1) (2020) 24.
  • [9] Konaklieva MI., Addressing Antimicrobial Resistance Through New Medicinal and Synthetic Chemistry Strategies, SLAS Discov., 24 (4) (2019) 419-439.
  • [10] Jain A., Gupta Y., Agrawal R., Khare P., Jain SK., Biofilms--A Microbial Life Perspective: A Critical Review, Crit Rev Ther Drug Carrier Syst., 24 (5) (2007) 393-443.
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  • [15] Şahin-Bölükbaşı S., Şahin N., Tahir MN., Arıcı C., Cevik E., Gürbüz N., Özdemir İ., Cummings BS., Novel N-heterocyclic Carbene Silver (I) Complexes: Synthesis, Structural Characterization, and Anticancer Activity, Inorganica Chim Acta., 486 (2019) 711-718.
  • [16] Şahin N., Şahin-Bölükbaşı S., Tahir MN., Arıcı C., Çevik E., Gürbüz N., Özdemir İ., Cummings BS., Synthesis, Characterization, and Anticancer Activity of Allyl Substituted N-heterocyclic Carbene Silver (I) Complexes, J Mol Struct., 1179 (2019) 92-99.
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  • [18] Tutar U., Çelik C., Antibiofilm and Antimicrobial Properties of 1-allyl-3-(2-diisopropylaminoethyl) Benzimidazolium Chloride and Its Silver(I)-NHC Complex, Cumhuriyet Sci J., 43 (3) (2022) 432-436.
  • [19] Lewis K., The Science of Antibiotic Discovery, Cell, 181 (1) (2020) 29-45.
  • [20] Wohlleben W., Mast Y., Stegmann E., Ziemert N., Antibiotic Drug Discovery, Microb Biotechnol., 9 (5) (2016) 541-548.
  • [21] Boström J., Brown DG., Young RJ., Keserü GM., Expanding the Medicinal Chemistry Synthetic Toolbox, Nat Rev Drug Discov., 17 (10) (2018) 709-727.
  • [22] Campos KR., Coleman PJ., Alvarez JC., Dreher SD., Garbaccio RM., Terrett NK., Tillyer RD., Truppo MD., Parmee ER., The Importance of Synthetic Chemistry in the Pharmaceutical Industry, Science, 363 (6424) (2019) eaat0805.
  • [23] Sakamoto R., Morozumi S., Yanagawa Y., Toyama M., Takayama A., Kasuga NC., Nomiya K., Synthesis, Characterization, and Structure-Activity Relationship of the Antimicrobial Activities of Dinuclear N-heterocyclic Carbene (NHC)-Silver(I) Complexes, J Inorg Biochem., 163 (2016) 110-117.
  • [24] Sarı Y., Akkoç S., Gök Y., Sifniotis V., Özdemir İ., Günal S., Kayser V., Benzimidazolium-Based Novel Silver N-heterocyclic Carbene Complexes: Synthesis, Characterization and In Vitro Antimicrobial Activity, J Enzyme Inhib Med Chem., 31 (6) (2016) 1527-1530.
  • [25] Gök Y., Akkoç S., Erdoğan H., Albayrak S., In Vitro Antimicrobial Studies of New Benzimidazolium Salts and Silver N-heterocyclic Carbene Complexes, J Enzyme Inhib Med Chem., 31 (6) (2016) 1322-1327.
  • [26] Butorac RR., Al-Deyab SS., Cowley AH., Antimicrobial Properties of Some Bis(iminoacenaphthene (BIAN)-Supported N-heterocyclic Carbene Complexes of Silver and Gold, Molecules, 16 (3) (2011) 2285-2292.
  • [27] Siegmund D., Lorenz N., Gothe Y., Spies C., Geissler B., Prochnow P., Nuernberger P., Bandow JE., Metzler-Nolte N., Benzannulated Re(i)-NHC Complexes: Synthesis, Photophysical Properties and Antimicrobial Activity, Dalton Trans., 46 (44) (2017) 15269-15279.
  • [28] Jiang Y., Geng M., Bai L., Targeting Biofilms Therapy: Current Research Strategies and Development Hurdles, Microorganisms, 8 (8) (2020) 1222.
  • [29] Roy R., Tiwari M., Donelli G., Tiwari V., Strategies for Combating Bacterial Biofilms: A Focus on Anti-biofilm Agents and Their Mechanisms of Action, Virulence, 9 (1) (2018) 522-554.
  • [30] Vasava MS., Bhoi MN., Rathwa SK., Jethava DJ., Acharya PT., Patel DB., Patel HD., Benzimidazole: A Milestone in the Field of Medicinal Chemistry, Mini Rev Med Chem., 20 (7) (2020) 532-565.
  • [31] Tessier J., Schmitzer AR., Benzimidazolium Salts Prevent and Disrupt Methicillin-Resistant Staphylococcus aureus Biofilms, RSC Adv., 10 (2020) 9420-9430.
  • [32] 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.
  • [33] Bernardi T., Badel S., Mayer P., Groelly J., de Frémont P., Jacques B., Braunstein P., Teyssot ML., Gaulier C., Cisnetti F., Gautier A., Roland S., High-Throughput Screening of Metal-N-heterocyclic Carbene Complexes Against Biofilm Formation by Pathogenic Bacteria, ChemMedChem., 9(6) (2014) 1140-1144.
  • [34] O'Beirne C., Piatek ME., Fossen J., Müller-Bunz H., Andes DR., Kavanagh K., Patil SA., Baumann M., Tacke M., Continuous Flow Synthesis and Antimicrobial Evaluation of NHC* Silver Carboxylate Derivatives of SBC3 In Vitro and In Vivo, Metallomics., 13 (2) (2021) mfaa011.
  • [35] Kaloğlu N., Kaloğlu M., Özdemir İ., Günal S., Özdemir İ., Silver–N-heterocyclic carbene complexes: Synthesis,characterization, and antimicrobial properties, J Chin Chem Soc., 64(4) (2017) 420–426.
  • [36] Nayak S., Gaonkar,S L., Coinage Metal N-Heterocyclic Carbene Complexes: Recent Synthetic Strategies and Medicinal Applications, ChemMedChem, 16(9) (2021) 1360–1390.

Year 2024, , 29 - 34, 28.03.2024

Uğur Tutar , Cem Çelik , Mehmet Ataş

https://doi.org/10.17776/csj.1390256

Abstract

References

  • [1] Kowalchuk GA., Jones SE., Blackall LL., Microbes Orchestrate Life on Earth, ISME J., 2(8) (2008) 795-796.
  • [2] Lorenzo JM., Munekata PE., Dominguez R., Pateiro M., Saraiva JA., Franco D., Main Groups of Microorganisms of Relevance for Food Safety and Stability, Innovative Technologies for Food Preservation., (2018) 53–107.
  • [3] Lindahl JF., Grace D., The Consequences of Human Actions on Risks for Infectious Diseases: a Review, Infect Ecol Epidemiol., (5) (2015) 30048.
  • [4] McEwen SA., Collignon PJ., Antimicrobial Resistance: A One Health Perspective, Microbiol Spectr., 6 (2) (2018) 10.1128.
  • [5] Topal M., Uslu Şenel G., Arslan Topal EI., Öbek E., Antibiotics and Usage Areas, Erciyes Üniversitesi Fen Bilimleri Enstitüsü Dergisi., 31(3) (2015) 121-127.
  • [6] Ventola CL., The Antibiotic Resistance Crisis: Part 1: Causes and Threats, P T., 40 (4) (2015) 277-283.
  • [7] Conly J., Johnston B., Where Are All the New Antibiotics? The New Antibiotic Paradox, Can J Infect Dis Med Microbiol., 16 (3) (2005) 159-160.
  • [8] Chen CH., Lu TK., Development and Challenges of Antimicrobial Peptides for Therapeutic Applications, Antibiotics (Basel)., 9 (1) (2020) 24.
  • [9] Konaklieva MI., Addressing Antimicrobial Resistance Through New Medicinal and Synthetic Chemistry Strategies, SLAS Discov., 24 (4) (2019) 419-439.
  • [10] Jain A., Gupta Y., Agrawal R., Khare P., Jain SK., Biofilms--A Microbial Life Perspective: A Critical Review, Crit Rev Ther Drug Carrier Syst., 24 (5) (2007) 393-443.
  • [11] Dumitru C., Bacterial Biofilms and Their Biological Significance, Rev Rom Med Vet., 28 (2) (2018) 35-40.
  • [12] Dincer S., Masume Uslu F., Delik A., Antibiotic Resistance in Biofilm. Bacterial Biofilms, London, UK: IntechOpen Limited, (2020).
  • [13] Hopkinson MN., Richter C., Schedler M., Glorius F., An Overview of N-heterocyclic Carbenes, Nature, 510 (7506) (2014) 485-496.
  • [14] Smith CA., Narouz MR., Lummis PA., Singh I., Nazemi A., Hung Li C., Crudden CM., N-heterocyclic Carbenes in Materials Chemistry, Chem Rev., 119 (8) (2019) 4986-5056.
  • [15] Şahin-Bölükbaşı S., Şahin N., Tahir MN., Arıcı C., Cevik E., Gürbüz N., Özdemir İ., Cummings BS., Novel N-heterocyclic Carbene Silver (I) Complexes: Synthesis, Structural Characterization, and Anticancer Activity, Inorganica Chim Acta., 486 (2019) 711-718.
  • [16] Şahin N., Şahin-Bölükbaşı S., Tahir MN., Arıcı C., Çevik E., Gürbüz N., Özdemir İ., Cummings BS., Synthesis, Characterization, and Anticancer Activity of Allyl Substituted N-heterocyclic Carbene Silver (I) Complexes, J Mol Struct., 1179 (2019) 92-99.
  • [17] Şahin N., Üstün E., Tutar U., Çelik C., Gürbüz N., Özdemir İ., Antimicrobial Activity, Inhibition of Biofilm Formation, and Molecular Docking Study of Novel Ag-NHC Complexes, J Organomet Chem., 954–955 (2021) 122082.
  • [18] Tutar U., Çelik C., Antibiofilm and Antimicrobial Properties of 1-allyl-3-(2-diisopropylaminoethyl) Benzimidazolium Chloride and Its Silver(I)-NHC Complex, Cumhuriyet Sci J., 43 (3) (2022) 432-436.
  • [19] Lewis K., The Science of Antibiotic Discovery, Cell, 181 (1) (2020) 29-45.
  • [20] Wohlleben W., Mast Y., Stegmann E., Ziemert N., Antibiotic Drug Discovery, Microb Biotechnol., 9 (5) (2016) 541-548.
  • [21] Boström J., Brown DG., Young RJ., Keserü GM., Expanding the Medicinal Chemistry Synthetic Toolbox, Nat Rev Drug Discov., 17 (10) (2018) 709-727.
  • [22] Campos KR., Coleman PJ., Alvarez JC., Dreher SD., Garbaccio RM., Terrett NK., Tillyer RD., Truppo MD., Parmee ER., The Importance of Synthetic Chemistry in the Pharmaceutical Industry, Science, 363 (6424) (2019) eaat0805.
  • [23] Sakamoto R., Morozumi S., Yanagawa Y., Toyama M., Takayama A., Kasuga NC., Nomiya K., Synthesis, Characterization, and Structure-Activity Relationship of the Antimicrobial Activities of Dinuclear N-heterocyclic Carbene (NHC)-Silver(I) Complexes, J Inorg Biochem., 163 (2016) 110-117.
  • [24] Sarı Y., Akkoç S., Gök Y., Sifniotis V., Özdemir İ., Günal S., Kayser V., Benzimidazolium-Based Novel Silver N-heterocyclic Carbene Complexes: Synthesis, Characterization and In Vitro Antimicrobial Activity, J Enzyme Inhib Med Chem., 31 (6) (2016) 1527-1530.
  • [25] Gök Y., Akkoç S., Erdoğan H., Albayrak S., In Vitro Antimicrobial Studies of New Benzimidazolium Salts and Silver N-heterocyclic Carbene Complexes, J Enzyme Inhib Med Chem., 31 (6) (2016) 1322-1327.
  • [26] Butorac RR., Al-Deyab SS., Cowley AH., Antimicrobial Properties of Some Bis(iminoacenaphthene (BIAN)-Supported N-heterocyclic Carbene Complexes of Silver and Gold, Molecules, 16 (3) (2011) 2285-2292.
  • [27] Siegmund D., Lorenz N., Gothe Y., Spies C., Geissler B., Prochnow P., Nuernberger P., Bandow JE., Metzler-Nolte N., Benzannulated Re(i)-NHC Complexes: Synthesis, Photophysical Properties and Antimicrobial Activity, Dalton Trans., 46 (44) (2017) 15269-15279.
  • [28] Jiang Y., Geng M., Bai L., Targeting Biofilms Therapy: Current Research Strategies and Development Hurdles, Microorganisms, 8 (8) (2020) 1222.
  • [29] Roy R., Tiwari M., Donelli G., Tiwari V., Strategies for Combating Bacterial Biofilms: A Focus on Anti-biofilm Agents and Their Mechanisms of Action, Virulence, 9 (1) (2018) 522-554.
  • [30] Vasava MS., Bhoi MN., Rathwa SK., Jethava DJ., Acharya PT., Patel DB., Patel HD., Benzimidazole: A Milestone in the Field of Medicinal Chemistry, Mini Rev Med Chem., 20 (7) (2020) 532-565.
  • [31] Tessier J., Schmitzer AR., Benzimidazolium Salts Prevent and Disrupt Methicillin-Resistant Staphylococcus aureus Biofilms, RSC Adv., 10 (2020) 9420-9430.
  • [32] 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.
  • [33] Bernardi T., Badel S., Mayer P., Groelly J., de Frémont P., Jacques B., Braunstein P., Teyssot ML., Gaulier C., Cisnetti F., Gautier A., Roland S., High-Throughput Screening of Metal-N-heterocyclic Carbene Complexes Against Biofilm Formation by Pathogenic Bacteria, ChemMedChem., 9(6) (2014) 1140-1144.
  • [34] O'Beirne C., Piatek ME., Fossen J., Müller-Bunz H., Andes DR., Kavanagh K., Patil SA., Baumann M., Tacke M., Continuous Flow Synthesis and Antimicrobial Evaluation of NHC* Silver Carboxylate Derivatives of SBC3 In Vitro and In Vivo, Metallomics., 13 (2) (2021) mfaa011.
  • [35] Kaloğlu N., Kaloğlu M., Özdemir İ., Günal S., Özdemir İ., Silver–N-heterocyclic carbene complexes: Synthesis,characterization, and antimicrobial properties, J Chin Chem Soc., 64(4) (2017) 420–426.
  • [36] Nayak S., Gaonkar,S L., Coinage Metal N-Heterocyclic Carbene Complexes: Recent Synthetic Strategies and Medicinal Applications, ChemMedChem, 16(9) (2021) 1360–1390.
There are 36 citations in total.

Details

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

Uğur Tutar 0000-0002-8058-0994

Cem Çelik 0000-0002-7141-5874

Mehmet Ataş 0000-0002-9425-0080

Publication Date March 28, 2024
Submission Date November 13, 2023
Acceptance Date March 12, 2024
Published in Issue Year 2024

Cite

APA Tutar, U., Çelik, C., & Ataş, M. (2024). Evaluation of Antibiofilm and Antimicrobial Activities of N-heterocyclic Carbene Complexes. Cumhuriyet Science Journal, 45(1), 29-34. https://doi.org/10.17776/csj.1390256