Synthesis, characterization, antimicrobial and antibiofilm activity, and molecular docking analysis of NHC precursors and their Ag-NHC complexes

Üstün, Elvan; Şahin, Neslihan; Çelik, Cem; Tutar, Uğur; Özdemir, Namık; Gürbüz, Nevin; Özdemır, İsmaıl

doi:10.1039/d1dt02003j

Cited by 22 publications

(14 citation statements)

References 67 publications

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“…All methyl carbon peaks of salts were observed at 20.7 ppm for. These values agree with reported data for similar N-heterocyclic carbenes [27]. The FT-IR, 1 H NMR, and 13 C{ 1 H} NMR spectra are presented in the details in the Supplementary Files (Figures S1, S6).…”

Section: Characterization Of N-heterocyclic Carbene Saltssupporting

confidence: 89%

Synthesis, and Characterization and In-Silico Analysis Against SARS CoV-2 of Novel Benzimidazolium Salts

Üstün

Şahin

2022

Orbital: Electron. J. Chem.

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N-heterocyclic carbene molecules are often used as the main scaffold in pharmaceutical chemistry, and one of the most important of these is benzimidazoles. Severe Acute Respiratory Syndrome Coronavirus Disease-2 is the cause of the ongoing pandemic, and a drug should be developed against this virus. Scientists have been investigated the antiviral effects of many not only known molecules but also new molecules. In this study, reactivity and anti-coronavirus disease properties of new benzimidazole derivative molecules were investigated by theoretical methods. Three new benzimidazole derivative molecules were synthesized and fully characterized by FT-IR, 1H NMR and, 13C{1H} NMR spectroscopies for this purpose. Density Functional Theory-based calculation methods were used for optimization and frontier orbitals analysis. Also, the interactions of the molecules were evaluated with coronavirus disease main protease, and severe acute respiratory syndrome coronavirus main peptidase and the results were compared with the results of well-known anti-viral drugs by molecular docking methods. According to the results, 1-allyl-3-(3-chlorobenzyl-5,6-dimethylbenzimidazolium chloride represent the best result against both main protease and main peptidase enzyme with -6.36 kcal/mol and -8.87 kcal/mol, respectively. Additionally, three of the molecules were give better binding results than the well-known anti-viral drugs.

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Section: Characterization Of N-heterocyclic Carbene Saltssupporting

confidence: 89%

Synthesis, and Characterization and In-Silico Analysis Against SARS CoV-2 of Novel Benzimidazolium Salts

Üstün

Şahin

2022

Orbital: Electron. J. Chem.

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“…Üstün et al [11] showed the antibiofilm activities of the Ag(I)-NHC compounds they synthesized on grampositive and negative bacteria and fungal strains. Celik et al [19] In their study, they reported that Ag(I)-NHC compounds inhibited the biofilm formation of grampositive and gram-negative bacteria and yeast strains by 32-84% while degrading mature biofilms by 14-66%.…”

Section: Resultsmentioning

confidence: 99%

“…The biofilm inhibition value at SubMIC was calculated with Eq. [11] Biofilm inhibition ( % ) = { ( Ac − As ) / Ac } 100 where As and Ac are the absorbance of sample and control, respectively. This test was performed in triplicate and the mean (n = 3) was taken.…”

Section: Reduction In Biofilm Formationmentioning

confidence: 99%

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

Tutar

Çelik

2022

Cumhuriyet Science Journal

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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.

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“…Ag(I)‐NHC complexes ( 2a–d ) were synthesized under argon gas atmosphere and according to the literature. [ 31 ]…”

Section: Methodsmentioning

confidence: 99%

Antimicrobial and antibiofilm activities and bovine serum albumin binding properties of benzimidazolium derivative NHC salts and their Ag(I)‐NHC complexes

Çelik

Üstün

Şahin

et al. 2022

Applied Organom Chemis

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Benzimidazole type N‐heterocyclic carbene molecules and their metal complexes have well‐known biological activity. Elemental silver and silver complexes also have antibacterial and antifungal activity. In this study, silver complexes with 1‐allyl 5,6‐dimethylbenzimidazolium derivative ligands were analyzed for their antimicrobial and antibiofilm activities. Additionally, bovine serum albumin (BSA) binding properties of the molecules were analyzed by spectrophotometric methods, and the details of interactions of the molecules with BSA were investigated by molecular docking methods. While N‐heterocyclic carbene salts showed moderate antifungal and antibiofilm activity, silver complexes of these salts have strong antimicrobial activity with <1.9–15.6 μg/ml minimal inhibitory concentration (MIC) values. On the other hand, carbene salts have better affinity against BSA than the complexes. Additionally, the interaction of the optimized complexes with SarA and BSA were analyzed by molecular docking methods. According to in vitro and in silico evaluation, the studied Ag complexes may be utilized for advanced studies.

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Synthesis, characterization, antimicrobial and antibiofilm activity, and molecular docking analysis of NHC precursors and their Ag-NHC complexes

Abstract: A series of novel silver(i)-NHC complexes are synthesized and characterized. The anticandidal activity of some complexes was found to be similar to that of Flucanozol.

Cited by 22 publications

References 67 publications

Synthesis, and Characterization and In-Silico Analysis Against SARS CoV-2 of Novel Benzimidazolium Salts

Synthesis, and Characterization and In-Silico Analysis Against SARS CoV-2 of Novel Benzimidazolium Salts

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

Antimicrobial and antibiofilm activities and bovine serum albumin binding properties of benzimidazolium derivative NHC salts and their Ag(I)‐NHC complexes

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