Allyl Functionalized Benzimidazolium-Derived Ag(I)-N-Heterocyclic Carbene Complexes: Anti-Biofilm and Antimicrobial Properties

Tutar, Uğur; Çelik, Cem; Şahin, Neslihan

doi:10.1007/s11094-022-02601-6

Cited by 4 publications

(2 citation statements)

References 31 publications

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“…Şahin et al [21] reported that the Ag(I) NHC compounds they synthesized found different concentrations of antibiofilm activity on two grampositive and two gram-negative bacteria and one yeast strain. Tutar et al [22] They reported that they found strong antibiofilm activity in their study with Ag(I) NHC complexes. Researchers have found up to 90% antibiofilm activity on gram-positive and gram-negative bacteria and yeast strains.…”

Section: Resultsmentioning

confidence: 93%

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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Section: Resultsmentioning

confidence: 93%

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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“…The best behavior of 160 can be attributed to the increase in the number of alkyl groups on benzyl moiety that increases in lipophilicity. Later Tutar et al expanded the investigation of this class of compounds synthesizing other six allyl-substituted benzimidazole-based Ag(I)-NHC complexes (161-166) [59]. All tested compounds showed strong and similar activity against E. coli ATCC 25922 at very low concentration (≤3.9 µgmL −1 ) as compared to ampicillin as well as they displayed the same or stronger activity against the A. baumannii isolate with MIC values of 15.6-31.25 µg mL −1 .…”

Section: Nhc-silver Complexes Bearing Aliphatic Substituentsmentioning

confidence: 99%

Structure–Activity Relationships in NHC–Silver Complexes as Antimicrobial Agents

2023

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Silver has a long history of antimicrobial activity and received an increasing interest in last decades owing to the rise in antimicrobial resistance. The major drawback is the limited duration of its antimicrobial activity. The broad-spectrum silver containing antimicrobial agents are well represented by N-heterocyclic carbenes (NHCs) silver complexes. Due to their stability, this class of complexes can release the active Ag+ cations in prolonged time. Moreover, the properties of NHC can be tuned introducing alkyl moieties on N-heterocycle to provide a range of versatile structures with different stability and lipophilicity. This review presents designed Ag complexes and their biological activity against Gram-positive, Gram-negative bacteria and fungal strains. In particular, the structure–activity relationships underlining the major requirements to increase the capability to induce microorganism death are highlighted here. Moreover, some examples of encapsulation of silver–NHC complexes in polymer-based supramolecular aggregates are reported. The targeted delivery of silver complexes to the infected sites will be the most promising goal for the future.

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Polymerized methyl imidazole silver bromide (CH₃C₆H₅AgBr)₆: Synthesis, crystal structures, and catalytic activity

Xin,

Yang,

Peng

et al. 2023

Open Chemistry

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One-pot synthesis of polymerized methyl imidazole silver bromide (CH3C6H5AgBr)6 Compound 1 was carried out by the reaction of methylimidazole, 1,2-dibromoethane, and Ag2O in tetrahydrofuran at 60°C for 2 h. Compound 1 was characterized by elemental analysis, 1 H nuclear magnetic resonance, and single crystal X-ray diffraction. The crystal cell parameters of Compound 1 are as follows: a = 8.916(4) Å, b = 17.655(9) Å, c = 9.024(4) Å, α = 90°, β = 103.621(7)°, γ = 90°, V = 1380.6(12) Å3, and Z = 4. The silver atoms in Compound 1 are pentacoordinated with three bromine atoms, one silver atom, and one nitrogen atom of methyl imidazole, and polymeric methyl imidazole silver bromide was formed based on this structure. The catalytic effects under optimized conditions were investigated in this study, and the results showed that Compound 1 possesses a strong catalytic effect on the oxidation of 2-methylnaphthalene with a conversion rate of 77.15% by using hydrogen peroxide as the oxidant at 80°C for 3 h. The catalytic mechanism was explored simultaneously.

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Allyl Functionalized Benzimidazolium-Derived Ag(I)-N-Heterocyclic Carbene Complexes: Anti-Biofilm and Antimicrobial Properties

Cited by 4 publications

References 31 publications

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

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

Structure–Activity Relationships in NHC–Silver Complexes as Antimicrobial Agents

Polymerized methyl imidazole silver bromide (CH₃C₆H₅AgBr)₆: Synthesis, crystal structures, and catalytic activity

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Allyl Functionalized Benzimidazolium-Derived Ag(I)-N-Heterocyclic Carbene Complexes: Anti-Biofilm and Antimicrobial Properties

Cited by 4 publications

References 31 publications

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

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

Structure–Activity Relationships in NHC–Silver Complexes as Antimicrobial Agents

Polymerized methyl imidazole silver bromide (CH3C6H5AgBr)6: Synthesis, crystal structures, and catalytic activity

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Polymerized methyl imidazole silver bromide (CH₃C₆H₅AgBr)₆: Synthesis, crystal structures, and catalytic activity