Silver (I) complexes of imidazolium based N-heterocyclic carbenes for antibacterial applications

Aher, Sainath Babaji; Das, Anamika; Muskawar, Prashant Narayan; Osborne, Jabez W.; Bhagat, Pundlik Rambhau

doi:10.1016/j.molliq.2017.01.109

Cited by 17 publications

(10 citation statements)

References 31 publications

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Section: Resultsmentioning

confidence: 99%

“…They reported that complexes were effective at inhibiting the growth of E. coli and S. aureus while their corresponding salts were inactive against both strains of bacteria. [ 60–66,75 ] Asekunowo et al [ 65 ] reported the MIC values of the silver complexes against both E. coli and S. aureus were in the range of 25–100 µg/ml. These Ag(I)–NHC complexes (1‐cyanopropyl‐3‐pentyl‐benzimidazolium‐silver hexafluorophosphate and 1‐cyanopropyl‐3‐(3‐cyanobenzyl)benzimidazolium‐silver(I) hexafluorophosphate) had better antibacterial qualities in comparison with silver nitrate.…”

Section: Resultsmentioning

confidence: 99%

“…The nitrile functionality on these ligands provides extra space for bonding or bridging to silver(I) center and this unique ability gave benefit either in coordination or in the formation of supramolecular architecture. [60][61][62][63][64][65][66] Other than that, the binding effect due to interaction or coordination between the nitrile functionality and the silver(I) center can result in more stable silver(I)-NHC complexes that S C H E M E 2 Synthesis of cyanopropylfunctionalized silver N-heterocyclic carbene complexes can slowly release silver ions at the wound site, thus preserving the antibacterial effect over a longer time. [67] The antibacterial activities of the prepared cyanopropyl functionalized benzimidazolium salts (1a-c) and their silver complexes (2a-c) were evaluated against a panel of Gram-positive (S. aureus, Enterococcus faecalis, and methicillin-resistant Staphylococcus aureus…”

Section: Antibacterial Activitiesmentioning

confidence: 99%

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Cyanopropyl functionalized benzimidazolium salts and their silver N‐heterocyclic carbene complexes: Synthesis, antimicrobial activity, and theoretical analysis

Türker

Üstün

Günal

et al. 2022

Archiv der Pharmazie

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The reaction of N-substituted benzimidazole with 4-bromobutyronitrile gives the corresponding benzimidazolium salts as N-heterocyclic carbene (NHC) precursors. Silver(I) carbene complexes are synthesized by the reaction of the corresponding benzimidazolium salts with Ag 2 O in dichloromethane. These new NHC precursors and Ag-NHC complexes were characterized by spectroscopy techniques and also screened for their antibacterial activities against the standard bacterial strains Escherichia coli, Pseudomonas aeruginosa, Acinetobacter baumannii, Klebsiella pneumoniae, Staphylococcus aureus, methicillin-resistant Staphylococcus aureus, and Enterococcus faecalis, and the standard fungal strains Candida albicans and Candida glabrata, and promising results were achieved. The compounds were also analyzed by density functional theory (DFT)/time-dependent DFT and docking methods.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Antibacterial Activitiesmentioning

confidence: 99%

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Cyanopropyl functionalized benzimidazolium salts and their silver N‐heterocyclic carbene complexes: Synthesis, antimicrobial activity, and theoretical analysis

Türker

Üstün

Günal

et al. 2022

Archiv der Pharmazie

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“…Actually, the activities of the NHC–silver complexesare considerably affected by the NHC ligand structures [ 13 ]. The factors such as hydrophobic substitution and steric bulk on imidazole ring can delay the rate of silver ions release [ 16 ]. Tacke’s group demonstrated that introducing lipophilic benzyl-substituents at the N 1 and N 3 positions, starting from 4,5-diphenylimidazol the resulting silver complexes show a minimum inhibitory concentration (MIC), ranging from 20 to 3.13 µg/mL (35.3 to 5.52 µM) for a variety of Gram-positive, Gram-negative and mycobacteria tested [ 17 ].…”

Section: Introductionmentioning

confidence: 99%

Silver (I) N-Heterocyclic Carbene Complexes: A Winning and Broad Spectrum of Antimicrobial Properties

Prencipe

Zanfardino

Napoli

et al. 2021

IJMS

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The evolution of antibacterial resistance has arisen as the main downside in fighting bacterial infections pushing researchers to develop novel, more potent and multimodal alternative drugs.Silver and its complexes have long been used as antimicrobial agents in medicine due to the lack of silver resistance and the effectiveness at low concentration as well as to their low toxicities compared to the most commonly used antibiotics. N-Heterocyclic Carbenes (NHCs) have been extensively employed to coordinate transition metals mainly for catalytic chemistry. However, more recently, NHC ligands have been applied as carrier molecules for metals in anticancer applications. In the present study we selected from literature two NHC-carbene based on acridinescaffoldand detailed nonclassicalpyrazole derived mono NHC-Ag neutral and bis NHC-Ag cationic complexes. Their inhibitor effect on bacterial strains Gram-negative and positivewas evaluated. Imidazolium NHC silver complex containing the acridine chromophore showed effectiveness at extremely low MIC values. Although pyrazole NHC silver complexes are less active than the acridine NHC-silver, they represent the first example of this class of compounds with antimicrobial properties. Moreover all complexesare not toxic and they show not significant activity againstmammalian cells (Hek lines) after 4 and 24 h. Based on our experimental evidence, we are confident that this promising class of complexes could represent a valuable starting point for developing candidates for the treatment of bacterial infections, delivering great effectiveness and avoiding the development of resistance mechanisms.

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“…Many substituted imidazolium nuclei with a proper counter ion have also been of interest in the field of ionic liquids . These compounds have biological applications because of their antibacterial activity and can also be used as sensors due to its fluorescence properties . The reliability of these applications is mainly based in two factors: the reactivity of the imidazolium nucleus and its capacity to establish supramolecular interactions.…”

Section: Introductionmentioning

confidence: 99%

Linkage between Fluorescence and Electrochemical Properties of Imidazolium Compounds in Acetonitrile Solution

et al. 2020

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The fluorescence properties of some imidazolium derivatives are relevant in photosensing and therefore, the structural analysis of them is a key point for its rational design, which would be useful to prepare new systems with novel applications. Herein we report a multidisciplinary study of the fluorescence and voltammetric properties of three imidazolium compounds {1,3‐bis[(R,R)‐1′‐chloro‐1′‐phenylpropan‐2′‐yl]‐imidazolium chloride (1), 1,3‐bis[(Z)‐1′‐phenylprop‐1′‐en‐2′‐yl]imidazolium chloride (2) 1,3‐bis[(R)‐1′‐chlorobutan‐2′‐yl]‐imidazolium chloride (3)}. Electronic structure calculations and Bader analyses were used to correlate both fluorescence and the capability of the molecules to be reduced through a heterogeneous electron transfer process. Both properties are strongly dependent on the proton in position two of the imidazolium ring, where the electron transfer as well as the excitation of the electrons are carried out. The reactivity in this position is controlled by the N‐substituents on the imidazolium ring and is due to single contacts H⋅⋅⋅Cl−, tricentric contacts Cl⋅⋅⋅Cl−⋅⋅⋅Cl, π‐electronic delocalization and π‐stacking interactions.

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Silver (I) complexes of imidazolium based N-heterocyclic carbenes for antibacterial applications

Cited by 17 publications

References 31 publications

Cyanopropyl functionalized benzimidazolium salts and their silver N‐heterocyclic carbene complexes: Synthesis, antimicrobial activity, and theoretical analysis

Cyanopropyl functionalized benzimidazolium salts and their silver N‐heterocyclic carbene complexes: Synthesis, antimicrobial activity, and theoretical analysis

Silver (I) N-Heterocyclic Carbene Complexes: A Winning and Broad Spectrum of Antimicrobial Properties

Linkage between Fluorescence and Electrochemical Properties of Imidazolium Compounds in Acetonitrile Solution

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