Antiviral and antimicrobial applications of chalcones and their derivatives: From nature to greener synthesis

Nematollahi, Mohammad Hadi; Mehrabani, Mehrnaz; Hozhabri, Yaser; Mirtajaddini, Maryamossadat; Iravani, Siavash

doi:10.1016/j.heliyon.2023.e20428

Cited by 8 publications

(4 citation statements)

References 162 publications

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“…This study presents a focused snapshot of antimicrobial activities and synergies within a specific context, guiding further exploration and refinement in antimicrobial research and strategies. The findings here contribute to the growing body of literature advocating for the development of selective antimicrobial agents, as highlighted in recent studies by Nematollahi et al [ 31 ] and Mezbege et al [ 32 ], which emphasize precision in antimicrobial therapy to minimize resistance development [ 31 , 32 ]. Future research should explore the clinical implications of these findings, particularly how they might influence current treatment protocols or contribute to the development of new, more effective therapies.…”

Section: Discussionsupporting

confidence: 65%

Selective in vitro Synergistic Evaluation of Probiotic Tolerant morpholinyl- and 4-ethylpiperazinyl-Imidazole-chalcone Derivatives on Gastrointestinal System Pathogens

Söylemez,

Kaplancıklı,

Osmaniye

et al. 2024

Curr Microbiol

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Imidazole-chalcone compounds are recognised for their broad-spectrum antimicrobial properties. Probiotic-friendly, selective new-generation antimicrobials prove to be more efficient in combating gastrointestinal system pathogens. The aim of this study is to identify imidazole-chalcone derivatives that probiotics tolerate and evaluate their in vitro synergistic antimicrobial effects on pathogens. In this study, fifteen previously identified imidazole-chalcone derivatives were analyzed for their in vitro antimicrobial properties against gastrointestinal microorganisms. Initially, the antimicrobial activity of pathogens was measured using the agar well diffusion method, while the susceptibility of probiotics was determined by microdilution. The chosen imidazole-chalcone derivatives were assessed for synergistic effects using the checkerboard method. Four imidazole-chalcone derivatives to which probiotic bacteria were tolerant exhibited antibacterial and antifungal activity against the human pathogens tested. To our knowledge, this study is the first to reveal the fractional inhibitory concentration (FIC) of combinations of imidazole-chalcone derivatives. Indeed, the minimum inhibitory concentrations (MIC) for morpholinyl- (ZDO-3f) and 4-ethylpiperazinyl- (ZDO-3 m) imidazole-chalcones were notably low when tested against E. coli and B. subtilis, with values of 31.25 μg/mL and 125 μg/mL, respectively. The combination of morpholinyl- and 4-ethylpiperazinyl derivatives demonstrated an indifferent effect against E. coli, but an additive effect was observed for B. subtilis. Additionally, it was observed that imidazole-chalcone derivatives did not exhibit any inhibitory effects on probiotic organisms like Lactobacillus fermentum (CECT-5716), Lactobacillus rhamnosus (GG), and Lactobacillus casei (RSSK-591). This study demonstrates that imidazole-chalcone derivatives that are well tolerated by probiotics can potentially exert a synergistic effect against gastrointestinal system pathogens.

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Section: Discussionsupporting

confidence: 65%

Selective in vitro Synergistic Evaluation of Probiotic Tolerant morpholinyl- and 4-ethylpiperazinyl-Imidazole-chalcone Derivatives on Gastrointestinal System Pathogens

Söylemez,

Kaplancıklı,

Osmaniye

et al. 2024

Curr Microbiol

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“…The synthesis of the chalcones involved potassium hydroxide (KOH)-promoted Claisen-Schmidt reaction between 2-hydroxy-4-methoxyacetophenone (3) and appropriate benzaldehyde (4) using ethanol as solvent (Scheme 2). The chalcones were characterized using UV/Visible, Fourier-Transform Infrared, 1 H NMR, 13 C NMR, and Mass spectroscopies; spectra provided in the Supporting Information.…”

Section: Chemistrymentioning

confidence: 99%

“…However, recent synthesis involving solid and functionalized reactants have generally used simple alcohols as solvents. Chalcones have demonstrated various biological activities including antioxidants, [3][4][5] anticancer, [6][7][8] antidiabetic, [9][10][11] antiviral, [12][13][14] antimalarial, [15][16][17] and many more. Aside the biological properties of chalcones, they have been employed in chemical industries as fluorescent active materials, [18][19][20] corrosion inhibitors, [21][22][23][24] and in the synthesis of liquid crystals.…”

Section: Introductionmentioning

confidence: 99%

Electrochemical and Theoretical Modelled Reduction of β‐Diketone Inspired Chalcones

Izuchukwu Ugwu,

Conradie

2024

ChemistrySelect

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The growing interest in synthesizing electrochemically active organic ligands stems from extensive reports highlighting the applications of redox‐active organic molecules. These molecules play a crucial role in capturing and converting CO2 into valuable organic compounds, including carbonates used as solvents in lithium batteries. In this study, we present an electrochemical investigation of two chalcone derivatives, referred to as (1) and (2). We explored the influence of different solvent systems, specifically acetonitrile and dimethyl sulfoxide, on the reduction potential of these chalcones. The reported chalcone derivatives were characterized using various analytical techniques, including UV/Visible spectroscopy, Fourier Transform Infrared spectroscopy, Proton and Carbon‐13 nuclear magnetic resonance, as well as mass spectrometry. The characterization of the reported chalcones, exhibiting properties of both β‐diketones and 2‐hydroxyphenones, is underscored by a density functional theory (DFT) study of chalcones (1) and (2). This research establishes a correlation between the energies calculated through DFT and the experimental reduction potentials of chalcones (1) and (2), in comparing them with a series of β‐diketones and 2‐hydroxyphenones.

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“…[27] Generally, the synthesis of chalcone is conducted by the conventional Claisen-Schmidt condensation, but also alternative approaches using green sources such as microwave and ultrasound have been introduced. [28] Compounds T1-20 were synthesized from the related acetophenones and benzaldehyde by the Claisen-Smidth method (Fandaklı et al 2018; Kahriman et al 2020). In vitro antimicrobial activity screening test of all synthesized compounds against Gram-positive, Gramnegative bacteria and yeast was performed.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Antimicrobial Activities, and Molecular Modeling Studies of Agents for the Sortase A Enzyme

Tatar Yilmaz,

Yayli,

Tüzüner

et al. 2024

Chemistry & Biodiversity

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Sortase A (SrtA) is an attractive target for developing new anti‐infective drugs that aim to interfere with essential virulence mechanisms, such as adhesion to host cells and biofilm formation. Herein, twenty hydroxy, nitro, bromo, fluoro, and methoxy substituted chalcone compounds T1‐20 were synthesized, antimicrobial activities and molecular modeling strategies against the SrtA enzyme were investigated. The most active compounds were found to be T2, T4, and T19 against Streptococcus mutans (S. mutans) with the MIC values; 1.93, 3.8, 3.94 µg/mL, and docking scores; ‐6.46, ‐6.63, ‐6.73 kcal/mol, respectively. Also, these three active compounds showed better activity than the chlorohexidine (CHX) (MIC value: 4.88 µg/mL, docking score: ‐6.29 kcal/mol) in both in vitro and in silico. Structural stability and binding free energy analysis of S.mutans SrtA with active compounds T2, T4, and T19 were measured by molecular dynamic (MD) simulations throughout 100 nanoseconds time. It was observed that the stability of the critical interactions between these compounds and the target enzyme was preserved. To prove further, in vivo biological evaluation studies could be conducted for the most promising precursor compounds T2, T4, and T19, and it might open new avenues to the discovery of more potent for SrtA inhibitors.

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Antiviral and antimicrobial applications of chalcones and their derivatives: From nature to greener synthesis

Cited by 8 publications

References 162 publications

Selective in vitro Synergistic Evaluation of Probiotic Tolerant morpholinyl- and 4-ethylpiperazinyl-Imidazole-chalcone Derivatives on Gastrointestinal System Pathogens

Selective in vitro Synergistic Evaluation of Probiotic Tolerant morpholinyl- and 4-ethylpiperazinyl-Imidazole-chalcone Derivatives on Gastrointestinal System Pathogens

Electrochemical and Theoretical Modelled Reduction of β‐Diketone Inspired Chalcones

Synthesis, Antimicrobial Activities, and Molecular Modeling Studies of Agents for the Sortase A Enzyme

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