Ferrocene derivatives as anti-infective agents

Ludwig, Beatrice Stefanie; Correia, João D. G.; Kühn, Fritz E.

doi:10.1016/j.ccr.2019.06.004

Cited by 101 publications

(65 citation statements)

References 260 publications

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“…Alternatively, many AMPs have been embellished with organometallic substituents including metallocenes, leading to improved activity [10–12] . Ferrocene in particular is inexpensive and known to display rather low toxicity (rat, oral LD 50 =1320 mg/kg); [13] accordingly, many ferrocene‐based antimicrobials have been reported and show improved efficacy as antimicrobial agents compared to their more traditional analogs [14–17] . In one example, synthetically derived ferrocene‐containing penems had superior anti‐MRSA activity, exhibiting as much as an approximately fourfold elevation, while also displaying a modest twofold enhancement in activity against Gram‐negative strains compared to their non‐organometallic antibiotic counterparts (Figure 1, left) [14,15] .…”

Section: Figurementioning

confidence: 99%

“…Ferrocene in particular is inexpensive and known to display rather low toxicity (rat, oral LD 50 =1320 mg/kg); [13] accordingly, many ferrocene‐based antimicrobials have been reported and show improved efficacy as antimicrobial agents compared to their more traditional analogs [14–17] . In one example, synthetically derived ferrocene‐containing penems had superior anti‐MRSA activity, exhibiting as much as an approximately fourfold elevation, while also displaying a modest twofold enhancement in activity against Gram‐negative strains compared to their non‐organometallic antibiotic counterparts (Figure 1, left) [14,15] . For other small molecule antibiotic mimics, the incorporation of ferrocene with dithiothione and dithioketone moieties resulted in good activity against both Escherichia coli and Streptococcus pyogenes (MIC=10 μg/mL; Figure 1, center) [16] .…”

Section: Figurementioning

confidence: 99%

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Metallocene QACs: The Incorporation of Ferrocene Moieties into monoQAC and bisQAC Structures

et al. 2020

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Inspired by the incorporation of metallocene functionalities into a variety of bioactive structures, particularly antimicrobial peptides, we endeavored to broaden the structural variety of quaternary ammonium compounds (QACs) by the incorporation of the ferrocene moiety. Accordingly, 23 ferrocene‐containing mono‐ and bisQACs were prepared in high yields and tested for activity against a variety of bacteria, including Gram‐negative strains and a panel of clinically isolated MRSA strains. Ferrocene QACs were shown to be effective antiseptics with some displaying single‐digit micromolar activity against all bacteria tested, demonstrating yet another step in the expansion of structural variety of antiseptic QACs.

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Section: Figurementioning

confidence: 99%

Section: Figurementioning

confidence: 99%

Metallocene QACs: The Incorporation of Ferrocene Moieties into monoQAC and bisQAC Structures

et al. 2020

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“…The drugs mentioned above were reported to exhibit improved therapeutic effects compared to their parent drugs. Ferroquine has reached the clinical trial phase (II), and ferrocifen is currently in a preclinical trial [24–26] . There are several research reports on ferrocene‐based compounds with various biological activities (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Hybrid Compounds Containing a Ferrocene Scaffold as Potential Antimalarials

2021

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Malaria is an infectious disease, and it remains a serious health problem globally. The drugs developed for its treatment suffer from several shortcomings such as low water solubility, poor bioavailability, drug toxicity, and resistance. Molecular hybridization of different bioactive agents is a promising approach for developing hybrid compounds with improved therapeutic effects. Ferrocene, an organometallic, has been hybridized with several pharmacophores resulting in compounds with potent biological activities. In this research, a modified ferrocene scaffold was hybridized with selected pharmacophores. The synthesized compounds were characterized by Fourier‐Transform Infrared Spectroscopy (FTIR), Nuclear Magnetic Resonance Spectroscopy (NMR), and Liquid Chromatography‐Mass Spectroscopy. The hybrid compounds were obtained in good yields (53–76 %). In vitro evaluation against NF54 (drug‐sensitive) strain of Plasmodium falciparum parasites revealed the compounds, 16 and 19 (hybrids containing artesunate scaffold), together with 18 and 21 (hybrids containing oleanolic acid scaffold), as promising antimalarial agents. These compounds displayed IC50 values of 116.73±3.18, 56.33±15.20, 78.22±21.05, and 58.22±15.20 nM, respectively. These findings revealed the potency of ferrocene as a precursor for the development of promising antimalarials.

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“…Since their discovery ferrocene (Fc) and its derivatives have been proved to be the excellent chemical reagents in organic and organometallic synthesis, electrochemistry, catalysts, and design of new chiral materials . Nowadays, they have wide applications, for example, medicine, electro‐optical devices, modified electrodes and capacitors, biosensors, and protective coating materials …”

Section: Introductionmentioning

confidence: 99%

2‐[(4‐Aminobutyl)ferrocenylmethylidene]‐5,6‐dimethoxy‐1‐indanone derivatives: Synthesis, characterization, and investigation of electro‐optical properties

Rahimpour

Shafagh‐Azar

Abbasi

et al. 2020

Applied Organom Chemis

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A ferrocenyl‐based, chromophore‐containing 1‐indanone derivative was synthesized through crotonic condensation between 4‐chlorobutylferrocenecarboxaldehyde and 5,6‐dimethoxy‐1‐indanone followed by the nucleophilic substitution of chlorine atom of the obtained dyad with different aromatic and aliphatic amines. The electrochemical and optical properties of the synthesized compounds were investigated to explore the relationship between their structures and optical and electrochemical properties. The bandgaps determined from optical absorption spectra ranged from 2.05 to 2.15 eV. The important electrochemical parameters, including the peak potential separation, peak current ratios, and the dependence of peak currents on the scan rate, were studied. Results showed an electrochemically reversible redox system with diffusion‐controlled redox process for the synthesized compounds. The study of quantum chemistry was performed on the synthesized compounds using the density functional theory approach. The B3LYP method and 6‐311 G(d) basis set were used for optimizing the structures in the gas phase. The theoretical and experimental results show that these compounds can be considered as candidates to be used in optical applications.

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Ferrocene derivatives as anti-infective agents

Cited by 101 publications

References 260 publications

Metallocene QACs: The Incorporation of Ferrocene Moieties into monoQAC and bisQAC Structures

Metallocene QACs: The Incorporation of Ferrocene Moieties into monoQAC and bisQAC Structures

Hybrid Compounds Containing a Ferrocene Scaffold as Potential Antimalarials

2‐[(4‐Aminobutyl)ferrocenylmethylidene]‐5,6‐dimethoxy‐1‐indanone derivatives: Synthesis, characterization, and investigation of electro‐optical properties

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