Quaternized and Thiazole‐Functionalized Free Radical‐Generating Organometallic Dendrimers as Antimicrobial Platform against Multidrug‐Resistant Microorganisms

Abd‐El‐Aziz, Alaa S.; Agatemor, Christian; Etkin, Nola; Bissessur, Rabin; Overy, David P.; Lanteigne, Martin; McQuillan, Katherine; Kerr, Russell G.

doi:10.1002/mabi.201700020

Cited by 17 publications

(4 citation statements)

References 90 publications

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“…The first decomposition is due to the losses of cationic cyclopentadienyl iron in the dendrimers’ arms, which exhibited around 15–25% loss at the temperature between 190–250 °C for as the first degradation of all dendrimers [ 31 , 56 , 57 ].…”

Section: Resultsmentioning

confidence: 99%

Design of Organoiron Dendrimers Containing Paracetamol for Enhanced Antibacterial Efficacy

2020

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Paracetamol (acetaminophen) is a common painkiller and antipyretic drug used globally. Attachment of paracetamol to a series of organoiron dendrimers was successfully synthesized. The aim of this study is to combine the benefits of the presence of these redox-active organoiron dendrimers, their antimicrobial activities against some human pathogenic Gram-positive, and the therapeutic characteristics of paracetamol. The antimicrobial activity of these dendrimers was investigated and tested with a minimum inhibitory concentration and this has been reported. Some of these newly synthesized dendrimers exhibited the highest inhibitory activity against methicillin-resistant Staphylococcus aureus (MRSA), vancomycin-resistant Enterococcus faecium (VRE), and Staphylococcus warneri compared to reference drugs. The results of this study indicate that the antimicrobial efficacy of the dendrimers is dependent on the size of the redox-active organoiron dendrimer and its terminal functionalities. The best result has been recorded for the fourth-generation dendrimer 11, which attached to 48 paracetamol end groups and has 90 units composed of the η6-aryl-η5-cyclopentadienyliron (II) complex. This dendrimer presented inhibition of 50% of the growth (IC50) of 0.52 μM for MRSA, 1.02 μM for VRE, and 0.73 μM for Staphylococcus warneri. The structures of the dendrimers were characterized by elemental analysis, Fourier transform infrared (FT-IR), nuclear magnetic resonance (1H-NMR), and 13C-NMR spectroscopic techniques. In addition, all synthesized dendrimers displayed good thermal stability in the range of 300–350 °C following the degradation of the cationic iron moieties which occurred around 200 °C.

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Section: Resultsmentioning

confidence: 99%

Design of Organoiron Dendrimers Containing Paracetamol for Enhanced Antibacterial Efficacy

2020

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“…For example, quaternization, the classic procedure for synthesizing most quaternary ammonium cations, takes 24-48 hours at elevated temperatures of 50-80 °C. [71] Such a high energyconsuming reaction is unsustainable from economic and environmental perspectives if the IL is required on a large scale. Also, most of the ILs used in the laboratory and industry are synthesized from non-renewable precursors.…”

Section: Economic Competitivenessmentioning

confidence: 99%

“…Unfortunately, many ILs’ and DESs’ precursors, such as quaternary ammonium, imidazolium, quaternary phosphonium, piperidinium, or pyrrolidinium cations, are synthesized via high energy‐consuming processes. For example, quaternization, the classic procedure for synthesizing most quaternary ammonium cations, takes 24–48 hours at elevated temperatures of 50–80 °C [71] . Such a high energy‐consuming reaction is unsustainable from economic and environmental perspectives if the IL is required on a large scale.…”

Section: Sustainable Solventsmentioning

confidence: 99%

Enabling Sustainable Chemistry with Ionic Liquids and Deep Eutectic Solvents: A Fad or the Future?

et al. 2022

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Ionic liquids (ILs) and deep eutectic solvents (DESs) debuted with a promise of a superior sustainability footprint due to their low vapor pressure. However, their toxicity and high cost compromise this footprint, impeding their real‐world applications. Fortunately, their property tunability through a rational selection of precursors, including bioderived ones, provides a strategy to ameliorate toxicity, lower cost, and endow new functions. This Review discusses whether ILs and DESs are sustainable solvents and how they contribute to sustainable chemical processes.

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“…The use of the organoiron sandwich complexes to construct several dendrimers has led to the development of novel drug carriers with potent activity against infection-causing microorganisms. Indeed, the presence of redox-active iron centers in the dendrimers structure has a key role in activating the formation of reactive oxygen species (ROS), which in turn eliminate microorganisms [ 25 , 26 ].…”

Section: Introductionmentioning

confidence: 99%

Aspirin-Based Organoiron Dendrimers as Promising Anti-Inflammatory, Anticancer, and Antimicrobial Drugs

et al. 2021

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Designing nanocarriers with actions directed at a specific organ or tissue is a very promising strategy since it can significantly reduce the toxicity of a bioactive drug. In this study, an organometallic dendrimer was used to synthesize a biocompatible drug delivery system by attaching aspirin to the periphery of the dendrimer. Our goal is to enhance the bioavailability and anticancer activity of aspirin and reduce its toxicity through successive generations of organoiron dendrimers. The biological activity of aspirin-based dendrimer complexes was evaluated. The result of antimicrobial activity of the synthesized dendrimers also demonstrated an increase in their antimicrobial activity with increased generation of the dendrimers for most types of microorganisms. This study reveals for the first time that organoiron dendrimers linked with aspirin exhibit an excellent Gram-negative activity comparable to the reference drug Gentamicin. All synthesized dendrimers were tested for their anticancer activity against breast cancer cell lines (MCF-7), hepatocellular cell lines (Hep-G2), and a non-cancer cell line, Human Embryonic Kidney (HEK293), using the MTT cell viability assay and compared against a standard anticancer drug, Doxorubicin. Compounds G3-D9-Asp and G4-D12-Asp exhibited noticeable activity against both cell lines, both of which were more effective than aspirin itself. In addition, the in vivo anti-inflammatory activity and histopathology of swollen paws showed that the designed aspirin-based dendrimers displayed significant anti-inflammatory activity; however, G2-D6-Asp showed the best anti-inflammatory activity, which was more potent than the reference drug aspirin during the same period. Moreover, the coupling of aspirin to the periphery of organoiron dendrimers showed a significant reduction in the toxicity of aspirin on the stomach.

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Quaternized and Thiazole‐Functionalized Free Radical‐Generating Organometallic Dendrimers as Antimicrobial Platform against Multidrug‐Resistant Microorganisms

Cited by 17 publications

References 90 publications

Design of Organoiron Dendrimers Containing Paracetamol for Enhanced Antibacterial Efficacy

Design of Organoiron Dendrimers Containing Paracetamol for Enhanced Antibacterial Efficacy

Enabling Sustainable Chemistry with Ionic Liquids and Deep Eutectic Solvents: A Fad or the Future?

Aspirin-Based Organoiron Dendrimers as Promising Anti-Inflammatory, Anticancer, and Antimicrobial Drugs

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