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

Abstract

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.

The effectiveness of newly synthesized quaternary ammonium salts differing in chain length and type of counterion against priority human pathogens

“…Our study indicates that the antimicrobial activity of mono-QAS increases with aliphatic chain length. This observation is consistent with previous literature 35 , 36 . As reported by Gozzelino et al .…”

“…those having the ability to oxidize proteins or lipids. Among the most active are compounds possessing chlorine, bromide, or iron atoms 33 , 36 , 42 . In contrast, studies indicate that the counterions of mono-QAS compounds are not as important as the aliphatic chain length for the activity of the compound 36 .…”

ε-Polylysine-Based Macromolecules with Catalase-Like Activity to Accelerate Wound Healing by Clearing Bacteria and Attenuating Inflammatory Response

“…For three kinds of EPL- g -Fc, the antibacterial activity increased with increasing the content of Fc in EPL- g -Fc, and EPL- g -Fc3 displayed the best antibacterial activity in this work. This may be attributed to the π–π stacking of Fc, which can promote the penetration of the macromolecule through the bacterial wall and exert an antibacterial effect . To further evaluate the antibacterial properties of EPL- g -Fc, photographs of bacteria colonies incubated with EPL- g -Fc were obtained.…”

“…This may be attributed to the π−π stacking of Fc, which can promote the penetration of the macromolecule through the bacterial wall and exert an antibacterial effect. 48 To further evaluate the antibacterial properties of EPL-g-Fc, photographs of bacteria colonies incubated with EPL-g-Fc were obtained. As displayed in Figure 2C, EPL-g-Fc3 showed little bit better sterilization than EPL-g-Fc1 and EPL-g-Fc2 at a concentration of 62.5 μg/ mL.…”

Quaternary Phosphonium Compounds: An Examination of Non-Nitrogenous Cationic Amphiphiles That Evade Disinfectant Resistance

“…Previous studies, including our own, have focused on elucidating structure–activity relationships (SARs) and structure–resistance relationships (SRRs) to enable the rational design of novel QAC compounds. These studies provided insights into the number and ratio of charges, length and types of side chains, core structural rigidity, and the inclusion of organometallic substituents have all contributed to the advancement of discovering next-generation QAC scaffolds. ,− …”