Synthesis and antimicrobial properties of monomeric and polymeric quaternary ammonium salts based on aminoalkyl esters of methacrylic acid

Introduction: Quaternary ammonium salts (QASs) are widely spread cationic surfactants applicable in various industrial branches. QASs manifesting antibacterial effect contain hydrophilic core and a long alkyl chain in the structure. These compounds have strong antimicrobial activity against certain bacteria strains especially non-spore forming, yeasts, or protozoa. S. Aureus&#160;is a frequent cause of nosocomial infections and&#160;plays an important role in the persistence of chronic infections, especially when it&#8217;s attached to medical implants and host tissue, and developed in mature biofilm.&#160;Either way, this pathogen represents a significant burden on the healthcare system and new antimicrobial compounds are always required in clinical practice. Hypothesis and aims: Our main research activity involves the synthesis of novel compounds based on QASs and evaluating their eradication ability against pathogenic S. Aureus in biofilm and free-floating form and subsequent effectivity comparison against these two different bacterial states.&#160; Methodology: All newly prepared compounds were prepared by the nucleophilic reaction, verified by Nuclear Magnetic Resonance (NMR) and High-Resolution Mass Spectrometry (HR-MS). The antimicrobial properties were evaluated by microdilution broth assay and by Calgary device based assay with MIC, MBC, and MBEC as outcomes. Results: Series of novel QAS were prepared and verified. The MICs, MBCs, and MBECs were measured for all substances and have shown antimicrobial potential against S. Aureus in both states, however higher concentration was needed for biofilm eradication. The activities of newly prepared compounds were comparable to QASs based disinfections already known and commonly used in practice. Conclusion: Series of synthesized compounds underwent antimicrobial evaluation and several compounds have shown antimicrobial potential against S. Aureus in planktonic and biofilm form.

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Synthesis and Correlation of Aggregation and Antimicrobial Properties of Homochiral Quaternary Ammonium Bromides Derived from Camphoric Acid

European Pharmaceutical Journal ◽

10.2478/afpuc-2020-0017 ◽

2021 ◽

Vol 0 (0) ◽

Author(s):

R. Mikláš ◽

N. Miklášová ◽

M. Bukovský

Keyword(s):

Quaternary Ammonium ◽

Cationic Surfactants ◽

Antifungal Agents ◽

Inhibitory Concentration ◽

Antimicrobial Properties ◽

Quaternary Ammonium Salts ◽

Ammonium Salts ◽

The Novel ◽

Benzalkonium Bromide ◽

Camphoric Acid

Abstract A group of homochiral quaternary ammonium salts bearing hydrophobic camphoric acid-derived moiety was synthesized and characterized. The aggregation properties of the prepared compounds were evaluated by surface tension measurements, and the critical micelle concentration (CMC) was calculated. The novel quaternary ammonium bromides were tested as antimicrobial and antifungal agents, and their minimal inhibitory concentration (MIC) was evaluated and compared to clinically used benzalkonium bromide (BAB). Correlation of MIC with CMC reveals that monomers of prepared cationic surfactants, instead of micelles, are primarily responsible for antimicrobial activity.

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Synthesis, Purification and Characterization of Polymerizable Multifunctional Quaternary Ammonium Compounds

Molecules ◽

10.3390/molecules24081464 ◽

2019 ◽

Vol 24 (8) ◽

pp. 1464 ◽

Cited By ~ 4

Author(s):

Ugochukwu C. Okeke ◽

Chad R. Snyder ◽

Stanislav A. Frukhtbeyn

Keyword(s):

Quaternary Ammonium ◽

Quantum Coherence ◽

Comprehensive Evaluation ◽

Antimicrobial Properties ◽

Quaternary Ammonium Salts ◽

Ammonium Salts ◽

Resonance Spectroscopy ◽

The Novel ◽

Scanning Calorimetry

Methacrylate analogs of quaternary ammonium salts functionalized with carboxylic (AMadh1 68.8% yield, AMadh2 53.2% yield) and methoxysilane (AMsil1 94.8% yield, AMsil2 36.0% yield) groups were synthesized via Menschutkin reaction. Fourier-transform infrared spectroscopy (FTIR), nuclear magnetic resonance spectroscopy (1H, 13C and 2D 1H-13C heteronuclear single quantum coherence (HSQC) NMR), mass spectrometry, thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC) were utilized to validate structures and characterize thermal properties of the novel multifunctional quaternary ammonium salts synthesized. The potential adhesive, coupling and antimicrobial properties of these multifunctional monomers encourage their further comprehensive evaluation in conventional and experimental copolymers and composites.

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Study of the Resistance of PVC Composite Materials Modified with Wollastonite Activated by QAS to Bacteria

Key Engineering Materials ◽

10.4028/www.scientific.net/kem.899.132 ◽

2021 ◽

Vol 899 ◽

pp. 132-136

Author(s):

Dilyara F. Sadykova ◽

Elena M. Gotlib ◽

Elena V. Perushkina ◽

Alla G. Sokolova

Keyword(s):

Quaternary Ammonium ◽

Antibacterial Properties ◽

Antimicrobial Properties ◽

Quaternary Ammonium Salts ◽

Ammonium Salts ◽

Gram Negative Bacteria ◽

Gram Positive ◽

Gram Negative ◽

Gram Positive Bacteria ◽

Materials Used

Evaluation of the antibacterial properties of PVC materials used, in particular, in medicine, is becoming increasingly important due to increased sanitary and hygienic requirements. One of the ways to ensure the resistance of PVC materials to microorganisms is modification with wollastonite, the surface of which is activated by quaternary ammonium salts (QASs). QASs are known for their antimicrobial properties. The results obtained indicate that the basic composition of linoleum is somewhat more resistant to gram-positive bacteria than to gram-negative bacteria. The introduction of wollastonite into the PVC compound formulation increases the resistance to the studied groups of microorganisms. It can be concluded that the surface treatment of Mivoll 10-97 by QAS generally improves the bactericidal properties of the material. The results obtained are consistent with the literature data on the activity of cationic QACs in relation to gram-positive and gram-negative bacteria. Quaternary ammonium salts have the ability to be attracted to the outer surface of the negatively charged bacterial membrane due to the positive charge of their molecules.

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Influence of cationic surfactants on physical and mechanical properties of polymer compositions

Proceedings of the Voronezh State University of Engineering Technologies ◽

10.20914/2310-1202-2020-1-225-229 ◽

2020 ◽

Vol 82 (1) ◽

pp. 225-229

Author(s):

N. S. Shmakova ◽

I. A. Kirsh ◽

V. A. Romanova

Keyword(s):

Mechanical Properties ◽

Quaternary Ammonium ◽

Cationic Surfactants ◽

Antimicrobial Properties ◽

Physical And Mechanical Properties ◽

Polymer Processing ◽

Quaternary Ammonium Salts ◽

Ammonium Salts ◽

Polymer Composition ◽

Packaging Materials

When creating filled polymer composite materials, difficulties often arise due to poor compatibility of polymers with modifying additives. To solve such problems, surface-active substances (SAS) are successfully used in many industries, but they are practically not used in polymer processing. This is largely due to the insufficient assortment of surfactants produced that are suitable for introduction into polymers, especially film-forming ones. Anionic and nonionic surfactants are used in the synthesis and processing of elastomers, but they are not used in the production of film materials. As for the use of cationic surfactants, there are still no data at all. They differ from other types of surfactants in a variety of structures, in the number and relative positions of cationic centers and hydrophobic radicals, and also in antimicrobial properties. The prospects of using quaternary ammonium salts for the modification of packaging materials are shown. The expediency of using cationic surfactants for the modification of polymeric materials is proved. It is shown that the use of quaternary ammonium salts improves the physical and mechanical properties of films based on polyethylene and polypropylene. It is proved that cationic surfactants are technologically compatible with polyolefins, which allows the processing of polymer compositions by extrusion. Today, the most common polymers for food packaging are polyethylene and polypropylene. This is due to their low cost, safety in contact with food products, and suitability for processing into films of different thicknesses. More and more attention is being paid to the creation of packaging materials with antimicrobial properties. The imparting of such properties is achieved by introducing an antimicrobial additive into the polymer melt. It is most expedient to introduce additives directly into the melt of the polymer composition during processing, since, for example, during the extrusion process, polymer homogenization with the additive.

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