Effects of Hydrophobicity on Antimicrobial Activity, Selectivity, and Functional Mechanism of Guanidinium‐Functionalized Polymers

Tan, Jason; Zhao, Yanli; Hedrick, James L.; Yang, Yi Yan

doi:10.1002/adhm.202100482

Cited by 27 publications

(31 citation statements)

References 59 publications

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“…The observed effect may be related to aggregation of C8‐ and C12‐ionenes, proved by CAC measurements (Table 1), or a detergent‐like mechanism executed on the lipid bilayer. [ 76 ] Selectivity index (SI) of the ionenes toward microorganisms over RBCs, defined as HC 50 /MIC, drops sharply with the alkyl group elongation above C4 (Table 2). Such an impact of the hydrophobicity on SI of SMAMPs and AMPs was already reported by other researcher.…”

Section: Resultsmentioning

confidence: 99%

Influence of PEG Subunit on the Biological Activity of Ionenes: Synthesis of Novel Polycations, Antimicrobial and Toxicity Studies

Kopiasz

Kulbacka

Drężek

et al. 2022

Macromolecular Bioscience

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An alarming increase of antibiotic resistance among pathogens creates an urgent need to develop new antimicrobial agents. Many reported polycations show high antimicrobial activity along with low hemolytic activity. Unfortunately, most of those molecules remain highly cytotoxic against various mammalian cells. In this work, a systematic study on the impact of triethylene glycol monomethyl ether side groups (short polyethylene glycol (PEG) analog) on antimicrobial, hemolytic, and cytotoxic properties of novel amphiphilic ionenes is presented. A detailed description of synthesis, leading to well‐defined alternating polymers, which differ in structural elements responsible for hydrophilicity (PEG) and hydrophobicity (alkyl chain), is presented. Obtained results show that the PEG moiety and fine‐tuned hydrophilic‐lipophilic balance of ionenes synergistically lead to low cytotoxic, low hemolytic molecules with high activity against S. aureus, including methicillin‐resistant strains (MRSA). Additionally, the results of mechanistic studies on bacterial cells and fluorescently labeled liposomes are also discussed.

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Section: Resultsmentioning

confidence: 99%

Influence of PEG Subunit on the Biological Activity of Ionenes: Synthesis of Novel Polycations, Antimicrobial and Toxicity Studies

Kopiasz

Kulbacka

Drężek

et al. 2022

Macromolecular Bioscience

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“…The main purpose of this work was to better understand how the hydrophilicity/hydrophobicity ratio of an antimicrobial compound may affect its effect. It is well known that the antimicrobial efficacy of cationic polymers can be improved by increasing their hydrophobicity [35]. The antimicrobial results presented here are compared to previous published work, where similar copolymers bearing more hydrophobic aliphatic chains with 16-carbon atoms were studied [27,28].…”

Section: Antimicrobial Activity Of the Polymeric Materialsmentioning

confidence: 90%

Preparation of Antimicrobial Coatings from Cross-Linked Copolymers Containing Quaternary Dodecyl-Ammonium Compounds

Druvari

Antonopoulou

Lainioti

et al. 2021

IJMS

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One of the concerns today’s societies face is the development of resistant pathogenic microorganisms. The need to tackle this problem has driven the development of innovative antimicrobial materials capable of killing or inhibiting the growth of microorganisms. The present study investigates the dependence of the antimicrobial activity and solubility properties on the hydrophilicity/hydrophobicity ratio of antimicrobial coatings based on quaternary ammonium compounds. In this line, suitable hydrophilic and hydrophobic structural units were selected for synthesizing the antimicrobial copolymers poly(4-vinylbenzyl dimethyldodecylammonium chloride-co-acrylic acid), P(VBCDDA-co-AA20) and poly(dodecyltrimethylammonium 4-styrene sulfonate-co-glycidyl methacrylate), P(SSAmC12-co-GMA20), bearing an alkyl chain of 12 carbons either through covalent bonding or through electrostatic interaction. The cross-linking reaction of the carboxylic group of acrylic acid (AA) with the epoxide group of glycidyl methacrylate (GMA) of these two series of reactive antimicrobial copolymers was explored in blends, obtained through solution casting after curing at various temperatures. The release of the final products in pure water and NaCl 1 M solutions (as analyzed by gravimetry and total organic carbon, TOC/total nitrogen, TN analyses), could be controlled by the coating composition. The cross-linked polymeric membranes of composition 60/40 w/w % ratios led to 97.8 and 99.7% mortality for Escherichia coli (E. coli) and Staphylococcus aureus (S. aureus), respectively, whereas the coating 20/80 w/w % resulted in 96.6 and 99.8% cell reduction. Despite the decrease in hydrophobicity (from a 16- to a 12-carbon alkyl chain), the new materials maintained the killing efficacy, while at the same time resulting in increased release to the aqueous solution.

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“…This phenomenon was also observed in other polymer systems. [15] The relatively more hydrophobic polyionenes might interact with the proteins present in the culture medium, masking their antimicrobial activity. Consistently, we observed that media containing polyionenes X1, X2, Y, Z1, Z2, and Z3 were cloudier with micrometer-sized aggregates than that of polyionenes A-E especially at high concentrations.…”

Section: Discussionmentioning

confidence: 99%

Potent Antiviral and Antimicrobial Polymers as Safe and Effective Disinfectants for the Prevention of Infections

Leong

Shi

Tan

et al. 2021

Adv Healthcare Materials

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Disinfection using effective antimicrobials is essential in preventing the spread of infectious diseases. This COVID‐19 pandemic has brought the need for effective disinfectants to greater attention due to the fast transmission of SARS‐CoV‐2. Current active ingredients in disinfectants are small molecules that microorganisms can develop resistance against after repeated long‐term use and may penetrate the skin, causing harmful side‐effects. To this end, a series of membrane‐disrupting polyionenes that contain quaternary ammoniums and varying hydrophobic components is synthesized. They are effective against bacteria and fungi. They are also fast acting against clinically isolated drug resistant strains of bacteria. Formulating them with thickeners and nonionic surfactants do not affect their killing efficiency. These polyionenes are also effective in preventing infections caused by nonenveloped and enveloped viruses. Their effectiveness against mouse coronavirus (i.e., mouse hepatitis virus‐MHV) depends on their hydrophobicity. The polyionenes with optimal compositions inactivates MHV completely in 30 s. More importantly, the polyionenes are effective in inhibiting SARS‐CoV‐2 by >99.999% within 30 s. While they are effective against the microorganisms, they do not cause damage to the skin and have a high oral lethal dose. Overall, these polyionenes are promising active ingredients for disinfection and prevention of viral and microbial infections.

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Effects of Hydrophobicity on Antimicrobial Activity, Selectivity, and Functional Mechanism of Guanidinium‐Functionalized Polymers

Cited by 27 publications

References 59 publications

Influence of PEG Subunit on the Biological Activity of Ionenes: Synthesis of Novel Polycations, Antimicrobial and Toxicity Studies

Influence of PEG Subunit on the Biological Activity of Ionenes: Synthesis of Novel Polycations, Antimicrobial and Toxicity Studies

Preparation of Antimicrobial Coatings from Cross-Linked Copolymers Containing Quaternary Dodecyl-Ammonium Compounds

Potent Antiviral and Antimicrobial Polymers as Safe and Effective Disinfectants for the Prevention of Infections

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