Antimicrobial activities of phosphonium containing polynorbornenes

Süer, N. Ceren; Demir, Ceren; Unubol, Nihan Aytekin; Yalçın, Özlem; Kocagoz, Tanil; Eren, Tarık

doi:10.1039/c6ra15545f

Cited by 41 publications

(28 citation statements)

References 49 publications

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“…[1] Drug development strategies inspired by antimicrobial peptides (AMPs) have been explored. [3] In response,synthetic, membrane-inserting mimics have been developed that capture some of the essential functions of AMPs,w hile overcoming certain limitations.E xamples include arylamide oligomers, [4] polynorbornenes, [5] polyme-thacrylates, [6] and an emerging class referred to as conjugated oligoelectrolytes (COEs). [3] In response,synthetic, membrane-inserting mimics have been developed that capture some of the essential functions of AMPs,w hile overcoming certain limitations.E xamples include arylamide oligomers, [4] polynorbornenes, [5] polyme-thacrylates, [6] and an emerging class referred to as conjugated oligoelectrolytes (COEs).…”

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confidence: 99%

Informed Molecular Design of Conjugated Oligoelectrolytes To Increase Cell Affinity and Antimicrobial Activity

Zhou¹,

Chia²,

et al. 2018

Angew Chem Int Ed

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Membrane-intercalating conjugated oligoelectrolytes (COEs) are emerging as potential alternatives to conventional, yet increasingly ineffective, antibiotics. Three readily accessible COEs, belonging to an unreported series containing a stilbene core, namely D4, D6, and D8, were designed and synthesized so that the hydrophobicity increases with increasing side-chain length. Decreased aqueous solubility correlates with increased uptake by E. coli. The minimum inhibitory concentration (MIC) of D8 is 4 μg mL against both E. coli and E. faecalis, with an effective uptake of 72 %. In contrast, the MIC value of the shortest COE, D4, is 128 μg mL owing to the low cellular uptake of 3 %. These findings demonstrate the application of rational design to generate efficacious antimicrobial COEs that have potential as low-cost antimicrobial agents.

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confidence: 99%

Informed Molecular Design of Conjugated Oligoelectrolytes To Increase Cell Affinity and Antimicrobial Activity

Zhou¹,

Chia²,

et al. 2018

Angew Chem Int Ed

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“…Most of the cases M n determined by GPC was underestimated compared to values derived by NMR end group analysis . Suer et al also observed same phenomenon for polar phosponiumbased ROMP polymer . GPC calibration with linear, non‐ionic pullulan standards resulted in different hydrodynamic volumes with respect to the cationic‐based copolymers, which can lead to a strong deviation .…”

Section: Resultsmentioning

confidence: 83%

“…Compared to these findings, when the alkyl group was longer, that is the increasing hydrophobicity, the polymers turned out to be effective and generally toxic . It was also observed that cationic charge density treshold also crucial for the activity against to S. aureus . Increasing the double charge density in each repeating unit resulted in high selectivity.…”

Section: Introductionmentioning

confidence: 94%

“…The cationic functionality may bind to anionic bacterial cell membranes by electrostatic interactions. Once the polymers bind to cell membranes, the hydrophobic groups of the polymers are inserted into the hydrophobic domains of membranes, and the polymer chains form active amphiphilic conformations capable of membrane disruption via carpet mechanism and active antibacterial polymers significantly kill bacteria by their active functional groups . As bacterial cell membranes are highly negatively charged as compared to human cell membranes, the polymers are expected to selectively bind to bacteria over human cells…”

Section: Introductionmentioning

confidence: 99%

“…[46] There are many reports that have been published on quaternary ammonium-based antibacterial polymers. [47][48][49] For polymer design, ring opening metathesis polymerization (ROMP) is one of the important techniques for the preparation of well-defined water-soluble polymer architectures [37,38,[50][51][52] and biologically active polymers. [53][54][55][56] Ilker et al studied ammonium-based polymers derived via ROMP and they found that antibacterial and hemolytic activity strongly depends on the length of alkyl substituent of the repeating units.…”

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confidence: 99%

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Amphiphilic water soluble cationic ring opening metathesis copolymer as an antibacterial agent

Islam

Aksu

Güncü

et al. 2020

Journal of Polymer Science

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Bacterial infection is a global problem, especially resistance acquired by bacteria against to antibiotics; there is urgent need for the development of antibiotics. Here, we proposed dendron‐grafted polymers via ring opening metathesis polymerization (ROMP) featuring different with tailored hydrophobicity/hydrophilicity and cationic charges. Dendritic oxanorbornene derivatives were synthesized having two and six carbon linkers and their corresponding random and block copolymers were prepared having pendant pyridinium salt moieties via ROMP. In total, 12 different water‐soluble dendronized cationic polymers featuring hexyl pyridinium moieties were prepared and investigated. Six carbon linker possessing triple charge density and hexyl pyridinium functionality each repeating unit copolymers exhibited high antibacterial activity against Gram‐positive bacteria (S. aureus). However, all the polymers were inactive against Gram‐negative bacteria (E. coli). Most of the copolymers are non‐hemolytic (>HC 50 = 1,000 μg/ml). It was also observed that, there is no significant effect between block copolymers and random copolymers keeping hydrophobicity and cationic charge density constant. Zeta potential was measured to investigate the mechanism in solution via the interaction of polymers with S. aureus, while scanning electron microscope (SEM) measurements image confirms damage of the bacterial cell wall after implementation of biocidal polymer.

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

Tan

Zhao

Hedrick

et al. 2021

Adv Healthcare Materials

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In this study, a series of guanidinium-functionalized polycarbonate random co-polymers is prepared from organocatalytic ring-opening polymerization to investigate the effect of the hydrophobic side chain (ethyl, propyl, isopropyl, benzyl, and hexyl) on their antimicrobial activity and selectivity. Although the polymers exhibit similar minimum inhibitory concentrations, the more hydrophobic polymers exhibit a faster rate of bacteria elimination. At higher percentage content (20 mol%), polymers with more hydrophobic side chains suffer from poor selectivity due to their high hemolytic activity. The highly hydrophobic co-polymer, containing the hydrophobic hexyl-functionalized cyclic carbonate, kills bacteria via a membrane-disruptive mechanism. Micelle formation leads to a lower extent of membrane disruption. This study unravels the effects of hydrophobic side chains on the activities of the polymers and their killing mechanism, providing insights into the design of new antimicrobial polymers.

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Antimicrobial activities of phosphonium containing polynorbornenes

Abstract: In this study, amphiphilic polyoxanorbornene with different alkyl and aromatic phosphonium side chains was synthesized and investigated their biocidal properties.

Cited by 41 publications

References 49 publications

Informed Molecular Design of Conjugated Oligoelectrolytes To Increase Cell Affinity and Antimicrobial Activity

Informed Molecular Design of Conjugated Oligoelectrolytes To Increase Cell Affinity and Antimicrobial Activity

Amphiphilic water soluble cationic ring opening metathesis copolymer as an antibacterial agent

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

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