Synthesis of Antibacterial Glycosylated Polycaprolactones Bearing Imidazoliums with Reduced Hemolytic Activity

Xu, Yuan; Zhang, Kaixi; Reghu, Sheethal; Lin, Yichao; Chan‐Park, Mary B.; Liu, Xuewei

doi:10.1021/acs.biomac.8b01577

Cited by 43 publications

(31 citation statements)

References 64 publications

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“…However, the toxicity toward host mammalian cells is not always as low as desired, in particular in polymers with high hydrophobic contents [15]. Attempts to improve the biocompatibility of antimicrobial polymers include the incorporation of non-ionic and biocompatible moieties such as polyethylene glycol (PEG) [16][17][18][19] and glycopolymers [20,21]. The toxicity of cationic amphiphilic polymers is typically evaluated by the hemolytic activity towards mammalian red blood cells (RBCs).…”

Section: Introductionmentioning

confidence: 99%

Hemolytic and Antimicrobial Activities of a Series of Cationic Amphiphilic Copolymers Comprised of Same Centered Comonomers with Thiazole Moieties and Polyethylene Glycol Derivatives

2020

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A series of well-defined antimicrobial polymers composed of comonomers bearing thiazole ring (2-(((2-(4-methylthiazol-5-yl)ethoxy)carbonyl)oxy)ethyl methacrylate monomer (MTZ)) and non-hemotoxic poly(ethylene glycol) side chains (poly(ethylene glycol) methyl ether methacrylate (PEGMA)) were synthesized by reversible addition-fragmentation chain transfer (RAFT) polymerization. By post-polymerization functionalization strategy, polymers were quaternized with either butyl or octyl iodides to result in cationic amphiphilic copolymers incorporating thiazolium groups, thus with variable hydrophobic/hydrophilic balance associated to the length of the alkylating agent. Likewise, the molar percentage of PEGMA was modulated in the copolymers, also affecting the amphiphilicity. The antimicrobial activities of these cationic polymers were determined against Gram-positive and Gram-negative bacteria and fungi. Minimum inhibitory concentration (MIC) was found to be dependent on both length of the alkyl hydrophobic chain and the content of PEGMA in the copolymers. More hydrophobic octylated copolymers were found to be more effective against all tested microorganisms. The incorporation of non-ionic hydrophilic units, PEGMA, reduces the hydrophobicity of the system and the activity is markedly reduced. This effect is dramatic in the case of butylated copolymers, in which the hydrophobic/hydrophilic balance is highly affected. The hemolytic properties of polymers analyzed against human red blood cells were greatly affected by the hydrophobic/hydrophilic balance of the copolymers and the content of PEGMA, which drastically reduces the hemotoxicity. The copolymers containing longer hydrophobic chain, octyl, are much more hemotoxic than their corresponding butylated copolymers.

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Section: Introductionmentioning

confidence: 99%

Hemolytic and Antimicrobial Activities of a Series of Cationic Amphiphilic Copolymers Comprised of Same Centered Comonomers with Thiazole Moieties and Polyethylene Glycol Derivatives

2020

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“…Chan group polymerized with NCA and chitosan to simulate the peptidoglycan component of the bacterial cell wall (Li et al, 2012;Hou et al, 2017). On these bases, they designed a variety of glycosylated cationic chitosan-based polymers, whose antibacterial activity and selectivity can be adjusted to meet application requirements through changing the glycosyl composition and cationic residues (Pranantyo et al, 2017;Xu et al, 2019). For example, glucosamine-functionalized star polymers (S-GSA 25) showed high bactericidal activity against Gram-positive bacteria while maintained good biocompatibility (Wong et al, 2016).…”

Section: Cationic Polymersmentioning

confidence: 99%

The Mechanisms and the Applications of Antibacterial Polymers in Surface Modification on Medical Devices

Qiu

Luo

et al. 2020

Front. Bioeng. Biotechnol.

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135

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Medical device contamination caused by microbial pathogens such as bacteria and fungi has posed a severe threat to the patients’ health in hospitals. Due to the increasing resistance of pathogens to antibiotics, the efficacy of traditional antibiotics treatment is gradually decreasing for the infection treatment. Therefore, it is urgent to develop new antibacterial drugs to meet clinical or civilian needs. Antibacterial polymers have attracted the interests of researchers due to their unique bactericidal mechanism and excellent antibacterial effect. This article reviews the mechanism and advantages of antimicrobial polymers and the consideration for their translation. Their applications and advances in medical device surface coating were also reviewed. The information will provide a valuable reference to design and develop antibacterial devices that are resistant to pathogenic infections.

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“…[ 5 ] Recently, our group have also developed a series of polycaprolactone (PCL) based glycopolymers exhibiting good potency against bacteria, including drug resistant strains. [ 6 ] Apart from degradability, the biocompatibility of glycosides in the polymers has also been systematically studied (Figure 1). A library of glycosylated PCLs has been prepared with different sugar moieties in various ratios through copper catalyzed click chemistry, and the results showed that the biological profile could be significantly improved by incorporating carbohydrates.…”

Section: Biocompatibility Of Carbohydratesmentioning

confidence: 99%

The versatility of carbohydrates in antimicrobial applications

Liu

2020

J Chinese Chemical Soc

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The worsening situation of global drug resistance is urgently demanding for novel antimicrobial agents. Considerable efforts have been concentrated on developing new antibacterial therapies with new mode of actions, exerting no selective pressure on bacterial mutation, and minimizing toxicity to host cells. In this context, active targeting can greatly contribute to selectivity between pathogens and mammalian cells in which carbohydrates, playing important roles in numerous biological processes, can be employed as targeting ligands or "trojan horse." This short account has discussed the recent results of carbohydrate-based antimicrobial agents developed by our group. Other excellent works by other scientists and possible directions in the future are also discussed.

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Synthesis of Antibacterial Glycosylated Polycaprolactones Bearing Imidazoliums with Reduced Hemolytic Activity

Cited by 43 publications

References 64 publications

Hemolytic and Antimicrobial Activities of a Series of Cationic Amphiphilic Copolymers Comprised of Same Centered Comonomers with Thiazole Moieties and Polyethylene Glycol Derivatives

Hemolytic and Antimicrobial Activities of a Series of Cationic Amphiphilic Copolymers Comprised of Same Centered Comonomers with Thiazole Moieties and Polyethylene Glycol Derivatives

The Mechanisms and the Applications of Antibacterial Polymers in Surface Modification on Medical Devices

The versatility of carbohydrates in antimicrobial applications

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