Antibacterial activity of cationic polymers: side-chain or main-chain type?

Guo, Jiangna; Qin, Jing; Ren, Yongyuan; Wang, Bin; Cui, Hengqing; Ding, Yingying; Mao, Haiyang; Yan, Feng

doi:10.1039/c8py00665b

Cited by 104 publications

(97 citation statements)

References 49 publications

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“…This effect may be related with the molecular weight, as the homopolymer PMTZ-BuI of the current work has an M n of 13,800 g/mol, while the previously reported polymer presented an M n of 78,300 g/mol. It is well known that the molecular weight of cationic amphiphilic polymers can affect the antimicrobial activity [1,[27][28][29], and in this case, it seems that low molecular weights demerit the antimicrobial performance against all the tested microorganisms. However, polymers with high molecular weights are typically more toxic because they could induce gen transfection, hemolysis, and hemagglutination, and are compounds that are difficult to eliminate by the kidney [30].…”

Section: Resultsmentioning

confidence: 86%

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: Resultsmentioning

confidence: 86%

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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“…Nano-drug carriers have many advantages, such as small size, large specific surface area, controlled release of matrix, targeted drug delivery, etc. Metal ion nanoparticles 2 , antibacterial hydrogel 3 , 4 , 5 , and cationic polymers 6 , 7 , 8 , have been widely explored for their applications particularly in the field of bacteriostasis. Among above nanocarriers, one of their common characteristics is the antibiotics prepared into/onto nano dosage forms to achieve drug delivery by pharmacy means.…”

Section: Introductionmentioning

confidence: 99%

Self-assembled natural phytochemicals for synergistically antibacterial application from the enlightenment of traditional Chinese medicine combination

Tian

Wang

et al. 2020

Acta Pharmaceutica Sinica B

103

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The application of nanotechnology for antimicrobial delivery has capacity to improve antibacterial efficacy. Currently, the usage of various inorganic and organic carriers, such as metal ions, nano-silicon and surfactants, might increase the potential toxicity of nanoparticles and make their clinical transformation more difficult. Herein, a nano-delivery system was constructed by direct self-assembly of antibacterial phytochemicals (berberine and rhein) originated from traditional Chinese medicine Coptis chinensis Franch. and Rheum palmatum L., respectively. Combining X-ray single crystal diffraction, nuclear magnetic resonance and other spectra characterizations, the stacked structure of nanoparticles was profoundly demonstrated. Briefly, rhein acted as the layered backbone and berberine embedded in it. In vitro bacteriostasis experiment showed the minimum bactericidal concentration of nanoparticles was 0.1 μmol/mL, which was lower than that of berberine and rhein. The results of confocal laser scanning microscope, biofilm quantitive assay and scanning electron microscopy indicated that nanoparticles had strong inhibitory effects on Staphylococcus aureus biofilm. More importantly, transmission electron microscopy and mass spectra indicated the further bacteriostatic mechanism of nanoparticles. Meanwhile, the nanoparticles had well biocompatibility and safety. Current study will open up new prospect that the design of self-assemblies between active phytochemicals can be originated from traditional Chinese medicine combination.

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“…Quaternary ammonium bottlebrush polymers are interesting materials for antimicrobial applications as their linear counterparts have been explored as antimicrobial materials due to their ionic interaction between ammonium groups and the cell membranes of bacteria 59,60. For example, quaternary ammonium small molecules and polymers with six‐carbon long alkyl groups show antimicrobial behavior with the polymers being more effective antimicrobial agents than the small molecules 61. Quaternary ammonium polymers with different architectures have been produced by direct polymerization of cationic monomers via controlled radical polymerization in aqueous media62–64 or post‐quaternization, which can be time‐consuming and result in incomplete ammonium functionalization 65.…”

Section: Introductionmentioning

confidence: 99%

Cationic Bottlebrush Polymers from Quaternary Ammonium Macromonomers by Grafting‐Through Ring‐Opening Metathesis Polymerization

Senkum

Gramlich

2020

Macro Chemistry & Physics

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Cationic bottlebrush homopolymers are polymerized using a grafting‐through approach by ring‐opening metathesis polymerization (ROMP) to afford well‐defined polymers. Quaternary ammonium macromonomers (MMs) are prepared by quaternizing tertiary amine MMs synthesized by reversible addition‐fragmentation chain transfer (RAFT) polymerization. The quaternary ammonium MMs undergo ROMP to target molecular weights (Mn = 30 000–100 000 g mol−1) and a low dispersity (Đ = 1.10–1.30). Halide‐ligand exchange between the third generation Grubbs catalyst (G3) and halide counter ions (bromide and iodide ions) of MMs changes the catalyst activity throughout ROMP, causing it to deviate from pseudo‐first order kinetic behavior; however, the polymerization still follows controlled behavior without significant catalyst termination. Increasing steric bulk of the MMs decreases the polymerization rate as well. Amphiphilic block copolymers are synthesized by sequential polymerization of quaternary ammonium MMs and polystyrene (PS) MMs. Using a PS macroinitiator affords block copolymers with lower Đ values as compared to the less active cationic macroinitiator.

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Antibacterial activity of cationic polymers: side-chain or main-chain type?

Abstract: Imidazolium (Im), quaternary ammonium (Qa), and 1,4-diazabicyclo[2.2.2]octane-1,4-diium (DABCO-diium) cation-based small molecule cationic compounds and their corresponding side-chain/main-chain cationic polymers were synthesized.

Cited by 104 publications

References 49 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

Self-assembled natural phytochemicals for synergistically antibacterial application from the enlightenment of traditional Chinese medicine combination

Cationic Bottlebrush Polymers from Quaternary Ammonium Macromonomers by Grafting‐Through Ring‐Opening Metathesis Polymerization

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