Increasing the Antimicrobial Activity of Amphiphilic Cationic Copolymers by the Facile Synthesis of High Molecular Weight Stars by Supplemental Activator and Reducing Agent Atom Transfer Radical Polymerization

Santos, Madson R. E.; Mendonça, Patrícia V.; Almeida, Mariana Cruz; Branco, Rita; Serra, Arménio C.; Morais, Paula V.; Coelho, Jorge F. J.

doi:10.1021/acs.biomac.8b00685

Cited by 41 publications

(41 citation statements)

References 48 publications

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“…Both of them proved to be more active of the corresponding starting small molecules monomers mainly against Gram-negative bacteria with an effectiveness that resulted enhanced by the increase of polymeric chain length and by the hydrophobicity of the macromolecules [79,102,109,110].…”

Section: Polymers Containing Quaternary Phosphonium And/or Ammonium Gmentioning

confidence: 99%

“…In addition, they proved higher activity of non-polymeric small antimicrobial drugs because, while their action consists in impairing the adhesion of bacteria by reducing their contact ability to the surface (without killing them), PQASs and PQPSs with quaternary ammonium or phosphonium units, commonly kill bacteria on contact [20,[110][111][112][113][114].…”

Section: Polymers Containing Quaternary Phosphonium And/or Ammonium Gmentioning

confidence: 99%

“…oligomeric guanidinium ↓MW ↓activity [130] quaternized N-hexyl-PVP, immobilized on a surface 160,000 full bactericidal effect [131] quaternized N-hexyl, N-methyl-PEI immobilized on a surface 25,000 full bactericidal effect [131] quaternized poly(2-(dimethylamino)ethyl methacrylate) (PDMEMA) Mn >10,000 100% killing efficiency [110] secondary and tertiary polydiallylamines (PDAAs) ↑MW ↓MIC100 [79] poly alkyldimethyl (vinylbenzyl) ammonium chloride alkyl C 12 chain ↑activity [64] cationic quaternary copolymers (vinylamine, aminoalkyl methacrylates, and N-vinyl pyrrolidone) with pendent quaternary ammonium groups any length not influenced by the length of the alkyl substituents at the nitrogen [132] alkylated quaternized PVP polymers alkyl > C 6 chain ↓activity [133] quaternized poly (4-vinyl pyridine) (P4VP)-poly (vinylidene fluoride) (PVDF) co-polymer C 4 >chain< C 10 ↑activity [134] quaternized alkyl pyridinium polyoxanorbornene Chain < C 4 minimal activity [88] quaternized alkyl pyridinium polyoxanorbornene Chain > C 6 ↑activity [88] As reported [134], the spatial separation of the positive charge and the presence of hydrophobic alkyl side chains, may influence both the antimicrobial properties and the hemolytic and cytotoxic effect to human cells. In particular, higher membrane-disrupting ability was observed when the charge is spatially separated from the alkyl chain [134].…”

Section: Type Of Caps Mw (Da) Alkylation Antimicrobial Activitymentioning

confidence: 99%

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Positively Charged Polymers as Promising Devices against Multidrug Resistant Gram-Negative Bacteria: A Review

2020

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Antibiotic resistance has increased markedly in Gram-negative bacteria, causing severe infections intractable with traditional drugs and amplifying mortality and healthcare costs. Consequently, to find novel antimicrobial compounds, active on multidrug resistant bacteria, is mandatory. In this regard, cationic antimicrobial peptides (CAMPs)—able to kill pathogens on contact—could represent an appealing solution. However, low selectivity, hemolytic toxicity and cost of manufacturing, hamper their massive clinical application. In the recent years—starting from CAMPs as template molecules—less toxic and lower-cost synthetic mimics of CAMPs, including cationic peptides, polymers and dendrimers, have been developed. Although the pending issue of hemolytic toxicity and biodegradability is still left not completely solved, cationic antimicrobial polymers (CAPs), compared to small drug molecules, thanks to their high molecular weight, own appreciable selectivity, reduced toxicity toward eukaryotic cells, more long-term activity, stability and non-volatility. With this background, an updated overview concerning the main manufactured types of CAPs, active on Gram-negative bacteria, is herein reported, including synthetic procedure and action’s mechanism. Information about their structures, antibacterial activity, advantages and drawbacks, was reported in the form of tables, which allow faster consultation and quicker learning concerning current CAPs state of the art, in order not to retrace reviews already available.

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Section: Polymers Containing Quaternary Phosphonium And/or Ammonium Gmentioning

confidence: 99%

Section: Polymers Containing Quaternary Phosphonium And/or Ammonium Gmentioning

confidence: 99%

Section: Type Of Caps Mw (Da) Alkylation Antimicrobial Activitymentioning

confidence: 99%

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Positively Charged Polymers as Promising Devices against Multidrug Resistant Gram-Negative Bacteria: A Review

2020

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“…For comparison, monomer M7 ( 7 ) was also analyzed under the same conditions. Although against various Gram-positive and Gram-negative strains M7 showed significantly lower MICs than those of the recently published cationic styrene monomer [ 13 ], accordingly to several articles [ 11 , 13 , 27 , 28 , 29 , 34 , 35 ] M7 was considered ineffective against all isolates evaluated in this study. On the contrary, the macromolecular compound P7 demonstrated very interesting results both on Gram-positive ( Table 2 ) and Gram-negative species ( Table 3 ), inhibiting the growth of bacteria regardless of their multidrug resistance pattern.…”

Section: Resultsmentioning

confidence: 63%

Broad-Spectrum Bactericidal Activity of a Synthetic Random Copolymer Based on 2-Methoxy-6-(4-Vinylbenzyloxy)-Benzylammonium Hydrochloride

Schito

Piatti

Caviglia

et al. 2021

IJMS

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Low-molecular-weight organic ammonium salts exert excellent antimicrobial effects by interacting lethally with bacterial membranes. Unfortunately, short-term functionality and high toxicity limit their clinical application. On the contrary, the equivalent macromolecular ammonium salts, derived from the polymerization of monomeric ammonium salts, have demonstrated improved antibacterial potency, a lower tendency to develop resistance, higher stability, long-term activity, and reduced toxicity. A water-soluble non-quaternary copolymeric ammonium salt (P7) was herein synthetized by copolymerizing 2-methoxy-6-(4-vinylbenzyloxy)-benzylammonium hydrochloride monomer with N, N-di-methyl-acrylamide. The antibacterial activity of P7 was assessed against several multidrug-resistant (MDR) clinical isolates of both Gram-positive and Gram-negative species. Except for colistin-resistant Pseudomonas aeruginosa, most isolates were susceptible to P7, also including some Gram-negative bacteria with a modified charge in the external membrane. P7 showed remarkable antibacterial activity against isolates of Enterococcus, Staphylococcus, Acinetobacter, and Pseudomonas, and on different strains of Escherichia coli and Stenotrophomonas maltophylia, regardless of their antibiotic resistance. The lowest minimal inhibitory concentrations (MICs) observed were 0.6–1.2 µM and the minimal bactericidal concentrations (MBC) were frequently overlapping with the MICs. In 24-h time–kill and turbidimetric studies, P7 displayed a rapid non-lytic bactericidal activity. P7 could therefore represent a novel and potent tool capable of counteracting infections sustained by several bacteria that are resistant to the presently available antibiotics.

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“…Cationic polymers, which have been used as DNA transfection reagents via facilitating the entry of DNA to target cells [20,21], are also known to have potent antimicrobial activity [22,23]. Polyethylenimine (PEI) is one such cationic polymer, and its novel anti-viral activity has been investigated in several studies [24,25,26,27].…”

Section: Introductionmentioning

confidence: 99%

The 40 kDa Linear Polyethylenimine Inhibits Porcine Reproductive and Respiratory Syndrome Virus Infection by Blocking Its Attachment to Permissive Cells

Wang

et al. 2019

Viruses

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Porcine reproductive and respiratory syndrome (PRRS) is one of the most economically devastating infectious diseases in pigs worldwide. The causative agent is the PRRS virus (PRRSV). In this study, we explored polyethylenimine (PEI), a cationic polymer with different forms (linear or branched), to inhibit the replication of PRRSV. Our results demonstrate that the linear but not the 40 kDa branched PEI, or the 25 kDa linear PEI, were well tolerated in cultured cells and exhibited a broad-spectrum inhibition of heterogeneous PRRSV-2 isolates in both MARC-145 cells and primary porcine pulmonary alveolar macrophages (PAMs). Further analysis suggests that PEI could prevent the attachment of PRRSV virions to the susceptible cells. Notably, PEI had a minimal effect on PRRSV internalization in MARC-145 cells, whereas PEI promoted the internalization of PRRSV virions in PAMs, which suggests that these two types of cells might have different internalization processes of PRRSV virions. In conclusion, our data demonstrate that PEI could be used as a novel inhibitor against PRRSV.

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Increasing the Antimicrobial Activity of Amphiphilic Cationic Copolymers by the Facile Synthesis of High Molecular Weight Stars by Supplemental Activator and Reducing Agent Atom Transfer Radical Polymerization

Cited by 41 publications

References 48 publications

Positively Charged Polymers as Promising Devices against Multidrug Resistant Gram-Negative Bacteria: A Review

Positively Charged Polymers as Promising Devices against Multidrug Resistant Gram-Negative Bacteria: A Review

Broad-Spectrum Bactericidal Activity of a Synthetic Random Copolymer Based on 2-Methoxy-6-(4-Vinylbenzyloxy)-Benzylammonium Hydrochloride

The 40 kDa Linear Polyethylenimine Inhibits Porcine Reproductive and Respiratory Syndrome Virus Infection by Blocking Its Attachment to Permissive Cells

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