Copolymers of acrylonitrile with quaternizable thiazole and triazole side-chain methacrylates as potent antimicrobial and hemocompatible systems

Tejero, Rubén; Gutiérrez, Beatriz; López, Daniel; López-Fabal, Fátima; Gómez-Garcés, José Luís; Fernández‐García, Marta

doi:10.1016/j.actbio.2015.07.037

Cited by 21 publications

(22 citation statements)

References 83 publications

(98 reference statements)

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“…The time‐kill curves suggest that MeI‐PDMAPMA has a stronger biocidal effect against E. coli than S. aureus , even though the MBC was shown to be the same for both species. This result is also contrary to the results of most previous reports, where a strain with lower MIC is associated with a faster killing rate …”

Section: Resultscontrasting

confidence: 99%

Antimicrobial anilinium polymers: The properties of poly(N,N‐dimethylaminophenylene methacrylamide) in solution and as coatings

Chen

Zhang

et al. 2019

J. Polym. Sci. Part A: Polym. Chem.

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Antimicrobial polymers have been widely reported to exert strong biocidal effects against bacteria. In contrast with antimicrobial polymers with aliphatic ammonium groups, polymers with anilinium groups have been rarely studied and applied as biocidal materials. In this study, a representative polymer with aniline side functional groups, poly(N,N‐dimethylaminophenylene methacrylamide) (PDMAPMA), was explored as a novel antimicrobial polymer. PDMAPMA was synthesized and its physicochemical properties evaluated. The methyl iodide‐quaternized polymer was tested against the Gram‐positive Staphylococcus aureus, with a minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) of 16–32 and 64–128 μg mL−1, respectively. Against the Gram‐negative Escherichia coli, the MIC and MBC were both 64–128 μg mL−1. To broaden the range of applications, PDMAPMA was coated on substrates via crosslinking to endow the surface with contact‐kill functionality. The effect of charge density of the coatings on the antimicrobial behavior was then investigated, and stronger biocidal performance was observed for films with higher charge density. This study of the biocidal behavior of PDMAPMA both in solution and as coatings is expected to broaden the application of polymers containing aniline side groups and provide more information on the antimicrobial behavior of such materials. © 2019 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2019, 57, 1908–1921

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Section: Resultscontrasting

confidence: 99%

Antimicrobial anilinium polymers: The properties of poly(N,N‐dimethylaminophenylene methacrylamide) in solution and as coatings

Chen

Zhang

et al. 2019

J. Polym. Sci. Part A: Polym. Chem.

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“…Some efficient measures have been taken to resolve the above problem, and it is well known that the invention and use of agrochemicals play an important role in reducing crop loss caused by plant diseases. However, many fungal, virus, oomycete, and bacteria species have developed resistance to some of the currently available agrochemicals due to long-term use of traditional pesticides with a single mode of action [3][4][5][6]. Moreover, the studies found that a large-scale outburst of drug resistance can be fast accelerated within a relatively short period once resistant populations emerge, which will further increase the difficulty in solving the severe problem and the potential risks on food production [7,8].…”

Section: Introductionmentioning

confidence: 99%

(R)-2-Phenyl-4,5-Dihydrothiazole-4-Carboxamide Derivatives Containing a Diacylhydrazine Group: Synthesis, Biological Evaluation, and SARs

Liu

Gong

et al. 2019

Molecules

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A series of (R)-2-phenyl-4,5-dihydrothiazole-4-carboxamide derivatives containing a diacylhydrazine moiety were designed and synthesized. Their structures were confirmed by melting points, 1H NMR, 13C NMR, and elemental analysis (EA). Their antifungal and insecticidal activities were evaluated. The antifungal activity result indicated that most title compounds against Cercospora arachidicola, Alternaria solani, Phytophthora capsici, and Physalospora piricola exhibited apparent antifungal activities at 50 mg/L, and better than chlorothalonil or carbendazim. The EC50 values of (R)-N’-benzoyl-2-(4-chlorophenyl)-4,5-dihydrothiazole-4-carbohydrazide (I-5) against six tested phytopathogenic fungi were comparable to those of chlorothalonil. The CoMSIA model showed that a proper hydrophilic group in the R1 position, as well as a proper hydrophilic and electron-donating group in the R2 position, could improve the antifungal activity against Physalospora piricola, which contributed to the further optimization of the structures. Meanwhile, most title compounds displayed good insecticidal activities, especially compound (R)-N’-(4-nitrobenzoyl)-2-(4-nitrophenyl)-4,5-dihydrothiazole-4-carbohydrazide (III-3). The insecticidal mechanism results indicated that compound III-3 can serve as effective insect Ca2+ level modulators by disrupting the cellular calcium homeostasis in Mythimna separata.

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“…In previous works, our group has tested the effectiveness in aqueous solution of different quaternized homopolymers and copolymers bearing two cationic groups per monomer units, thiazole and triazole moieties. These polymers were synthesized by both conventional radical polymerization and by controlled techniques via simultaneous ATRP and click chemistry [12,[21][22][23]. In addition, the block copolymers bearing these cationic structures were employed as surfactant in emulsion polymerization of butyl methacrylate and subsequently antimicrobial coating were also prepared from the resulting latex [20].…”

Section: Introductionmentioning

confidence: 99%

“…This method involves the preparation of active surfaces by the physical incorporation of the antimicrobial agent in relatively low concentration into a polymer matrix. In contrast to other approaches consisting in the covalent attachment of the antimicrobial agent onto the surface [23,24], this approach is an easy and straightforward method that avoids multiple chemical and modification steps which are generally needed in other strategies. Another advantage of the blending approach is that the surface composition can be controlled by surface segregation.…”

Section: Introductionmentioning

confidence: 99%

“…From MIC values, the antimicrobial activity seems to increase as cationic segment length (PQMTA) augments, being more effective against gram-positive S. aureus bacteria. [12,23] This could be due to a self-assembly effect as a result of the relatively reduced solubility of these copolymers in water. Taking into consideration these weak results found in solution, we prepared films from these copolymers expecting a different behavior at the surfaces.…”

mentioning

confidence: 99%

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Antimicrobial surfaces obtained from blends of block copolymers synthesized by simultaneous ATRP and click chemistry reactions

Álvarez-Paino

Bonilla

Cuervo-Rodríguez

et al. 2017

European Polymer Journal

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A series of amphiphilic block copolymers based on styrene (S) and a monomer bearing both thiazole and triazole groups (MTA) were synthesized by combination of ATRP and click chemistry. In particular, two approaches were followed; the direct ATRP from a PS macroinitiator of the pre-synthesized MTA antimicrobial monomer; and the simultaneous synthesis and polymerization of the MTA through a one-step 'click chemistry'/ATRP process. Both strategies conduct to well-defined block copolymers with controlled molecular weight and low polydispersity. Subsequent quaternization of the thiazole and triazole groups of MTA units with butyl iodine renders systems with antimicrobial properties. Although these systems presented relatively low antimicrobial activity against bacteria and fungi in aqueous media, the preparation of surfaces functionalized with these copolymers leads to potent antimicrobial surfaces, especially against gram-positive bacteria.

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Copolymers of acrylonitrile with quaternizable thiazole and triazole side-chain methacrylates as potent antimicrobial and hemocompatible systems

Cited by 21 publications

References 83 publications

Antimicrobial anilinium polymers: The properties of poly(N,N‐dimethylaminophenylene methacrylamide) in solution and as coatings

Antimicrobial anilinium polymers: The properties of poly(N,N‐dimethylaminophenylene methacrylamide) in solution and as coatings

(R)-2-Phenyl-4,5-Dihydrothiazole-4-Carboxamide Derivatives Containing a Diacylhydrazine Group: Synthesis, Biological Evaluation, and SARs

Antimicrobial surfaces obtained from blends of block copolymers synthesized by simultaneous ATRP and click chemistry reactions

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