Characterization and antibacterial properties of N-halamine-derivatized cross-linked polymethacrylamide nanoparticles

Gutman, Ori; Natan, Michal; Banin, Ehud; Margel, Shlomo

doi:10.1016/j.biomaterials.2014.02.056

Cited by 68 publications

(97 citation statements)

References 45 publications

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“…Further advantages of polymeric antibacterial agents are that they are non‐volatile, chemically stable, and have low penetration through the skin . These polymeric antimicrobial agents could be utilized in a variety of applications such as water treatment, food packaging, sanitary, medical applications, and health care‐related materials …”

Section: Introductionsupporting

confidence: 81%

“…Vinylic monomers are routinely used for preparing organic polymeric microparticles because they may contain many possible functional side groups. Dispersion polymerization is a common method for preparing uniform nonporous microparticles in a single step . In this technique, the monomer, initiator, and surfactant are dissolved in an organic‐based continuous phase, forming a homogeneous solution.…”

Section: Introductionmentioning

confidence: 99%

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Engineering of crosslinked poly(isothiouronium methylstyrene) microparticles of narrow size distribution for antibacterial applications

Cohen

Laitman

Tennenbaum

et al. 2016

Polym. Adv. Technol.

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Isothiouronium salts are well known for their biocidal activity; however, their environmental toxicity is problematic. The current manuscript describes the synthesis of the antibacterial vinylic monomer, isothiouronium methylstyrene (ITMS), as well as its dispersion co‐polymerization with the crosslinking monomer divinylbenzene to form micrometer‐sized crosslinked poly(isothiouronium methylstyrene) (PITMS) particles of narrow size distribution. The effect of crosslinking monomer, initiator, and stabilizer concentrations on the size and size distribution of the formed microparticles was also elucidated. The incorporation of the isothiouronium salts into microparticles significantly reduces their toxicity. The bactericidal activity of PITMS microspheres of 380 ± 40‐nm diameter was demonstrated against four common bacterial pathogens: Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, and Listeria innocua. The minimum bactericidal concentration of PITMS microparticles needed for total killing was found, and their potent antibacterial activity demonstrates the potential of these particles as new types of antibacterial additive for various industrial and biomedical materials. Copyright © 2016 John Wiley & Sons, Ltd.

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Section: Introductionsupporting

confidence: 81%

Section: Introductionmentioning

confidence: 99%

Engineering of crosslinked poly(isothiouronium methylstyrene) microparticles of narrow size distribution for antibacterial applications

Cohen

Laitman

Tennenbaum

et al. 2016

Polym. Adv. Technol.

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“…27 These chloramine-derivatized NPs were found to be extremely potent against Escherichia coli and Staphylococcus aureus as well as against multidrug-resistant bacteria, establishing the efficacy of this newly synthesized material. 27 In the current study, we further characterized the antibacterial potential of P(MAA-MBAA)-Cl NPs in comparison to NaOCl (bleach), one of the most widely used disinfectants in medical, industrial, and domestic settings. We show that the nanoscale P(MAA-MBAA)-Cl retains potent antibacterial activity even after exposure to organic materials and repetitive bacterial loading cycles as compared to bleach, which is highly labile under these conditions, losing its biocidal activity rapidly.…”

mentioning

confidence: 95%

Killing Mechanism of Stable N-Halamine Cross-Linked Polymethacrylamide Nanoparticles That Selectively Target Bacteria

et al. 2015

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Increased resistance of bacteria to disinfection and antimicrobial treatment poses a serious public health threat worldwide. This has prompted the search for agents that can inhibit both bacterial growth and withstand harsh conditions (e.g., high organic loads). In the current study, N-halamine-derivatized cross-linked polymethacrylamide nanoparticles (NPs) were synthesized by copolymerization of the monomer methacrylamide (MAA) and the cross-linker monomer N,N-methylenebis(acrylamide) (MBAA) and were subsequently loaded with oxidative chlorine using sodium hypochlorite (NaOCl). The chlorinated NPs demonstrated remarkable stability and durability to organic reagents and to repetitive bacterial loading cycles as compared with the common disinfectant NaOCl (bleach), which was extremely labile under these conditions. The antibacterial mechanism of the cross-linked P(MAA-MBAA)-Cl NPs was found to involve generation of reactive oxygen species (ROS) only upon exposure to organic media. Importantly, ROS were not generated upon suspension in water, revealing that the mode of action is target-specific. Further, a unique and specific interaction of the chlorinated NPs with Staphylococcus aureus was discovered, whereby these microorganisms were all specifically targeted and marked for destruction. This bacterial encircling was achieved without using a targeting module (e.g., an antibody or a ligand) and represents a highly beneficial, natural property of the P(MAA-MBAA)-Cl nanostructures. Our findings provide insights into the mechanism of action of P(MAA-MBAA)-Cl NPs and demonstrate the superior efficacy of the NPs over bleach (i.e., stability, specificity, and targeting). This work underscores the potential of developing sustainable P(MAA-MBAA)-Cl NP-based devices for inhibiting bacterial colonization and growth.

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“…The FTIR spectra of Figure 1 A,B showed p(Thi‐g‐MAm) polymer coated ITO electrode surface (black line) and anti‐NSE antibodies immobilized ITO electrode surface (purple line), respectively. In the FTIR spectrum of polymer P(Thi‐g‐MAm), coated electrode surface had symmetric and asymmetric stretching of NH (3347 cm −1 ) and C(O)NH 2 (3211 cm −1 ) (Figure A) . The new band at 1653 cm −1 is originated from the carboxyl groups of P(Thi‐g‐MAm) polymer .…”

Section: Resultsmentioning

confidence: 87%

A Highly Selective Poly(thiophene)‐graft‐Poly(methacrylamide) Polymer Modified ITO Electrode for Neuron Specific Enolase Detection in Human Serum

Aydın

Sezgintürk

2019

Macromolecular Bioscience

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In this study, an impedimetric immunosensor based on polymer poly(thiophene)‐graft‐poly(methacrylamide) polymer (P(Thi‐g‐MAm)) modified indium tin oxide (ITO) electrode is developed for the detection of the Neuron Specific Enolase (NSE) cancer biomarker. First, the P(Thi‐g‐MAm) polymer is synthesized and coated on the ITO electrode by using a spin‐coating technique. P(Thi‐g‐MAm) polymer acts as an immobilization platform for immobilization of NSE‐specific monoclonal antibodies. Anti‐NSE antibodies are utilized as biosensing molecules and they bind to the amino groups of P(Thi‐g‐Mam) polymer via glutaraldehyde cross‐linking. Spin‐coating technique is employed for bioelectrode fabrication and this technique provides a thin and uniform film on the ITO electrode surface. This bioelectrode fabrication technique is simple and it generates a suitable platform for large‐scale loadings of anti‐NSE antibodies. This immunosensor exhibits a wide linear detection range from 0.02 to 4 pg mL−1 and with an ultralow detection limit of 6.1 fg mL−1. It reveals a good long‐term stability (after 8 weeks, 78% of its initial activity), an excellent reproducibility (1.29% of relative standard deviation (RSD)), a good repeatability (5.55% of RSD), and a high selectivity. In addition, the developed immunosensor is proposed as a robust diagnostic tool for the clinical detection of NSE and other cancer biomarkers.

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Characterization and antibacterial properties of N-halamine-derivatized cross-linked polymethacrylamide nanoparticles

Cited by 68 publications

References 45 publications

Engineering of crosslinked poly(isothiouronium methylstyrene) microparticles of narrow size distribution for antibacterial applications

Engineering of crosslinked poly(isothiouronium methylstyrene) microparticles of narrow size distribution for antibacterial applications

Killing Mechanism of Stable N-Halamine Cross-Linked Polymethacrylamide Nanoparticles That Selectively Target Bacteria

A Highly Selective Poly(thiophene)‐graft‐Poly(methacrylamide) Polymer Modified ITO Electrode for Neuron Specific Enolase Detection in Human Serum

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