New polymeric biocides: synthesis and antibacterial activities of polycations with pendant biguanide groups

Ikeda, Tomiki; Yamaguchi, Hideki; Tazuke, S

doi:10.1128/aac.26.2.139

Cited by 191 publications

(144 citation statements)

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“…centrifuged at 3000 x g for 10 min at 4°C, washed 3 times in PBS then resuspended in 1 ml PBS. 50 µl from each time point was resuspended in 10 ml PBS at 2.5 x 10 6 CFU/ml and another 50 µl was resuspended in 10 ml of 1 mg/ml trypan blue (Beckman Coulter, CA, USA) in PBS at 2.5 x 10 6 CFU/ml 37 . Samples were incubated at ambient temperature for at least 30 min, but not more than 6 hours to ensure bacterial survival.…”

Section: Synthesis Of 50 % Quaternised Pdmaemamentioning

confidence: 99%

“…The mode of action of cationic biocides has been suggested to progress as follows: (1) adsorption onto the bacterial cell surface, (2) diffusion through the cell wall, (3) binding to the cytoplasmic membrane, (4) disruption of the cytoplasmic membrane, (5) release of cell cytoplasmic constituents and (6) cell death 37 . pDMAEMA may work in a similar manner by adsorbing to the cell surface through electrostatic interactions and disrupting the cytoplasmic membrane through hydrophobic interactions 28,30 .…”

Section: Introductionmentioning

confidence: 99%

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Antibacterial Effects of Poly(2-(dimethylamino ethyl)methacrylate) against Selected Gram-Positive and Gram-Negative Bacteria

et al. 2009

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Antimicrobial coatings can reduce the occurrence of medical device-related bacterial infections. Poly(2-(dimethylamino ethyl)methacrylate) (pDMAEMA) is one such polymer that is being researched in this regard. The aims of this study were to (1) elucidate pDMAEMA’s antimicrobial activity against a range of Gram-positive and Gram-negative bacteria and (2) to investigate its antimicrobial mode of action. The methods used include determination of minimum inhibitory concentration (MIC) values against various bacteria and the effect of pH and temperature on antimicrobial activity. The ability of pDMAEMA to permeabilise bacterial membranes was determined using the dyes 1-N-phenyl-naphthylamine and calcein-AM. Flow cytometry was used to investigate pDMAEMA’s capacity to be internalized by bacteria and to determine effects on bacterial cell cycling. pDMAEMA was bacteriostatic against Gram-negative bacteria with MIC values between 0.1−1 mg/mL. MIC values against Gram-positive bacteria were variable. pDMAEMA was active against Gram-positive bacteria around its pK a and at lower pH values, while it was active against Gram-negative bacteria around its pK a and at higher pH values. pDMAEMA inhibited bacterial growth by binding to the outside of the bacteria, permeabilizing the outer membrane and disrupting the cytoplasmic membrane. By incorporating pDMAEMA with erythromycin, it was found that the efficacy of the latter was increased against Gram-negative bacteria. Together, the results illustrate that pDMAEMA acts in a similar fashion to other cationic biocides.

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Section: Synthesis Of 50 % Quaternised Pdmaemamentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Antibacterial Effects of Poly(2-(dimethylamino ethyl)methacrylate) against Selected Gram-Positive and Gram-Negative Bacteria

et al. 2009

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“…In previous papers, we reported that in a clean system where there are no interfering materials such as negatively charged macromolecules, polycations having biguanide units or quaternary ammonium salts exhibit much higher antibacterial activity than the monomeric analogs (4,5). In view of the fact that many properties of polymers depend strongly on their molecular weights (MW) and MW distributions, it is reasonable to expect that the antibacterial activity of such polycations is MW dependent.…”

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confidence: 99%

Polycationic biocides with pendant active groups: molecular weight dependence of antibacterial activity

Ikeda¹,

Hirayama²,

Yamaguchi³

et al. 1986

Antimicrob Agents Chemother

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173

138

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Two types of polycations with pendant active groups were synthesized: one is polymethacrylate containing pendant biguanide units, and the other is poly(vinylbenzyl ammonium chloride). The two polycations were found to exhibit higher bactericidal activity against Staphylococcus aureus than the corresponding monomers.Fractionation of the polycations was successfully performed on gel filtration chromatography, and examination of the antibacterial activity against S. aureus of the well-characterized polymer samples with various molecular weights (MW) revealed that the activity was strongly dependent on the MW of the polycations and that there existed an optimal MW range for the cidal action of the polymeric biocides. Experiments on the lysis of protoplasts ofBacillus subtilis in contact with the polycations have shown that the target sites of the polycationic biocides are cytoplasmic membranes of bacteria.In previous papers, we reported that in a clean system where there are no interfering materials such as negatively charged macromolecules, polycations having biguanide units or quaternary ammonium salts exhibit much higher antibacterial activity than the monomeric analogs (4, 5). In view of the fact that many properties of polymers depend strongly on their molecular weights (MW) and MW distributions, it is reasonable to expect that the antibacterial activity of such polycations is MW dependent. In fact, in the oligomers of in-chain quaternary ammonium salts ranging from monomer to tetramer, a strong MW dependence has been observed (T. Ikeda, H. Yamaguchi, and S. Tazuke, submitted for publication).In this paper, we describe the preparation of wellcharacterized polycationic samples with various MW and narrow MW distributions. In addition, we report on the effect of MW of the polycations on bactericidal activity, focusing our attention on the high-MW polymers. Various physiological events were observed in intact cells and protoplasts when they were exposed to various polycations. The effects are discussed in terms of the mode of action of these polycationic biocides. MATERIALS AND METHODSPreparation. The synthetic route for the methacrylate monomer with a pendant biguanide is shown in Fig. 1. 2-Hydroxyethylphenyldicyandiamide (compound 1) was prepared as reported previously (5). To prepare 4-(2-methacryloyloxyethyl)phenyldicyandiamide (compound 2), a solution of compound 1 (14 g, 0.07 mol) dissolved in tetrahydrofuran-water (10:1, 93 ml) was cooled in an ice bath; to this solution, freshly distilled methacryloyl chloride (52 ml, 0.54 mol) was added dropwise with stirring over a period of 2 h; and the reaction mixture was left overnight at room temperature. It was then poured into a large excess of water, and the precipitate was collected and dried under vacuum (yield, 90%). The product was recrystallized from 2-propanol. mp 181-182°C; NMR (dimethyl sulfoxide-d6, 8)

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“…Biguanides of the polyhexamethylene biguanide hydrochloride type were originally developed as surface disinfectant in the food and beverage industry. Its antimicrobial action is based on the binding of the cationic molecules to the anionically charged bacteria, leading to membrane rupture and denaturation of proteins [18][19][20]. Complete destruction of S. aureus was found after 5-10 min of exposure to 0.2% biguanide solution [21].…”

Section: Discussionmentioning

confidence: 99%

Influence of Mucin on the Activity of the Antiseptic Lavasept<sup>®</sup> against <i>Staphylococcus aureus</i>

Ansorg¹,

Azem²,

Fabry³

et al. 2002

Chemotherapy

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Background: Lavasept^®, containing the polymeric biguanide polyhexanide, may be effective against Staphylococcus aureus colonizing the nasal mucosa. To obtain basic data on its suitability for that purpose, its antimicrobial activity was examined in the presence of mucin. Methods: A disk diffusion test was applied using Mueller-Hinton agar, and disks soaked with a therapeutic and a 10-fold higher concentration of Lavasept. Commercially available mucin preparations from porcine stomach were added to the test system. Reference strains and 20 clinically isolates of S. aureus, and reference strains of Escherichia coli, Pseudomonas aeruginosa, Enterococcusfaecalis, and Candida albicans were tested. Results: Supplementation of the test medium with 1% mucin completely abolished the activity of disks loaded with the therapeutically used concentration of the antiseptic. The neutralizing effect of mucin occurred with all test strains. Conclusions: The inactivation of Lavaseptby mucin may hamper a reliable clearance of nasal S. aureus carriage.

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New polymeric biocides: synthesis and antibacterial activities of polycations with pendant biguanide groups

Cited by 191 publications

References 12 publications

Antibacterial Effects of Poly(2-(dimethylamino ethyl)methacrylate) against Selected Gram-Positive and Gram-Negative Bacteria

Antibacterial Effects of Poly(2-(dimethylamino ethyl)methacrylate) against Selected Gram-Positive and Gram-Negative Bacteria

Polycationic biocides with pendant active groups: molecular weight dependence of antibacterial activity

Influence of Mucin on the Activity of the Antiseptic Lavasept<sup>®</sup> against <i>Staphylococcus aureus</i>

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