Bactericidal Properties of Flat Surfaces and Nanoparticles Derivatized with Alkylated Polyethylenimines

Lin, Jiunn-Yuan; Qiu, Shuyi; Lewis, Kim; Klibanov, Alexander M.

doi:10.1021/bp025597w

Cited by 238 publications

(231 citation statements)

References 32 publications

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“…35 The immobilization was followed by alkylation, acylation, or carboxyalkylation to generate cationic (quaternary ammonium), neutral (amide), and zwitter-ionic (quaternary ammonium carboxylic acid) functional groups, respectively. Alkylation was performed with a range of chainlengths (ethyl, Butyl, hexyl, dodecyl, and octadecyl) followed by subsequent methylation to quaternize the amine.…”

Section: Aliphatic Quaternary Ammonium Polymersmentioning

confidence: 99%

“…Irreversible immobilization of the antimicrobial agents in the device offers an alternative motif that eliminates patient exposure to elutable active agents and potentially increases the duration of antimicrobial efficacy. 8,9 A wide range of antimicrobial agents have been immobilized, including small molecules (e.g., quaternary ammonium silanes), [10][11][12][13][14][15][16][17] quaternary ammonium polymers, [18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35] polyamines, [36][37][38][39][40][41][42] chitosan, [43][44][45][46][47][48][49] enzymes, [50][51][52][53][54][55] peptides, and peptide mimetics. …”

Section: Introductionmentioning

confidence: 99%

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A review of immobilized antimicrobial agents and methods for testing

2011

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Antimicrobial surfaces for food and medical applications have historically involved antimicrobial coatings that elute biocides for effective kill in solution or at surfaces. However, recent efforts have focused on immobilized antimicrobial agents (iAMA) to avoid toxicity, compatibility and reservoir limitations common to elutable agents. This review critically examines the assorted AMAs reported to have been immobilized with an emphasis around interpretation of antimicrobial testing as it pertains to discriminating between eluting and immobilized agents. Immobilization techniques and modes of antimicrobial action are also discussed.

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Section: Aliphatic Quaternary Ammonium Polymersmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

A review of immobilized antimicrobial agents and methods for testing

2011

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“…Helander et al demonstrated that PEI increased cell permeability to the fluorescent dye 1-Nphenylnaphthylamine (19). Several papers by Klibanov and colleagues (26,27) have shown that alkylated derivatives of PEI can exert an antimicrobial effect when incorporated into surfaces and textiles. This was proposed to occur due to the fact that the alkyl chains were long enough to penetrate from the surface to the bacterial membrane (28).…”

Section: Vol 50 2006 Photoinactivation With Pei-chlorin(e6) Conjugamentioning

confidence: 99%

Protease-Stable Polycationic Photosensitizer Conjugates between Polyethyleneimine and Chlorin(e6) for Broad-Spectrum Antimicrobial Photoinactivation

Tegos

Anbe

Yang

et al. 2006

Antimicrob Agents Chemother

161

146

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We previously showed that covalent conjugates between poly-L-lysine and chlorin(e6) were efficient photosensitizers (PS) of both gram-positive and gram-negative bacteria. The polycationic molecular constructs increased binding and penetration of the PS into impermeable gram-negative cells. We have now prepared a novel set of second-generation polycationic conjugates between chlorin(e6) and three molecular forms of polyethyleneimine (PEI): a small linear, a small cross-linked, and a large cross-linked molecule. The conjugates were characterized by high-pressure liquid chromatography and tested for their ability to kill a panel of pathogenic microorganisms, the gram-positive Staphylococcus aureus and Streptococcus pyogenes, the gramnegative Escherichia coli and Pseudomonas aeruginosa, and the yeast Candida albicans, after exposure to low levels of red light. The large cross-linked molecule efficiently killed all organisms, while the linear conjugate killed gram-positive bacteria and C. albicans. The small cross-linked conjugate was the least efficient antimicrobial PS and its remarkably low activity could not be explained by reduced photochemical quantum yield or reduced cellular uptake. In contrast to polylysine conjugates, the PEI conjugates were resistant to degradation by proteases such as trypsin that hydrolyze lysine-lysine peptide bonds, The advantage of protease stability combined with the ready availability of PEI suggests these molecules may be superior to polylysine-PS conjugates for photodynamic therapy of localized infections.Photodynamic therapy (PDT) employs a nontoxic dye termed a photosensitizer (PS) and low-intensity visible light, which in the presence of oxygen produce cytotoxic species (4-6). PDT has the advantage of dual selectivity in that the PS can be targeted to its destination cell or tissue, and in addition the illumination can be spatially directed to the lesion. PDT was originally discovered over 100 years ago by its effect on microorganisms (35) but since then has been principally developed as a treatment for cancer (11) and age-related macular degeneration (3).Because of the well-known increase in multiantibiotic resistance among pathogenic microbes of all classes, PDT has attracted attention as a possible treatment for localized infections (9, 14, 46). It is known that gram-negative bacteria are resistant to PDT with many commonly used PS that will readily lead to phototoxicity for gram-positive species (29) and that PS bearing a cationic charge (33) or the use of agents that increase the permeability of the outer membrane will increase the efficacy of killing of gram-negative organisms (29).In 1997 our laboratory formed the hypothesis that by covalently conjugating a suitable PS such as chlorin(e6) (ce6) to a poly-L-lysine (pL) chain, a bacterially targeted PS delivery vehicle could be constructed that would efficiently inactivate both gram-positive and gram-negative species (42). Because the resulting polycationic entity is a macromolecule, it is taken up by mammalian cells by th...

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“…A number of polycations possessing antimicrobial properties were developed for this purpose including ion exchange fibers [8], alkoxysilanes [9], soluble and insoluble pyridinium-type polymers [10,11], polyionenes [12], polymer surfaces derivatized with poly(vinyl-N-pyridinium) [13,14], and immobilized N-alkylated polyethyleneimine [15][16][17].…”

Section: Introductionmentioning

confidence: 99%

Quaternary Ammonium Polyethyleneimine: Antibacterial Activity

Yudovin-Farber

Golenser

Beyth

et al. 2010

Journal of Nanomaterials

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Quaternary ammonium polyethyleneimine-(QA-PEI-) based nanoparticles were synthesized using two synthetic methods, reductive amination and N-alkylation. According to the first method, QA-PEI nanoparticles were synthesized by cross-linking with glutaraldehyde followed by reductive amination with octanal and further N-methylation with methyl iodide. The second method is based on crosslinking with dialkyl halide followed by N-alkylation with octyl halide and further N-methylation with methyl iodide. QA-PEI nanoparticles completely inhibited bacterial growth (>10 6 bacteria), including both Gram-positive, that is, Staphylococcus aureus at 80 μg/mL, and Gram-negative, that is, Escherichia coli at 320 μg/mL. Activity analysis revealed that the degree of alkylation and N-methylation of the QA-PEI nanoparticles plays a significant role in antibacterial activity of the reagent. The most potent compound was octyl alkylated QA-PEI alkylated at 1 : 1 mole ratio (primary amine of PEI monomer units/alkylating agent). Also, cytotoxicity studies on MAT-LyLu and MBT cell lines were performed with QA-PEI nanoparticles. These findings confirm previous reports that polycations bearing quaternary ammonium moieties inhibit bacterial growth in vitro and have a potential use as additives in medical devices which need antibacterial properties.

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Bactericidal Properties of Flat Surfaces and Nanoparticles Derivatized with Alkylated Polyethylenimines

Cited by 238 publications

References 32 publications

A review of immobilized antimicrobial agents and methods for testing

A review of immobilized antimicrobial agents and methods for testing

Protease-Stable Polycationic Photosensitizer Conjugates between Polyethyleneimine and Chlorin(e6) for Broad-Spectrum Antimicrobial Photoinactivation

Quaternary Ammonium Polyethyleneimine: Antibacterial Activity

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