Novel polycationic biocides: Synthesis and antibacterial activity of polymeric phosphonium salts

Kanazawa, Akihiko; Ikeda, Tomiki; Endō, Takeshi

doi:10.1002/pola.1993.080310205

Cited by 209 publications

(208 citation statements)

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“…The polymeric phosphonium salts were found to exhibit a higher bactericidal activity than the polymeric quaternary ammonium salts with the same structure except the cationic part (7). However, for polymers, various factors such as molecular weight distribution and repulsion between positively charged atoms are expected to affect the antibacterial activity.…”

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confidence: 99%

“…We have previously reported the antibacterial activity of polymeric phosphonium salts and low-molecular-weight model compounds having various alkyl chains against Staphylococcus aureus and Escherichia coli, evaluated by the viable cell counting method in sterile distilled water (7,8). The polymeric phosphonium salts were found to exhibit a higher bactericidal activity than the polymeric quaternary ammonium salts with the same structure except the cationic part (7).…”

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confidence: 99%

“…This is partly because synthesis of such phosphonium salts is difficult in comparison with nitrogen compounds, resulting from less availability of trialkylphosphines as starting materials. This problem evidently depressed research in phosphonium salts as cationic biocides, which was solved recently by the establishment of a simple route of synthesis of di-and trimethylsubstituted trialkylphosphines containing long alkyl chains (10).We have previously reported the antibacterial activity of polymeric phosphonium salts and low-molecular-weight model compounds having various alkyl chains against Staphylococcus aureus and Escherichia coli, evaluated by the viable cell counting method in sterile distilled water (7,8). The polymeric phosphonium salts were found to exhibit a higher bactericidal activity than the polymeric quaternary ammonium salts with the same structure except the cationic part (7).…”

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Synthesis and antimicrobial activity of dimethyl- and trimethyl-substituted phosphonium salts with alkyl chains of various lengths

Kanazawa

Ikeda

Endō

1994

Antimicrob Agents Chemother

112

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Various phosphonium salts possessing single or double alkyl chains of various lengths (C1O to C18) were prepared as cationic biocides, and their antimicrobial activities against 11 typical strains of microorganisms including methicillin-resistant Staphylococcus aureus (MRSA) were evaluated. The phosphonium salts with long alkyl chains were found to show high levels of antimicrobial activity. Their activities depended strongly on the molecular structure, and a correlation between antimicrobial activity and molecular structure was observed. In the alkyltrimethylphosphonium salts, the bactericidal activity against S. aureus and Escherichia coli increased with increasing alkyl chain length, and the compound with the longest alkyl chain (C18) killed all the bacterial cells (ca. 107 cells per ml) within 30 min of contact at concentrations of 2.8 and 28 ,uM, respectively. In contrast, the bactericidal activity of dialkyldimethylphosphonium salts was found to decrease as the chain length of the substituents increased. It is significant that the phosphonium biocide containing double decyl groups exhibited the broadest spectrum of activity against microorganisms tested and showed the greatest bacteriostatic activity against MRSA (MIC = 0.78 ,ug/ml). Furthermore, we systematically investigated differences in bactericidal activity between the phosphonium salts and commonly available ammonium salts with the same hydrophobic structure. It was observed that the phosphonium salts showed an advantage over the corresponding ammonium salts in bactericidal activity and killing rate. For example, tetradecyltrimethyl-and didecyldimethylphosphonium chlorides killed all S. aureus organisms (ca. 107 cells per ml) within 60 and 30 min of exposure at 28 and 2.8 ,uM, respectively, while tetradecyltrimethyl-and didecyldimethylammonium chlorides which are representative of the existing cationic disinfectants did not kill all the bacteria even at the longest exposure time (120 min).At present, positively charged compounds such as quaternary ammonium salt derivatives are widely used as disinfectants in agriculture, the food processing industry, and clinics, etc. Use of the organic cations as disinfectants is particularly important because they possess a high antibacterial activity and a broad spectrum of antimicrobial activity. Quaternary ammonium salts used as cationic biocides have a common structure of long alkyl chains in the molecule. Trimethyl-n-alkylammonium salts are representative of this group. On the other hand, few studies of the antibacterial activity of phosphonium salts have been done (4). In particular, no study on the antibacterial activity of di-and trimethyl-substituted phosphonium salts with long alkyl chains has been reported except in U.S. patents in which no details of their activity were given (15, 15a). This is partly because synthesis of such phosphonium salts is difficult in comparison with nitrogen compounds, resulting from less availability of trialkylphosphines as starting materials. This problem evidently depress...

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Synthesis and antimicrobial activity of dimethyl- and trimethyl-substituted phosphonium salts with alkyl chains of various lengths

Kanazawa

Ikeda

Endō

1994

Antimicrob Agents Chemother

112

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“…Preparation of the macroinitiator [9] The hydroxyl end-group of the commercially available poly[isoprene-block-(ethyleneco-butylene)] oligomer (PI-b-PEB-OH) has been reacted with 2-bromoisobutyryl bromide, in order to make a macroinitiator, PI-b-PE-Br, available to ATRP of DMAEMA, TBAEMA and MMA, respectively. Moreover, the short polyisoprene block of this macroinitiator (c. 10 double bonds/chain) makes the amphiphilic copolymer cross-linkable upon UV exposure.…”

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confidence: 99%

Antimicrobial activity of polystyrene particles coated by photo-crosslinked block copolymers containing a biocidal polymethacrylate block

et al. 2005

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A commercially available poly(ethylene-co-butylene) copolymer, endcapped by a short polyisoprene block and a hydroxyl group (PI-b-PEB-OH), has been derivatized into a macroinitiator for atom transfer radical polymerization (ATRP) by esterification of the hydroxyl end-group by an activated bromidecontaining acyl bromide. Two types of triblock copolymers, PI-b-PEB-b-poly-(dimethylaminoethyl methacrylate) (PDMAEMA) and PI-b-PEB-b-poly[2-(tert-butylamino)ethyl methacrylate] (PTBAEMA), have been synthesized and used to coat polystyrene particles. These coatings have been permanently immobilized by UV cross-linking of the isoprene units. They exhibit a biocidal activity against Gramnegative bacteria either intrinsically in case of the PTBAEMA block or upon quaternization of the PDMAEMA block by octyl bromide. The antimicrobial activity is directly related to the concentration of coated PS particles in the medium.

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“…The lengths of the alkyl chains on phosphonium and ammonium salts are known to affect the antibacterial activity of the small molecules, 32 so it was desirable to explore this in the context of phosphonium-functionalized polymer assemblies. Initial attempts to prepare the alkynefunctionalized phosphonium salts by reaction of trialkylphosphines with propargyl bromide resulted in complex and inseparable product mixtures.…”

Section: Synthesis Of Alkyne-functionalized Phosphonium Saltsmentioning

confidence: 99%

Phosphonium-Functionalized Polymer Micelles with Intrinsic Antibacterial Activity

2017

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New approaches to treat bacterial infections are badly needed to address the increasing problem of antibiotic-resistance. This study explores phosphonium-functionalized block copolymer micelles as intrinsically antibacterial polymer assemblies. Phosphonium cations with varying alkyl lengths were conjugated to the terminus of a poly(ethylene oxide)-polycaprolactone block copolymer and the phosphonium-functionalized block copolymers were self-assembled to form micelles in aqueous solution. The size, morphology, and z-potential of the assemblies were studied and their abilities to kill Escherichia coli and Staphylococcus aureus were evaluated. It was found that the minimum bactericidal concentration depended on the phosphonium alkyl chain length and different trends were observed for Gram-negative and Gram-positive bacteria.The most active assemblies exhibited no hemolysis of red blood cells above the bactericidal 2 concentrations, indicating that they can selectively disrupt the membranes of bacteria.Furthermore, it was possible to encapsulate and release the antibiotic tetracycline using the assemblies, providing a potential multi-mechanistic approach to bacterial killing.

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Novel polycationic biocides: Synthesis and antibacterial activity of polymeric phosphonium salts

Cited by 209 publications

References 9 publications

Synthesis and antimicrobial activity of dimethyl- and trimethyl-substituted phosphonium salts with alkyl chains of various lengths

Synthesis and antimicrobial activity of dimethyl- and trimethyl-substituted phosphonium salts with alkyl chains of various lengths

Antimicrobial activity of polystyrene particles coated by photo-crosslinked block copolymers containing a biocidal polymethacrylate block

Phosphonium-Functionalized Polymer Micelles with Intrinsic Antibacterial Activity

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