Influence of amphiphilic compounds on membranes.

Przestalski, S.; Sarapuk, Janusz; Kleszczyńska, Halina; Gabrielska, Janina; Hładyszowski, Jerzy; Trela, Zenon; Kuczera, J

doi:10.18388/abp.2000_3984

Cited by 62 publications

(39 citation statements)

References 29 publications

(19 reference statements)

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“…For example, DABCO derivatives containing one long alkyl chain were active against Gram‐positive and Gram‐negative bacteria as well as fungi 30, 31. When attached to insoluble carbohydrate and protein‐based materials, they also showed very high antimicrobial activities 31–33. However, the activity of the DABCO group depends on the length of the alkyl chain attached to it, and an increase in alkyl chain length was shown to increase the antimicrobial activity 30, 33.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and antimicrobial activities of new water‐soluble bis‐quaternary ammonium methacrylate polymers

Dizman

Elasri

Mathias

2004

J of Applied Polymer Sci

156

135

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New methacrylate monomers containing pendant quaternary ammonium moieties based on 1,4-diazabicyclo-[2.2.2]-octane (DABCO) were synthesized. The DABCO group contains either a butyl or a hexyl pendant group comprising the hydrophobic segment of the monomers and one tether group to the methacrylate moiety. The monomers were homopolymerized in water by using 2,2Ј-azobis(2-methylpropionamide) dihydrochloride (V-50) as an initiator. The monomers and polymers were characterized by elemental analysis, thermogravimetric analysis (TGA), differential scanning calorimetry (DSC), FTIR, and 13 C-NMR. The antimicrobial activities of the corresponding small molecules (bis-quaternary ammonium monocarboxylates) and polymers were investigated against Staphylococcus aureus and Escherichia coli. Although the small molecules did not show any antimicrobial activity, the polymers were moderately effective against both Gram-positive and Gramnegative bacteria. The minimum inhibitory concentration (MIC) values of the polymers with butyl and hexyl hydrocarbon chains against S. aureus and E. coli were found to be 250 and 62.5 g/mL, respectively. The minimum bactericidal concentration (MBC) value for the polymer with the butyl group was higher than 1 mg/mL, whereas the MBC value for the polymer with hexyl group was found to be 62.5 g/mL. Thus, an increase of the alkyl chain length from 4 to 6 significantly increased the antimicrobial activity of the polymer.

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Section: Introductionmentioning

confidence: 99%

Synthesis and antimicrobial activities of new water‐soluble bis‐quaternary ammonium methacrylate polymers

Dizman

Elasri

Mathias

2004

J of Applied Polymer Sci

156

135

View full text Add to dashboard Cite

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“…The hydrophobic chain length between 12 and 18 carbons processed an excellent antimicrobial activity. 33,34 DMAE-CB has a long lipophilic chain with 16 carbons according to the previous studies, 17 but chain length of DMAEMA-PMDPM salt is very short, so this might be the reason why DMAEMA-PMDPM salt has a higher MIC/ MBC. The anionic part of QSA monomer could affect the bactericidal activity but the law is not very clear now.…”

Section: Discussionmentioning

confidence: 92%

“…The activity depends both on the character of the polar heads (size, electric charge distribution) and hydrocarbon chains (length, saturation, multiple chains). 33 The results showed that the antimicrobial property of the new monomer is lower than DMAE-CB, especially for C. albicans. There may be some reasons for this phenomenon.…”

Section: Discussionmentioning

confidence: 93%

Synthesis and properties of a polymerizable quaternary ammonium salt

Zhou

Tang

et al. 2014

J of Applied Polymer Sci

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Novel polymerizable monomer N,N‐dimethyl‐2‐[(2‐methylacryloyl)oxy] ethanaminium 5‐carboxy‐2,4‐bis benzoate (DMAEMA‐PMDPM salt) was synthesized by acid‐alkali neutralizing reaction and was proved to be successful by Fourier transform infrared spectroscopy. The antibacterial activity and cytotoxicity of monomer were assessed by determination of the minimal inhibitory concentration and minimal bactericidal concentration, time–kill study and methyltetrazolium test assay. Polymerizable efficiency was determined by measurement of degree of conversion. The results indicated that DMAEMA‐PMDPM salt which is a kind of liquid polymerizable has some antimicrobial activity and similar cytotoxicity to common dental resin monomers. The new monomer also has a high polymerizable ability. Therefore it might have a great potential to prepare antimicrobial coatings on denture base and soft lining materials, as well as some biomedical applications. © 2014 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2014, 131, 41002.

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“…[41] Since the F O rotor of F 1 F O complex is embedded in the inner membrane, any change in the bilayer properties can modulate the catalytic activity and also affect its sensitivity to inhibitors. [42] Butyltins are amphiphilic [43] and their butyl arms facilitate their incorporation within phospholipid acyl chains ( Fig. 1).…”

Section: Effects Of Butyltin (Iv) N+ Compounds On Membrane Bilayer Prmentioning

confidence: 99%

“…[25][26][27] Any decrease in the negative charges (or increase in positive charges) on the membrane surface decreases the accessibility of organotins for electrostatic reasons and conversely an increase of negative charges (and decrease of positive charges) favours their incorporation. [43,44] Accordingly, electrostatic interactions could also explain synergistic or antagonist effects of other co-present xenobiotics, including butyltin derivatives. [45] In model systems, butyltins are incorporated into phospholipids such as phosphatidylcholine, phosphatidylethanolamine and phosphatidylserine, where they perturb the thermotropic and structural properties.…”

Section: Effects Of Butyltin (Iv) N+ Compounds On Membrane Bilayer Prmentioning

confidence: 99%

Modulation of the F₁F_O‐ATPase function by butyltin compounds

Nesci

Ventrella

Pagliarani

2013

Applied Organom Chemis

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Among butyltin compounds, tributyltin (TBT), widely exploited in the past in antifouling paints for its biocidal properties, is long known as one of the most harmful sea contaminants. Among the ascertained and universal toxicity mechanisms, TBT targeting F1FO‐ATPase and thus impairing cell bioenergetics, is here reviewed. While TBT effects on F1FO‐ATPase have been investigated for decades, the possible impact of the derivatives dibutyltin (DBT) and monobutyltin (MBT), produced by abiotic and/or biotic dealkylation of TBT and usually considered far less toxic, have been poorly explored up until now. Butyltin effects on F1FO‐ATPase and their underlying action mechanism seem to be tightly structure dependent. Butyltins are membrane‐active toxicants. Owing to its more pronounced lipophilicity TBT targets the transmembrane FO sector, blocks ionic translocation and causes a dose‐dependent loss of sensitivity to FO inhibitors such as oligomycin and N,N′‐dicyclohexylcarbodiimide. DBT strongly inhibits F1FO‐ATPase activity by competing with the Mg+2 cofactor in the F1 catalytic site but is ineffective on the enzyme sensitivity to FO inhibitors. MBT is apparently ineffective. The possible contribution of DBT to the overall butyltin toxicity on membrane systems may not be neglectable since usually TBT coexists with its derivatives in organotin‐exposed animal tissues. Copyright © 2013 John Wiley & Sons, Ltd.

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Influence of amphiphilic compounds on membranes.

Cited by 62 publications

References 29 publications

Synthesis and antimicrobial activities of new water‐soluble bis‐quaternary ammonium methacrylate polymers

Synthesis and antimicrobial activities of new water‐soluble bis‐quaternary ammonium methacrylate polymers

Synthesis and properties of a polymerizable quaternary ammonium salt

Modulation of the F₁F_O‐ATPase function by butyltin compounds

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Influence of amphiphilic compounds on membranes.

Cited by 62 publications

References 29 publications

Synthesis and antimicrobial activities of new water‐soluble bis‐quaternary ammonium methacrylate polymers

Synthesis and antimicrobial activities of new water‐soluble bis‐quaternary ammonium methacrylate polymers

Synthesis and properties of a polymerizable quaternary ammonium salt

Modulation of the F1FO‐ATPase function by butyltin compounds

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Product

Resources

About

Modulation of the F₁F_O‐ATPase function by butyltin compounds