Most cited article - PubMed ID 2699283
Interaction of amine oxides and quaternary ammonium salts with membrane and membrane-associated processes in E. coli cells: mode of action
Resistant strains of Escherichia coli were obtained by stepwise cultivation in media with increasing concentration of antimicrobially active 1-(methyldodecyl)dimethylamine oxide and 1-(methyldodecyl)trimethylammonium bromide. Adaptive changes were determined in the fatty-acid (FA) composition in an isolated lipopolysaccharide sample from the outer membrane of these strains. The composition of this FA mixture from adapted strains was compared with that of FA from a sensitive strain. The differences were found in level of palmitic, heptadecanoic, heptadecenoic, heptadecadienoic and nonadecenoic acids. In addition, the adapted strains differed from each other in the content of myristic, pentadecanoic, stearic and linoleic acids.
- MeSH
- Drug Resistance, Bacterial MeSH
- Dimethylamines pharmacology MeSH
- Escherichia coli drug effects metabolism MeSH
- Adaptation, Physiological drug effects MeSH
- Quaternary Ammonium Compounds pharmacology MeSH
- Lipopolysaccharides metabolism MeSH
- Fatty Acids metabolism MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- Dimethylamines MeSH
- Quaternary Ammonium Compounds MeSH
- Lipopolysaccharides MeSH
- Fatty Acids MeSH
- N-(1-methyldodecyl)-N,N,N-trimethylammonium MeSH Browser
- N,N-dimethyl-1-methyldodecylamine oxide MeSH Browser
Antimicrobial activity of 19 commercially manufactured disinfectant substances on a Salmonella enteritidis strain was determined. The substances represented 8 quaternary ammonium salts (QAS) and 10 QAS combined with other additives. The antimicrobial efficacy was characterized by influencing the growth of bacterial cells expressed as MIC and ED50 values as well as by the inhibition of the incorporation rate of 14C-adenine and 14C-leucine. According to their efficacy the disinfectants were divided into three groups: (1) substances with strong inhibitory effect (MIC 6-45 micrograms/L) such as Diesin forte, Hexaquart plus, Neoquat S, Triquart, Almyrol, Hexaquart S, ID212, ID213 and Microbac forte; (2) substances with good antibacterial efficacy (MIC 90-780 micrograms/L); (3) substances with MIC values > 780 micrograms/L (up to 3120 micrograms/L). Cetrimide had very low activity (MIC 3.12-6.25 mg/L). The effect of disinfectants on the biosynthetic processes was expressed by R values (IC50(Ade):IC50(Leu)); all these values were < 1 except Benzalkonium chloride, FD312, Divoquat forte, 5P plus, Almyrol, Hexaquart S and Hexaquart plus. Low R values suggested interference of these substances with the synthesis of both nucleic acids and proteins. All substances except 5P plus caused an inhibition of endogenous respiration. The most effective were Almyrol, Diesin forte, Microbac forte and Neoquat which completely inhibited respiration at 190 mg/L. Kvart showed the lowest effect on the respiration over the whole concentration range. The disinfectants also suppressed growth of S. enteritidis, probably by interfering with energy-yielding and-requiring processes in the cells.
- MeSH
- Adenine pharmacokinetics MeSH
- Disinfectants pharmacology MeSH
- Gastroenteritis microbiology prevention & control MeSH
- Leucine pharmacokinetics MeSH
- Humans MeSH
- Carbon Radioisotopes MeSH
- Salmonella enteritidis drug effects metabolism MeSH
- In Vitro Techniques MeSH
- Check Tag
- Humans MeSH
- Publication type
- Journal Article MeSH
- Comparative Study MeSH
- Names of Substances
- Adenine MeSH
- Disinfectants MeSH
- Leucine MeSH
- Carbon Radioisotopes MeSH
The effects of subinhibitory concentrations (1/4, 1/8, 1/16 of the MIC) of 12 organic ammonium salts of A (hard-alkyltrimethylammonium bromides) and B (soft--2-(dodecanoylamino)ethylalkyldimethylammonium bromides) homologous series on phospholipase C, proteinase, elastase and permeability activity were studied. The substances with longer substituents were more effective in reducing phospholipase C activity (hard and soft series) as well as proteinase (hard series). Phospholipase C was the most frequently and the most markedly inhibited enzyme. The organic ammonium salts were less effective in inhibiting elastase and permeability activity. Only one of the substances under study reduced all the tested activities.
- MeSH
- Anti-Bacterial Agents pharmacology MeSH
- Type C Phospholipases antagonists & inhibitors MeSH
- Protease Inhibitors pharmacology MeSH
- Capillary Permeability MeSH
- Quaternary Ammonium Compounds pharmacology MeSH
- Microbial Sensitivity Tests MeSH
- Pancreatic Elastase antagonists & inhibitors MeSH
- Pseudomonas aeruginosa drug effects enzymology pathogenicity MeSH
- Virulence MeSH
- Structure-Activity Relationship MeSH
- Publication type
- Journal Article MeSH
- Names of Substances
- Anti-Bacterial Agents MeSH
- Type C Phospholipases MeSH
- Protease Inhibitors MeSH
- Quaternary Ammonium Compounds MeSH
- Pancreatic Elastase MeSH
New surface-active bisquaternary ammonium salts derived from bis-(2-dimethylaminoethyl) ester of glutaric acid are highly effective against representatives of Gram-positive, Gram-negative bacteria and yeasts. Relationships between structure, lipophilicity and antimicrobial effectiveness were demonstrated by quantitative structure-activity methodology. The non-linear dependence of biological activity on the structure as well as lipophilicity (expressed as critical micelle concentration-CMC) was shown using Kubinyi's bilinear model. The most effective compounds were those with the alkyl chain of 11-12 carbon atoms and with the CMC values around 0.7-1.0 mmol/L. These derivatives possessed higher antimicrobial activity particularly to Gram-negative bacteria.
- MeSH
- Anti-Bacterial Agents MeSH
- Antifungal Agents chemical synthesis pharmacology MeSH
- Anti-Infective Agents chemical synthesis pharmacology MeSH
- Candida albicans drug effects MeSH
- Escherichia coli drug effects MeSH
- Quaternary Ammonium Compounds pharmacology MeSH
- Microbial Sensitivity Tests MeSH
- Surface-Active Agents pharmacology MeSH
- Staphylococcus aureus drug effects MeSH
- Structure-Activity Relationship MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- Anti-Bacterial Agents MeSH
- Antifungal Agents MeSH
- Anti-Infective Agents MeSH
- Quaternary Ammonium Compounds MeSH
- Surface-Active Agents MeSH
A change in interaction with spores of Bacillus cereus occurred in the range of critical concentrations of micelle formation. With 1-methyldodecyldimethylamine-N-oxide and N,N'-bis(dodecyldimethyl)-1,2-ethanediammonium dibromide, the induced release of dipicolinic acid was blocked and the adsorption dynamics changed, respectively.
- MeSH
- Adsorption MeSH
- Bacillus cereus drug effects metabolism MeSH
- Bacterial Adhesion drug effects MeSH
- Dimethylamines pharmacokinetics pharmacology MeSH
- Quaternary Ammonium Compounds pharmacokinetics pharmacology MeSH
- Micelles MeSH
- Surface-Active Agents pharmacokinetics pharmacology MeSH
- Spores, Bacterial drug effects metabolism MeSH
- Publication type
- Journal Article MeSH
- Names of Substances
- Dimethylamines MeSH
- Quaternary Ammonium Compounds MeSH
- Micelles MeSH
- N,N-dimethyl-1-methyldodecylamine oxide MeSH Browser
- N,N'-bis(dodecyldimethyl)-1,2-ethanediammonium MeSH Browser
- Surface-Active Agents MeSH