1887

Abstract

Hydrolysis of tetradecyl betainate (B14), a fast-acting (QAC) being an ester of betaine and tetradecanol, occurred after binding to resulting in release of the water-soluble betaine portion and retention of the lipophilic tetradecanol. The rate of the hydrolysis was significant but retarded in comparison to B14 in solution. As in free solution, the hydrolysis of substance bound to was increased in an alkaline environment and by heat. At pH 6.0 and 20 ° the hydrolysis of bound ester was about 10% after 180 min, whereas at pH 9.0 and 50 ° it was about 50% after 60 min. These results are consistent with a model where amphiphilic QACs are inserted into the bacterial outer membrane (OM) with the quaternary ammonium head group facing outwards and the lipophilic portion, including the ester bond, being in the membrane lipid environment enough for retarding the hydrolysis. However, calculation of the mean concentration of B14 in the bacteria at MBC (minimum bactericidal concentration required to kill 99% of cells) showed a 7000-8000 times greater concentration than in the medium. At this concentration, when most B14 is considered to be bound to the OM, the available surface area for each molecule was only 2 å. This is only 6-7% of that required for close packing of the quaternary ammonium head group (30 å), indicating that a three-dimensional, presumably continuous arrangement was formed. Since B14 is hydrolysed after its binding to bacteria with microbicidal effect, it may be used under conditions where stable QACs might be harmful to the close or the common environment.

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1998-09-01
2024-04-24
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References

  1. Ahlstrüm B., Edebo L. 1994; Selective release of the periplasmic enzyme β-lactamase from Escherichia coli with tetradecyl betainate.. FEMS Microbiol Lett 119:7–12
    [Google Scholar]
  2. Andersson S., Hyde S.T., Larsson K., Lidin S. 1988; Minimal surfaces and structures: from inorganic and metal crystals to cell membranes and biopolymers.. Chem Rev 88:221–242
    [Google Scholar]
  3. Association of Official Analytical Chemists 1984; Disinfectants. In Official Methods of Analysis, 14th. pp. 65–77 Arlington, VA;: Association of Official Analytical Chemists;
    [Google Scholar]
  4. Bodor N., Kaminski J.K., Selk S. 1980; Soft drugs. 1. Labile quaternary ammonium salts as soft antimicrobials.. J Med Chem 23:469–474
    [Google Scholar]
  5. Braun V., Gnirke H., Henning U., Rehn K. 1973; Model for the structure of the shape-maintaining layer of the Escherichia coli cell envelope.. J Bacteriol 114:1264–1270
    [Google Scholar]
  6. Edebo L., Kihlstrom E., Magnusson K.-E., Stendahi O. 1980; The hydrophobic effect and charge effects in the adhesion of enterobacteria to animal cell surfaces and the influence of antibodies of different immunoglobulin classes.. In Cell Adhesion and Motility. 3rd Symposium of the British Society for Cell Biology pp. 65–101 Curtis A. S. G., Pitts J.D. Edited by Cambridge: Cambridge University Press;
    [Google Scholar]
  7. Edebo L., Ahlstrüm B., Chelminska-Bertilsson M., Lange S., Lindstedt M., Thompson R.A. 1992; Betaine esters: quaternary ammonium compounds with time-limited activity.. In Industrial Applications of Surfactants III, pp. 184–207 Karsa D. R. Edited by Cambridge: Royal Society of Chemistry;
    [Google Scholar]
  8. Lindstedt M., Allenmark S., Thompson R.A., Edebo L. 1990; Antimicrobial activity of betaine esters, quaternary ammonium amphiphiles which spontaneously hydrolyse into nontoxic components.. Antimicrob Agents Chemother 43:1949–1954
    [Google Scholar]
  9. Mitchell P. 1966; Chemiosmotic coupling in oxidative and photosynthetic phosphorylation.. Biol Rev 41:445–502
    [Google Scholar]
  10. Neidhardt F.C. 1987; Chemical composition of Escherichia coli. . In Escherichia coli and Salmonella typhimurium: Cellular and Molecular Biology pp. 3–6 Neidhardt F. C., Ingraham J. L., Brooks Low K., Magasanik B., Schaechter M., Umbarger H. E. Edited by Washington, DC: American Society for Microbiology;
    [Google Scholar]
  11. Nikaido H., Vaara M. 1987; Outer membrane.. In Escherichia coli and Salmonella typhimurium: Cellular and Molecular Biology, pp. 7–22 Neidhardt F. C., Ingraham J. L., Brooks Low K., Magasanik B., Schaechter M., Umbarger H.E. Edited by Washington, DC: American Society for Microbiology;
    [Google Scholar]
  12. Rennie A.R., Lee E.M., Simister E.A., Thomas R.K. 1990; Structure of a cationic surfactant layer at the silica-water interface.. Langmuir 6:1031–1034
    [Google Scholar]
  13. Robson Wright M. 1968; Arrhenius parameter for the alkaline hydrolysis of esters in aqueous solution. Part III. Methyl betaine methyl ester.. J Chem Soc B 5:548–550
    [Google Scholar]
  14. Salt W.G., Wiseman D. 1970; The relation between the uptake of cetyltrimethylammonium bromide by Escherichia coli and its effects on cell growth and viability.. J Pharm Pharmacol 22:261–264
    [Google Scholar]
  15. Salton M.R.J. 1951; The adsorption of cetyltrimethylammonium bromide by bacteria, its action in releasing cellular constituents and its bactericidal effect.. J Gen Microbiol 5:391–404
    [Google Scholar]
  16. Thompson R.A. 1989; Effects of molecular association on the rates of hydrolysis of long-chain alkyl betainates (alkoxycarbonyl-N,N,N-trialkylmethanaminium halides).. Acta Chem Scand 43:690–693
    [Google Scholar]
  17. Thompson R.A., Allenmark S. 1992; Factors influencing the micellar catalyzed hydrolysis of long-chain betainates.. J Colloid Interface Sci 148:241–246
    [Google Scholar]
  18. Thompson R.A., Lindstedt M., Allenmark S. 1990; A liquid radiochromatographic method for following the synthesis and hydrolysis of a double (3H14C) radiolabeled alkyl betainate.. Anal Lett 23:787–798
    [Google Scholar]
  19. Vitzthum J., Rupprecht H. 1990; Coadsorption of cationic surfactants and sodium ethylene diamine tetraacetate on silica surfaces and Escherichia coli. . Acta Pharm Technol 36:67–73
    [Google Scholar]
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