Abstract
Resistant strains ofEscherichia 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.
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Abbreviations
- AO:
-
amine oxide(s)
- FA:
-
fatty acid(s)
- FAME:
-
fatty acid methyl ester(s)
- MTB:
-
1-(methyldodecyl)trimethylammonium bromide
- LPS:
-
lipopolysaccharide(s)
- OM:
-
outer membrane
- QAS:
-
quaternary ammonium salt(s)
- MDO:
-
1-(methyldodecyl)dimethylamine oxide
References
Alexander C., Rietschel E.T.: Bacterial lipopolysaccharides and innate immunity.J.Endotox.Res. 7, 167–202 (2001).
Bukovský M., Mlynarčík D., Nagy A., Bella J.: Outer membrane alterations inEscherichia coli cells adapted to amine oxides.Acta Fac.Pharm. 46, 153–167 (1991).
Bukovský M., Mlynarčík D., Koščová H.: Change of immunomodulating properties ofEscherichia coli caused by artificial resistance to amine oxides. (In Slovak)Farm.Obzor 57, 59–68 (1998).
Carty S.M., Sreekumar K.R., Raetz C.R.: Effect of cold shock on lipid A biosynthesis inEscherichia coli. Induction at 12 degrees C of an acyltransferase specific for palmitoleyl-acyl carrier protein.J.Biol.Chem. 274, 9677–9685 (1999).
Chladková K., Hendrych T., Gášková D., Goroncy-Bermes P., Sigler K.: Effect of biocides onS. cerevisiae: relationship between short-term membrane affliction and long-term cell killing.Folia Microbiol. 49, 718–724 (2004).
Čupková V., Vinter V., Devínsky F., Lacko I., Mlynarčík D.: Inhibitory effect of 1-methyldodecyldimethylamine oxide andN,N-bis(dodecyldimethyl)-1,2-ethanediammonium dibromide on the spores ofBacillus cereus.Folia Microbiol. 33, 433–439 (1988).
Dubničková M., Bukovský M., Mlynarčík D.: Activation of human leukocytes by lipid A fromE. coli strains adapted to quaternary ammonium salt and amine oxide.Folia Microbiol. 48, 543–547 (2003).
Dubois-Brissonnet F., Malgrange S., Guérin-Méchin L., Heyd B., Leveau J.Y.: Changes in fatty acid composition ofPseudomonas aeruginosa ATCC 15442 induced by growth conditions: consequences of resistance to quaternary ammonium compounds.Microbios 106, 97–110 (2001).
Ferenčík M., Lacko I., Devinsky F.: Immunomodulatory activity of some amphiphilic compounds.Pharmazie 45, 695–696 (1990).
Guérin-Mechin L., Dubois-Brissonnet F., Heyd B., Leveau J.Y.: Specific variations of fatty acid composition ofPseudomonas aeruginosa ATCC 15442 induced by quaternary ammonium compounds and relation with resistance to bactericidal activity.J.Appl.Microbiol. 87, 735–742 (1999).
Hoštacká A., Majtán V.: Enzymic and permeability activity ofPseudomonas aeruginosa after treatment with sub-MICs of organic ammonium salts.Folia Microbiol. 39, 197–202 (1994).
Hoštacká A., Majtán V., Hybenová D.: Antimicrobial efficacy of quaternary bisammonium salts and the effect of their sub-MICs onPseudomonas aeruginosa virulence factors.Folia Microbiol. 40, 283–287 (1995).
Kawahara K., Tsukano H., Watanabe H., Lindner B., Matsuura M.: Modification of the structure and activity of lipid A inYersinia pestis lipopolysaccharide by growth temperature.Infect.Immun. 70, 4092–4098 (2002).
Kopecká-Leitmanová A., Devinsky F., Lacko I., Mlynarčík D.: Interaction of amine oxides and quaternary ammonium salts with membrane and membrane associated processes inE. coli cells. Mode of action.Drug Metab.Drug Interact. 7, 29–51 (1989).
Kuželová M., Mladonická M., Šperglová L., Stankovič M., Jusko M., Dubničková M., Bukovský M., Adameová A., Stankovičová T., Seginko J.: Modified lipid A influences myocardial ischemia reperfusion injury at bothin vitro andin vivo conditions. (In Slovak)Farm.Obzor. 74, 251–256 (2005).
Majtánová L’., Majtán V., Hoštacká A.: Effects of amphiphilic compounds on metabolic and biological activities ofSalmonella typhimurium.Arzneim.Forsch.Drug Res. 46, 64–67 (1996).
McQuillen K., Roberts R.B.: The utilization of acetate for synthesis inEscherichia coli.J.Biol.Chem. 207, 81–95 (1954).
Metcalfe L.D., Wang C.N.: Rapid preparation of fatty-acid methyl-esters using organic base-catalyzed trans-esterification.J.Chromatogr.Sci. 19, 530–535 (1981).
Mueller M., Lindner B., Kusumoto S., Fukase K., Schromm A.B., Seydel U.: Aggregates are the biologically active units of endotoxin.J.Biol.Chem. 279, 26307–26313 (2004).
Rodriguez-Carvajal M.A., Tejero-Mateo P., Espartero J.L., Ruiz-Sainz J.E., Buendía-Clavería A.M., Ollero F.J., Yang S.S., Gil-Serrano A.M.: Determination of the chemical structure of the capsular polysaccharide of strain B33, a fast growing soy bean-modulating bacterium isolated from an acid region of China.Biochem.J. 357, 505–511 (2001).
Somerville J.E. Jr.,Cassiano L., Bainbridge B., Cunningham M.D.P., Darveau R.P.: A novelE. coli lipid a mutant that produces an antiinflammatory lipopolysaccharide.J.Clin.Invest. 97, 359–365 (1997).
Westphal O., Jann K.: Bacterial lipopolysaccharides. Extraction with phenol-water and further applications of the procedure, pp. 83–91 in R.L. Whistler, J.N. BeMiller, M. Wolfrom (Eds):Methods in Carbohydrate Chemistry, Vol. 5. Academic Press, New York-London 1965.
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Dubničková, M., Řezanka, T. & Koščová, H. Adaptive changes in fatty acids ofE. coli strains exposed to a quaternary ammonium salt and an amine oxide. Folia Microbiol 51, 371–374 (2006). https://doi.org/10.1007/BF02931578
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DOI: https://doi.org/10.1007/BF02931578