Gemini ester quat surfactants and their biological activity

• Autorzy: Luczynski J. , Frackowiak R. , Wloch A. , Kleszczynska H. , Witek S.
• Języki publikacji: EN

Abstrakty

EN

Cationic gemini surfactants are an important class of surface-active compounds that exhibit much higher surface activity than their monomeric counterparts. This type of compound architecture lends itself to the compound being easily adsorbed at interfaces and interacting with the cellular membranes of microorganisms. Conventional cationic surfactants have high chemical stability but poor chemical and biological degradability. One of the main approaches to the design of readily biodegradable and environmentally friendly surfactants involves inserting a bond with limited stability into the surfactant molecule to give a cleavable surfactant. The best-known example of such a compound is the family of ester quats, which are cationic surfactants with a labile ester bond inserted into the molecule. As part of this study, a series of gemini ester quat surfactants were synthesized and assayed for their biological activity. Their hemolytic activity and changes in the fluidity and packing order of the lipid polar heads were used as the measures of their biological activity. A clear correlation between the hemolytic activity of the tested compounds and their alkyl chain length was established. It was found that the compounds with a long hydrocarbon chain showed higher activity. Moreover, the compounds with greater spacing between their alkyl chains were more active. This proves that they incorporate more easily into the lipid bilayer of the erythrocyte membrane and affect its properties to a greater extent. A better understanding of the process of cell lysis by surfactants and of their biological activity may assist in developing surfactants with enhanced selectivity and in widening their range of application.

Słowa kluczowe

EN

surfactant; surface active substance; gemini ester quat surfactant; biological activity; cationic amphiphile; hemolytic activity; membrane fluidity; anisotropy; erythrocyte membrane; hemolysis

• Wydawca: -
• Czasopismo: Cellular and Molecular Biology Letters
• Rocznik: 2013
• Tom: 18
• Numer: 1
• Opis fizyczny: p.89-101,fig.,ref.

Twórcy

autor

Luczynski J.

• Faculty of Chemistry, Wroclaw University of Technology, Wybrzeze Wyspianskiego 27, 50-370 Wroclaw, Poland

autor

Frackowiak R.

• Faculty of Chemistry, Wroclaw University of Technology, Wybrzeze Wyspianskiego 27, 50-370 Wroclaw, Poland

autor

Wloch A.

• Department of Physics and Biophysics, Wroclaw University of Environmental and Life Sciences, Norwida 25, 50-375 Wroclaw, Poland

autor

Kleszczynska H.

• Department of Physics and Biophysics, Wroclaw University of Environmental and Life Sciences, Norwida 25, 50-375 Wroclaw, Poland

autor

Witek S.

• Faculty of Chemistry, Wroclaw University of Technology, Wybrzeze Wyspianskiego 27, 50-370 Wroclaw, Poland

Bibliografia

• 1. Haldar, J., Kondaiah, P. and Bhattacharya, S. Synthesis and antibacterial properties of novel hydrolyzable cationic amphiphiles. Incorporation of multiple head groups leads to impressive antibacterial activity. J. Med. Chem. 48 (2005) 3823-3831.
• 2. Meister, A. and Blume, A. Self-assembly of bipolar amphiphiles. Curr. Opin. Colloid Interface Sci. 12 (2007) 138-147.
• 3. Tucker, I., Penfold, J., Thomas, R.K., Grillo, I., Barker, J.G. and Mildner, D.F.R. The surface and solution properties of dihexadecyl dimethylammonium bromide. Langmuir 24 (2008) 6509-6520.
• 4. Para, G., Hamerska-Dudra, A., Wilk, K.A. and Warszyński, P. Mechanism of cationic surfactant adsorption – Effect of molecular structure and multiple charge. Colloids Surf. A 383 (2011) 67-72.
• 5. Para, G., Hamerska-Dudra, A., Wilk, K.A. and Warszynski, P. Surface activity of cationic surfactants, influence of molecular structure. Colloids Surf. A 365 (2010) 215-221.
• 6. Węgrzyńska, J., Para, G., Chlebicki, J., Warszyński, P. and Wilk, K.A. Adsorption of multiple ammonium salts at the air/solution interface. Langmuir 24 (2008) 3171-3180.
• 7. Chlebicki, J., Węgrzyńska, J. and Wilk, K.A. Surface-active, micellar, and antielectrostatic properties of bis-ammonium salts. J. Colloid Interface Sci. 323 (2008) 372-378.
• 8. Llies, M.A., Seitz, W.A., Johnson, B.H., Ezell, E.L., Miller, A.L., Thompson, E.B. and Balaban, A.T. Lipophilic pyrylium salts in the synthesis of efficient pyridinium-based cationic lipids, gemini surfactants, and lipophilic oligomers for gene delivery. J. Med. Chem. 49 (2006) 3872-3887.
• 9. Vyas, S.M., Turánek, J., Knötigová, P., Kašná, A., Kvardová, V., Rankin, E.S., Knutson, B.L. and Lehmler, H. J. Synthesis and biocompatibility evaluation of partially fluorinated pyridinium bromides. New J. Chem. 30 (2006) 944-951.
• 10. Heyes, J.A., Nicolescu-Duvaz, D., Cooper, R.G. and Springer, C.J. Synthesis of novel cationic lipids: effect of structural modification on the efficiency of gene transfer. J. Med. Chem. 45 (2002) 99-114.
• 11. Kirby, A.J., Camilleri, P., Engberts, J.B.F.N., Feiters, M.C., Nolte, R.J.M., Söderman, O., Bergsma, M., Bell, P.C., Fielden, L.M., Rodriguez, C.L.G., Guédat, P., Kremer, A., McGregor, C., Perrin, C., Ronsin, G. and van Eijk, M.C.P. Gemini surfactants: new synthetic vectors for gene transfection. Angew. Chem. Int. Ed. Engl. 42 (2003) 1448-1457.
• 12. Stephenson, B.C., Rangel-Yagui, C.O., Pessoa, A., Tavares, L.C., Beers, K. and Blankschtein, D. Experimental and theoretical investigation of the micellar-assisted solubilization of ibuprofen in aqueous media. Langmuir 22 (2006) 1514-1525.
• 13. Bramer, T., Dew, N. and Edsman, K. Pharmaceutical applications for catanionic mixtures. J. Pharm. Pharmacol. 59 (2007) 1319-1334.
• 14. Bombelli, C., Caracciolo, G., Di Profio, P., Diociaiuti, M., Luciani, P., Mancini, G., Mazzuca, C., Marra, M., Molinari, A., Monti, D., Toccacieli, L. and Venanzi, M. Inclusion of a photosensitizer in liposomes formed by DMPC/gemini surfactant: correlation between physicochemical and biological features of the complexes. J. Med. Chem. 48 (2005) 4882-4891.
• 15. Sakai, E.N.K., Takamatsu, Y., Sharma, S.C., Torigoe, K., Yoshimura, T., Esumi, K., Sakai, H. and Abe, M. Adsorption of cationic monomeric and gemini surfactants on montmorillonite and adsolubilization of vitamin E. J. Oleo Sci. 57 (2008) 423-429.
• 16. Macián, M., Seguer, J., Infante, M.R., Selve, C. and Vinardell, M.P. Preliminary studies of the toxic effects of non-ionic surfactants derived from lysine. Toxicology 106 (1996) 1-9.
• 17. Caillier, L., de Givenchy, E.T., Levy, R., Vandenberghe, Y., Geribaldi, S. and Guittard, F. Polymerizable semi-fluorinated gemini surfactants designed for antimicrobial materials. J. Colloid Interface Sci. 332 (2009) 201-207.
• 18. Obłąk, E., Gamian, A., Adamski, R. and Ułaszewski, S. The physiological and morphological phenotype of a yeast mutant resistant to the quaternary ammonium salt N-(dodecyloxycarboxymethyl)-N,N,N-trimethyl ammonium chloride. Cell. Mol. Biol. Lett. 15 (2010) 215-233.
• 19. Benavides, T., Martinez, V., Mitjans, M., Infante, M.R., Moran, C., Clapes, P., Clothier, R. and Vinardell, M.P. Assessment of the potential irritation and photoirritation of novel amino acid-based surfactants by in vitro methods as alternative to the animal tests. Toxicology 201 (2004) 87-93.
• 20. Mitjans, M., Martinez, V., Clapes, P., Perez, L., Infante, M.R. and Vinardell, M.P. Low potential ocular irritation of argininebased gemini surfactants and their mixtures with nonionic and zwitterionic surfactants. Pharm. Res. 20 (2003) 1697-1701.
• 21. Tehrani-Bagha, A.R. and Holmberg, K. Cleavable surfactants. Curr. Opin. Colloid Interface Sci. 12 (2007) 81-91.
• 22. Tehrani-Bagha, A.R., Oskarsson, H., van Ginkel, C.G. and Holmberg, K. Cationic ester-containing gemini surfactants: Chemical hydrolysis and biodegradation. J. Colloid Interface Sci. 312 (2007) 444-452.
• 23. Tehrani-Bagha, A.R., Kärnbratt, J., Löfroth, J.E. and Holmberg, K. Cationic ester-containing gemini surfactants: Determination of aggregation numbers by time-resolved fluorescence quenching. J. Colloid Interface Sci. 376 (2012) 126-132.
• 24. Auzély-Velty, R. and Rinaudo, M. Synthesis of starch derivation with labile cationic groups. Int. J. Biol. Macromol. 31 (2003) 123-129.
• 25. Obłąk, E., Lachowicz, T.M., Łuczyński, J. and Witek, S. Lysosomotropic N,N-dimethyl aminoesters and their quaternary ammonium salts as plasma membrane and mitochondrial ATPase inhibitors. Cell. Mol. Biol. Lett. 7 (2002) 1121-1129.
• 26. Kołaczkowski, M., Kołaczkowska, A., Łuczyński, J., Witek, S. and Goffeau, A. In vivo characterization of the drug resistant profile of the major ABC transporters and other components of the yeast pleiotropic drug resistance network. Microb. Drug Resistance 4 (1998) 143-158.
• 27. Kleszczyńska, H., Sarapuk, J., Przestalski, S. and Kilian, M. Mechanical properties of red cells and blm in the presence of some mono- and bisquaternary ammonium salts. Studia Biophysica 135 (1990) 191-199.
• 28. Dodge, J.T., Mitchell, C. and Hanahan, D.J. The preparation and chemical characteristics of hemoglobin-free ghosts of erythrocytes. Arch. Biochem. Biophys. 100 (1963) 119-130.
• 29. Lakowicz, J.R. Fluorescence polarization. In: Principles of fluorescence spectroscopy. Plenum Press. New York. London, 2006, 353-382.
• 30. Parasassi, T., Krasnowska, E.K., Bagatolli, L. and Gratton, E. Laurdan and prodan as polarity-sensitive fluorescent membrane probes. J. Fluorescence 8 (1998) 365-373.
• 31. Kleszczyńska, H., Łuczyński, J., Witek, S. and Przestalski, S. Hemolytic activity of aminoethyl – dodecanoates. Z. Naturforsch. 53c (1998) 101-106.
• 32. Kleszczyńska, H., Sarapuk, J., Przestalski, S. and Kilian, M. Mechanical properties of red cel and BLM in the presence of some mono- and bisquaternary ammonium salts. Studia Biophysica 135 (1990) 191-199.
• 33. Hagerstrand, H. and Isomaa, B. Morphological characterization of exovesicles and endovesicles released from human erythrocytes following treatment with amphiphiles. Biochim. Biophys. Acta 1109 (1992) 117-126.
• 34. Isomaa, B. Interactions of surface-active alkyltrimethylammonium salts with the erythrocyte membrane. Biochem. Pharmacol. 28 (1979) 9975-9980.