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Gemini ester quat surfactants and their biological activity

Abstract

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.

Abbreviations

DMALM-12:

n-dodecylalaninate N,N,N-trimethyl ammonium bromide

DPH:

1,6-diphenyl-1,3,5-hexatriene

GP:

generalized polarization

Laurdan:

6-dodecanoyl-2-dimethylaminonaphthalene

TMEAL-n (Br):

ethylene-bis-alanine-nalkylesterquats bromides

TMPAL-n (Br):

1,3-propylene-bis-alanine-n-alkylesterquats bromides

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Correspondence to Jacek Łuczyński.

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Łuczyński, J., Frąckowiak, R., Włoch, A. et al. Gemini ester quat surfactants and their biological activity. Cell Mol Biol Lett 18, 89–101 (2013). https://doi.org/10.2478/s11658-012-0041-4

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  • DOI: https://doi.org/10.2478/s11658-012-0041-4

Key words

  • Gemini surfactants
  • Cationic amphiphiles
  • Hemolytic activity
  • Membrane fluidity
  • Generalized polarization
  • Anisotropy
  • Erythrocyte membrane
  • Lipid packing order
  • Hemolysis
  • Fluorescent probes