Amino Acids

, Volume 46, Issue 8, pp 1893–1898 | Cite as

Biological and surface-active properties of double-chain cationic amino acid-based surfactants

  • Katarzyna E. GreberEmail author
  • Małgorzata Dawgul
  • Wojciech Kamysz
  • Wiesław Sawicki
  • Jerzy Łukasiak
Original Article


Cationic amino acid-based surfactants were synthesized via solid phase peptide synthesis and terminal acylation of their α and ε positions with saturated fatty acids. Five new lipopeptides, N-α-acyl-N-ε-acyl lysine analogues, were obtained. Minimum inhibitory concentration and minimum bactericidal (fungicidal) concentration were determined on reference strains of bacteria and fungi to evaluate the antimicrobial activity of the lipopeptides. Toxicity to eukaryotic cells was examined via determination of the haemolytic activities. The surface-active properties of these compounds were evaluated by measuring the surface tension and formation of micelles as a function of concentration in aqueous solution. The cationic surfactants demonstrated diverse antibacterial activities dependent on the length of the fatty acid chain. Gram-negative bacteria and fungi showed a higher resistance than Gram-positive bacterial strains. It was found that the haemolytic activities were also chain length-dependent values. The surface-active properties showed a linear correlation between the alkyl chain length and the critical micelle concentration.


Lipopeptides Surfactants Antimicrobial activity Critical micelle concentration 





Colony forming units


Critical micelle concentration












Minimum bactericidal concentration


Minimum fungicidal concentration


Minimum inhibitory concentration


Trifluoroacetic acid





This research was supported by the Medical University of Gdańsk, Project W-117 and the Ministry of Science and Higher Education, Project NN 305 412438.

Conflict of interest

The authors declare that they have no conflict of interest.


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Copyright information

© Springer-Verlag Wien 2014

Authors and Affiliations

  • Katarzyna E. Greber
    • 1
    Email author
  • Małgorzata Dawgul
    • 2
  • Wojciech Kamysz
    • 2
  • Wiesław Sawicki
    • 1
  • Jerzy Łukasiak
    • 1
  1. 1.Department of Physical Chemistry, Faculty of PharmacyMedical University of GdańskGdańskPoland
  2. 2.Department of Inorganic Chemistry, Faculty of PharmacyMedical University of GdańskGdańskPoland

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