Amino Acids

, Volume 46, Issue 8, pp 1893–1898

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

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

DOI: 10.1007/s00726-014-1744-9

Cite this article as:
Greber, K.E., Dawgul, M., Kamysz, W. et al. Amino Acids (2014) 46: 1893. doi:10.1007/s00726-014-1744-9

Abstract

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.

Keywords

Lipopeptides Surfactants Antimicrobial activity Critical micelle concentration 

Abbreviations

Boc

tert-Butoxycarbonyl

CFU

Colony forming units

CMC

Critical micelle concentration

DCM

Dichloromethane

DIC

Diisopropylcarbodiimide

DMF

N,N-dimethylformamide

Fmoc

9-fluorenylmethoxycarbonyl

HOBt

1-Hydroxybenzotriazole

MBC

Minimum bactericidal concentration

MFC

Minimum fungicidal concentration

MIC

Minimum inhibitory concentration

TFA

Trifluoroacetic acid

TIS

Triisopropylosilane

Copyright information

© Springer-Verlag Wien 2014

Authors and Affiliations

  • Katarzyna E. Greber
    • 1
  • 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