Biochemistry (Moscow)

, Volume 73, Issue 4, pp 432–441 | Cite as

Interaction of chitosans and their N-acylated derivatives with lipopolysaccharide of gram-negative bacteria

  • G. A. Naberezhnykh
  • V. I. Gorbach
  • G. N. Likhatskaya
  • V. N. Davidova
  • T. F. Solov’eva
Article

Abstract

The interactions of lipopolysaccharide (LPS) with the natural polycation chitosan and its derivatives—high molecular weight chitosans (80 kD) with different degree of acetylation, low molecular weight chitosan (15 kD), acylated oligochitosan (5.5 kD) and chitooligosaccharides (biose, triose, and tetraose)—were studied using ligand-enzyme solid-phase assay. The LPS-binding activity of chitosans (80 kD) decreased with increase in acetylation degree. Affinity of LPS interaction with chitosans increased after introduction of a fatty acid residue at the reducing end of chitosan. Activity of N-monoacylated chitooligosaccharides decreased in the order: oligochitosan → tetra-→ tri-→ disaccharides. The three-dimensional structures of complexes of R-LPS and chitosans with different degree of acetylation, chitooligosaccharides, and their N-monoacylated derivatives were generated by molecular modeling. The number of bonds stabilizing the complexes and the energy of LPS binding with chitosans decreased with increase in acetate group content in chitosans and resulted in changing of binding sites. It was shown that binding sites of chitooligosaccharides on R-LPS overlapped and chitooligosaccharide binding energies increased with increase in number of monosaccharide residues in chitosan molecules. The input of the hydrophobic fragment in complex formation energy is most prominent for complexes in water phase and is due to the hydrophobic interaction of chitooligosaccharide acyl fragment with fatty acid residues of LPS.

Key words

lipopolysaccharide chitosan binding computer simulation molecular docking 

Abbreviations

B-LC

biotinylated low molecular weight chitosan

COL

oligochitosan

COS

chitooligosaccharide

HC

high molecular weight chitosan

LESPA

ligand-enzyme solid-phase assay

LC

low molecular weight chitosan

LPS

lipopolysaccharide

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Copyright information

© MAIK Nauka 2008

Authors and Affiliations

  • G. A. Naberezhnykh
    • 1
  • V. I. Gorbach
    • 1
  • G. N. Likhatskaya
    • 1
  • V. N. Davidova
    • 1
  • T. F. Solov’eva
    • 1
  1. 1.Pacific Institute of Bioorganic ChemistryFar East Division of the Russian Academy of SciencesVladivostokRussia

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