Lysine-spermine conjugates: hydrophobic polyamine amides as potent lipopolysaccharide sequestrants

Bioorg Med Chem. 2005 Apr 1;13(7):2523-36. doi: 10.1016/j.bmc.2005.01.038.

Abstract

Lipopolysaccharides (LPS), otherwise termed 'endotoxins', are outer-membrane constituents of Gram-negative bacteria. Lipopolysaccharides play a key role in the pathogenesis of 'Septic Shock', a major cause of mortality in the critically ill patient. Therapeutic options aimed at limiting downstream systemic inflammatory processes by targeting lipopolysaccharide do not exist at the present time. We have defined the pharmacophore necessary for small molecules to specifically bind and neutralize LPS and, using animal models of sepsis, have shown that the sequestration of circulatory LPS by small molecules is a therapeutically viable strategy. In this paper, the interactions of a focused library of lysine-spermine conjugates with lipopolysaccharide (LPS) have been characterized. Lysine-spermine conjugates with the epsilon-amino terminus of the lysinyl moiety derivatized with long-chain aliphatic hydrophobic substituents in acyl or alkyl linkage bind and neutralize bacterial lipopolysaccharides, and may be of use in the prevention or treatment of endotoxic shock states.

Publication types

  • Comparative Study
  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Amides / chemistry
  • Amides / pharmacology*
  • Animals
  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology
  • Binding, Competitive
  • Cell Line
  • Cytokines / antagonists & inhibitors
  • Cytokines / blood
  • Disease Models, Animal
  • Female
  • Humans
  • Lipopolysaccharides / antagonists & inhibitors*
  • Lipopolysaccharides / chemistry
  • Lipopolysaccharides / classification
  • Lysine / chemical synthesis*
  • Lysine / chemistry
  • Lysine / pharmacology
  • Mice
  • Nitric Oxide / antagonists & inhibitors
  • Polyamines / chemistry
  • Polyamines / pharmacology*
  • Sepsis / mortality
  • Sepsis / prevention & control
  • Spermine / chemical synthesis*
  • Spermine / chemistry
  • Spermine / pharmacology
  • Structure-Activity Relationship

Substances

  • Amides
  • Anti-Bacterial Agents
  • Cytokines
  • Lipopolysaccharides
  • Polyamines
  • Spermine
  • Nitric Oxide
  • Lysine