Synthesis of Lipoamino acids and their activity against cerebral ischemic injury

Molecules. 2009 Oct 12;14(10):4051-64. doi: 10.3390/molecules14104051.

Abstract

A series of lipoamino acids were synthesized and their neuroprotective effect against brain ischemia induced by oxygen-glucose deprivation (OGD) on rat cerebral slices was evaluated. Among these compounds, N-stearoyl-L-tyrosine (4), N-stearoyl-L-serine (5) and N-stearoyl-L-threonine (6) exhibited good neuroprotective activity. We found that the neuroprotective activity of lipoamino acids depended on the acyl group, the presence of a free carboxylic function and a free hydroxyl group at the branched chain of the amino acids. The results also showed that 5 was the most active compound, protecting rat brain slices against OGD as well as hydrogen peroxide (H(2)O(2)) insult at the range of 1-10 M.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anaerobiosis
  • Animals
  • Brain / blood supply
  • Brain / drug effects*
  • Brain Ischemia / prevention & control*
  • Hydrogen Peroxide / toxicity
  • Neuroprotective Agents / chemical synthesis
  • Neuroprotective Agents / chemistry
  • Neuroprotective Agents / pharmacology*
  • Rats
  • Serine / analogs & derivatives*
  • Serine / chemical synthesis
  • Serine / chemistry
  • Serine / pharmacology
  • Threonine / analogs & derivatives*
  • Threonine / chemical synthesis
  • Threonine / chemistry
  • Threonine / pharmacology
  • Tyrosine / analogs & derivatives*
  • Tyrosine / chemical synthesis
  • Tyrosine / chemistry
  • Tyrosine / pharmacology

Substances

  • N-stearoyl-L-serine
  • N-stearoyl-L-threonine
  • Neuroprotective Agents
  • Threonine
  • Tyrosine
  • Serine
  • N-stearoyltyrosine
  • Hydrogen Peroxide