(3R,5S,7as)-(3,5-Bis(4-fluorophenyl)tetrahydro-1H-oxazolo[3,4-c]oxazol-7a-yl)methanol, a novel neuroprotective agent

J Med Chem. 2009 Dec 10;52(23):7537-43. doi: 10.1021/jm900254k.

Abstract

Compounds that interact with microtubules, such as paclitaxel, have been shown to possess protective properties against beta-amyloid (Abeta) induced neurodegeneration associated with Alzheimer's disease. In this work, the novel agent (3R,5S,7as)-(3,5-bis(4-fluorophenyl)tetrahydro-1H-oxazolo[3,4-c]oxazol-7a-yl)methanol was investigated for effectiveness in protecting neurons against several toxic stimuli and its interaction with the microtubule network. Exposure of neuronal cultures to Abeta peptide in the presence of 5 nM (3R,5S,7as)-(3,5-bis(4-fluorophenyl)tetrahydro-1H-oxazolo[3,4-c]oxazol-7a-yl)methanol resulted in a 50% increase in survival. Neuronal cultures treated with other toxic stimuli such as staurosporine, thapsigargin, paraquat, and H(2)O(2) showed significantly enhanced survival in the presence of (3R,5S,7as)-(3,5-bis(4-fluorophenyl)tetrahydro-1H-oxazolo[3,4-c]oxazol-7a-yl)methanol. Microtubule binding and tubulin assembly studies revealed differences compared to paclitaxel but confirmed the interaction of (3R,5S,7as)-(3,5-bis(4-fluorophenyl)tetrahydro-1H-oxazolo[3,4-c]oxazol-7a-yl)methanol with microtubules. Furthermore, in vitro studies using bovine brain microvessel endothelial cells experiments suggest that (3R,5S,7as)-(3,5-bis(4-fluorophenyl)tetrahydro-1H-oxazolo[3,4-c]oxazol-7a-yl)methanol can readily cross the blood-brain barrier in a passive manner.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Amyloid beta-Peptides / toxicity
  • Animals
  • Biological Transport / drug effects
  • Blood-Brain Barrier / metabolism
  • Cattle
  • Cell Death / drug effects
  • Cells, Cultured
  • Microtubules / metabolism
  • Neurons / drug effects
  • Neurons / metabolism
  • Neuroprotective Agents / chemistry
  • Neuroprotective Agents / metabolism
  • Neuroprotective Agents / pharmacology*
  • Oxazoles / chemistry
  • Oxazoles / metabolism
  • Oxazoles / pharmacology*
  • Permeability
  • Protein Binding / drug effects
  • Protein Stability
  • Rats
  • Rhodamine 123 / metabolism
  • Stereoisomerism

Substances

  • (3,5-bis(4-fluorophenyl)tetrahydro-1H-oxazolo(3,4-c)oxazol-7a-yl)methanol
  • Amyloid beta-Peptides
  • Neuroprotective Agents
  • Oxazoles
  • Rhodamine 123