Synthesis and evaluation of diverse thio avarol derivatives as potential UVB photoprotective candidates

Bioorg Med Chem Lett. 2007 May 1;17(9):2561-5. doi: 10.1016/j.bmcl.2007.02.007. Epub 2007 Feb 7.

Abstract

Semisynthesis of 13 new thio avarol derivatives (4-16) and in vitro evaluation on the photodamage response induced by UVB irradiation are described. Their ability to inhibit NF-kappaB activation and TNF-alpha generation in HaCaT cells as well as their antioxidant capacity in human neutrophils has also been studied. Among them we have identified two monophenyl thio avarol derivatives (4-5) lacking cytotoxicity which can be considered promising UVB photoprotective agents through the potent inhibition of NF-kappaB activation with a mild antioxidant pharmacological profile.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antioxidants / pharmacology*
  • Cell Line, Tumor
  • Chemistry, Pharmaceutical / methods*
  • Drug Design
  • Humans
  • Magnetic Resonance Spectroscopy
  • Models, Chemical
  • Molecular Conformation
  • NF-kappa B / antagonists & inhibitors
  • Neutrophils / drug effects
  • Photochemistry / methods*
  • Reactive Oxygen Species
  • Sesquiterpenes / chemical synthesis*
  • Sesquiterpenes / pharmacology*
  • Tumor Necrosis Factor-alpha / antagonists & inhibitors
  • Ultraviolet Rays

Substances

  • Antioxidants
  • NF-kappa B
  • Reactive Oxygen Species
  • Sesquiterpenes
  • Tumor Necrosis Factor-alpha
  • avarol