Synthesis and application of a novel sunscreen-antioxidant

Free Radic Res. 2006 May;40(5):485-94. doi: 10.1080/10715760600590065.

Abstract

Background information on the inefficacy of sunscreens to provide free radical protection in skin, despite their usefulness in preventing sunburn/erythema, prompted us to synthesize a compound which would display in the same molecule both UV-absorbing and antioxidant capacities. For this purpose, the UVB absorber, 2-ethylhexyl-4-methoxycinnamate (OMC) was combined with the piperidine nitroxide TEMPOL, which has antioxidant properties. The spectral properties of the new nitroxide-based sunscreen (MC-NO) as well as its efficacy to prevent photo-oxidative damage to lipids induced by UVA, natural sunlight and 4-tert-butyl-4-methoxydibenzoylmethane (BMDBM), a photo-unstable sunscreen which generates free radicals upon UV radiation, was studied. The results obtained demonstrate that MC-NO: (a) absorbs in the UVB region even after UVA irradiation; (b) acts as free radical scavenger as demonstrated by EPR experiments; (c) strongly reduces both UVA-, sunlight- and BMDBM-induced lipid peroxidation in liposomes, measured as reduced TBARS levels; and (d) has comparable antioxidant activity to that of commonly used vitamin E and BHT in skin care formulations. These results suggest that the use of the novel sunscreen-antioxidant or of other nitroxide-based sunscreens in formulations aimed at reducing photoinduced skin damage may be envisaged.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antioxidants / chemical synthesis
  • Antioxidants / pharmacology*
  • Cinnamates / chemical synthesis
  • Cinnamates / pharmacology*
  • Cyclic N-Oxides / chemical synthesis
  • Cyclic N-Oxides / pharmacology*
  • Electron Spin Resonance Spectroscopy
  • Free Radical Scavengers / chemical synthesis
  • Free Radical Scavengers / pharmacology
  • Lipid Peroxidation / drug effects
  • Liposomes
  • Oxidation-Reduction / drug effects
  • Spin Labels / chemical synthesis
  • Sunscreening Agents / chemical synthesis
  • Sunscreening Agents / pharmacology*
  • Thiobarbituric Acid Reactive Substances / analysis
  • Ultraviolet Rays

Substances

  • Antioxidants
  • Cinnamates
  • Cyclic N-Oxides
  • Free Radical Scavengers
  • Liposomes
  • Spin Labels
  • Sunscreening Agents
  • Thiobarbituric Acid Reactive Substances
  • octylmethoxycinnamate
  • tempol