Evaluation of scavenging rate constants of DOPA and tyrosine enantiomers against multiple reactive oxygen species and methyl radical as measured with ESR trapping method

Bioorganic & Medicinal Chemistry Letters
Yoshimi Sueishi, Tsubasa Takemoto

Abstract

The scavenging rates of DOPA (dl- and l-3-(3,4-dihydroxyphenyl)alanine) and Tyr (tyrosine (dl- and l-3-(4-hydroxyphenyl)alanine)) against five reactive oxygen species (ROS) and methyl radical were measured with the use of electron spin resonance (ESR) spin-trapping method and the scavenging rate constants of DOPA and Tyr were determined. The scavenging rate constants for multiple active species increased in the order of O2(-)<RO<(1)O2<H3C<HO for Tyr and RO≈O2(-)<(1)O2≈H3C<HO for DOPA, and the differences in the radical scavenging abilities for l-enantiomers and dl-mixtures of DOPA and Tyr were shown. Further, based on the redox potentials, we have suggested that the primary chemical process of antioxidant reactions with O2(-) and (1)O2 can be characterized with the electron transfer of antioxidants (DOPA and Tyr).

References

Jun 25, 1999·Free Radical Biology & Medicine·S FoleyC A Rice-Evans
Feb 5, 2003·Biochemical and Biophysical Research Communications·Paul Georg FurtmüllerChristian Obinger
Oct 2, 2003·Journal of Agricultural and Food Chemistry·Ana JiménezFrancisca Sevilla
Aug 20, 2005·Free Radical Biology & Medicine·Kazuo MukaiKeishi Ohara
Mar 28, 2012·Dalton Transactions : an International Journal of Inorganic Chemistry·Carla R GarcíaJulia L Brumaghim
Apr 2, 2014·Journal of Clinical Biochemistry and Nutrition·Yoshimi SueishiKeishi Ohara

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Citations

Mar 13, 2015·Environmental Science & Technology·Sonja MilićIvan Spasojević
Oct 1, 2016·Journal of Ovarian Research·J BlohbergerA Mayerhofer
Jun 13, 2017·Analytical Sciences : the International Journal of the Japan Society for Analytical Chemistry·Aoi MiyamotoNaotaka Kuroda
May 6, 2017·Journal of Chemical Information and Modeling·Orkid Coskuner, Vladimir N Uversky

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