How lipid unsaturation, peroxyl radical partitioning, and chromanol lipophilic tail affect the antioxidant activity of α-tocopherol: direct visualization via high-throughput fluorescence studies conducted with fluorogenic α-tocopherol analogues

Journal of the American Chemical Society
Katerina KrumovaGonzalo Cosa

Abstract

The preparation of two highly sensitive fluorogenic α-tocopherol (TOH) analogues which undergo >30-fold fluorescence intensity enhancement upon reaction with peroxyl radicals is reported. The probes consist of a chromanol moiety coupled to the meso position of a BODIPY fluorophore, where the use of a methylene linker (BODIPY-2,2,5,7,8-pentamethyl-6-hydroxy-chroman adduct, H(2)B-PMHC) vs an ester linker (meso-methanoyl BODIPY-6-hydroxy-2,5,7,8-tetramethylchromane-2-carboxylic acid, H(2)B-TOH) enables tuning their reactivity toward H-atom abstraction by peroxyl radicals. The development of a high-throughput fluorescence assay for monitoring kinetics of peroxyl radical reactions in liposomes is subsequently described where the evolution of the fluorescence intensity over time provides a rapid, facile method to conduct competitive kinetic studies in the presence of TOH and its analogues. A quantitative treatment is formulated for the temporal evolution of the intensity in terms of relative rate constants of H-atom abstraction (k(inh)) from the various tocopherol analogues. Combined, the new probes, the fluorescence assay, and the data analysis provide a new method to obtain, in a rapid, parallel format, relative antioxidant activit...Continue Reading

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Citations

May 25, 2013·Journal of the American Chemical Society·Alan T MaccaroneStephen J Blanksby
Oct 12, 2013·Journal of the American Chemical Society·Katerina KrumovaGonzalo Cosa
May 15, 2014·The Journal of Physical Chemistry Letters·Julian GarrecMounir Tarek
Aug 11, 2016·Journal of the American Chemical Society·Lana E GreeneGonzalo Cosa
Oct 25, 2016·International Journal of Molecular Sciences·Fereidoon Shahidi, Adriano Costa de Camargo
Jun 10, 2017·The Journal of Physical Chemistry. B·Alexis AspéeEmilio I Alarcon
Aug 29, 2018·Chemical Society Reviews·Verónica Almeida-MarreroAndrés de la Escosura
Nov 28, 2018·Photochemistry and Photobiology·Lana E GreeneGonzalo Cosa
Oct 6, 2017·American Journal of Physiology. Cell Physiology·Francis H WongJohn W Hanrahan
Jan 29, 2021·Free Radical Research·Yuta Matsuoka, Ken-Ichi Yamada
Oct 19, 2017·Journal of the American Chemical Society·Lana E GreeneGonzalo Cosa
Dec 22, 2016·Journal of the American Chemical Society·Mei-Ni BelzileGonzalo Cosa
Aug 27, 2014·Langmuir : the ACS Journal of Surfaces and Colloids·Robert GodinGonzalo Cosa
Jul 11, 2018·Journal of the American Chemical Society·Isabel O L BacellarMauricio S Baptista

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