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Probing the Formation of a Seleninic Acid in Living Cells by the Fluorescence Switching of a Glutathione Peroxidase Mimetic
Author(s) -
Ungati Harinarayana,
Govindaraj Vijayakumar,
Narayanan Megha,
Mugesh Govindasamy
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201903958
Subject(s) - ebselen , chemistry , fluorophore , fluorescence , peroxidase , glutathione , moiety , glutathione peroxidase , oxidative stress , photoinduced electron transfer , electron transfer , photochemistry , enzyme , biochemistry , stereochemistry , physics , quantum mechanics
Glutathione peroxidase (GPx) is a selenoenzyme that protects cells against oxidative damage. Although the formation of a seleninic acid (‐SeO 2 H) by this enzyme during oxidative stress has been proposed, a selenic acid has not been identified in cells. Herein, we report that the formation of a seleninic acid can be monitored in living cells by using a redox‐active ebselen analogue with a naphthalimide fluorophore. The probe reacts with H 2 O 2 to generate the highly fluorescent seleninic acid. The electron withdrawing nature of the ‐SeO 2 H moiety and strong Se⋅⋅⋅O interactions, which prevent the photoinduced electron transfer, are responsible for the fluorescence.