A Diselenide Turn-On Fluorescent Probe for the Detection of Thioredoxin Reductase
Tendai J. Mafireyi
Department of Chemistry, Portland State University, 1719 SW 10th Avenue, Portland, OR, 97201 USA
Search for more papers by this authorMadeleine Laws
Department of Dermatology, Oregon Health & Science University, Portland, OR, 97201 USA
Search for more papers by this authorJohn W. Bassett
Department of Dermatology, Oregon Health & Science University, Portland, OR, 97201 USA
Search for more papers by this authorCorresponding Author
Pamela B. Cassidy
Department of Dermatology, Oregon Health & Science University, Portland, OR, 97201 USA
Search for more papers by this authorDr. Jorge O. Escobedo
Department of Chemistry, Portland State University, 1719 SW 10th Avenue, Portland, OR, 97201 USA
Search for more papers by this authorCorresponding Author
Prof. Dr. Robert M. Strongin
Department of Chemistry, Portland State University, 1719 SW 10th Avenue, Portland, OR, 97201 USA
Search for more papers by this authorTendai J. Mafireyi
Department of Chemistry, Portland State University, 1719 SW 10th Avenue, Portland, OR, 97201 USA
Search for more papers by this authorMadeleine Laws
Department of Dermatology, Oregon Health & Science University, Portland, OR, 97201 USA
Search for more papers by this authorJohn W. Bassett
Department of Dermatology, Oregon Health & Science University, Portland, OR, 97201 USA
Search for more papers by this authorCorresponding Author
Pamela B. Cassidy
Department of Dermatology, Oregon Health & Science University, Portland, OR, 97201 USA
Search for more papers by this authorDr. Jorge O. Escobedo
Department of Chemistry, Portland State University, 1719 SW 10th Avenue, Portland, OR, 97201 USA
Search for more papers by this authorCorresponding Author
Prof. Dr. Robert M. Strongin
Department of Chemistry, Portland State University, 1719 SW 10th Avenue, Portland, OR, 97201 USA
Search for more papers by this authorAbstract
We report the first diselenide-based probe for the selective detection of thioredoxin reductase (TrxR), an enzyme commonly overexpressed in melanomas. The probe design involves conjugation of a seminaphthorhodafluor dye with a diselenide moiety. TrxR reduces the diselenide bond, triggering a fluorescence turn-on response of the probe. Kinetic studies reveal favorable binding of the probe with TrxR with a Michaelis–Menten constant (Km) of 15.89 μm. Computational docking simulations predict a greater binding affinity to the TrxR active site in comparison to its disulfide analogue. In vitro imaging studies further confirmed the diselenide probe exhibited improved signaling of TrxR activity compared to the disulfide analogue.
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