A Diselenide Turn-On Fluorescent Probe for the Detection of Thioredoxin Reductase

Tendai J. Mafireyi, Madeleine Laws, John W. Bassett, Pamela B. Cassidy, Jorge O. Escobedo, Robert M. Strongin

Research output: Contribution to journalArticle

Abstract

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.

Original languageEnglish (US)
Pages (from-to)15259-15263
Number of pages5
JournalAngewandte Chemie
Volume132
Issue number35
DOIs
StatePublished - Aug 24 2020

Keywords

  • diagnostics
  • melanoma
  • selenium probes
  • seminaphthorhodafluor
  • thioredoxin reductase

ASJC Scopus subject areas

  • Engineering(all)

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  • Cite this

    Mafireyi, T. J., Laws, M., Bassett, J. W., Cassidy, P. B., Escobedo, J. O., & Strongin, R. M. (2020). A Diselenide Turn-On Fluorescent Probe for the Detection of Thioredoxin Reductase. Angewandte Chemie, 132(35), 15259-15263. https://doi.org/10.1002/ange.202004094