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 journalArticlepeer-review

29 Scopus citations

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)15147-15151
Number of pages5
JournalAngewandte Chemie - International Edition
Volume59
Issue number35
DOIs
StatePublished - Aug 24 2020

Keywords

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

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry

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