Highly Sensitive Bioluminescent Probe for Thiol Detection in Living Cells

Mayu Hemmi, Yuma Ikeda, Yutaka Shindo, Takahiro Nakajima, Shigeru Nishiyama, Kotaro Oka, Moritoshi Sato, Yuki Hiruta, Daniel Citterio, Koji Suzuki

Research output: Contribution to journalArticlepeer-review

13 Citations (Scopus)

Abstract

The sensitive detection of thiols including glutathione and cysteine is desirable owing to their roles as indispensable biomolecules in maintaining intracellular biological redox homeostasis. Herein, we report the design and synthesis of SEluc-1 (sulfinate ester luciferin), a chemoselective probe exhibiting a ratiometric and turn-on response towards thiols selectively in fluorescence and bioluminescence, respectively. The probe, which was designed based on the “caged” luciferin strategy, displays excellent selectivity, high signal/noise ratio (>240 in the case of bioluminescence), and a biologically relevant limit of detection (LOD, 80 nm for cysteine), which are all desirable traits for a sensitive bioluminescent sensor. SEluc-1 was further applied to fluorescence imaging of thiol activity in living human cervical cancer HeLa cell cultures, and was successfully able to detect fluctuations in thiol concentrations induced by oxidative stress in a bioluminescent assay utilizing African green monkey fibroblast COS-7 cells and human breast adenocarcinoma MCF-7 cells.

Original languageEnglish
Pages (from-to)648-655
Number of pages8
JournalChemistry - An Asian Journal
Volume13
Issue number6
DOIs
Publication statusPublished - 2018 Mar 16

Keywords

  • bioluminescence
  • fluorescence
  • imaging agents
  • luciferin
  • thiol

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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