Rational Design of a Ratiometric Fluorescent Probe Based on Arene-Metal-Ion Contact for Endogenous Hydrogen Sulfide Detection in Living Cells

Ryosuke Kawagoe, Ippei Takashima, Kazuteru Usui, Anna Kanegae, Yusuke Ozawa, Akio Ojida

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

We report the design and development of a fluorescent CdII ion complex that is capable of the ratiometric detection of H2S in living cells. This probe exploits the metal-ion-induced emission red shift resulting from direct contact between the aromatic ring of a fluorophore and a metal ion (i.e., arene-metal-ion or "AM" contact). The CdII complex displays a large emission blue shift upon interaction with H2S as the CdII-free ligand is released by the formation of cadmium sulfide. Screening of potential ligands and fluorophores led to the discovery of a pyronine-type probe, 6CdII, that generated a sensitive and rapid ratio value change upon interaction with H2S, without interference from the glutathione that is abundant in the cell. The membrane-impermeable 6CdII was successfully translocated into live cells by using an oligo-arginine peptide and pyrenebutylate as carriers. As such, 6CdII was successfully applied to the ratiometric detection of both exogenous and endogenous H2S produced by the enzymes in living cells, thus demonstrating the utility of 6CdII in biological fluorescence analysis.

Original languageEnglish
Pages (from-to)1608-1615
Number of pages8
JournalChemBioChem
Volume16
Issue number11
DOIs
Publication statusPublished - Jul 1 2015

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Hydrogen Sulfide
Fluorescent Dyes
Metal ions
Fluorophores
Metals
Cells
Ions
Pyronine
Ligands
Glutathione
Arginine
Screening
Fluorescence
Membranes
Peptides
Enzymes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Organic Chemistry

Cite this

Rational Design of a Ratiometric Fluorescent Probe Based on Arene-Metal-Ion Contact for Endogenous Hydrogen Sulfide Detection in Living Cells. / Kawagoe, Ryosuke; Takashima, Ippei; Usui, Kazuteru; Kanegae, Anna; Ozawa, Yusuke; Ojida, Akio.

In: ChemBioChem, Vol. 16, No. 11, 01.07.2015, p. 1608-1615.

Research output: Contribution to journalArticle

Kawagoe, Ryosuke ; Takashima, Ippei ; Usui, Kazuteru ; Kanegae, Anna ; Ozawa, Yusuke ; Ojida, Akio. / Rational Design of a Ratiometric Fluorescent Probe Based on Arene-Metal-Ion Contact for Endogenous Hydrogen Sulfide Detection in Living Cells. In: ChemBioChem. 2015 ; Vol. 16, No. 11. pp. 1608-1615.
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