Unexpected Photo-instability of 2,6-Sulfonamide-Substituted BODIPYs and Its Application to Caged GABA

Aoi Takeda, Toru Komatsu, Hiroshi Nomura, Masamitsu Naka, Norio Matsuki, Yuji Ikegaya, Takuya Terai, Tasuku Ueno, Kenjiro Hanaoka, Tetsuo Nagano, Yasuteru Urano

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

Investigation of the unexpected photo-instability of 2,6-sulfonamide-substituted derivatives of the boron dipyrromethene (BODIPY) fluorophore led to the discovery of a photoreaction accompanied by multiple bond scissions. We characterized the photoproducts and utilized the photoreaction to design a caged γ-aminobutyric acid (GABA) derivative that can release GABA upon irradiation in the visible range (>450 nm). This allowed us to stimulate neural cells in mouse brain slices.

Original languageEnglish
Pages (from-to)1233-1240
Number of pages8
JournalChemBioChem
DOIs
Publication statusPublished - 2016 Jul 1
Externally publishedYes

Keywords

  • BODIPY
  • cage compounds
  • chemical biology
  • photolysis
  • sulfonamides

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Organic Chemistry

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