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

doi:10.1002/cbic.201600097

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 journal › Article › peer-review

12 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 language	English
Pages (from-to)	1233-1240
Number of pages	8
Journal	ChemBioChem
DOIs	https://doi.org/10.1002/cbic.201600097
Publication status	Published - 2016 Jul 1
Externally published	Yes

Keywords

BODIPY
cage compounds
chemical biology
photolysis
sulfonamides

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Organic Chemistry

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10.1002/cbic.201600097

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

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.",

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doi = "10.1002/cbic.201600097",

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T1 - Unexpected Photo-instability of 2,6-Sulfonamide-Substituted BODIPYs and Its Application to Caged GABA

AU - Takeda, Aoi

AU - Komatsu, Toru

AU - Nomura, Hiroshi

AU - Naka, Masamitsu

AU - Matsuki, Norio

AU - Ikegaya, Yuji

AU - Terai, Takuya

AU - Ueno, Tasuku

AU - Hanaoka, Kenjiro

AU - Nagano, Tetsuo

AU - Urano, Yasuteru

PY - 2016/7/1

Y1 - 2016/7/1

N2 - 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.

AB - 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.

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KW - cage compounds

KW - chemical biology

KW - photolysis

KW - sulfonamides

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

Abstract

Keywords

ASJC Scopus subject areas

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