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Chembiochem. 2016 Jul 1;17(13):1233-40. doi: 10.1002/cbic.201600097. Epub 2016 May 23.

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

Author information

1
Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1, Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan.
2
Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1, Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan. tkomatsu@mol.f.u-tokyo.ac.jp.
3
PRESTO (Japan) Science and Technology Agency (JST), 4-1-8 Honcho Kawaguchi, Saitama, 332-0012, Japan. tkomatsu@mol.f.u-tokyo.ac.jp.
4
CREST (Japan) Agency for Medicinal Research and Development (AMED), 1-7-1 Otemachi, Chiyoda-ku, Tokyo, 100-0004, Japan.
5
Drug Discovery Initiative, The University of Tokyo, 7-3-1, Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan.
6
Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1, Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan. uranokun@m.u-tokyo.ac.jp.
7
Graduate School of Medicine, The University of Tokyo, 7-3-1, Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan. uranokun@m.u-tokyo.ac.jp.
8
CREST (Japan) Agency for Medicinal Research and Development (AMED), 1-7-1 Otemachi, Chiyoda-ku, Tokyo, 100-0004, Japan. uranokun@m.u-tokyo.ac.jp.

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.

KEYWORDS:

BODIPY; cage compounds; chemical biology; photolysis; sulfonamides

PMID:
27038199
DOI:
10.1002/cbic.201600097
[Indexed for MEDLINE]

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