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

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

Authors

Aoi Takeda¹, Toru Komatsu^{2

3}, Hiroshi Nomura¹, Masamitsu Naka¹, Norio Matsuki¹, Yuji Ikegaya¹, Takuya Terai^{1

4}, Tasuku Ueno^{1

4}, Kenjiro Hanaoka¹, Tetsuo Nagano⁵, Yasuteru Urano^{6

7

8}

Affiliations

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.

PMID: 27038199
DOI: 10.1002/cbic.201600097

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acetaldehyde / analysis
Animals
Baclofen / pharmacology
Basolateral Nuclear Complex / drug effects
Basolateral Nuclear Complex / physiology
Boron Compounds / chemical synthesis
Boron Compounds / chemistry
Boron Compounds / radiation effects*
Formaldehyde / analysis
GABA Antagonists / pharmacology
HeLa Cells
Humans
Light
Methylamines / analysis
Mice
Picrotoxin / pharmacology
Sulfonamides / chemical synthesis
Sulfonamides / chemistry
Sulfonamides / radiation effects*
gamma-Aminobutyric Acid / analogs & derivatives*
gamma-Aminobutyric Acid / pharmacology*

Substances

4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
Boron Compounds
GABA Antagonists
Methylamines
Sulfonamides
Picrotoxin
Formaldehyde
gamma-Aminobutyric Acid
methylamine
Acetaldehyde
Baclofen