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.
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1, Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan.
authors.forename: Aoi
authors.initials: A
authors.lastname: Takeda
authors.affiliation: 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.|PRESTO (Japan) Science and Technology Agency (JST), 4-1-8 Honcho Kawaguchi, Saitama, 332-0012, Japan. tkomatsu@mol.f.u-tokyo.ac.jp.
authors.forename: Toru
authors.initials: T
authors.lastname: Komatsu
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1, Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan.
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Nomura
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1, Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan.
authors.forename: Masamitsu
authors.initials: M
authors.lastname: Naka
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1, Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan.
authors.forename: Norio
authors.initials: N
authors.lastname: Matsuki
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1, Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan.
authors.forename: Yuji
authors.initials: Y
authors.lastname: Ikegaya
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1, Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan.|CREST (Japan) Agency for Medicinal Research and Development (AMED), 1-7-1 Otemachi, Chiyoda-ku, Tokyo, 100-0004, Japan.
authors.forename: Takuya
authors.initials: T
authors.lastname: Terai
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1, Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan.|CREST (Japan) Agency for Medicinal Research and Development (AMED), 1-7-1 Otemachi, Chiyoda-ku, Tokyo, 100-0004, Japan.
authors.forename: Tasuku
authors.initials: T
authors.lastname: Ueno
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1, Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan.
authors.forename: Kenjiro
authors.initials: K
authors.lastname: Hanaoka
authors.affiliation: Drug Discovery Initiative, The University of Tokyo, 7-3-1, Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan.
authors.forename: Tetsuo
authors.initials: T
authors.lastname: Nagano
authors.affiliation: 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.|Graduate School of Medicine, The University of Tokyo, 7-3-1, Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan. uranokun@m.u-tokyo.ac.jp.|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.
authors.forename: Yasuteru
authors.initials: Y
authors.lastname: Urano
mesh_terms: D000079:Acetaldehyde / Q000032:analysis; D000818:Animals; D001418:Baclofen / Q000494:pharmacology; D066272:Basolateral Nuclear Complex / Q000187:drug effects / Q000502:physiology; D001896:Boron Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000528:radiation effects*; D005557:Formaldehyde / Q000032:analysis; D018756:GABA Antagonists / Q000494:pharmacology; D006367:HeLa Cells; D006801:Humans; D008027:Light; D008744:Methylamines / Q000032:analysis; D051379:Mice; D010852:Picrotoxin / Q000494:pharmacology; D013449:Sulfonamides / Q000138:chemical synthesis / Q000737:chemistry / Q000528:radiation effects*; D005680:gamma-Aminobutyric Acid / Q000031:analogs & derivatives* / Q000494:pharmacology*
chemical_list: D000079:Acetaldehyde; D001418:Baclofen; D001896:Boron Compounds; D005557:Formaldehyde; D018756:GABA Antagonists; D008744:Methylamines; D010852:Picrotoxin; D013449:Sulfonamides; D005680:gamma-Aminobutyric Acid; C095489:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; C027451:methylamine
keywords: BODIPY; cage compounds; chemical biology; photolysis; sulfonamides