title: A double bond-conjugated dimethylnitrobenzene-type photolabile nitric oxide donor with improved two-photon cross section.
abstract: Photocontrollable NO donors enable precise spatiotemporal release of NO under physiological conditions. We designed and synthesized a novel dimethylnitrobenzene-type NO donor, Flu-DNB-DB, which contains a carbon-carbon double bond in place of the amide bond of previously reported Flu-DNB. Flu-DNB-DB releases NO in response to one-photon activation in the blue wavelength region, and shows a greatly increased two-photon cross-section (δu) at 720 nm (Flu-DNB: 0.12 GM, Flu-DNB-DB: 0.98 GM). We show that Flu-DNB-DB enables precisely controlled intracellular release of NO in response to 950 nm pulse laser irradiation for as little as 1s. This near-infrared-light-controllable NO source should be a valuable tool for studies on the biological roles of NO.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Nagoya City University, 467-8603, Japan.
authors.forename: Naoya
authors.initials: N
authors.lastname: Ieda
authors.affiliation: Graduate School of Pharmaceutical Sciences, Nagoya City University, 467-8603, Japan.
authors.forename: Kazuhiro
authors.initials: K
authors.lastname: Hishikawa
authors.affiliation: National Institute of Physiological Sciences, 444-8585, Japan.
authors.forename: Kei
authors.initials: K
authors.lastname: Eto
authors.affiliation: Graduate School of Pharmaceutical Sciences, Nagoya City University, 467-8603, Japan.
authors.forename: Kai
authors.initials: K
authors.lastname: Kitamura
authors.affiliation: Graduate School of Pharmaceutical Sciences, Nagoya City University, 467-8603, Japan.
authors.forename: Mitsuyasu
authors.initials: M
authors.lastname: Kawaguchi
authors.affiliation: Graduate School of Medical Science, Kyoto Prefectural University of Medicine, 606-0823, Japan.
authors.forename: Takayoshi
authors.initials: T
authors.lastname: Suzuki
authors.affiliation: Showa University School of Pharmacy, 142-8555, Japan.
authors.forename: Kiyoshi
authors.initials: K
authors.lastname: Fukuhara
authors.affiliation: Graduate School of Pharmaceutical Sciences, Nagoya City University, 467-8603, Japan.
authors.forename: Naoki
authors.initials: N
authors.lastname: Miyata
authors.affiliation: Department of Biomolecular Science, Toho University, 274-8510, Japan.
authors.forename: Toshiaki
authors.initials: T
authors.lastname: Furuta
authors.affiliation: National Institute of Physiological Sciences, 444-8585, Japan.
authors.forename: Junichi
authors.initials: J
authors.lastname: Nabekura
authors.affiliation: Graduate School of Pharmaceutical Sciences, Nagoya City University, 467-8603, Japan. Electronic address: deco@phar.nagoya-cu.ac.jp.
authors.forename: Hidehiko
authors.initials: H
authors.lastname: Nakagawa
mesh_terms: D004578:Electron Spin Resonance Spectroscopy; D005452:Fluoresceins / Q000737:chemistry / Q000378:metabolism; D045325:HCT116 Cells; D006801:Humans; D008856:Microscopy, Fluorescence; D009569:Nitric Oxide / Q000378:metabolism; D020030:Nitric Oxide Donors / Q000737:chemistry* / Q000378:metabolism; D009578:Nitrobenzenes / Q000737:chemistry* / Q000378:metabolism
chemical_list: C000595255:Flu-DNB; D005452:Fluoresceins; D020030:Nitric Oxide Donors; D009578:Nitrobenzenes; D009569:Nitric Oxide; C036077:nitrobenzene
keywords: Near infrared controllable compound; Nitric oxide donor; Two photon excitation