A double bond-conjugated dimethylnitrobenzene-type photolabile nitric oxide donor with improved two-photon cross section. Issue 16 (15th August 2015)

• Record Type: Journal Article
• Authors: Ieda, Naoya; Hishikawa, Kazuhiro; Eto, Kei; Kitamura, Kai; Kawaguchi, Mitsuyasu; Suzuki, Takayoshi; Fukuhara, Kiyoshi; Miyata, Naoki; Furuta, Toshiaki; Nabekura, Junichi; Nakagawa, Hidehiko
• Is Part Of: Bioorganic & medicinal chemistry letters. Volume 25:Issue 16(2015)
• Page Start: 3172
• Page End: 3175
• Publication Date: 2015-08-15
• Subjects: Nitric oxide donor -- Two photon excitation -- Near infrared controllable compound; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1016/j.bmcl.2015.05.095
• Languages: English
• ISSNs: 0960-894X

Abstract

Graphical abstract: 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 ( δ u ) 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 1 s. This near-infrared-light-controllable NO source should be a valuable tool for studies on the biological roles of NO.