title: Visible-light-triggered release of nitric oxide from N-pyramidal nitrosamines.
abstract: Although many organic/inorganic compounds that release nitric oxide (NO) upon photoirradiation (phototriggered caged-NOs) have been reported, their photoabsorption wavelengths mostly lie in the UV region, because X-NO bonds (X=heteroatom and metal) generally have rather strong π-bond character. Thus, it is intrinsically difficult to generate organic compounds that release NO under visible light irradiation. Herein, the structures and properties of N-pyramidal nitrosamine derivatives of 7-azabicyclo[2.2.1]heptanes that release NO under visible light irradiation are described. Bathochromic shifts of the absorptions of these nitrosamines, attributed to HOMO (n)-LUMO (π*) transitions associated with the nonplanar structure of the N-NO moiety, enable the molecules to absorb visible light, which results in N-NO bond cleavage. Thus, these compounds are innate organic caged-NOs that are uncaged by visible light.
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
authors.forename: Fumika
authors.initials: F
authors.lastname: Karaki
authors.forename: Yoji
authors.initials: Y
authors.lastname: Kabasawa
authors.forename: Takahiro
authors.initials: T
authors.lastname: Yanagimoto
authors.forename: Nobuhiro
authors.initials: N
authors.lastname: Umeda
authors.lastname: Firman
authors.forename: Yasuteru
authors.initials: Y
authors.lastname: Urano
authors.forename: Tetsuo
authors.initials: T
authors.lastname: Nagano
authors.forename: Yuko
authors.initials: Y
authors.lastname: Otani
authors.forename: Tomohiko
authors.initials: T
authors.lastname: Ohwada
mesh_terms: D003500:Cyclization; D008027:Light; D008958:Models, Molecular; D015394:Molecular Structure; D009569:Nitric Oxide / Q000737:chemistry*; D009602:Nitrosamines / Q000737:chemistry*
chemical_list: D009602:Nitrosamines; D009569:Nitric Oxide