title: Photomanipulation of vasodilation with a blue-light-controllable nitric oxide releaser.
abstract: Spatiotemporally controllable nitric oxide (NO)-releasers allow us to analyze the physiological effects of NO, a gaseous mediator that modulates many biological signaling networks, and are also candidate chemotherapeutic agents. We designed and synthesized a blue-light-controllable NO releaser, named NOBL-1, which bears an N-nitrosoaminophenol moiety for NO release tethered to a BODIPY dye moiety for harvesting blue light. Photoinduced electron transfer from N-nitrosoaniline to the antenna moiety upon irradiation with relatively noncytotoxic blue light (470-500 nm) should result in NO release with formation of a stable quinone moiety. NO release from NOBL-1 was confirmed by ESR spin trapping and fluorescence detection. Spatially controlled NO release in cells was observed with DAR-4M AM, a fluorogenic NO probe. We also demonstrated temporally controlled vasodilation of rat aorta ex vivo by blue-light-induced NO release from NOBL-1. This compound should be useful for precise examination of the functions of NO with excellent spatiotemporal control.
authors.affiliation: Graduate School of Pharmaceutical Science, Nagoya City University , 3-1, Tanabe-dori, Mizuho-ku, Nagoya, Aichi 467-8603, Japan.
authors.forename: Naoya
authors.initials: N
authors.lastname: Ieda
authors.forename: Yuji
authors.initials: Y
authors.lastname: Hotta
authors.forename: Naoki
authors.initials: N
authors.lastname: Miyata
authors.forename: Kazunori
authors.initials: K
authors.lastname: Kimura
authors.forename: Hidehiko
authors.initials: H
authors.lastname: Nakagawa
mesh_terms: D000627:Aminophenols / Q000737:chemistry*; D000818:Animals; D001011:Aorta / Q000187:drug effects / Q000502:physiology; D001896:Boron Compounds / Q000737:chemistry*; D003692:Delayed-Action Preparations / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000737:chemistry*; D057809:HEK293 Cells; D006801:Humans; D008027:Light; D009569:Nitric Oxide / Q000008:administration & dosage / Q000737:chemistry / Q000494:pharmacology*; D020030:Nitric Oxide Donors / Q000008:administration & dosage / Q000737:chemistry / Q000494:pharmacology*; D009603:Nitroso Compounds / Q000737:chemistry; D051381:Rats; D012235:Rhodamines / Q000737:chemistry; D014664:Vasodilation / Q000187:drug effects
chemical_list: C095489:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; D000627:Aminophenols; D001896:Boron Compounds; D003692:Delayed-Action Preparations; D005456:Fluorescent Dyes; D020030:Nitric Oxide Donors; D009603:Nitroso Compounds; D012235:Rhodamines; C532273:diaminorhodamine-4M acetoxymethyl ester; D009569:Nitric Oxide