A caged nicotine with nanosecond range kinetics and visible light sensitivity.
We report the synthesis, characterization and applications of a ruthenium-bipyridine based caged nicotine. The complex [Ru(bpy)(2)(nic)(2)](2+) (where bpy = 2,2' bipyridine and nic = nicotine (3-[(2S)-1-methylpyrrolidin-2-yl] pyridine)) releases nicotine with a quantum yield ϕ = 0.23 upon irradiation with biologically harmless, blue (473 nm) or green (532 nm) light. The photolysis reaction is clean and very fast, with a time constant of 17 ns. The synthesis is simple and the obtained compound is characterized by NMR, UV-Vis spectroscopy and cyclic voltammetry. We find that this compound is active in biological systems, being able to elicit action potentials in leech neurons.
Filevich
Oscar
O
Departamento de Química Inorgánica, Analítica y Química Física, INQUIMAE, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria Pabellón 2 Piso 3, C1428EHA, Buenos Aires, Argentina.
Salierno
Marcelo
M
Etchenique
Roberto
R
D000818:Animals; D004594:Electrophysiology; D007865:Leeches / Q000166:cytology; D008027:Light; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D009474:Neurons / Q000187:drug effects / Q000378:metabolism; D009538:Nicotine / Q000737:chemistry* / Q000494:pharmacology*; D010777:Photochemistry / Q000379:methods; D010782:Photolysis; D012428:Ruthenium / Q000737:chemistry
D009538:Nicotine; D012428:Ruthenium