title: Seminaphthofluorescein-based fluorescent probes for imaging nitric oxide in live cells.
abstract: Fluorescent turn-on probes for nitric oxide based on seminaphthofluorescein scaffolds were prepared and spectroscopically characterized. The Cu(II) complexes of these fluorescent probes react with NO under anaerobic conditions to yield a 20-45-fold increase in integrated emission. The seminaphthofluorescein-based probes emit at longer wavelengths than the parent FL1 and FL2 fluorescein-based generations of NO probes, maintaining emission maxima between 550 and 625 nm. The emission profiles depend on the excitation wavelength; maximum fluorescence turn-on is achieved at excitations between 535 and 575 nm. The probes are highly selective for NO over other biologically relevant reactive nitrogen and oxygen species including NO(3)(-), NO(2)(-), HNO, ONOO(-), NO(2), OCl(-), and H(2)O(2). The seminaphthofluorescein-based probes can be used to visualize endogenously produced NO in live cells, as demonstrated using Raw 264.7 macrophages.
authors: Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.
authors: Michael D
authors: MD
authors: Pluth
authors: Maria R
authors: MR
authors: Chan
authors: Lindsey E
authors: LE
authors: McQuade
authors: Stephen J
authors: SJ
authors: Lippard
mesh_terms: D000818:Animals; D002460:Cell Line; D003300:Copper / Q000737:chemistry*; D018360:Crystallography, X-Ray; D005452:Fluoresceins / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D008264:Macrophages / Q000737:chemistry*; D051379:Mice; D008856:Microscopy, Fluorescence; D015394:Molecular Structure; D009569:Nitric Oxide / Q000032:analysis*; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D013056:Spectrophotometry, Ultraviolet
chemical_list: D005452:Fluoresceins; D005456:Fluorescent Dyes; D009942:Organometallic Compounds; C401959:seminaphthofluorescein; D009569:Nitric Oxide; D003300:Copper