title: SpiroZin1: a reversible and pH-Insensitive, reaction-based, red-fluorescent probe for imaging biological mobile zinc.
abstract: A reversible, reaction-based sensor for biological mobile zinc was designed, prepared, and characterized. The sensing mechanism of this probe is based on the zinc-induced, ring-opening reaction of spirobenzopyran to give a cyanine fluorophore that emits in the deep-red region of the electromagnetic spectrum. This probe is not activated by protons and operates efficiently in aqueous solution at pH 7 and high ionic strength. The mechanism of this reaction was studied by using a combination of kinetics experiments and DFT calculations. The biocompatibility of the probe was demonstrated in live HeLa cells.
authors.affiliation: Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Ave, Cambridge, MA 02139 (USA) http://web.mit.edu/lippardlab/
authors.forename: Pablo
authors.initials: P
authors.lastname: Rivera-Fuentes
authors.forename: Stephen J
authors.initials: SJ
authors.lastname: Lippard
mesh_terms: D001578:Benzopyrans / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D056831:Coordination Complexes / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D005456:Fluorescent Dyes / Q000737:chemistry*; D006367:HeLa Cells; D006801:Humans; D006863:Hydrogen-Ion Concentration; D018613:Microscopy, Confocal; D011725:Pyridines / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D013050:Spectrometry, Fluorescence; D013816:Thermodynamics; D015032:Zinc / Q000737:chemistry / Q000378:metabolism*
chemical_list: D001578:Benzopyrans; D056831:Coordination Complexes; D005456:Fluorescent Dyes; D011725:Pyridines; C000594506:SpiroZin1; D015032:Zinc
keywords: bioinorganic chemistry; biosensors; coordination chemistry; spirobenzopyran