title: pH-dependent Si-fluorescein hypochlorous acid fluorescent probe: spirocycle ring-opening and excess hypochlorous acid-induced chlorination.
abstract: We report the synthesis and characterization of a fluorescent probe (Hypo-SiF) designed for the detection of hypochlorous acid (HOCl) using a silicon analogue of fluorescein (SiF). The probe is regulated in an "off-on" fashion by a highly selective thioether spirocyclic nonfluorescent structure that opens to form a mixture of fluorescent products in the presence of HOCl. Over a range of pH values, the probe reacts with a stoichiometric amount of HOCl, resulting in a mixture of two pH-dependent fluorescent species, a SiF disulfide product and a SiF sulfonate product. The unique colorimetric properties of the individual SiF fluorophores were utilized to perform simultaneous detection of HOCl and pH. When an excess of HOCl is present, the SiF fluorophores become chlorinated, via an intermediate halohydrin, resulting in a more pH independent and red-shifted fluorophore.
authors.affiliation: Department of Chemistry and Biochemistry, Southern Illinois University , Carbondale, Illinois 62901, United States.
authors.forename: Quinn A
authors.initials: QA
authors.lastname: Best
authors.forename: Narsimha
authors.initials: N
authors.lastname: Sattenapally
authors.forename: Daniel J
authors.initials: DJ
authors.lastname: Dyer
authors.forename: Colleen N
authors.initials: CN
authors.lastname: Scott
authors.forename: Matthew E
authors.initials: ME
authors.lastname: McCarroll
mesh_terms: D019793:Fluorescein / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D006997:Hypochlorous Acid / Q000737:chemistry*; D015394:Molecular Structure; D012825:Silicon / Q000737:chemistry*
chemical_list: D005456:Fluorescent Dyes; D006997:Hypochlorous Acid; D019793:Fluorescein; D012825:Silicon