title: The Development of Fluorescent Probes for Visualizing Intracellular Hydrogen Polysulfides.
abstract: Endogenous hydrogen polysulfides (H2Sn; n>1) have been recognized as important regulators in sulfur-related redox biology. H2Sn can activate tumor suppressors, ion channels, and transcription factors with higher potency than H2S. Although H2Sn are drawing increasing attention, their exact mechanisms of action are still poorly understood. A major hurdle in this field is the lack of reliable and convenient methods for H2Sn detection. Herein we report a H2Sn-mediated benzodithiolone formation under mild conditions. This method takes advantage of the unique dual reactivity of H2Sn as both a nucleophile and an electrophile. Based on this reaction, three fluorescent probes (PSP-1, PSP-2, and PSP-3) were synthesized and evaluated. Among the probes prepared, PSP-3 showed a desirable off/on fluorescence response to H2Sn and high specificity. The probe was successfully applied in visualizing intracellular H2Sn.
authors.affiliation: Department of Chemistry, Washington State University, Pullman, WA 99164 (USA).
authors.forename: Wei
authors.initials: W
authors.lastname: Chen
authors.affiliation: Department of Chemistry, Washington State University, Pullman, WA 99164 (USA).
authors.forename: Ethan W
authors.initials: EW
authors.lastname: Rosser
authors.affiliation: Department of Environmental Health Sciences and Molecular Toxicology, Tohoku University Graduate School of Medicine, Sendai, 980-8575 (Japan).
authors.forename: Tetsuro
authors.initials: T
authors.lastname: Matsunaga
authors.affiliation: Department of Chemistry, Washington State University, Pullman, WA 99164 (USA).
authors.forename: Armando
authors.initials: A
authors.lastname: Pacheco
authors.affiliation: Department of Environmental Health Sciences and Molecular Toxicology, Tohoku University Graduate School of Medicine, Sendai, 980-8575 (Japan).
authors.forename: Takaaki
authors.initials: T
authors.lastname: Akaike
authors.affiliation: Department of Chemistry, Washington State University, Pullman, WA 99164 (USA). mxian@wsu.edu.
authors.forename: Ming
authors.initials: M
authors.lastname: Xian
mesh_terms: D000818:Animals; D002460:Cell Line; D002522:Chlorocebus aethiops; D005453:Fluorescence; D005456:Fluorescent Dyes / Q000032:analysis / Q000138:chemical synthesis* / Q000737:chemistry; D006367:HeLa Cells; D006801:Humans; D006859:Hydrogen / Q000032:analysis*; D051379:Mice; D015394:Molecular Structure; D013440:Sulfides / Q000032:analysis*; D014709:Vero Cells
chemical_list: D005456:Fluorescent Dyes; D013440:Sulfides; D006859:Hydrogen; C032915:polysulfide
keywords: cyclization; fluorescence; fluorescent probes; hydrogen polysulfides; imaging agents