title: A Ratiometric Fluorescent Probe Based on a Through-Bond Energy Transfer (TBET) System for Imaging HOCl in Living Cells.
abstract: A simple ratiometric probe (Naph-Rh) has been designed and synthesized based on a through-bond energy transfer (TBET) system for sensing HOCl. In this probe, rhodamine thiohydrazide and naphthalene formyl were connected by simple synthesis methods to construct a structure of monothio-bishydrazide. Free probe Naph-Rh showed only the emission of naphthalene. When probe Naph-Rh reacted with HOCl, monothio-bishydrazide could be converted into 1,2,4-oxadiazole, which not only ensured that the donor and the acceptor were connected with electronically conjugated bonds, but also resulted in the spiro-ring opening and the emission of rhodamine. Therefore, a typical TBET process took place. The probe possessed high-energy transfer efficiency and large pseudo-Stokes shifts. As the first TBET probe for HOCl, Naph-Rh showed excellent selectivity and sensitivity toward HOCl over other reactive oxygen species (ROS)/reactive nitrogen species (RNS), and could respond fast to a low concentration of HOCl in the real sample. In addition, the probe was suitable for imaging HOCl in living cells due to its real-time response, excellent resolution, and reduced cytotoxicity.
authors.affiliation: Institute of Organic Chemistry, School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100 (P.R. China).
authors.forename: Yan-Ru
authors.initials: YR
authors.lastname: Zhang
authors.affiliation: Institute of Developmental Biology, School of Life Science, Shandong University, Jinan 250100 (P.R. China).|School of Biological Science and Technology, University of Jinan, Jinan 250022 (P.R. China).
authors.forename: Ning
authors.initials: N
authors.lastname: Meng
authors.affiliation: Institute of Developmental Biology, School of Life Science, Shandong University, Jinan 250100 (P.R. China). miaojy@sdu.edu.cn.
authors.forename: Jun-Ying
authors.initials: JY
authors.lastname: Miao
authors.affiliation: Institute of Organic Chemistry, School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100 (P.R. China). bxzhao@sdu.edu.cn.
authors.forename: Bao-Xiang
authors.initials: BX
authors.lastname: Zhao
mesh_terms: D003952:Diagnostic Imaging; D031541:Fluorescence Resonance Energy Transfer; D005456:Fluorescent Dyes / Q000737:chemistry*; D006367:HeLa Cells; D006801:Humans; D006997:Hypochlorous Acid / Q000737:chemistry*; D009281:Naphthalenes / Q000737:chemistry*; D010069:Oxadiazoles / Q000737:chemistry*
chemical_list: D005456:Fluorescent Dyes; D009281:Naphthalenes; D010069:Oxadiazoles; D006997:Hypochlorous Acid
keywords: fluorescent probes; hypochlorous acid; naphthalene; rhodamine; through-bond energy transfer