title: Molecular Engineering of Aqueous Soluble Triarylboron-Compound-Based Two-Photon Fluorescent Probe for Mitochondria H2S with Analyte-Induced Finite Aggregation and Excellent Membrane Permeability.
abstract: Hydrogen sulfide (H2S) is a multifunctional signaling molecule that participates in many important biological processes. Herein, by functionalizing triarylboron with cyclen and diphenylamine, we synthesized TAB-1, TAB-2, and TAB-3 for H2S recongnization by rational design of molecular structures. Among them, aqueous soluble TAB-2 possesses excellent properties, including large two-photon action cross section, membrane permeability and can effectively complex with Cu(2+). The complex of TAB-2-Cu(2+) can selectively detect H2S with an instant response and mitochondria targeted. Moreover, the H2S-induced finite aggregation of indicators enhances their photostability and causes variation of the fluorescence lifetime. TAB-2-Cu(2+) has also been successfully applied for the mitochondria H2S imaging in NIH/3T3 fibroblast cells by TPM and FLIM.
authors.affiliation: Beijing National Laboratory for Molecular Sciences, Key laboratory of Photochemistry, Institute of Chemistry, Chinese Academy of Sciences , Beijing 100190, China.
authors.forename: Jun
authors.initials: J
authors.lastname: Liu
authors.affiliation: Beijing National Laboratory for Molecular Sciences, Key laboratory of Photochemistry, Institute of Chemistry, Chinese Academy of Sciences , Beijing 100190, China.
authors.forename: Xudong
authors.initials: X
authors.lastname: Guo
authors.affiliation: Beijing National Laboratory for Molecular Sciences, Key laboratory of Photochemistry, Institute of Chemistry, Chinese Academy of Sciences , Beijing 100190, China.
authors.forename: Rui
authors.initials: R
authors.lastname: Hu
authors.affiliation: Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry Chinese Academy of Sciences , Beijing 100190, China.
authors.forename: Xinyang
authors.initials: X
authors.lastname: Liu
authors.affiliation: Beijing National Laboratory for Molecular Sciences, Key laboratory of Photochemistry, Institute of Chemistry, Chinese Academy of Sciences , Beijing 100190, China.
authors.forename: Shuangqing
authors.initials: S
authors.lastname: Wang
authors.affiliation: Beijing National Laboratory for Molecular Sciences, Key laboratory of Photochemistry, Institute of Chemistry, Chinese Academy of Sciences , Beijing 100190, China.
authors.forename: Shayu
authors.initials: S
authors.lastname: Li
authors.affiliation: Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry Chinese Academy of Sciences , Beijing 100190, China.
authors.forename: Yi
authors.initials: Y
authors.lastname: Li
authors.affiliation: Beijing National Laboratory for Molecular Sciences, Key laboratory of Photochemistry, Institute of Chemistry, Chinese Academy of Sciences , Beijing 100190, China.
authors.forename: Guoqiang
authors.initials: G
authors.lastname: Yang
mesh_terms: D000818:Animals; D001896:Boron Compounds / Q000737:chemistry* / Q000378:metabolism; D002463:Cell Membrane Permeability; D002470:Cell Survival; D002478:Cells, Cultured; D003300:Copper / Q000737:chemistry / Q000378:metabolism; D000080027:Cyclams; D004159:Diphenylamine / Q000737:chemistry / Q000378:metabolism; D005347:Fibroblasts / Q000737:chemistry* / Q000166:cytology / Q000378:metabolism; D005453:Fluorescence; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D006571:Heterocyclic Compounds / Q000737:chemistry / Q000378:metabolism; D006862:Hydrogen Sulfide / Q000032:analysis* / Q000378:metabolism; D051379:Mice; D008928:Mitochondria / Q000737:chemistry* / Q000378:metabolism; D015394:Molecular Structure; D041681:NIH 3T3 Cells; D011522:Protons; D012995:Solubility; D014867:Water / Q000737:chemistry
chemical_list: D001896:Boron Compounds; D000080027:Cyclams; D005456:Fluorescent Dyes; D006571:Heterocyclic Compounds; D011522:Protons; D014867:Water; D003300:Copper; C038072:cyclen; D004159:Diphenylamine; D006862:Hydrogen Sulfide