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.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Animals
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Boron Compounds / chemistry*
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Boron Compounds / metabolism
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Cell Membrane Permeability*
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Cell Survival
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Cells, Cultured
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Copper / chemistry
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Copper / metabolism
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Cyclams
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Diphenylamine / chemistry
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Diphenylamine / metabolism
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Fibroblasts / chemistry*
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Fibroblasts / cytology
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Fibroblasts / metabolism
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Fluorescence
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Fluorescent Dyes / chemical synthesis
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Fluorescent Dyes / chemistry*
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Fluorescent Dyes / metabolism
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Heterocyclic Compounds / chemistry
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Heterocyclic Compounds / metabolism
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Hydrogen Sulfide / analysis*
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Hydrogen Sulfide / metabolism
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Mice
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Mitochondria / chemistry*
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Mitochondria / metabolism
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Molecular Structure
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NIH 3T3 Cells
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Protons
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Solubility
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Water / chemistry
Substances
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Boron Compounds
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Cyclams
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Fluorescent Dyes
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Heterocyclic Compounds
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Protons
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Water
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Copper
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cyclen
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Diphenylamine
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Hydrogen Sulfide