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Molecular Engineering Of Aqueous Soluble Triarylboron-Compound-Based Two-Photon Fluorescent Probe For Mitochondria H2S With Analyte-Induced Finite Aggregation And Excellent Membrane Permeability.

J. Liu, Xudong Guo, R. Hu, Xinyang Liu, Shuangqing Wang, Shayu Li, Y. Li, Guoqiang Yang
Published 2016 · Chemistry, Medicine

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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.
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