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Development of Lysosome‐Targeted Fluorescent Probes for Cys by Regulating the Boron‐dipyrromethene (BODIPY) Molecular Structure
Author(s) -
Gao Jinhua,
Tao Yuanfang,
Zhang Jian,
Wang Nannan,
Ji Xin,
He Jinling,
Si Yubing,
Zhao Weili
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201902301
Subject(s) - bodipy , fluorescence , chemistry , moiety , intersystem crossing , photochemistry , lysosome , hela , excited state , quenching (fluorescence) , singlet state , boron , lyso , stereochemistry , in vitro , enzyme , biochemistry , organic chemistry , physics , quantum mechanics , nuclear physics , scintillator , detector , electrical engineering , engineering
Our previous discovery suggested that substituents on the 1,7 positions delicately modulate the sensing ability of the meso ‐arylmercapto boron‐dipyrromethene (BODIPY) to biothiols. In this work, the impact of delicate modulations on the sensing ability is investigated. Therefore, 1,7‐dimethyl, 3,5‐diaryl substituted BODIPY is designed and developed and its conformationally restricted species with a meso ‐arylmercapto moiety ( DM‐BDP‐SAr and DM‐BDP‐R‐SAr ) as selective fluorescent probes for Cys. Moreover, the lysosome‐target probes ( Lyso‐S and Lyso‐D ) based on DM‐BDP‐SAr carrying one or two morpholinoethoxy moieties were developed. They were able to detect Cys selectively in vitro with low detection limits. Both Lyso‐S and Lyso‐D localized nicely in lysosomes in living HeLa cells and exhibited red fluorescence for Cys. Moreover, a novel fluorescence quenching mechanism was proposed from the calculations by density functional theory (DFT). The probes may go through intersystem crossing (from singlet excited state to triplet excited state) to result in fluorescence quenching.