Ratiometric Near-Infrared Fluorescent Probes Based On Through-Bond Energy Transfer and π-Conjugation Modulation between Tetraphenylethene and Hemicyanine Moieties for Sensitive Detection of pH Changes in Live Cells

Bioconjugate Chemistry
Jianbo WangHaiying Liu

Abstract

In this paper, we present three ratiometric near-infrared fluorescent probes (A-C) for accurate, ratiometric detection of intracellular pH changes in live cells. Probe A consists of a tetraphenylethene (TPE) donor and near-infrared hemicyanine acceptor in a through-bond energy transfer (TBET) strategy, while probes B and C are composed of TPE and hemicyanine moieties through single and double sp2 carbon-carbon bond connections in a π-conjugation modulation strategy. The specific targeting of the probes to lysosomes in live cells was achieved by introducing morpholine residues to the hemicyanine moieties to form closed spirolactam ring structures. Probe A shows aggregation-induced emission (AIE) property at neutral or basic pH, while probes B and C lack AIE properties. At basic or neutral pH, the probes only show fluorescence of TPE moieties with closed spirolactam forms of hemicyanine moieties, and effectively avoid blind fluorescence imaging spots, an issue which typical intensity-based pH fluorescent probes encounter. Three probes show ratiometric fluorescence responses to pH changes from 7.0 to 3.0 with TPE fluorescence decreases and hemicyanine fluorescence increases, because acidic pH makes the spirolactam rings open to en...Continue Reading

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Citations

Sep 5, 2018·Chembiochem : a European Journal of Chemical Biology·Alejandro Méndez-ArdoyJavier Montenegro
Apr 25, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Mingxi FangHaiying Liu
Jan 17, 2020·Chemistry : a European Journal·Alejandro Méndez-ArdoyJavier Montenegro
Oct 21, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Yibin ZhangHaiying Liu
Sep 16, 2020·Analytical Methods : Advancing Methods and Applications·Lingling LiWen Zhang
Dec 29, 2020·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Wafa MaziHaiying Liu
Apr 8, 2021·Topics in Current Chemistry·Lei DongQing-Zheng Yang
May 1, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Yunnan YanHaiying Liu
May 14, 2021·Chembiochem : a European Journal of Chemical Biology·Yibin ZhangHaiying Liu
Jun 17, 2021·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Shulin WanHaiying Liu
Apr 8, 2020·ACS Applied Materials & Interfaces·Yibin ZhangHaiying Liu
Oct 26, 2021·Chembiochem : a European Journal of Chemical Biology·Pankaj E HandeSantosh J Gharpure

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