Novel Pyrazine-Bridged D-A-D Type Charge Neutral Probe for Membrane Permeable Long-Term Live Cell Imaging

Pei Liu; Suna Chen; Wenxuan Zhao; Qiutang Wang; Shuqi Wu; Liang Xu; Dan Bai; Dan Bai; Dan Bai

doi:10.3389/fchem.2021.782827

Frontiers in Chemistry (Dec 2021)

Novel Pyrazine-Bridged D-A-D Type Charge Neutral Probe for Membrane Permeable Long-Term Live Cell Imaging

Pei Liu,
Suna Chen,
Wenxuan Zhao,
Qiutang Wang,
Shuqi Wu,
Liang Xu,
Dan Bai,
Dan Bai,
Dan Bai

Affiliations

Pei Liu: Department of Chemistry and Chemical Engineering, School of Natural Sciences, Northwestern Polytechnical University, Xi'an, China
Suna Chen: Frontiers Science Center for Flexible Electronics (FSCFE), Institute of Flexible Electronics (IFE), MIIT Key Laboratory of Flexible Electronics (KLoFE), Xi'an Key Laboratory of Special Medicine and Health Engineering, Northwestern Polytechnical University, Northwestern Polytechnical University, Xi'an, China
Wenxuan Zhao: School of Material Science and Engineering, Northwestern Polytechnical University, Xi'an, China
Qiutang Wang: School of Medicine, Xi'an Jiaotong University, Xi'an, China
Shuqi Wu: School of Life Sciences, Northwestern Polytechnical University, Xi'an, China
Liang Xu: School of Chemistry and Chemical Engineering, Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, Shihezi University, Shihezi, China
Dan Bai: Frontiers Science Center for Flexible Electronics (FSCFE), Institute of Flexible Electronics (IFE), MIIT Key Laboratory of Flexible Electronics (KLoFE), Xi'an Key Laboratory of Special Medicine and Health Engineering, Northwestern Polytechnical University, Northwestern Polytechnical University, Xi'an, China
Dan Bai: Research and Development Institute of Northwestern Polytechnical University in Shenzhen, Northwestern Polytechnical University, Xi'an, China
Dan Bai: Research Institute of Xi'an Jiaotong University (Zhejiang), Hangzhou, China

DOI: https://doi.org/10.3389/fchem.2021.782827
Journal volume & issue: Vol. 9

Abstract

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A novel donor–acceptor–donor (D-A-D) type compound containing pyrazine as the acceptor and triphenylamine as the donor has been designed and synthesized. The photophysical properties and biocompatibility of this probe, namely (OMeTPA)2-Pyr for live cell imaging were systematically investigated, with observed large Stokes shifts, high photostability, and low cytotoxicity. Furthermore, we demonstrated that (OMeTPA)2-Pyr could permeate live cell membranes for labeling. The proposed mechanism of this probe was the binding and shafting through membrane integral transport proteins by electrostatic and hydrophobic interactions. These salient and novel findings can facilitate the strategic design of new pyrazine-fused charge-neutral molecular platforms as fluorescent probes, for long-term in situ dynamic monitoring in live cells.

Published in Frontiers in Chemistry

ISSN: 2296-2646 (Online)
Publisher: Frontiers Media S.A.
Country of publisher: Switzerland
LCC subjects: Science: Chemistry
Website: http://journal.frontiersin.org/journal/chemistry

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