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Synthesis of a Novel Pyrazine-Pyridone Biheteroaryl-Based Fluorescence Sensor and Detection of Endogenous Labile Zinc Ions in Lung Cancer Cells


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Title: Synthesis of a Novel Pyrazine-Pyridone Biheteroaryl-Based Fluorescence Sensor and Detection of Endogenous Labile Zinc Ions in Lung Cancer Cells
Authors: Hagimori, Masayori / Taniura, Mana / Mizuyama, Naoko / Karimine, Yasushi / Kawakami, Shigeru / Saji, Hideo / Mukai, Takahiro
Issue Date: 2-May-2019
Publisher: MDPI
Citation: Sensors, 19(9), art.no.2049; 2019
Abstract: A small extent of endogenous labile zinc is involved in many vital physiological roles in living systems. However, its detailed functions have not been fully elucidated. In this study, we developed a novel biheteroaryl-based low molecular weight fluorescent sensor, 3-(phenylsulfonyl)-pyrazine-pyridone (5b), and applied it for the detection of endogenous labile zinc ions from lung cancer cells during apoptosis. The electron-withdrawing property of the sulfonyl group between the phenyl ring as an electron donor and the pyridone ring as a fluorophore inhibited the intramolecular charge transfer state, and the background fluorescence of the sensor was decreased in aqueous media. From the structure-fluorescence relationship analysis of the substituent effects with/without Zn 2+ , compound 5b acting as a sensor possessed favorable properties, including a longer emission wavelength, a large Stokes shift (over 100 nm),a large fluorescence enhancement in response to Zn 2+ under physical conditions, and good cell membrane permeability in living cells. Fluorescence imaging studies of human lung adenocarcinoma cells (A549) undergoing apoptosis revealed that compound 5b could detect endogenous labile zinc ions. These experiments suggested that the low molecular weight compound 5b is a potential fluorescence sensor for Zn 2+ toward understanding its functions in living systems.
Keywords: Cellular imaging / Endogenous Zn 2+ / Low background fluorescence / Pyrazine-pyridone biheteroaryl / Sulfonyl group
URI: http://hdl.handle.net/10069/39215
DOI: 10.3390/s19092049
Rights: © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
Type: Journal Article
Text Version: publisher
Appears in Collections:Articles in academic journal

Citable URI : http://hdl.handle.net/10069/39215

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