Next Article in Journal
An Enhanced Source Location Privacy based on Data Dissemination in Wireless Sensor Networks (DeLP)
Previous Article in Journal
Edge-Computing Video Analytics for Real-Time Traffic Monitoring in a Smart City
Article

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

1
Department of Biophysical Chemistry, Kobe Pharmaceutical University, 4-19-1 Motoyamakita Machi, Higashinada Ku, Kobe 658-8558, Japan
2
Graduate School of Biomedical Sciences, Nagasaki University, 1-7-1 Sakamoto, Nagasaki 852-8501, Japan
3
Clinical Research Center, Nagasaki University Hospital, 1-7-1 Sakamoto, Nagasaki 852-8501, Japan
4
Graduate School of Pharmaceutical Sciences, Kyoto University, 46–29 Yoshida-Shimoadachi-cho, Sakyo-ku, Kyoto 606-8501, Japan
*
Authors to whom correspondence should be addressed.
Sensors 2019, 19(9), 2049; https://doi.org/10.3390/s19092049
Received: 7 April 2019 / Revised: 29 April 2019 / Accepted: 1 May 2019 / Published: 2 May 2019
(This article belongs to the Section Chemical Sensors)
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 Zn2+, 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 Zn2+ 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 Zn2+ toward understanding its functions in living systems. View Full-Text
Keywords: endogenous Zn2+; pyrazine–pyridone biheteroaryl; low background fluorescence; sulfonyl group; cellular imaging endogenous Zn2+; pyrazine–pyridone biheteroaryl; low background fluorescence; sulfonyl group; cellular imaging
Show Figures

Figure 1

MDPI and ACS Style

Hagimori, M.; Taniura, M.; Mizuyama, N.; Karimine, Y.; Kawakami, S.; Saji, H.; Mukai, T. Synthesis of a Novel Pyrazine–Pyridone Biheteroaryl-Based Fluorescence Sensor and Detection of Endogenous Labile Zinc Ions in Lung Cancer Cells. Sensors 2019, 19, 2049. https://doi.org/10.3390/s19092049

AMA Style

Hagimori M, Taniura M, Mizuyama N, Karimine Y, Kawakami S, Saji H, Mukai T. Synthesis of a Novel Pyrazine–Pyridone Biheteroaryl-Based Fluorescence Sensor and Detection of Endogenous Labile Zinc Ions in Lung Cancer Cells. Sensors. 2019; 19(9):2049. https://doi.org/10.3390/s19092049

Chicago/Turabian Style

Hagimori, Masayori, Mana Taniura, Naoko Mizuyama, Yasushi Karimine, Shigeru Kawakami, Hideo Saji, and Takahiro Mukai. 2019. "Synthesis of a Novel Pyrazine–Pyridone Biheteroaryl-Based Fluorescence Sensor and Detection of Endogenous Labile Zinc Ions in Lung Cancer Cells" Sensors 19, no. 9: 2049. https://doi.org/10.3390/s19092049

Find Other Styles
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Article Access Map by Country/Region

1
Back to TopTop