Selective fluorescent recognition of Zn2+ by using chiral binaphthol-pyrene probes

Mukesh Eknath Shirbhate; Yerin Jeong; Gyeongju Ko; Gain Baek; Gyoungmi Kim; Yong Uk Kwon; Kwan Mook Kim; Juyoung Yoon

doi:10.1016/j.dyepig.2019.03.063

Selective fluorescent recognition of Zn²⁺ by using chiral binaphthol-pyrene probes

Mukesh Eknath Shirbhate, Yerin Jeong, Gyeongju Ko, Gain Baek, Gyoungmi Kim, Yong Uk Kwon, Kwan Mook Kim, Juyoung Yoon

Chemistry & Nanoscience

Research output: Contribution to journal › Article › peer-review

28 Scopus citations

Abstract

The bis-binaphthol-pyrene derivative 1 (R isomer) and 2 (S isomer) selectively sense Zn²⁺ by undergoing a reversible fluorescent emission enhancement at 550 nm. Moreover, upon addition of Zn²⁺, the magnitude of the peak in the CD spectrum of 1 at 289 nm increases and the intensity of the peak at 272 nm decreases. Opposite changes were observed for 2 upon the addition Zn²⁺. The distinctive fluorescence and ratiometric CD spectral changes are attributed to a change in the dihedral angle between the binaphthol groups in 1 and 2 caused by Zn²⁺ binding. Probe 1 was further employed to image Zn²⁺ in cells.

Original language	English
Pages (from-to)	29-35
Number of pages	7
Journal	Dyes and Pigments
Volume	167
DOIs	https://doi.org/10.1016/j.dyepig.2019.03.063
State	Published - Aug 2019

Bibliographical note

Funding Information:
This study was supported financially by a grant from the National Creative Research Initiative Program of the National Research Foundation of Korea , which is funded by the Korean government (MSIP) (No. 2012R1A3A2048814 ). K.M.K. thanks to the National Research Foundation of Korea (NRF) grant funded by the Korean government (MSIP) (NO. NRF-2017R1A2B2009672 ). The Korea Basic Science Institute is acknowledged for the LC/MS data. FAB mass spectral data were obtained from the Korea Basic Science Institute on a Jeol JMS 700 high resolution mass spectrometer.

Funding Information:
This study was supported financially by a grant from the National Creative Research Initiative Program of the National Research Foundation of Korea, which is funded by the Korean government (MSIP) (No. 2012R1A3A2048814). K.M.K. thanks to the National Research Foundation of Korea (NRF) grant funded by the Korean government (MSIP) (NO. NRF-2017R1A2B2009672). The Korea Basic Science Institute is acknowledged for the LC/MS data. FAB mass spectral data were obtained from the Korea Basic Science Institute on a Jeol JMS 700 high resolution mass spectrometer.

Publisher Copyright:
© 2019 Elsevier Ltd

Keywords

Binapthol
Circular dichroism
Fluorescent chemosensor for Zn
Fluorescent probe for Zn
Zn imaging in cells

Access to Document

10.1016/j.dyepig.2019.03.063

Cite this

@article{5274b150a099457386e25eb4599b1219,

title = "Selective fluorescent recognition of Zn2+ by using chiral binaphthol-pyrene probes",

abstract = "The bis-binaphthol-pyrene derivative 1 (R isomer) and 2 (S isomer) selectively sense Zn2+ by undergoing a reversible fluorescent emission enhancement at 550 nm. Moreover, upon addition of Zn2+, the magnitude of the peak in the CD spectrum of 1 at 289 nm increases and the intensity of the peak at 272 nm decreases. Opposite changes were observed for 2 upon the addition Zn2+. The distinctive fluorescence and ratiometric CD spectral changes are attributed to a change in the dihedral angle between the binaphthol groups in 1 and 2 caused by Zn2+ binding. Probe 1 was further employed to image Zn2+ in cells.",

keywords = "Binapthol, Circular dichroism, Fluorescent chemosensor for Zn, Fluorescent probe for Zn, Zn imaging in cells",

author = "Shirbhate, {Mukesh Eknath} and Yerin Jeong and Gyeongju Ko and Gain Baek and Gyoungmi Kim and Kwon, {Yong Uk} and Kim, {Kwan Mook} and Juyoung Yoon",

note = "Funding Information: This study was supported financially by a grant from the National Creative Research Initiative Program of the National Research Foundation of Korea , which is funded by the Korean government (MSIP) (No. 2012R1A3A2048814 ). K.M.K. thanks to the National Research Foundation of Korea (NRF) grant funded by the Korean government (MSIP) (NO. NRF-2017R1A2B2009672 ). The Korea Basic Science Institute is acknowledged for the LC/MS data. FAB mass spectral data were obtained from the Korea Basic Science Institute on a Jeol JMS 700 high resolution mass spectrometer. Funding Information: This study was supported financially by a grant from the National Creative Research Initiative Program of the National Research Foundation of Korea, which is funded by the Korean government (MSIP) (No. 2012R1A3A2048814). K.M.K. thanks to the National Research Foundation of Korea (NRF) grant funded by the Korean government (MSIP) (NO. NRF-2017R1A2B2009672). The Korea Basic Science Institute is acknowledged for the LC/MS data. FAB mass spectral data were obtained from the Korea Basic Science Institute on a Jeol JMS 700 high resolution mass spectrometer. Publisher Copyright: {\textcopyright} 2019 Elsevier Ltd",

year = "2019",

month = aug,

doi = "10.1016/j.dyepig.2019.03.063",

language = "English",

volume = "167",

pages = "29--35",

journal = "Dyes and Pigments",

issn = "0143-7208",

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T1 - Selective fluorescent recognition of Zn2+ by using chiral binaphthol-pyrene probes

AU - Shirbhate, Mukesh Eknath

AU - Jeong, Yerin

AU - Ko, Gyeongju

AU - Baek, Gain

AU - Kim, Gyoungmi

AU - Kwon, Yong Uk

AU - Kim, Kwan Mook

AU - Yoon, Juyoung

N1 - Funding Information: This study was supported financially by a grant from the National Creative Research Initiative Program of the National Research Foundation of Korea , which is funded by the Korean government (MSIP) (No. 2012R1A3A2048814 ). K.M.K. thanks to the National Research Foundation of Korea (NRF) grant funded by the Korean government (MSIP) (NO. NRF-2017R1A2B2009672 ). The Korea Basic Science Institute is acknowledged for the LC/MS data. FAB mass spectral data were obtained from the Korea Basic Science Institute on a Jeol JMS 700 high resolution mass spectrometer. Funding Information: This study was supported financially by a grant from the National Creative Research Initiative Program of the National Research Foundation of Korea, which is funded by the Korean government (MSIP) (No. 2012R1A3A2048814). K.M.K. thanks to the National Research Foundation of Korea (NRF) grant funded by the Korean government (MSIP) (NO. NRF-2017R1A2B2009672). The Korea Basic Science Institute is acknowledged for the LC/MS data. FAB mass spectral data were obtained from the Korea Basic Science Institute on a Jeol JMS 700 high resolution mass spectrometer. Publisher Copyright: © 2019 Elsevier Ltd

PY - 2019/8

Y1 - 2019/8

N2 - The bis-binaphthol-pyrene derivative 1 (R isomer) and 2 (S isomer) selectively sense Zn2+ by undergoing a reversible fluorescent emission enhancement at 550 nm. Moreover, upon addition of Zn2+, the magnitude of the peak in the CD spectrum of 1 at 289 nm increases and the intensity of the peak at 272 nm decreases. Opposite changes were observed for 2 upon the addition Zn2+. The distinctive fluorescence and ratiometric CD spectral changes are attributed to a change in the dihedral angle between the binaphthol groups in 1 and 2 caused by Zn2+ binding. Probe 1 was further employed to image Zn2+ in cells.

AB - The bis-binaphthol-pyrene derivative 1 (R isomer) and 2 (S isomer) selectively sense Zn2+ by undergoing a reversible fluorescent emission enhancement at 550 nm. Moreover, upon addition of Zn2+, the magnitude of the peak in the CD spectrum of 1 at 289 nm increases and the intensity of the peak at 272 nm decreases. Opposite changes were observed for 2 upon the addition Zn2+. The distinctive fluorescence and ratiometric CD spectral changes are attributed to a change in the dihedral angle between the binaphthol groups in 1 and 2 caused by Zn2+ binding. Probe 1 was further employed to image Zn2+ in cells.

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KW - Fluorescent probe for Zn

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