A fluorinated azine as a versatile scaffold for the development of Cu(II)-specific multi-functional imaging probes

Weijian Ye; Mengting Xie; Junjie Wei; Guocong Li; Yongjin Tang; Lu Hou; Lu Wang; Huijuan Yu; Chi Sing Lee; Hao Xu

doi:10.1016/j.snb.2021.130106

A fluorinated azine as a versatile scaffold for the development of Cu(II)-specific multi-functional imaging probes

Weijian Ye, Mengting Xie, Junjie Wei, Guocong Li, Yongjin Tang, Lu Hou, Lu Wang, Huijuan Yu, Chi Sing Lee^*, Hao Xu^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

7 Citations (Scopus)

Abstract

Copper is vital to many physiological activities, and its dyshomeostasis is related to cancers as well as neurodegenerative diseases. Copper targeting probes with single imaging modality have been extensively reported and employed in specific aspects. Herein, we delineate the development of Cu(II)-specific multi-functional imaging probes based on a fluorinated azine FN. The azine selectively binds to a Cu²⁺ ion, forming a 1:1 FN-Cu²⁺ complex, and induces a substantial fluorescence quenching, which can be resumed upon addition of H₂S (Na₂S as the source of H₂S). The binding of the paramagnetic Cu²⁺ ions also leads to the relaxation enhancement of the ¹⁹F nuclei in the FN-Cu²⁺ complex and improve the signal-to-noise ratio of the phantom images. The ¹⁸F-radiolabeled analogue, [¹⁸F]FN, is synthesized for the first time and used in PET/CT imaging on cynomolgus for a preliminary study of pharmacokinetics.

Original language	English
Article number	130106
Journal	Sensors and Actuators B: Chemical
Volume	343
DOIs	https://doi.org/10.1016/j.snb.2021.130106
Publication status	Published - 15 Sept 2021

User-Defined Keywords

F magnetic resonance
Azine
Copper ion
Fluorescent probe
Positron emission tomography

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This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.snb.2021.130106

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@article{dd9a9364eedb489e893a1e23d1f5a9eb,

title = "A fluorinated azine as a versatile scaffold for the development of Cu(II)-specific multi-functional imaging probes",

abstract = "Copper is vital to many physiological activities, and its dyshomeostasis is related to cancers as well as neurodegenerative diseases. Copper targeting probes with single imaging modality have been extensively reported and employed in specific aspects. Herein, we delineate the development of Cu(II)-specific multi-functional imaging probes based on a fluorinated azine FN. The azine selectively binds to a Cu2+ ion, forming a 1:1 FN-Cu2+ complex, and induces a substantial fluorescence quenching, which can be resumed upon addition of H2S (Na2S as the source of H2S). The binding of the paramagnetic Cu2+ ions also leads to the relaxation enhancement of the 19F nuclei in the FN-Cu2+ complex and improve the signal-to-noise ratio of the phantom images. The 18F-radiolabeled analogue, [18F]FN, is synthesized for the first time and used in PET/CT imaging on cynomolgus for a preliminary study of pharmacokinetics.",

keywords = "F magnetic resonance, Azine, Copper ion, Fluorescent probe, Positron emission tomography",

author = "Weijian Ye and Mengting Xie and Junjie Wei and Guocong Li and Yongjin Tang and Lu Hou and Lu Wang and Huijuan Yu and Lee, {Chi Sing} and Hao Xu",

note = "Funding Information: The authors gratefully acknowledge the support of K.C. Wong Education Foundation (China) , and the Project of Innovative Team for the Guangdong Universities ( 2018KCXTD001 , China). This work was financially supported by Postdoctoral Fund of the First Affiliated Hospital, Jinan University (No. 809028 ), Hong Kong Baptist University ( RC-SGT2/18-19/SCI/005 and RC-ICRS-18-19-01A ), the National Natural Science Foundation of China (Nos. 81871383 and 82071974 ), Guangdong Basic and Applied Basic Research Foundation ( 2020A1515011192 , China) and the Fundamental Research Funds for the Central Universities ( 21619104 ). We thank Jianzhou Li from Ge healthcare for the assistant on radio labeling and supplying Fig. S13. Publisher Copyright: {\textcopyright} 2021 Elsevier B.V.",

year = "2021",

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doi = "10.1016/j.snb.2021.130106",

language = "English",

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T1 - A fluorinated azine as a versatile scaffold for the development of Cu(II)-specific multi-functional imaging probes

AU - Ye, Weijian

AU - Xie, Mengting

AU - Wei, Junjie

AU - Li, Guocong

AU - Tang, Yongjin

AU - Hou, Lu

AU - Wang, Lu

AU - Yu, Huijuan

AU - Lee, Chi Sing

AU - Xu, Hao

N1 - Funding Information: The authors gratefully acknowledge the support of K.C. Wong Education Foundation (China) , and the Project of Innovative Team for the Guangdong Universities ( 2018KCXTD001 , China). This work was financially supported by Postdoctoral Fund of the First Affiliated Hospital, Jinan University (No. 809028 ), Hong Kong Baptist University ( RC-SGT2/18-19/SCI/005 and RC-ICRS-18-19-01A ), the National Natural Science Foundation of China (Nos. 81871383 and 82071974 ), Guangdong Basic and Applied Basic Research Foundation ( 2020A1515011192 , China) and the Fundamental Research Funds for the Central Universities ( 21619104 ). We thank Jianzhou Li from Ge healthcare for the assistant on radio labeling and supplying Fig. S13. Publisher Copyright: © 2021 Elsevier B.V.

PY - 2021/9/15

Y1 - 2021/9/15

N2 - Copper is vital to many physiological activities, and its dyshomeostasis is related to cancers as well as neurodegenerative diseases. Copper targeting probes with single imaging modality have been extensively reported and employed in specific aspects. Herein, we delineate the development of Cu(II)-specific multi-functional imaging probes based on a fluorinated azine FN. The azine selectively binds to a Cu2+ ion, forming a 1:1 FN-Cu2+ complex, and induces a substantial fluorescence quenching, which can be resumed upon addition of H2S (Na2S as the source of H2S). The binding of the paramagnetic Cu2+ ions also leads to the relaxation enhancement of the 19F nuclei in the FN-Cu2+ complex and improve the signal-to-noise ratio of the phantom images. The 18F-radiolabeled analogue, [18F]FN, is synthesized for the first time and used in PET/CT imaging on cynomolgus for a preliminary study of pharmacokinetics.

AB - Copper is vital to many physiological activities, and its dyshomeostasis is related to cancers as well as neurodegenerative diseases. Copper targeting probes with single imaging modality have been extensively reported and employed in specific aspects. Herein, we delineate the development of Cu(II)-specific multi-functional imaging probes based on a fluorinated azine FN. The azine selectively binds to a Cu2+ ion, forming a 1:1 FN-Cu2+ complex, and induces a substantial fluorescence quenching, which can be resumed upon addition of H2S (Na2S as the source of H2S). The binding of the paramagnetic Cu2+ ions also leads to the relaxation enhancement of the 19F nuclei in the FN-Cu2+ complex and improve the signal-to-noise ratio of the phantom images. The 18F-radiolabeled analogue, [18F]FN, is synthesized for the first time and used in PET/CT imaging on cynomolgus for a preliminary study of pharmacokinetics.

KW - F magnetic resonance

KW - Azine

KW - Copper ion

KW - Fluorescent probe

KW - Positron emission tomography

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U2 - 10.1016/j.snb.2021.130106

DO - 10.1016/j.snb.2021.130106

M3 - Journal article

AN - SCOPUS:85105751559

SN - 0925-4005

VL - 343

JO - Sensors and Actuators B: Chemical

JF - Sensors and Actuators B: Chemical

M1 - 130106

ER -

A fluorinated azine as a versatile scaffold for the development of Cu(II)-specific multi-functional imaging probes

Abstract

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