Cancer-specific hNQO1-responsive biocompatible naphthalimides providing a rapid fluorescent turn-on with an enhanced enzyme affinity

Sun Young Park; Eugeine Jung; Jong Seung Kim; Sung Gil Chi; Min Hee Lee

doi:10.3390/s20010053

Cancer-specific hNQO1-responsive biocompatible naphthalimides providing a rapid fluorescent turn-on with an enhanced enzyme affinity

Sun Young Park, Eugeine Jung, Jong Seung Kim, Sung Gil Chi, Min Hee Lee

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

16 Citations (Scopus)

Abstract

Human NAD(P)H:quinone oxidoreductase 1 (hNQO1) is overexpressed in cancer cells and associated with the drug resistance factor of cancer. The objective of this work is the development of fluorescent probes for the efficient detection of hNQO1 activity in cancer cells, which can be employed for the cancer diagnosis and therapeutic agent development. Herein, we report naphthalimide-based fluorescent probes 1 and 2 that can detect hNQO1. For hNQO1 activity, the probes showed a significant fluorescence increase at 540 nm. In addition, probe 1, the naphthalimide containing a triphenylphosphonium salt, showed an enhanced enzyme efficiency and rapid detection under a physiological condition. The detection ability of probe 1 was superior to that of other previously reported probes. Moreover, probe 1 was less cytotoxic during the cancer cell imaging and readily provided a strong fluorescence in hNQO1-overexpressed cancer cells (A549). We proposed that probe 1 can be used to detect hNQO1 expression in live cells and it will be applied to develop the diagnosis and customized treatment of hNQO1-related disease.

Original language	English
Article number	53
Journal	Sensors (Switzerland)
Volume	20
Issue number	1
DOIs	https://doi.org/10.3390/s20010053
Publication status	Published - 2020 Jan 1

Bibliographical note

Funding Information:
Funding: This research was supported by the CRI project (2018R1A3B1052702, J.S.K.), National Research Foundation of Korea (NRF) (2018R1C1B6006110, M.H.L.) and the Sookmyung Women’s University BK21 Plus Scholarship.

Publisher Copyright:
© 2019 by the authors. Licensee MDPI, Basel, Switzerland.

Keywords

Fluorescent off-on naphthalimides
Human NAD(P)H:quinone oxidoreductase 1 (hNQO1)
Trimethyl lock quinone
Triphenylphosphonium salt

ASJC Scopus subject areas

Analytical Chemistry
Biochemistry
Atomic and Molecular Physics, and Optics
Instrumentation
Electrical and Electronic Engineering

UN SDGs

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

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10.3390/s20010053

Cite this

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title = "Cancer-specific hNQO1-responsive biocompatible naphthalimides providing a rapid fluorescent turn-on with an enhanced enzyme affinity",

abstract = "Human NAD(P)H:quinone oxidoreductase 1 (hNQO1) is overexpressed in cancer cells and associated with the drug resistance factor of cancer. The objective of this work is the development of fluorescent probes for the efficient detection of hNQO1 activity in cancer cells, which can be employed for the cancer diagnosis and therapeutic agent development. Herein, we report naphthalimide-based fluorescent probes 1 and 2 that can detect hNQO1. For hNQO1 activity, the probes showed a significant fluorescence increase at 540 nm. In addition, probe 1, the naphthalimide containing a triphenylphosphonium salt, showed an enhanced enzyme efficiency and rapid detection under a physiological condition. The detection ability of probe 1 was superior to that of other previously reported probes. Moreover, probe 1 was less cytotoxic during the cancer cell imaging and readily provided a strong fluorescence in hNQO1-overexpressed cancer cells (A549). We proposed that probe 1 can be used to detect hNQO1 expression in live cells and it will be applied to develop the diagnosis and customized treatment of hNQO1-related disease.",

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author = "Park, {Sun Young} and Eugeine Jung and Kim, {Jong Seung} and Chi, {Sung Gil} and Lee, {Min Hee}",

note = "Funding Information: Funding: This research was supported by the CRI project (2018R1A3B1052702, J.S.K.), National Research Foundation of Korea (NRF) (2018R1C1B6006110, M.H.L.) and the Sookmyung Women{\textquoteright}s University BK21 Plus Scholarship. Publisher Copyright: {\textcopyright} 2019 by the authors. Licensee MDPI, Basel, Switzerland.",

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AU - Chi, Sung Gil

AU - Lee, Min Hee

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N2 - Human NAD(P)H:quinone oxidoreductase 1 (hNQO1) is overexpressed in cancer cells and associated with the drug resistance factor of cancer. The objective of this work is the development of fluorescent probes for the efficient detection of hNQO1 activity in cancer cells, which can be employed for the cancer diagnosis and therapeutic agent development. Herein, we report naphthalimide-based fluorescent probes 1 and 2 that can detect hNQO1. For hNQO1 activity, the probes showed a significant fluorescence increase at 540 nm. In addition, probe 1, the naphthalimide containing a triphenylphosphonium salt, showed an enhanced enzyme efficiency and rapid detection under a physiological condition. The detection ability of probe 1 was superior to that of other previously reported probes. Moreover, probe 1 was less cytotoxic during the cancer cell imaging and readily provided a strong fluorescence in hNQO1-overexpressed cancer cells (A549). We proposed that probe 1 can be used to detect hNQO1 expression in live cells and it will be applied to develop the diagnosis and customized treatment of hNQO1-related disease.

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Cancer-specific hNQO1-responsive biocompatible naphthalimides providing a rapid fluorescent turn-on with an enhanced enzyme affinity

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

UN SDGs

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