A thiocoumarin-based turn-on fluorescent probe for hypochlorite detection and its application to live-cell imaging

Van Nghia Nguyen; Seonye Heo; Sangin Kim; K. M.K. Swamy; Jeongsun Ha; Sungnam Park; Juyoung Yoon

doi:10.1016/j.snb.2020.128213

A thiocoumarin-based turn-on fluorescent probe for hypochlorite detection and its application to live-cell imaging

Van Nghia Nguyen, Seonye Heo, Sangin Kim, K. M.K. Swamy, Jeongsun Ha, Sungnam Park, Juyoung Yoon

Department of Chemistry & Nanoscience

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

55 Scopus citations

Abstract

A thiocoumarin-based turn-on fluorescence probe for the detection of hypochlorite anion (ClO⁻) was prepared and characterized. Coumarin dye (CZCN-O) exhibited intense fluorescence with good quantum yields (Φ_PL = 0.98) in acetonitrile. Contrastingly, the fluorescence of thiocoumarin dye (CZCN-S) was almost completely quenched (Φ_PL < 0.01) because of the efficient intersystem crossing from the emissive singlet excited state to the non-emissive triplet state. The addition of ClO⁻ to the PBS buffer (pH = 7.4, containing 50% ACN) of thiocoumarin resulted in a remarkable fluorescence enhancement with an emission maximum at 486 nm, indicating the sensitive OFF–ON fluorescence sensing of ClO⁻. The calculated detection limit of ClO⁻ in 50% aqueous ACN was 0.17 μM. An investigation of the sensing behavior to various analytes revealed that thiocoumarin dye had an excellent selectivity for ClO⁻. The recognition mechanism was attributed to the ClO⁻-induced conversion of thiocarbonyl coumarin into its oxo analogue through oxidative desulfurization. In particular, cell studies demonstrated that thiocoumarin dye could be used as an effective fluorescent probe for the detection of ClO⁻ in living cells.

Original language	English
Article number	128213
Journal	Sensors and Actuators, B: Chemical
Volume	317
DOIs	https://doi.org/10.1016/j.snb.2020.128213
State	Published - 15 Aug 2020

Bibliographical note

Funding Information:
This study was supported by grants from the National Research Foundation of Korea (NRF) funded by the Korean government (MSIP) (No. 2012R1A3A2048814 for J.Y. and No. 2019R1A6A1A11044070 for S.P.). High-resolution mass spectrometer analysis was performed on the Synapt G2-HDMS mass spectrometer (Waters, Manchester, UK), which was operated on the MassLynx 4.1 software at KBSI (Korea Basic Science Institue, Ochang, Center of Research Equipment).

Publisher Copyright:
© 2020 Elsevier B.V.

Keywords

Desulfurization
Fluorescence imaging
Fluorescent probe
Hypochlorite
Sulfur-substituted coumarin

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10.1016/j.snb.2020.128213

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title = "A thiocoumarin-based turn-on fluorescent probe for hypochlorite detection and its application to live-cell imaging",

abstract = "A thiocoumarin-based turn-on fluorescence probe for the detection of hypochlorite anion (ClO−) was prepared and characterized. Coumarin dye (CZCN-O) exhibited intense fluorescence with good quantum yields (ΦPL = 0.98) in acetonitrile. Contrastingly, the fluorescence of thiocoumarin dye (CZCN-S) was almost completely quenched (ΦPL < 0.01) because of the efficient intersystem crossing from the emissive singlet excited state to the non-emissive triplet state. The addition of ClO− to the PBS buffer (pH = 7.4, containing 50% ACN) of thiocoumarin resulted in a remarkable fluorescence enhancement with an emission maximum at 486 nm, indicating the sensitive OFF–ON fluorescence sensing of ClO−. The calculated detection limit of ClO− in 50% aqueous ACN was 0.17 μM. An investigation of the sensing behavior to various analytes revealed that thiocoumarin dye had an excellent selectivity for ClO−. The recognition mechanism was attributed to the ClO−-induced conversion of thiocarbonyl coumarin into its oxo analogue through oxidative desulfurization. In particular, cell studies demonstrated that thiocoumarin dye could be used as an effective fluorescent probe for the detection of ClO− in living cells.",

keywords = "Desulfurization, Fluorescence imaging, Fluorescent probe, Hypochlorite, Sulfur-substituted coumarin",

author = "Nguyen, {Van Nghia} and Seonye Heo and Sangin Kim and Swamy, {K. M.K.} and Jeongsun Ha and Sungnam Park and Juyoung Yoon",

note = "Funding Information: This study was supported by grants from the National Research Foundation of Korea (NRF) funded by the Korean government (MSIP) (No. 2012R1A3A2048814 for J.Y. and No. 2019R1A6A1A11044070 for S.P.). High-resolution mass spectrometer analysis was performed on the Synapt G2-HDMS mass spectrometer (Waters, Manchester, UK), which was operated on the MassLynx 4.1 software at KBSI (Korea Basic Science Institue, Ochang, Center of Research Equipment). Publisher Copyright: {\textcopyright} 2020 Elsevier B.V.",

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doi = "10.1016/j.snb.2020.128213",

language = "English",

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T1 - A thiocoumarin-based turn-on fluorescent probe for hypochlorite detection and its application to live-cell imaging

AU - Nguyen, Van Nghia

AU - Heo, Seonye

AU - Kim, Sangin

AU - Swamy, K. M.K.

AU - Ha, Jeongsun

AU - Park, Sungnam

AU - Yoon, Juyoung

N1 - Funding Information: This study was supported by grants from the National Research Foundation of Korea (NRF) funded by the Korean government (MSIP) (No. 2012R1A3A2048814 for J.Y. and No. 2019R1A6A1A11044070 for S.P.). High-resolution mass spectrometer analysis was performed on the Synapt G2-HDMS mass spectrometer (Waters, Manchester, UK), which was operated on the MassLynx 4.1 software at KBSI (Korea Basic Science Institue, Ochang, Center of Research Equipment). Publisher Copyright: © 2020 Elsevier B.V.

PY - 2020/8/15

Y1 - 2020/8/15

N2 - A thiocoumarin-based turn-on fluorescence probe for the detection of hypochlorite anion (ClO−) was prepared and characterized. Coumarin dye (CZCN-O) exhibited intense fluorescence with good quantum yields (ΦPL = 0.98) in acetonitrile. Contrastingly, the fluorescence of thiocoumarin dye (CZCN-S) was almost completely quenched (ΦPL < 0.01) because of the efficient intersystem crossing from the emissive singlet excited state to the non-emissive triplet state. The addition of ClO− to the PBS buffer (pH = 7.4, containing 50% ACN) of thiocoumarin resulted in a remarkable fluorescence enhancement with an emission maximum at 486 nm, indicating the sensitive OFF–ON fluorescence sensing of ClO−. The calculated detection limit of ClO− in 50% aqueous ACN was 0.17 μM. An investigation of the sensing behavior to various analytes revealed that thiocoumarin dye had an excellent selectivity for ClO−. The recognition mechanism was attributed to the ClO−-induced conversion of thiocarbonyl coumarin into its oxo analogue through oxidative desulfurization. In particular, cell studies demonstrated that thiocoumarin dye could be used as an effective fluorescent probe for the detection of ClO− in living cells.

AB - A thiocoumarin-based turn-on fluorescence probe for the detection of hypochlorite anion (ClO−) was prepared and characterized. Coumarin dye (CZCN-O) exhibited intense fluorescence with good quantum yields (ΦPL = 0.98) in acetonitrile. Contrastingly, the fluorescence of thiocoumarin dye (CZCN-S) was almost completely quenched (ΦPL < 0.01) because of the efficient intersystem crossing from the emissive singlet excited state to the non-emissive triplet state. The addition of ClO− to the PBS buffer (pH = 7.4, containing 50% ACN) of thiocoumarin resulted in a remarkable fluorescence enhancement with an emission maximum at 486 nm, indicating the sensitive OFF–ON fluorescence sensing of ClO−. The calculated detection limit of ClO− in 50% aqueous ACN was 0.17 μM. An investigation of the sensing behavior to various analytes revealed that thiocoumarin dye had an excellent selectivity for ClO−. The recognition mechanism was attributed to the ClO−-induced conversion of thiocarbonyl coumarin into its oxo analogue through oxidative desulfurization. In particular, cell studies demonstrated that thiocoumarin dye could be used as an effective fluorescent probe for the detection of ClO− in living cells.

KW - Desulfurization

KW - Fluorescence imaging

KW - Fluorescent probe

KW - Hypochlorite

KW - Sulfur-substituted coumarin

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U2 - 10.1016/j.snb.2020.128213

DO - 10.1016/j.snb.2020.128213

M3 - Article

AN - SCOPUS:85084345702

SN - 0925-4005

VL - 317

JO - Sensors and Actuators, B: Chemical

JF - Sensors and Actuators, B: Chemical

M1 - 128213

ER -

A thiocoumarin-based turn-on fluorescent probe for hypochlorite detection and its application to live-cell imaging

Abstract

Bibliographical note

Keywords

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