Naphthoquinone-Based Colorimetric and Fluorometric Dual-Channel Chemosensor for the Detection of Fe2+ Ion and Its Application in Bio-Imaging of Live Cells and Zebrafish

Palanisamy Ravichandiran; Anna Boguszewska-Czubara; Maciej Masłyk; Antony Paulraj Bella; Sivakumar Allur Subramaniyan; Princy Merlin Johnson; Kwan Seob Shim; Hwan Gyu Kim; Dong Jin Yoo

doi:10.1021/acssuschemeng.9b03822

Naphthoquinone-Based Colorimetric and Fluorometric Dual-Channel Chemosensor for the Detection of Fe²⁺ Ion and Its Application in Bio-Imaging of Live Cells and Zebrafish

Palanisamy Ravichandiran
, Anna Boguszewska-Czubara
, Maciej Masłyk
, Antony Paulraj Bella
, Sivakumar Allur Subramaniyan
, Princy Merlin Johnson
, Kwan Seob Shim
, Hwan Gyu Kim
, Dong Jin Yoo^*

^*Corresponding author for this work

Jeonbuk National University
Medical University of Lublin
John Paul II Catholic University of Lublin
Bharathidasan University

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

93 Scopus citations

Abstract

A new naphthoquinone-based chemosensor 2-((3-hydroxyphenyl)amino)-3-(phenylthio)naphthalene-1,4-dione (2HPN) was successfully synthesized for the selective detection of Fe²⁺. The sensing property of the chemosensor 2HPN was evaluated in aqueous acetonitrile (CH₃CN) medium by a fluorescence emission method. The metal-binding studies of the ligand 2HPN showed selective "turn-on" fluorescence responses for Fe²⁺ (K_a = 1.0 × 10⁶ M^-1). The detection limit of the ligand 2HPN to Fe²⁺ was calculated to be 0.272 μM, which is lower than the World Health Organization recommendation (0.3 mg/L) in drinking water. The most significant feature of the obtained chemosensor 2HPN is its ability to sense Fe²⁺ via naked-eye detection over various metal ions. The chemosensor operated via the intramolecular charge transfer effect, which was supported by Fourier transform infrared analysis, NMR titrations, and quantum chemical calculations. The efficiency of the chemosensor 2HPN as a biomarker for Fe²⁺ was successfully proven by imaging in human cancer cells and zebrafish. Thus, the chemosensor 2HPN could be a useful biomarker for the precise sensing of Fe²⁺ in clinical diagnosis.

Original language	English
Pages (from-to)	17210-17219
Number of pages	10
Journal	ACS Sustainable Chemistry and Engineering
Volume	7
Issue number	20
DOIs	https://doi.org/10.1021/acssuschemeng.9b03822
State	Published - 2019.10.21

UN SDGs

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

SDG 3 Good Health and Well-being

Keywords

breast cancer cells
fluorescence sensor
metal binding
quinone
turn-on

Quacquarelli Symonds(QS) Subject Topics

Environmental Sciences
Engineering - Electrical & Electronic
Engineering - Petroleum
Engineering - Chemical
Chemistry

Access to Document

10.1021/acssuschemeng.9b03822

Cite this

Ravichandiran, P., Boguszewska-Czubara, A., Masłyk, M., Bella, A. P., Subramaniyan, S. A., Johnson, P. M., Shim, K. S., Kim, H. G., & Yoo, D. J. (2019). Naphthoquinone-Based Colorimetric and Fluorometric Dual-Channel Chemosensor for the Detection of Fe²⁺ Ion and Its Application in Bio-Imaging of Live Cells and Zebrafish. ACS Sustainable Chemistry and Engineering, 7(20), 17210-17219. https://doi.org/10.1021/acssuschemeng.9b03822

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title = "Naphthoquinone-Based Colorimetric and Fluorometric Dual-Channel Chemosensor for the Detection of Fe2+ Ion and Its Application in Bio-Imaging of Live Cells and Zebrafish",

abstract = "A new naphthoquinone-based chemosensor 2-((3-hydroxyphenyl)amino)-3-(phenylthio)naphthalene-1,4-dione (2HPN) was successfully synthesized for the selective detection of Fe2+. The sensing property of the chemosensor 2HPN was evaluated in aqueous acetonitrile (CH3CN) medium by a fluorescence emission method. The metal-binding studies of the ligand 2HPN showed selective {"}turn-on{"} fluorescence responses for Fe2+ (Ka = 1.0 × 106 M-1). The detection limit of the ligand 2HPN to Fe2+ was calculated to be 0.272 μM, which is lower than the World Health Organization recommendation (0.3 mg/L) in drinking water. The most significant feature of the obtained chemosensor 2HPN is its ability to sense Fe2+ via naked-eye detection over various metal ions. The chemosensor operated via the intramolecular charge transfer effect, which was supported by Fourier transform infrared analysis, NMR titrations, and quantum chemical calculations. The efficiency of the chemosensor 2HPN as a biomarker for Fe2+ was successfully proven by imaging in human cancer cells and zebrafish. Thus, the chemosensor 2HPN could be a useful biomarker for the precise sensing of Fe2+ in clinical diagnosis.",

keywords = "breast cancer cells, fluorescence sensor, metal binding, quinone, turn-on",

author = "Palanisamy Ravichandiran and Anna Boguszewska-Czubara and Maciej Mas{\l}yk and Bella, \{Antony Paulraj\} and Subramaniyan, \{Sivakumar Allur\} and Johnson, \{Princy Merlin\} and Shim, \{Kwan Seob\} and Kim, \{Hwan Gyu\} and Yoo, \{Dong Jin\}",

note = "Publisher Copyright: Copyright {\textcopyright} 2019 American Chemical Society.",

year = "2019",

month = oct,

day = "21",

doi = "10.1021/acssuschemeng.9b03822",

language = "English",

volume = "7",

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Ravichandiran, P, Boguszewska-Czubara, A, Masłyk, M, Bella, AP, Subramaniyan, SA, Johnson, PM, Shim, KS , Kim, HG & Yoo, DJ 2019, 'Naphthoquinone-Based Colorimetric and Fluorometric Dual-Channel Chemosensor for the Detection of Fe²⁺ Ion and Its Application in Bio-Imaging of Live Cells and Zebrafish', ACS Sustainable Chemistry and Engineering, vol. 7, no. 20, pp. 17210-17219. https://doi.org/10.1021/acssuschemeng.9b03822

Naphthoquinone-Based Colorimetric and Fluorometric Dual-Channel Chemosensor for the Detection of Fe²⁺ Ion and Its Application in Bio-Imaging of Live Cells and Zebrafish. / Ravichandiran, Palanisamy; Boguszewska-Czubara, Anna; Masłyk, Maciej et al.
In: ACS Sustainable Chemistry and Engineering, Vol. 7, No. 20, 21.10.2019, p. 17210-17219.

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

TY - JOUR

T1 - Naphthoquinone-Based Colorimetric and Fluorometric Dual-Channel Chemosensor for the Detection of Fe2+ Ion and Its Application in Bio-Imaging of Live Cells and Zebrafish

AU - Ravichandiran, Palanisamy

AU - Boguszewska-Czubara, Anna

AU - Masłyk, Maciej

AU - Bella, Antony Paulraj

AU - Subramaniyan, Sivakumar Allur

AU - Johnson, Princy Merlin

AU - Shim, Kwan Seob

AU - Kim, Hwan Gyu

AU - Yoo, Dong Jin

PY - 2019/10/21

Y1 - 2019/10/21

N2 - A new naphthoquinone-based chemosensor 2-((3-hydroxyphenyl)amino)-3-(phenylthio)naphthalene-1,4-dione (2HPN) was successfully synthesized for the selective detection of Fe2+. The sensing property of the chemosensor 2HPN was evaluated in aqueous acetonitrile (CH3CN) medium by a fluorescence emission method. The metal-binding studies of the ligand 2HPN showed selective "turn-on" fluorescence responses for Fe2+ (Ka = 1.0 × 106 M-1). The detection limit of the ligand 2HPN to Fe2+ was calculated to be 0.272 μM, which is lower than the World Health Organization recommendation (0.3 mg/L) in drinking water. The most significant feature of the obtained chemosensor 2HPN is its ability to sense Fe2+ via naked-eye detection over various metal ions. The chemosensor operated via the intramolecular charge transfer effect, which was supported by Fourier transform infrared analysis, NMR titrations, and quantum chemical calculations. The efficiency of the chemosensor 2HPN as a biomarker for Fe2+ was successfully proven by imaging in human cancer cells and zebrafish. Thus, the chemosensor 2HPN could be a useful biomarker for the precise sensing of Fe2+ in clinical diagnosis.

AB - A new naphthoquinone-based chemosensor 2-((3-hydroxyphenyl)amino)-3-(phenylthio)naphthalene-1,4-dione (2HPN) was successfully synthesized for the selective detection of Fe2+. The sensing property of the chemosensor 2HPN was evaluated in aqueous acetonitrile (CH3CN) medium by a fluorescence emission method. The metal-binding studies of the ligand 2HPN showed selective "turn-on" fluorescence responses for Fe2+ (Ka = 1.0 × 106 M-1). The detection limit of the ligand 2HPN to Fe2+ was calculated to be 0.272 μM, which is lower than the World Health Organization recommendation (0.3 mg/L) in drinking water. The most significant feature of the obtained chemosensor 2HPN is its ability to sense Fe2+ via naked-eye detection over various metal ions. The chemosensor operated via the intramolecular charge transfer effect, which was supported by Fourier transform infrared analysis, NMR titrations, and quantum chemical calculations. The efficiency of the chemosensor 2HPN as a biomarker for Fe2+ was successfully proven by imaging in human cancer cells and zebrafish. Thus, the chemosensor 2HPN could be a useful biomarker for the precise sensing of Fe2+ in clinical diagnosis.

KW - breast cancer cells

KW - fluorescence sensor

KW - metal binding

KW - quinone

KW - turn-on

UR - https://www.scopus.com/pages/publications/85073155647

U2 - 10.1021/acssuschemeng.9b03822

DO - 10.1021/acssuschemeng.9b03822

M3 - Journal article

AN - SCOPUS:85073155647

SN - 2168-0485

VL - 7

SP - 17210

EP - 17219

JO - ACS Sustainable Chemistry and Engineering

JF - ACS Sustainable Chemistry and Engineering

IS - 20

ER -

Ravichandiran P, Boguszewska-Czubara A, Masłyk M, Bella AP, Subramaniyan SA, Johnson PM et al. Naphthoquinone-Based Colorimetric and Fluorometric Dual-Channel Chemosensor for the Detection of Fe²⁺ Ion and Its Application in Bio-Imaging of Live Cells and Zebrafish. ACS Sustainable Chemistry and Engineering. 2019 Oct 21;7(20):17210-17219. doi: 10.1021/acssuschemeng.9b03822