Volume 84, Issue 3 p. 252-259
Full Paper

A Near-Infrared Fluorescence Chemosensor Based on Isothiocyanate-Aza-BODIPY for Cyanide Detection at the Parts per Billion Level: Applications in Buffer Media and Living Cell Imaging

Pornthip Piyanuch

Pornthip Piyanuch

Department of Chemistry, Faculty of Science, Silpakorn University, Nakhon Pathom, 73000 Thailand

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Prof. Jitnapa Sirirak

Prof. Jitnapa Sirirak

Department of Chemistry, Faculty of Science, Silpakorn University, Nakhon Pathom, 73000 Thailand

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Dr. Anyanee Kamkaew

Dr. Anyanee Kamkaew

School of Chemistry, Institute of Science, Suranaree University of Technology, Nakhon Ratchasima, 30000 Thailand

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Dr. Oratai Weeranantanapan

Dr. Oratai Weeranantanapan

School of Preclinical Science, Institute of Science, Suranaree University of Technology, Nakhon Ratchasima, 30000 Thailand

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Prof. Vinich Promarak

Prof. Vinich Promarak

School of Molecular Science and Engineering, Vidyasirimedhi Institute of Science and Technology Wangchan, Rayong, 21210 Thailand

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Prof. Kevin Burgess

Prof. Kevin Burgess

Department of Chemistry, Texas A & M University College Station, TX 77842 USA

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Prof. Nantanit Wanichacheva

Corresponding Author

Prof. Nantanit Wanichacheva

Department of Chemistry, Faculty of Science, Silpakorn University, Nakhon Pathom, 73000 Thailand

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First published: 11 January 2019
Citations: 20

Graphical Abstract

Green light given: A novel near-infrared sensor contains an aza-BODIPY core with two isothiocyanate groups for CN sensing and provides both near-infrared (NIR) fluorometric and colorimetric responses with a low detection limit of 19 ppb in buffer media. The sensor was also utilized as an intracellular CN sensor with low cytotoxicity.

Abstract

A near-infrared chemodosimeter based on an aza-BODIPY dye was designed and synthesized. The sensor contains isothiocyanate groups for cyanide ion sensing. The sensing function was illustrated via the fluorescence changes in near-infrared frequencies as well as chromogenic changes which could be easily visualized with a detection limit of 19 ppb. The sensor provides high selectivity to CN and discriminates other anions such as CH3COO, HPO4, HSO4, ClO3, CO32−, SO42−, NO3, Cl, F, Br, I, and phenylalanine (Phe) in 50 % PBS buffer/acetonitrile at physiological pH. The potential of the sensor for CN detection in both aqueous buffer solutions and living cells imaging was demonstrated.

Conflict of interest

The authors declare no conflict of interest.