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A Novel Fluorescent Probe for the Detection of Cyanide Ions in Solutions and Studies on Its Biophysical Interactions with ctDNA and Proteases

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Abstract

A new cationic indolium based styryl dye (Ci) as a fluorescent probe was synthesized and its anions selectivity/sensitivity properties/molecular interactions with protease enzymes (pepsin/trypsin) and ctDNA has been studied by spectroscopic and computational methods. The fluorescence measurements at different temperatures indicated that quenching mechanism of enzymes by Ci was static. ΔH and ΔS data pointed out electrostatic/hydrophobic interactions with pepsin, and also hydrogen bonds/van der Waals forces with trypsin of Ci. According to Förster’s non-radiative energy transfer, binding distances (r) were calculated as 3.53/3.27 nm for pepsin/trypsin. It was also investigated that groove binding is effective in interaction with ctDNA. The results were supported with molecular docking analyzes which have same tendency. Ci has been demonstrated hypsochromic effect with a decrease in polarity of solvents and it showed highly selective colorimetric and fluorometric sensing behavior for cyanide in organic solvent and in aqueous solution. 1H NMR titration was performed to examine the interaction mechanism between Ci and cyanide. The LOD values of cyanide ion were reported as 4.87 × 10–9 M and 9.70 × 10–7 M in DMSO and DMSO/H2O binary mixture, respectively. In addition, sensitivity of Ci as a chemosensor to cyanide was investigated in bitter almond samples.

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Acknowledgements

The numerical calculations reported were partially performed at TUBITAK ULAKBIM, High Performance and Grid Computing Center (TRUBA resources).

Funding

This study was partially supported by Hacettepe University Scientific Research Fund (Project number: FBA2017-12854).

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Authors and Affiliations

  1. Department of Chemistry, Hacettepe University, 06800, Ankara, Turkey

    Bensu Doyuran & Elmas Gökoğlu

  2. Department of Chemistry, Gazi University, 06560, Ankara, Turkey

    Ayman Zouitini, Ergin Keleş & Zeynel Seferoğlu

  3. Technological Dyes and Materials Application and Research Center (TEBAM), Gazi University, 06560, Ankara, Turkey

    Ergin Keleş, Nurgül Seferoğlu & Zeynel Seferoğlu

  4. Department of Chemistry, Gaziantep University, 27310, Gaziantep, Turkey

    Tugba Taskin-Tok

  5. Department of Bioinformatics and Computational Biology, Gaziantep University, 27310, Gaziantep, Turkey

    Tugba Taskin-Tok

  6. Department of Advanced Technology, Gazi University, 06560, Ankara, Turkey

    Nurgül Seferoğlu

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  1. Bensu Doyuran
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  2. Elmas Gökoğlu
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Contributions

Bensu Doyuran: Investigation, Writing-original draft. Elmas Gökoğlu: Data curation, Review & Editing. Ayman Zouitini: Synthesis, Investigation, Characterization. Ergin Keleş: Synthesis, Investigation, Characterization. Tugba Taskin-Tok: The theoretical calculations. Nurgül Seferoğlu: The theoretical calculations. Zeynel Seferoğlu: Data curation, Writing-original draft.

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Correspondence to Elmas Gökoğlu.

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Doyuran, B., Gökoğlu, E., Zouitini, A. et al. A Novel Fluorescent Probe for the Detection of Cyanide Ions in Solutions and Studies on Its Biophysical Interactions with ctDNA and Proteases. J Fluoresc 32, 2173–2188 (2022). https://doi.org/10.1007/s10895-022-03014-0

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