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Evaluation of the Binding Properties of A New Phenylurea Appended Carbazole Compound to Pepsin/Trypsin by Computational and Multi-Spectral Analysis

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Abstract

A novel carbazole compound, named 1-(9-ethyl-9H-carbazol-3-yl)-3-phenylurea (Cpu) was synthesized and its binding properties with protease enzymes (pepsin and trypsin) has been examined by steady-state fluorescence measurements, UV/vis absorption, infrared (FT-IR) and circular dicroism (CD) spectroscopies and also computational methods. The fluorescence experimental results indicated that the quenching mechanism of enzyme by Cpu is static process. The thermodynamic parameters (both negative ΔH/ΔS) and molecular docking results suggested that the binding of Cpu to pepsin/trypsin were driven by hydrogen bonds and van der Waals forces. Based on Förster’s theory, the binding distance (r) between pepsin/trypsin and Cpu was calculated to be 3.072/2.784 nm, which implies that non-radiative energy transfer occurs from enzyme to Cpu. Furthermore, absorption, CD, and FT-IR spectral analysis provided an evidence that the presence of Cpu induced notable changes in the secondary structures and microenvironmental of both pepsin and trypsin, supporting its significant influence on these enzymes.

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Data Availability

All data generated or analysed during this study are included in this published article.

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Funding

This work was partially supported by Hacettepe University Scientific Research Fund (BAP Project ID: FBA2017-12854).

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Authors and Affiliations

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

    Elmas Gökoğlu, Bensu Doyuran & Gülşah Özen

  2. Department of Chemistry, Gebze Technical University, 41400, Kocaeli, Turkey

    Halil Duyar

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

    Tugba Taskin-Tok

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

    Tugba Taskin-Tok

  5. Department of Chemistry, Gazi University, 06800, Ankara, Turkey

    Zeynel Seferoğlu

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  1. Elmas Gökoğlu
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  2. Bensu Doyuran
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Contributions

Elmas Gökoğlu: Data curation, Review & Editing. Bensu Doyuran: Investigation, spectroscopic studies, writing-original draft. Gülşah Özen: Investigation, spectroscopic studies. Halil Duyar: Investigation, synthesis and spectral characterizations. Tugba Taskin-Tok: The theoretical calculations. Zeynel Seferoğlu: Data curation.

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Correspondence to Elmas Gökoğlu.

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Gökoğlu, E., Doyuran, B., Özen, G. et al. Evaluation of the Binding Properties of A New Phenylurea Appended Carbazole Compound to Pepsin/Trypsin by Computational and Multi-Spectral Analysis. J Fluoresc (2023). https://doi.org/10.1007/s10895-023-03451-5

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