Synthesis of Carbazole–Thiazole Dyes via One-Pot Tricomponent Reaction: Exploring Photophysical Properties, Tyrosinase Inhibition, and Molecular Docking

Krawczyk, Przemysław; Jędrzejewska, Beata; Cytarska, Joanna; Seklecka, Klaudia; Łączkowski, Krzysztof Z.

doi:10.3390/s24196368

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Synthesis of Carbazole–Thiazole Dyes via One-Pot Tricomponent Reaction: Exploring Photophysical Properties, Tyrosinase Inhibition, and Molecular Docking

by

Przemysław Krawczyk

^1,*

,

Beata Jędrzejewska

²

,

Joanna Cytarska

³

,

Klaudia Seklecka

³ and

Krzysztof Z. Łączkowski

³

¹

Department of Physical Chemistry, Faculty of Pharmacy, Collegium Medicum, Nicolaus Copernicus University, Kurpińskiego 5, 85-950 Bydgoszcz, Poland

²

Faculty of Chemical Technology and Engineering, Bydgoszcz University of Science and Technology, Seminaryjna 3, 85-326 Bydgoszcz, Poland

³

Department of Chemical Technology and Pharmaceuticals, Faculty of Pharmacy, Collegium Medicum, Nicolaus Copernicus University, Jurasza 2, 85-089 Bydgoszcz, Poland

^*

Author to whom correspondence should be addressed.

Sensors 2024, 24(19), 6368; https://doi.org/10.3390/s24196368 (registering DOI)

Submission received: 7 August 2024 / Revised: 25 September 2024 / Accepted: 29 September 2024 / Published: 30 September 2024

(This article belongs to the Special Issue Recent Advances in Fluorescence Sensing and Imaging)

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Abstract

Carbazole is an aromatic heterocyclic organic compound consisting of two fused benzene rings and a pyrrole ring and is a very valuable building structure for the design of many compounds for use in various fields of chemistry and medicine. This study presents three new carbazole-based thiazole derivatives that differ in the presence of a different halogen atom: chlorine, bromine, and fluorine. Experimental studies and quantum-chemical simulations show the effect of changing a halogen atom on the physicochemical, biological, and linear and nonlinear optical properties. We have also found that carbazoles C-Cl, C-Br, and C-F exhibit high tyrosinase inhibitory activity, with IC₅₀ values in the range of 68–105 µM with mixed mechanism of action. Finally, molecular docking to the active site of Concanavalin A (ConA) and bioavailability for all compounds were evaluated.

Keywords: carbazole derivatives; optical functional materials; linear optical properties; NLO properties; tyrosinase; toxicology; bioimaging; protein affinity; TD-DFT method

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MDPI and ACS Style

Krawczyk, P.; Jędrzejewska, B.; Cytarska, J.; Seklecka, K.; Łączkowski, K.Z. Synthesis of Carbazole–Thiazole Dyes via One-Pot Tricomponent Reaction: Exploring Photophysical Properties, Tyrosinase Inhibition, and Molecular Docking. Sensors 2024, 24, 6368. https://doi.org/10.3390/s24196368

AMA Style

Krawczyk P, Jędrzejewska B, Cytarska J, Seklecka K, Łączkowski KZ. Synthesis of Carbazole–Thiazole Dyes via One-Pot Tricomponent Reaction: Exploring Photophysical Properties, Tyrosinase Inhibition, and Molecular Docking. Sensors. 2024; 24(19):6368. https://doi.org/10.3390/s24196368

Chicago/Turabian Style

Krawczyk, Przemysław, Beata Jędrzejewska, Joanna Cytarska, Klaudia Seklecka, and Krzysztof Z. Łączkowski. 2024. "Synthesis of Carbazole–Thiazole Dyes via One-Pot Tricomponent Reaction: Exploring Photophysical Properties, Tyrosinase Inhibition, and Molecular Docking" Sensors 24, no. 19: 6368. https://doi.org/10.3390/s24196368

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Synthesis of Carbazole–Thiazole Dyes via One-Pot Tricomponent Reaction: Exploring Photophysical Properties, Tyrosinase Inhibition, and Molecular Docking

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