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Some Azo Dyes Containing Uracil: DFT Study and Antiparasitic Activity for Leishmania promastigotes and Trichomonas vaginalis

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Abstract

In this study 6-aminopyrimidine-2,4,5(3)-trione-5-[(phenyl)hydrazone] (dye 1) and 6-aminopyrimidine-2,4,5(3)-trione-5-[(4-methoxyphenyl)hydrazone] (dye 2) were resynthesized by method given in the literature and confirmed structurally using Fourier transform infrared (FT-IR) and proton nuclear magnetic resonance (1H NMR) spectroscopic methods. For the first time, for dyes 1 and 2, both theoretical studies were performed and investigated in terms of antiparasitic activity. The density functional theory (DFT) calculations for possible tautomeric forms of dyes 1 and 2 were carried out by using DFT/B3LYP/6-311++G (d,p) method. Thus, optimized geometries, IR and 1H NMR spectral data were obtained and compared with experimental ones. Therefore, the most possible tautomeric forms were determined for dyes 1 and 2. Results show that in the gas phase and dimethyl sulfoxide (DMSO) solvent for both dyes, the amine-diketo-hydrazone forms (T-I-H) are the lowest energy and therefore the most stable form. Leishmania spp. and Trichomonas vaginalis are flagellated protozoan parasites that cause parasitic infections in humans. In vitro antiparasitic activity of dye 1 and dye 2 against Trichomonas vaginalis trophozoites, Leishmania tropica, Leishmania major, and Leishmania infantum promastigotes were determined for the first time. The in vitro antileishmanial and antitrichomonal activity was performed by microdilution method. Amphotericin B and Metronidazole were used for Leishmania spp. promastigotes, and T. vaginalis trophozoites, as a control drug, respectively. The Minimum Lethal Concentration (MLC) was determined and compared with the control.

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ACKNOWLEDGMENTS

The numerical calculations reported in this paper werefully performed at TUBITAK ULAKBIM, High Performance and Grid Computing Center (TRUBA resources).

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Authors and Affiliations

  1. Department of Medical Microbiology, Faculty of Medicine, Giresun University, 28100, Giresun, Turkey

    Şahin Direkel

  2. Graduate School of Natural and Applied Sciences, Advanced Technologies, Gazi University, 06500, Ankara, Turkey

    Nevin Süleymanoğlu

  3. Department of Chemistry, Faculty of Sciences, Aydın Adnan Menderes University, 09100, Aydın, Turkey

    Fatih Eyduran

  4. Department of Parasitology, Faculty of Medicine, Aydın Adnan Menderes University, 09010, Aydın, Turkey

    Evren Tileklioğlu & Hatice Ertabaklar

  5. Department of Parasitology, Faculty of Medicine, Ordu University, 52200, Ordu, Turkey

    Ülkü Karaman

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  1. Şahin Direkel
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Contributions

Author ŞD—methodology, antileishmanial activity study. Author NS—methodology, DFT study. Author FE—sample synthesis, FTIR, and NMR spectroscopy. Authors ET, HE, and ÜK—antitrichomonal activity study. All authors contributed to manuscript preparation (writing and editing). All authors participated in the discussions.

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This work was supported by ongoing institutional funding. No additional grants to carry out or direct thisparticular research were obtained.

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Correspondence to Şahin Direkel.

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The data that support the findings of this study are available from the corresponding author upon reasonable request. This article does not contain any studies involving animals or human participants performed by any of the authors. Informed consent was not required for this article. No conflict of interest was declared by the authors.

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Direkel, Ş., Süleymanoğlu, N., Eyduran, F. et al. Some Azo Dyes Containing Uracil: DFT Study and Antiparasitic Activity for Leishmania promastigotes and Trichomonas vaginalis. Russ J Bioorg Chem 49, 1408–1421 (2023). https://doi.org/10.1134/S1068162023060213

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