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Synthesis, biological properties, and acid dissociation constant of novel naphthoquinone-triazole hybrids.
Nural, Yahya; Ozdemir, Sadin; Doluca, Osman; Demir, Bunyamin; Yalcin, Mustafa Serkan; Atabey, Hasan; Kanat, Beyza; Erat, Selma; Sari, Hayati; Seferoglu, Zeynel.
Afiliação
  • Nural Y; Department of Analytical Chemistry, Faculty of Pharmacy, Mersin University, Mersin 33169, Turkey; Advanced Technology, Research and Application Center, Mersin University, 33343 Mersin, Turkey. Electronic address: yahyanural@mersin.edu.tr.
  • Ozdemir S; Food Processing Programme, Technical Science Vocational School, Mersin University, Mersin 33343, Turkey.
  • Doluca O; Department of Biomedical Engineering, Izmir University of Economics, Izmir 35330, Turkey.
  • Demir B; Advanced Technology, Research and Application Center, Mersin University, 33343 Mersin, Turkey; Department of Mechanical Engineering, Faculty of Engineering, Mersin University, Mersin 33169, Turkey.
  • Yalcin MS; Department of Chemistry and Chemical Processing Technologies, Technical Science Vocational School, Mersin University, Mersin 33343, Turkey.
  • Atabey H; Mersin National Education Directorate, Department of Analytical Chemistry, Mersin, Turkey.
  • Kanat B; Department of Biomedical Engineering, Izmir University of Economics, Izmir 35330, Turkey.
  • Erat S; Advanced Technology, Research and Application Center, Mersin University, 33343 Mersin, Turkey; Department of Medical Services and Techniques, Vocational School of Technical Sciences, Mersin University, Mersin 33343, Turkey.
  • Sari H; Department of Chemistry, Faculty of Science and Arts, Tokat Gaziosmanpasa University, Tokat 60250, Turkey.
  • Seferoglu Z; Department of Chemistry, Faculty of Science, Gazi University, Ankara 06500, Turkey. Electronic address: znseferoglu@gazi.edu.tr.
Bioorg Chem ; 105: 104441, 2020 12.
Article em En | MEDLINE | ID: mdl-33181409
A series of novel 1,4-naphthoquinone-triazole hybrids, N-(3-amino-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-2-(4-R-1H-1,2,3-triazol-1-yl)acetamide, was synthesized by click chemistry in the presence of sodium ascorbate and copper(II) sulfate pentahydrate in 81-94% yield. Various biological properties of the synthesized compounds including DNA binding/cleavage, antioxidant, antibacterial and antifungal properties were evaluated. The DNA binding study was performed using dsDNA and G-quadruplex DNA. All of the compounds showed fluorescence increase in the presence of DNA, regardless of the structure. Up to 2.9 and 2.5 times fluorescence increase upon incubation with double stranded or G-quadruplex DNA was detected for 5f and 5g, respectively. The docking studies performed on dsDNA and G-quadruplex structures suggested compounds' mode of interactions were populated around the grooves. All of the compounds showed excellent DNA cleavage activity and 5e was almost degraded the plasmid DNA. The highest radical scavenging activity was obtained as 89.9% at 200 mg/L with 5d. However, the highest ferrous chelating activity was obtained as 68.1% at 200 mg/L with 5g. The compounds exhibited antimicrobial activity against Bacillus cereus, Legionella pneumophila subsp. pneumophila, Staphylococcus aureus, Pseudomonas aeruginosa, Escherichia coli and Enterococcus hirae as bacteria strains and Candida albicans and Candida tropicalis as microfungus strains. The compounds exhibited antibacterial and antifungal activity in the range of 4-128 µg/mL and 16-128 µg/mL, respectively. The best antimicrobial activity was obtained with 5d and 5e with a MIC value of 4 µg/mL against Enterococcus hirae. The acid dissociation constants (pKa) were determined potentiometrically in 20% (v/v) dimethyl sulfoxide-water hydro-organic solvent at an ionic background of 0.1 mol/L of NaCl, at 25 ± 0.1 °C. Five pKa values were obtained for each ligand.
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Triazóis / Naftoquinonas / Corantes Fluorescentes / Anti-Infecciosos Idioma: En Revista: Bioorg Chem Ano de publicação: 2020 Tipo de documento: Article

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Triazóis / Naftoquinonas / Corantes Fluorescentes / Anti-Infecciosos Idioma: En Revista: Bioorg Chem Ano de publicação: 2020 Tipo de documento: Article