Design, Synthesis, Biological Evaluation, and Antioxidant and Cytotoxic Activity of Heteroatom-Substituted 1,4-Naphtho- and Benzoquinones

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  • Deniz Nahide Gülşah
    Division of Organic Chemistry, Department of Chemistry, Engineering Faculty, Istanbul University
  • Ibis Cemil
    Division of Organic Chemistry, Department of Chemistry, Engineering Faculty, Istanbul University
  • Gokmen Zeliha
    Division of Organic Chemistry, Department of Chemistry, Engineering Faculty, Istanbul University
  • Stasevych Maryna
    Institute of Chemistry and Chemical Technology, Department of Technology of Biologically Active Substances, Pharmacy and Biotechnology, Lviv Polytechnic National University
  • Novikov Volodymyr
    Institute of Chemistry and Chemical Technology, Department of Technology of Biologically Active Substances, Pharmacy and Biotechnology, Lviv Polytechnic National University
  • Komarovska-Porokhnyavets Olena
    Institute of Chemistry and Chemical Technology, Department of Technology of Biologically Active Substances, Pharmacy and Biotechnology, Lviv Polytechnic National University
  • Ozyurek Mustafa
    Division of Analytical Chemistry, Department of Chemistry, Engineering Faculty, Istanbul University
  • Guclu Kubilay
    Division of Analytical Chemistry, Department of Chemistry, Engineering Faculty, Istanbul University
  • Karakas Didem
    Department of Biology, Faculty of Arts and Sciences, Uludag University
  • Ulukaya Engin
    Department of Clinical Biochemistry, Faculty of Medicine, Uludag University

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In the present paper, we report the synthesis, characterization, and biological evaluation as antifungal, antibacterial, antioxidant, and cytotoxic/anticancer agents of N-, S-, O-substituted-1,4-naphtho- and 2,5-bis(amino-substituted)-1,4-benzoquinone derivatives. In the synthesized compounds, antimicrobial activity at low concentrations against Escherichia coli B-906, Staphylococcus aureus 209-P, and Mycobacterium luteum B-917 bacteria and Candida tenuis VKM Y-70 and Aspergillus niger F-1119 fungi in comparison with controls was identified. 2-(N-Diphenylmethylpiperazin-1-yl)-3-chloro-1,4-naphthoquinone 9a was the most potent, with a minimum inhibitory concentration value of 3.9 µg/mL against test culture M. luteum. The synthesized compounds were screened for their antioxidant capacity using the cupric-reducing antioxidant capacity (CUPRAC) method. 2,2′-[1-(2-Aminoethyl)piperazin-1-yl]-3,3′-dichloro-bis(1,4-naphthoquinone) 10 showed the highest antioxidant capacity, with a 0.455 CUPRAC-trolox equivalent antioxidant capacity (TEAC) coefficient. Other parameters of antioxidant activity (scavenging effects on OH·, O2·－, and H2O2) of these compounds were also determined. The cytotoxic activity of the compounds was investigated by employing the sulforhodamine B cell viability assay against A549 (lung), MCF-7 (breast), DU145 (prostate), and HT-29 (colon) cancer cell lines. Compound 10 exhibited the most powerful cytotoxic activity at a concentration of 20 µM against all cell lines. In addition to the strongest antioxidant activity of compound 10, it also had lowest IC50 values (<3 µM), warranting further in vivo studies due to its anticancer activity.

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