Design, synthesis, biological evaluation, and antioxidant and cytotoxic activity of heteroatom-substituted 1,4-naphtho- and benzoquinones
Loading...
Date
2015-12
Authors
Deniz, Nahide Gülşah
İbiş, Cemil
Gökmen, Zeliha
Stasevych, Maryna
Novikov, Volodymyr
Porokhnyavets, Olena Komarovska
Özyürek, Mustafa
Güçlü, Kubilay
Journal Title
Journal ISSN
Volume Title
Publisher
Pharmaceutical Soc Japan
Abstract
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 tennis 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, mu g/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 center dot, O-2(center dot-), 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 mu m against all cell lines. In addition to the strongest antioxidant activity of compound 10, it also had lowest IC50 values (<3 mu m), warranting further in vivo studies due to its anticancer activity.
Description
Keywords
Antimicrobial activity, Antioxidant activity, Cupric-reducing antioxidant capacity method, Cytotoxicity, Quinone, Reactive oxygen species-scavenging activity, Radical radical scavenging activity, Naphthoquinone derivatives, Antifungal activity, Spectral properties, Anticancer agents, Mechanisms, Inhibitors, Qsar, Pharmacology & pharmacy, Chemistry
Citation
Deniz, N. G. vd. (2015). "Design, synthesis, biological evaluation, and antioxidant and cytotoxic activity of heteroatom-substituted 1,4-naphtho- and benzoquinones". Chemical and Pharmaceutical Bulletin, 63(12), 1029-1039.