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Research Article Open access CC BY 4.0

Synthesis and Evaluation of Cytotoxicity and Antioxidant Properties of Polyfluorinated Phosphorus-containing 1,4-Benzoquinones and 1,4-Naphthoquinones

O. D. Zakharova, L. P. Ovchinnikova, S. I. Zhivetyeva, L. I. Goryunov, V. D. Shteingarts, E. V. Tretyakov, G. A. Nevinsky

Advances in Research · pp. 1–12 · Published 15 Mar 2016

10.9734/AIR/2016/24265

Abstract

Aim: Synthesis and analysis of antioxidant and antitumor properties of fluorinated phosphorus-containing derivatives of tetrafluoro-1,4-benzoquinone and hexafluoro-1,4-naphthoquinone. Methodology: All compounds were synthesized by amino- and phosphanodefluorination with corresponding amines and phosphanes. The cytotoxicity of these fluorinated benzoquinones and naphthoquinones was compared using human myeloma and human mammary adenocarcinoma as target tumors, as well as normal mouse fibroblasts cells. Their mutagenic and antioxidant properties in a Salmonella tester strain were also evaluated. Results: All the benzoquinones suppressed the growth of the two lines of tumor cells at approximately 3.2–90-fold higher concentrations than the naphthoquinones. In addition, the naphthoquinones were universal, while the benzoquinones were selective toward suppression of different tumor cells. At the same time, the benzoquinones and naphthoquinones demonstrated similar antioxidant properties, and protected bacterial cells against spontaneous and H2O2-dependent mutagenesis at comparable concentrations. Conclusion: All compounds are effective antioxidants and suppress the growth of tumor cells.

Polyfluorinated phosphorus-containing 1,4-benzoquinones and 1,4-naphthoquinones nucleophilic substitution antioxidant properties cytotoxicity

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Cited by 6

Metal‐Free C−C Bond Cleavage: One‐Pot Access to 1,4‐Benzoquinone‐linked N‐Formyl Amides/Sulfonamides/Carbamates using Oxone

P. V. Sri Ramya, Srinivas Angapelly, Bathini Nagendra Babu · Asian Journal of Organic Chemistry · 2017

Synthesis of novel phosphonium betaines and bis-betaines derived from hexafluoro-1,4-naphthoquinone

S.I. Zhivetyeva, E.V. Tretyakov, I.Yu. Bagryanskaya · Journal of Fluorine Chemistry · 2018

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