Synthesis of amino acid-naphthoquinones and in vitro studies on cervical and breast cell lines Article uri icon

abstract

  • We performed an extensive analysis about the reaction conditions of the 1,4-Michael addition of amino acids to 1,4-naphthoquinone and substitution to 2,3-dichloronaphthoquinone, and a complete evaluation of stoichiometry, use of different bases, and the pH influence was performed. We were able to show that microwave-assisted synthesis is the best method for the synthesis of naphthoquinone-amino acid and chloride-naphthoquinone-amino acid derivatives with 79-91%25 and 78-91%25 yields, respectively. The cyclic voltammetry profiles showed that both series of naphthoquinone-amino acid derivatives mainly display one quasi-reversible redox reaction process. Interestingly, it was shown that naphthoquinone derivatives possess a selective antitumorigenic activity against cervix cancer cell lines and chloride-naphthoquinone-amino acid derivatives against breast cancer cell lines. Furthermore, the newly synthetized compounds with asparagine-naphthoquinones (3e and 4e) inhibited ∼85%25 of SiHa cell proliferation. These results show promising compounds for specific cervical and breast cancer treatment. © 2019 by the authors. Licensee MDPI, Basel, Switzerland.

publication date

  • 2019-01-01