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Synthesis of Amino Acid-Naphthoquinones and In Vitro Studies on Cervical and Breast Cell Lines.


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% and 78-91% 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% of SiHa cell proliferation. These results show promising compounds for specific cervical and breast cancer treatment.

SUBMITTER: Rivera-Avalos E 

PROVIDER: S-EPMC6930466 | biostudies-literature | 2019 Nov

REPOSITORIES: biostudies-literature

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Synthesis of Amino Acid-Naphthoquinones and In Vitro Studies on Cervical and Breast Cell Lines.

Rivera-Ávalos Ernesto E   de Loera Denisse D   Araujo-Huitrado Jorge Gustavo JG   Escalante-García Ismailia Leilani IL   Muñoz-Sánchez Miguel Antonio MA   Hernández Hiram H   López Jesús Adrián JA   López Lluvia L  

Molecules (Basel, Switzerland) 20191125 23


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% and 78-91% yields, respectively. T  ...[more]

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