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Molecules 2014, 19(9), 13188-13199; doi:10.3390/molecules190913188

Synthesis and Cytotoxic Evaluation of a Series of 2-Amino-Naphthoquinones against Human Cancer Cells

1
Departamento de Morfologia e Fisiologia Animal-UFRPE, Universidade Federal Rural de Pernambuco-UFRPE, Rua Dom Manoel de, s/n, Dois Irmãos, Recife, Pernambuco PE 52171-900, Brazil
2
Departamento de Ciencias Moleculares-UFRPE, Universidade Federal Rural de Pernambuco-UFRPE, Rua Dom Manoel de Medeiros, s/n, Dois Irmãos, Recife, Pernambuco PE 52171-900, Brazil
3
Departamento de Farmacologia e Fisiologia, Universidade Federal do Ceará-UFC, Rua Coronel Nunes de Melo, 1127, Rodolfo Teófilo, CP 3157, Fortaleza, Ceará CE 60430-270, Brazil
*
Authors to whom correspondence should be addressed.
Received: 9 June 2014 / Revised: 22 August 2014 / Accepted: 22 August 2014 / Published: 26 August 2014
(This article belongs to the Section Medicinal Chemistry)
View Full-Text   |   Download PDF [765 KB, uploaded 26 August 2014]   |  

Abstract

The cytotoxicity of a series of aminonaphthoquinones resulting from the reaction of suitable aminoacids with 1,4-naphthoquinone was assayed against SF-295 (glioblastoma), MDAMB-435 (breast), HCT-8 (colon), HCT-116 (colon), HL-60 (leukemia), OVCAR-8 (ovarian), NCI-H358M (bronchoalveolar lung carcinoma) and PC3-M (prostate) cancer cells and also against PBMC (peripheral blood mononuclear cells). The results demonstrated that all the synthetic aminonaphthoquinones had relevant cytotoxic activity against all human cancer lines used in this experiment. Five of the compounds showed high cytotoxicity and selectivity against all cancer cell lines tested (IC50 = 0.49 to 3.89 µg·mL−1). The title compounds were less toxic to PBMC, since IC50 was 1.5 to eighteen times higher (IC50 = 5.51 to 17.61 µg·mL−1) than values shown by tumour cell lines. The mechanism of cell growth inhibition and structure–activity relationships remains as a target for future investigations. View Full-Text
Keywords: naphthoquinones; aminoacid naphthoquinones; cytotoxicity; cancer cells naphthoquinones; aminoacid naphthoquinones; cytotoxicity; cancer cells
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This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

de Moraes, T.A.P.; Filha, M.J.S.; Camara, C.A.; Silva, T.M.S.; Soares, B.M.; Bomfim, I.S.; Pessoa, C.; Ximenes, G.C.; Silva, V.A., Jr. Synthesis and Cytotoxic Evaluation of a Series of 2-Amino-Naphthoquinones against Human Cancer Cells. Molecules 2014, 19, 13188-13199.

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