2. Academic Validation
  3. Hybrid compounds with two redox centres: modular synthesis of chalcogen-containing lapachones and studies on their antitumor activity

Hybrid compounds with two redox centres: modular synthesis of chalcogen-containing lapachones and studies on their antitumor activity

  • Eur J Med Chem. 2015 Aug 28:101:254-65. doi: 10.1016/j.ejmech.2015.06.044.
André A Vieira 1,  Igor R Brandão 2,  Wagner O Valença 3,  Carlos A de Simone 4,  Bruno C Cavalcanti 5,  Claudia Pessoa 6,  Teiliane R Carneiro 5,  Antonio L Braga 7,  Eufrânio N da Silva 8
Affiliations

Affiliations

  • 1 Departamento de Química, UFSC, 88040-900, Florianópolis, SC, Brazil; Instituto de Química, Departamento de Química Orgânica, UFBA, 40170-290, Salvador, BA, Brazil.
  • 2 Departamento de Química, UFSC, 88040-900, Florianópolis, SC, Brazil.
  • 3 Instituto de Ciências Exatas, Departamento de Química, UFMG, 31270-901, Belo Horizonte, MG, Brazil.
  • 4 Departamento de Física e Informática, Instituto de Física, USP, 13560-160, São Carlos, SP, Brazil.
  • 5 Departamento de Fisiologia e Farmacologia, UFC, 60430-270, Fortaleza, CE, Brazil.
  • 6 Departamento de Fisiologia e Farmacologia, UFC, 60430-270, Fortaleza, CE, Brazil; Fiocruz - Ceará, 60180-900, Fortaleza, CE, Brazil.
  • 7 Departamento de Química, UFSC, 88040-900, Florianópolis, SC, Brazil. Electronic address: braga.antonio@ufsc.br.
  • 8 Instituto de Ciências Exatas, Departamento de Química, UFMG, 31270-901, Belo Horizonte, MG, Brazil. Electronic address: eufranio@ufmg.br.
PMID: 26142490 DOI: 10.1016/j.ejmech.2015.06.044
Abstract

Chalcogen-containing β-lapachone derivatives were synthesized using a straightforward methodology and evaluated against several Cancer cell lines (leukaemia, human colon carcinoma, prostate, human metastatic prostate, ovarian, central nervous system and breast), showing, in some cases, IC50 values below 1 μM. The cytotoxic potential of the lapachones evaluated was also assayed using non-tumor cells: human peripheral blood mononuclear cells, two murine fibroblast lines (L929 and V79 cells) and MDCK (canine kidney epithelial cells). These compounds could provide promising new lead derivatives for Anticancer drug development. This manuscript reports important findings since few authors have described C-3 substituted β-lapachone with potent antitumor activity. The methodology employed allowed the preparation of the compounds from lapachol within a few minutes in a green approach.

Keywords

Anticancer; Antitumor; Quinone; Selenide; Selenium; Sulfur; β-lapachone.

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