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  3. On the synthesis of quinone-based BODIPY hybrids: New insights on antitumor activity and mechanism of action in cancer cells

On the synthesis of quinone-based BODIPY hybrids: New insights on antitumor activity and mechanism of action in cancer cells

  • Bioorg Med Chem Lett. 2017 Sep 15;27(18):4446-4456. doi: 10.1016/j.bmcl.2017.08.007.
Talita B Gontijo 1,  Rossimiriam P de Freitas 1,  Flavio S Emery 2,  Leandro F Pedrosa 3,  José B Vieira Neto 4,  Bruno C Cavalcanti 4,  Claudia Pessoa 5,  Aaron King 6,  Fabio de Moliner 6,  Marc Vendrell 7,  Eufrânio N da Silva Júnior 8
Affiliations

Affiliations

  • 1 Institute of Exact Sciences, Department of Chemistry, Federal University of Minas Gerais, Belo Horizonte 31270-901, MG, Brazil.
  • 2 Faculty of Pharmaceutical Sciences at Ribeirao Preto, University of São Paulo, CEP 14040-903, Ribeirão Preto, SP, Brazil.
  • 3 Institute of Exact Sciences, Department of Chemistry, Fluminense Federal University, CEP 27213-145, Volta Redonda, RJ, Brazil.
  • 4 Department of Physiology and Pharmacology, Federal University of Ceará, CEP 60180-900 Fortaleza, CE, Brazil.
  • 5 Department of Physiology and Pharmacology, Federal University of Ceará, CEP 60180-900 Fortaleza, CE, Brazil; Fiocruz-Ceará, CEP 60180-900 Fortaleza, CE, Brazil.
  • 6 MRC/UoE Centre for Inflammation Research, The University of Edinburgh, EH16 4TJ Edinburgh, United Kingdom.
  • 7 MRC/UoE Centre for Inflammation Research, The University of Edinburgh, EH16 4TJ Edinburgh, United Kingdom. Electronic address: mvendrel@staffmail.ed.ac.uk.
  • 8 Institute of Exact Sciences, Department of Chemistry, Federal University of Minas Gerais, Belo Horizonte 31270-901, MG, Brazil. Electronic address: eufranio@ufmg.br.
PMID: 28818447 DOI: 10.1016/j.bmcl.2017.08.007
Abstract

Fluorescent quinone-based BODIPY hybrids were synthesised and characterised by NMR analysis and mass spectrometry. We measured their cytotoxic activity against Cancer and normal cell lines, performed mechanistic studies by lipid peroxidation and determination of reduced (GSH) and oxidized (GSSG) glutathione, and imaged their subcellular localisation by confocal microscopy. Cell imaging experiments indicated that nor-β-lapachone-based BODIPY derivatives might preferentially localise in the lysosomes of Cancer cells. These results assert the potential of hybrid quinone-BODIPY derivatives as promising prototypes in the search of new potent lapachone antitumor drugs.

Keywords

BODIPY; Cancer; Lapachone; Quinone; Subcellular localization.

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