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

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.

• Authors: Talita B Gontijo, Rossimiriam P de Freitas, Flavio S Emery, Leandro F Pedrosa, José B Vieira Neto, Bruno C Cavalcanti, Claudia Pessoa, Aaron King, Fabio de Moliner, Marc Vendrell, Eufrânio N da Silva Júnior
• Journal: Bioorganic & medicinal chemistry letters (Bioorg Med Chem Lett) Vol. 27 Issue 18 Pg. 4446-4456 (09 15 2017) ISSN: 1464-3405 [Electronic] England
• PMID: 28818447 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
• Copyright: Copyright © 2017 Elsevier Ltd. All rights reserved.

Chemical References

• 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
• Antineoplastic Agents
• Benzoquinones
• Boron Compounds
• quinone

Topics

• Antineoplastic Agents (chemical synthesis, chemistry, pharmacology)
• Benzoquinones (chemical synthesis, chemistry, pharmacology)
• Boron Compounds (chemistry, pharmacology)
• Cell Line, Tumor
• Cell Proliferation (drug effects)
• Dose-Response Relationship, Drug
• Drug Screening Assays, Antitumor
• Humans
• Molecular Structure
• Structure-Activity Relationship