On the Synthesis of Quinone-based BODIPY Hybrids: New Insights on Antitumor Activity and Mechanism of Action in Cancer Cells

Talita B Gontigo; Rossimiriam P  de Freitas; Flavio S Emery; Leandro F Pedrosa; Jose B Vieira Neto; Bruno C Cavalcanti; Claudia Pessoa; Aaron King; Fabio De Moliner; Marc Vendrell Escobar; Eufranio N da Silva Junior

doi:10.1016/j.bmcl.2017.08.007

On the Synthesis of Quinone-based BODIPY Hybrids: New Insights on Antitumor Activity and Mechanism of Action in Cancer Cells

Talita B Gontigo, Rossimiriam P de Freitas, Flavio S Emery, Leandro F Pedrosa, Jose B Vieira Neto, Bruno C Cavalcanti, Claudia Pessoa, Aaron King, Fabio De Moliner, Marc Vendrell Escobar, Eufranio N da Silva Junior

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Journal	Bioorganic & Medicinal Chemistry Letters
Volume	25
Issue number	18
Early online date	4 Aug 2017
DOIs	https://doi.org/10.1016/j.bmcl.2017.08.007
Publication status	Published - 15 Sept 2017

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10.1016/j.bmcl.2017.08.007

BMCL-acceptedAccepted author manuscript, 942 KBLicence: Creative Commons: Attribution-NonCommercial-NoDerivatives (CC BY-NC-ND)

ENDOIMAGE - Activatable Fluorescent Probes as Smart Diagnostic Tools for Microendoscopy Imaging
Vendrell Escobar, M. (Principal Investigator)
EU other
1/08/13 → 31/07/17
Project: Research

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Gontigo, T. B., de Freitas, R. P., Emery, F. S., Pedrosa, L. F., Vieira Neto, J. B., Cavalcanti, B. C., Pessoa, C., King, A., De Moliner, F., Vendrell Escobar, M., & da Silva Junior, E. N. (2017). On the Synthesis of Quinone-based BODIPY Hybrids: New Insights on Antitumor Activity and Mechanism of Action in Cancer Cells. Bioorganic & Medicinal Chemistry Letters, 25(18). https://doi.org/10.1016/j.bmcl.2017.08.007

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title = "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 andcharacterised 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.",

author = "Gontigo, {Talita B} and {de Freitas}, {Rossimiriam P} and Emery, {Flavio S} and Pedrosa, {Leandro F} and {Vieira Neto}, {Jose B} and Cavalcanti, {Bruno C} and Claudia Pessoa and Aaron King and {De Moliner}, Fabio and {Vendrell Escobar}, Marc and {da Silva Junior}, {Eufranio N}",

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doi = "10.1016/j.bmcl.2017.08.007",

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Gontigo, TB, de Freitas, RP, Emery, FS, Pedrosa, LF, Vieira Neto, JB, Cavalcanti, BC, Pessoa, C, King, A, De Moliner, F , Vendrell Escobar, M & da Silva Junior, EN 2017, 'On the Synthesis of Quinone-based BODIPY Hybrids: New Insights on Antitumor Activity and Mechanism of Action in Cancer Cells', Bioorganic & Medicinal Chemistry Letters, vol. 25, no. 18. https://doi.org/10.1016/j.bmcl.2017.08.007

TY - JOUR

T1 - On the Synthesis of Quinone-based BODIPY Hybrids: New Insights on Antitumor Activity and Mechanism of Action in Cancer Cells

AU - Gontigo, Talita B

AU - de Freitas, Rossimiriam P

AU - Emery, Flavio S

AU - Pedrosa, Leandro F

AU - Vieira Neto, Jose B

AU - Cavalcanti, Bruno C

AU - Pessoa, Claudia

AU - King, Aaron

AU - De Moliner, Fabio

AU - Vendrell Escobar, Marc

AU - da Silva Junior, Eufranio N

PY - 2017/9/15

Y1 - 2017/9/15

N2 - Fluorescent quinone-based BODIPY hybrids were synthesised andcharacterised 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.

AB - Fluorescent quinone-based BODIPY hybrids were synthesised andcharacterised 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.

U2 - 10.1016/j.bmcl.2017.08.007

DO - 10.1016/j.bmcl.2017.08.007

M3 - Article

SN - 0960-894X

VL - 25

JO - Bioorganic & Medicinal Chemistry Letters

JF - Bioorganic & Medicinal Chemistry Letters

IS - 18

ER -

On the Synthesis of Quinone-based BODIPY Hybrids: New Insights on Antitumor Activity and Mechanism of Action in Cancer Cells

Abstract

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ENDOIMAGE - Activatable Fluorescent Probes as Smart Diagnostic Tools for Microendoscopy Imaging

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