Structurally optimised BODIPY derivatives for imaging of mitochondrial dysfunction in cancer and heart cells

Shubhanchi Nigam; Benjamin P Burke; Laura H Davies; Juozas Domarkas; Jennifer F Wallis; Paul G Waddell; Jennifer S Waby; David M Benoit; Anne-Marie Seymour; Christopher Cawthorne; Lee J Higham; Stephen J Archibald

doi:10.1039/c5cc08325g

Structurally optimised BODIPY derivatives for imaging of mitochondrial dysfunction in cancer and heart cells

Chem Commun (Camb). 2016 May 24;52(44):7114-7. doi: 10.1039/c5cc08325g.

Affiliations

¹ Department of Chemistry, University of Hull, Cottingham Road, Hull, HU6 7RX, UK. S.J.Archibald@Hull.ac.uk and Positron Emission Tomography Research Centre, University of Hull, Cottingham Road, Hull, HU6 7RX, UK.
² School of Chemistry, Newcastle University, Bedson Building, Newcastle upon Tyne, NE1 7RU, UK.
³ Positron Emission Tomography Research Centre, University of Hull, Cottingham Road, Hull, HU6 7RX, UK and Centre for Cardiovascular and Metabolic Research, University of Hull, Cottingham Road, Hull, HU6 7RX, UK.
⁴ School of Biological, Biomedical and Environmental Sciences, University of Hull, Cottingham Road, HU6 7RX, UK.
⁵ Department of Chemistry, University of Hull, Cottingham Road, Hull, HU6 7RX, UK. S.J.Archibald@Hull.ac.uk.
⁶ Centre for Cardiovascular and Metabolic Research, University of Hull, Cottingham Road, Hull, HU6 7RX, UK and School of Biological, Biomedical and Environmental Sciences, University of Hull, Cottingham Road, HU6 7RX, UK.
⁷ Positron Emission Tomography Research Centre, University of Hull, Cottingham Road, Hull, HU6 7RX, UK and School of Biological, Biomedical and Environmental Sciences, University of Hull, Cottingham Road, HU6 7RX, UK.

PMID: 27166476
DOI: 10.1039/c5cc08325g

Abstract

The structural features required for mitochondrial uptake of BODIPY-based optical imaging agents have been explored. The first derivatives of this class of dyes shown to have mitochondrial membrane potential-dependent uptake in both cancer and heart cells have been developed.

MeSH terms

Animals
Boron Compounds / chemistry*
Boron Compounds / pharmacokinetics
Cell Line
Fluorescent Dyes / chemistry*
Fluorescent Dyes / pharmacokinetics
Heart / drug effects*
Humans
MCF-7 Cells
Membrane Potential, Mitochondrial / drug effects
Microscopy, Confocal
Mitochondria / drug effects*
Mitochondria / metabolism
Molecular Structure
Myocytes, Cardiac / drug effects*
Myocytes, Cardiac / metabolism
Rats

Substances

4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
Boron Compounds
Fluorescent Dyes