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Issue 14, 2018
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Mitochondria-localizing BODIPY–copper(II) conjugates for cellular imaging and photo-activated cytotoxicity forming singlet oxygen

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Abstract

Copper(II) acetylacetonates of N,N,N-donor dipicolylamine (dpa) ligands, viz. [Cu(L1)(acac)]ClO4 (1), [Cu(L2)(acac)]ClO4 (2) and [Cu(L3)(acac)]ClO4 (3), where L1 is benzyldipicolylamine (bzdpa), L2 and L3 are non-iodinated and diiodinated BODIPY (borondipyrromethene) ligands and Hacac is acetylacetone, were synthesized and characterized and their photocytotoxicity was studied. The BODIPY complex 2, structurally characterized by X-ray crystallography, has copper(II) in a distorted square-pyramidal geometry (degree of trigonality, τ5 = 0.28). The one-electron paramagnetic and redox active copper(II) complexes displayed 1 : 1 electrolytic behaviour in polar organic solvents. The BODIPY complexes 2 and 3 showed respective visible bands at 498 and 539 nm in 5% DMSO–phosphate buffered saline (PBS). Complex 2 displayed an emission band at 511 nm in 5% DMSO–PBS (λex = 465 nm) with a fluorescence quantum yield (ΦF) value of 0.15. Cellular imaging using this complex showed significant mitochondrial localization in HeLa and MCF-7 cancer cells. Complex 3 with a diiodo-BODIPY moiety was non-emissive (ΦF = 0.01) but acted as an efficient photosensitizer with a singlet oxygen quantum yield value of 0.59 (ΦΔ). Complex 3 showed a remarkable PDT effect with apoptotic cell death due to singlet oxygen giving IC50 values within 0.04–0.06 μM in HeLa and MCF-7 cells using visible light (400–700 nm), while being less toxic in the dark.

Graphical abstract: Mitochondria-localizing BODIPY–copper(ii) conjugates for cellular imaging and photo-activated cytotoxicity forming singlet oxygen

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Publication details

The article was received on 20 Jan 2018, accepted on 27 Feb 2018 and first published on 28 Feb 2018


Article type: Paper
DOI: 10.1039/C8DT00255J
Citation: Dalton Trans., 2018,47, 5019-5030
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    Mitochondria-localizing BODIPY–copper(II) conjugates for cellular imaging and photo-activated cytotoxicity forming singlet oxygen

    A. Bhattacharyya, A. Jameei, A. Garai, R. Saha, A. A. Karande and A. R. Chakravarty, Dalton Trans., 2018, 47, 5019
    DOI: 10.1039/C8DT00255J

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