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Molecules 2017, 22(5), 809;

Mitochondria Targeting with Luminescent Rhenium(I) Complexes

Faculty of Chemistry, Department of Organic Chemistry, University of Łódź, Tamka 12, 91-403 Łódź, Poland
Nencki Institute of Experimental Biology, Polish Academy of Sciences, ul. Pasteura 3, 02-093 Warszawa, Poland
Faculty of Chemistry, Biological and Chemical Research Centre, University of Warsaw, Żwirki i Wigury 101, 02-089 Warszawa, Poland
Department of Chemical Sciences, University of Naples Federico II, Complesso Univ. di Monte Sant’ Angelo, Via Cintia, I-80126 Napoli, Italy
Department of Pharmacy, University of Naples Federico II, Via Mezzocannone 16, 80134 Napoli, Italy
CIRPEB: Centro Interuniversitario di Ricerca sui Peptidi Bioattivi, Via Mezzocannone 16, I-80134 Napoli, Italy
CNR Institute of Biostructures and Bioimages, Via Mezzocannone 16, I-80134 Napoli, Italy
Department of Technology of Organic Synthesis, Institute of Chemical Engineering, Ural Federal University, 19 Mira Str., 620002 Ekaterinburg, Russia
Institut für Physikalische und Theoretische Chemie, Universität Regensburg, Universitätsstraße 31, D-93040 Regensburg, Germany
Lehrstuhl für Anorganische Chemie I, University of Bayreuth, D-95440 Bayreuth, Germany
Authors to whom correspondence should be addressed.
Academic Editor: Roman Dembinski
Received: 19 April 2017 / Revised: 10 May 2017 / Accepted: 11 May 2017 / Published: 15 May 2017
(This article belongs to the Section Organometallic Chemistry)
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Two new neutral fac-[Re(CO)3(phen)L] compounds (1,2), with phen = 1,10-phenanthroline and L = O2C(CH2)5CH3 or O2C(CH2)4C≡CH, were synthetized in one-pot procedures from fac-[Re(CO)3(phen)Cl] and the corresponding carboxylic acids, and were fully characterized by IR and UV-Vis absorption spectroscopy, 1H- and 13C-NMR, mass spectrometry and X-ray crystallography. The compounds, which display orange luminescence, were used as probes for living cancer HeLa cell staining. Confocal microscopy revealed accumulation of both dyes in mitochondria. To investigate the mechanism of mitochondrial staining, a new non-emissive compound, fac-[Re(CO)3(phen)L], with L = O2C(CH2)3((C5H5)Fe(C5H4), i.e., containing a ferrocenyl moiety, was synthetized and characterized (3). 3 shows the same mitochondrial accumulation pattern as 1 and 2. Emission of 3 can only be possible when ferrocene-containing ligand dissociates from the metal center to produce a species containing the luminescent fac­[Re(CO)3(phen)]+ core. The release of ligands from the Re center was verified in vitro through the conjugation with model proteins. These findings suggest that the mitochondria accumulation of compounds 13 is due to the formation of luminescent fac-[Re(CO)3(phen)]+ products, which react with cellular matrix molecules giving secondary products and are uptaken into the negatively charged mitochondrial membranes. Thus, reported compounds feature a rare dissociation-driven mechanism of action with great potential for biological applications. View Full-Text
Keywords: bioorganometallics; rhenium complexes; ferrocene; confocal microscopy; luminescence; mitochondria staining; phototoxicity bioorganometallics; rhenium complexes; ferrocene; confocal microscopy; luminescence; mitochondria staining; phototoxicity

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Skiba, J.; Bernaś, T.; Trzybiński, D.; Woźniak, K.; Ferraro, G.; Marasco, D.; Merlino, A.; Shafikov, M.Z.; Czerwieniec, R.; Kowalski, K. Mitochondria Targeting with Luminescent Rhenium(I) Complexes. Molecules 2017, 22, 809.

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