Description

• Title:
  Mitochondria Targeting with Luminescent Rhenium(I) Complexes
• Creator:
  Skiba, Joanna;
  Kowalski, Konrad;
  Bernaś, Tytus;
  Trzybiński, Damian;
  Woźniak, Krzysztof;
  Ferraro, Giarita;
  Merlino, Antonello;
  Marasco, Daniela;
  Shafikov, Marsel Z.;
  Czerwieniec, Rafał
• Contributor:
  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
• Description:
  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 1–3 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.;
  The X-ray single-crystal diffraction studies were carried out at the Biological and Chemical Research Centre, University of Warsaw, established within the project co-financed by European Union from the European Regional Development Fund under the Operational Programme ‘Innovative Economy’, 2007–2013. This study was also supported by the National Science Centre Poland MAESTRO grant-DEC-2012/04/A/ST5/00609 (D.T. and K.W.), which enabled the X-ray structural analysis to be performed. RC thanks the European Research Council (ERC) for support in the framework of the MSCA RISE Project no. 645628.
• Object availability:
  free access
• Rights:
  Uznanie autorstwa 4.0 Międzynarodowe;
  http://creativecommons.org/licenses/by/4.0
• Date:
  2021.10.13;
  2017
• Type:
  Article
• Language:
  English
• Format:
  application/pdf
• Publisher:
  MDPI
• Relation:
  Molecules;22(5);
  809
• Subject:
  bioorganometallics;
  rhenium complexes;
  ferrocene;
  confocal microscopy;
  luminescence;
  mitochondria staining;
  phototoxicity
• Identifier: http://hdl.handle.net/11089/39374 ;
  1420-3049;
  10.3390/molecules22050809
• Data provider:
  Repozytorium Uniwersytetu Łódzkiego
• Can I use it?:
  check license
• Type:
  image