Design and synthesis of lipid-mimetic cationic iridium complexes and their liposomal formulation for in vitro and in vivo application in luminescent bioimaging

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Shakirova , J R , Sadeghi , A , Koblova , A A , Chelushkin , P S , Toropainen , E , Tavakoli , S , Kontturi , L-S , Lajunen , T , Tunik , S P & Urtti , A 2020 , ' Design and synthesis of lipid-mimetic cationic iridium complexes and their liposomal formulation for in vitro and in vivo application in luminescent bioimaging ' , RSC Advances , vol. 10 , no. 24 , pp. 14431-14440 . https://doi.org/10.1039/d0ra01114b

Title: Design and synthesis of lipid-mimetic cationic iridium complexes and their liposomal formulation for in vitro and in vivo application in luminescent bioimaging
Author: Shakirova, Julia R.; Sadeghi, Amir; Koblova, Alla A.; Chelushkin, Pavel S.; Toropainen, Elisa; Tavakoli, Shirin; Kontturi, Leena-Stiina; Lajunen, Tatu; Tunik, Sergey P.; Urtti, Arto
Other contributor: University of Helsinki, University of Eastern Finland (UEF)
University of Helsinki, Drug Delivery Unit
University of Helsinki, Helsinki Institute of Life Science HiLIFE
University of Helsinki, Division of Pharmaceutical Biosciences
University of Helsinki, Drug Research Program





Date: 2020-04-07
Language: eng
Number of pages: 10
Belongs to series: RSC Advances
ISSN: 2046-2069
DOI: https://doi.org/10.1039/d0ra01114b
URI: http://hdl.handle.net/10138/315044
Abstract: Two iridium [Ir(NC)(2)(NN)](+) complexes with the diimine NN ligand containing a long polymethylene hydrophobic chain were synthesized and characterized by using NMR and ESI mass-spectrometry: NN - 2-(1-hexadecyl-1H-imidazol-2-yl)pyridine, NC - methyl-2-phenylquinoline-4-carboxylate (Ir1) and 2-phenylquinoline-4-carboxylic acid (Ir2). These complexes were used to prepare the luminescent PEGylated DPPC liposomes (DPPC/DSPE-PEG2000/Ir-complex = 95/4.5/1 mol%) using a thin film hydration method. The narrowly dispersed liposomes had diameters of about 110 nm. The photophysics of the complexes and labeled liposomes were carefully studied. Ir1 and Ir2 give red emission (lambda(em) = 667 and 605 nm) with a lifetime in the microsecond domain and quantum yields of 4.8% and 10.0% in degassed solution. Incorporation of the complexes into the liposome lipid bilayer results in shielding of the emitters from interaction with molecular oxygen and partial suppression of excited state nonradiative relaxation due to the effect of the relatively rigid bilayer matrix. Delivery of labeled liposomes to the cultured ARPE-19 cells demonstrated the usefulness of Ir1 and Ir2 in cellular imaging. Labeled liposomes were then injected intravitreally into rat eyes and imaged successfully with optical coherence tomography and funduscopy. In conclusion, iridium complexes enabled the successful labeling and imaging of liposomes in cells and animals.
Subject: OPTICAL COHERENCE TOMOGRAPHY
DRUG-DELIVERY
PHOTOPHYSICAL PROPERTIES
LOADED LIPOSOMES
FLUORESCENT
LIGANDS
PEG
116 Chemical sciences
317 Pharmacy
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