Mitochondria Targeting with Luminescent Rhenium(I) Complexes

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Joanna SkibaKonrad Kowalski

Abstract

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)]⁺...Continue Reading

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Citations

Feb 17, 2019·International Journal of Molecular Sciences·Daniele FlorioDaniela Marasco
Sep 3, 2019·Current Pharmaceutical Design·Philippe ColleryVeena Vijaykumar
Jun 16, 2018·Dalton Transactions : an International Journal of Inorganic Chemistry·Chilaluck C KonkankitJustin J Wilson
Feb 8, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Marsel Z ShafikovHartmut Yersin
Sep 16, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Daniel ÁlvarezRamón López
Jan 22, 2021·Dalton Transactions : an International Journal of Inorganic Chemistry·Ahmed M MansourOla R Shehab
Apr 4, 2021·International Journal of Molecular Sciences·Sara La MannaDaniela Marasco
Jan 23, 2020·Inorganic Chemistry·Alexandra A ShmakovaMaxim N Sokolov

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Methods Mentioned

BETA
X-ray
confocal microscopy
surface plasmon resonance
NMR
column chromatography
chip

Software Mentioned

SCALE3 ABSPACK
CrysAlis RED
ORTEP
SVP
Bioworks
Gaussian
XLMP
HyD
CrysAlis RED CCD
BioMass

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