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Light‐activated carbon monoxide prodrugs based on bipyridyl dicarbonyl ruthenium(II) complexes


Geri, Stepan; Krunclova, Tereza; Janouskova, Olga; Panek, Jiri; Hruby, Martin; Hernández‐Valdés, Daniel; Probst, Benjamin; Alberto, Roger A; Mamat, Constantin; Kubeil, Manja; Stephan, Holger (2020). Light‐activated carbon monoxide prodrugs based on bipyridyl dicarbonyl ruthenium(II) complexes. Chemistry - A European Journal, 26(48):10992-11006.

Abstract

Two photoactivatable dicarbonyl ruthenium(II) complexes based on an amide‐functionalised bipyridine scaffold (4‐position) equipped with an alkyne functionality or a green‐fluorescent BODIPY (boron‐dipyrromethene) dye have been prepared and used to investigate their light‐induced decarbonylation. UV/Vis, FTIR and 13C NMR spectroscopies as well as gas chromatography and multivariate curve resolution alternating least‐squares analysis (MCR‐ALS) were used to elucidate the mechanism of the decarbonylation process. Release of the first CO molecule occurs very quickly, while release of the second CO molecule proceeds more slowly. In vitro studies using two cell lines A431 (human squamous carcinoma) and HEK293 (human embryonic kidney cells) have been carried out in order to characterise the anti‐proliferative and anti‐apoptotic activities. The BODIPY‐labelled compound allows for monitoring the cellular uptake, showing fast internalisation kinetics and accumulation at the endoplasmic reticulum and mitochondria.

Abstract

Two photoactivatable dicarbonyl ruthenium(II) complexes based on an amide‐functionalised bipyridine scaffold (4‐position) equipped with an alkyne functionality or a green‐fluorescent BODIPY (boron‐dipyrromethene) dye have been prepared and used to investigate their light‐induced decarbonylation. UV/Vis, FTIR and 13C NMR spectroscopies as well as gas chromatography and multivariate curve resolution alternating least‐squares analysis (MCR‐ALS) were used to elucidate the mechanism of the decarbonylation process. Release of the first CO molecule occurs very quickly, while release of the second CO molecule proceeds more slowly. In vitro studies using two cell lines A431 (human squamous carcinoma) and HEK293 (human embryonic kidney cells) have been carried out in order to characterise the anti‐proliferative and anti‐apoptotic activities. The BODIPY‐labelled compound allows for monitoring the cellular uptake, showing fast internalisation kinetics and accumulation at the endoplasmic reticulum and mitochondria.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Scopus Subject Areas:Physical Sciences > Catalysis
Physical Sciences > Organic Chemistry
Uncontrolled Keywords:General Chemistry
Language:English
Date:26 August 2020
Deposited On:27 Aug 2020 15:36
Last Modified:06 Sep 2020 12:20
Publisher:Wiley-VCH Verlag
ISSN:0947-6539
OA Status:Hybrid
Publisher DOI:https://doi.org/10.1002/chem.202002139
PubMed ID:32700815
Project Information:
  • : FunderFP7
  • : Grant ID627113
  • : Project TitleLIGHT-CORM-CAT - Development of novel Near-infrared Light-triggered CORMs for Cancer Treatment
  • : FunderDAAD
  • : Grant ID57448291
  • : Project Title
  • : FunderCzech Science Foundation
  • : Grant ID19‐01438S
  • : Project Title

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