In vitro anticancer activity and biologically relevant metabolization of organometallic ruthenium complexes with carbohydrate-based ligands.

Détails

ID Serval
serval:BIB_7E083338AFB7
Type
Article: article d'un périodique ou d'un magazine.
Collection
Publications
Institution
Titre
In vitro anticancer activity and biologically relevant metabolization of organometallic ruthenium complexes with carbohydrate-based ligands.
Périodique
Chemistry
Auteur⸱e⸱s
Berger I., Hanif M., Nazarov A.A., Hartinger C.G., John R.O., Kuznetsov M.L., Groessl M., Schmitt F., Zava O., Biba F., Arion V.B., Galanski M., Jakupec M.A., Juillerat-Jeanneret L., Dyson P.J., Keppler B.K.
ISSN
0947-6539
Statut éditorial
Publié
Date de publication
2008
Peer-reviewed
Oui
Volume
14
Numéro
29
Pages
9046-57
Langue
anglais
Notes
Publication types: Journal Article ;
Résumé
The synthesis and in vitro anticancer activity of dihalogenido(eta6-p-cymene)(3,5,6-bicyclophosphite-alpha-D-glucofuranoside)ruthenium(II) complexes are described. The compounds were characterized by NMR spectroscopy and ESI mass spectrometry, and the molecular structures of dichlorido-, dibromido- and diiodido(eta6-p-cymene)(3,5,6-bicyclophosphite-1,2-O-isopropylidene-alpha-D-glucofuranoside)ruthenium(II) were determined by X-ray diffraction analysis. The complexes were shown to undergo aquation of the first halido ligand in aqueous solution, followed by hydrolysis of a P--O bond of the phosphite ligand, and finally formation of dinuclear species. The hydrolysis mechanism was confirmed by DFT calculations. The aquation of the complexes was markedly suppressed in 100 mM NaCl solution, and notably only very slow hydrolysis of the P--O bond was observed. The complexes showed affinity towards albumin and transferrin and monoadduct formation with 9-ethylguanine. In vitro studies revealed that the 3,5,6-bicyclophosphite-1,2-O-cyclohexylidene-alpha-D-glucofuranoside complex is the most cytotoxic compound in human cancer cell lines (IC50 values from 30 to 300 microM depending on the cell line).
Mots-clé
Antineoplastic Agents, Carbohydrate Metabolism, Carbohydrates, Cell Line, Cell Survival, Humans, Hydrolysis, Kinetics, Ligands, Magnetic Resonance Spectroscopy, Models, Molecular, Molecular Structure, Organic Chemistry Phenomena, Ruthenium Compounds
Pubmed
Web of science
Création de la notice
03/10/2008 12:29
Dernière modification de la notice
20/08/2019 15:39
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