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Published on: May 28, 2014
Exploring the Impact of Phenanthroline-Based Glycoconjugated Ru(II) Polypyridyl Photosensitizers on
Elena de la Torre-Rubio1,2, María-Selma Arias-Pérez1, Lourdes Gude1,2
1Departamento de Química Orgánica y Química Inorgánica, Universidad de Alcalá, Instituto de Investigación Química "Andrés M. del Río" (IQAR), Alcalá de Henares, Madrid, 28805, Spain.
Abstract:
Novel water-soluble, phosphorescent ruthenium(II) polypyridyl-glycoconjugates of general formula [Ru{N-(1,10-phenanthroline)}2{N-(1,10-phenanthrolin-5-yl)-β-glycopyranosylamine}][Cl]2 (glycopyranosyl = D-glucopyranosyl (1), D-mannopyranosyl (2), L-rhamnopyranosyl (3), L-xylopyranosyl (4), and 2,3,4-tri-O-acetyl-L-xylopyranosyl (5)) and corresponding aglycone [Ru{N-(1,10-phenanthroline)}2{N-(1,10-phenanthrolin-5-amine)}][Cl]2 (6) have been synthesized and fully characterized. Their stability and behavior in physiological media have been assessed using ultraviolet visible spectroscopy (UV-Vis) and 1H nuclear magnetic resonance (¹H-NMR), revealing minor N-glycosidic cleavage and high photostability. The photocytotoxicity of the complexes has been evaluated in two different cancer (PC-3 and MCF-7) and one nontumorigenic (HFF-1) cell lines. While exhibiting no toxicity in the dark, some glycoconjugates achieve photoselectivity indexes of up to 40 upon blue-light irradiation. Remarkably, complexes 1-6 potently affect the metastatic phenotype of PC-3 cells, evidenced by the inhibition of migration in the wound healing assay and the increased resistance to trypsin detachment following photoactivation.
