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Issue 7, 2017
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Glyco-functionalized dinuclear rhenium(i) complexes for cell imaging

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Abstract

The design, synthesis and photophysical characterization of four new luminescent glycosylated luminophores based on dinuclear rhenium complexes, namely Glyco-Re, are described. The derivatives have the general formula [Re2(μ-Cl)2(CO)6(μ-pydz-R)] (R-pydz = functionalized 1,2-pyridazine), where a sugar residue (R) is covalently bound to the pyridazine ligand in the β position. Different synthetic pathways have been investigated including the so-called neo-glycorandomization procedure, affording stereoselectively glyco-conjugates containing glucose and maltose in a β anomeric configuration. A multivalent dinuclear rhenium glycodendron bearing three glucose units is also synthesized. All the Glyco-Re conjugates are comprehensively characterized and their photophysical properties and cellular internalization experiments on human cervical adenocarcinoma (HeLa) cells are reported. The results show that such Glyco-Re complexes display interesting bio-imaging properties, i.e. high cell permeability, organelle selectivity, low cytotoxicity and fast internalization. These findings make the presented Glyco-Re derivatives efficient phosphorescent probes suitable for cell imaging application.

Graphical abstract: Glyco-functionalized dinuclear rhenium(i) complexes for cell imaging

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Supplementary files

Article information


Submitted
22 Nov 2016
Accepted
19 Jan 2017
First published
30 Jan 2017

Org. Biomol. Chem., 2017,15, 1686-1699
Article type
Paper

Glyco-functionalized dinuclear rhenium(I) complexes for cell imaging

A. Palmioli, A. Aliprandi, D. Septiadi, M. Mauro, A. Bernardi, L. De Cola and M. Panigati, Org. Biomol. Chem., 2017, 15, 1686
DOI: 10.1039/C6OB02559E

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