Issue 7, 2017

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

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

Supplementary files

Article information

Article type
Paper
Submitted
22 Nov 2016
Accepted
19 Jan 2017
First published
30 Jan 2017

Org. Biomol. Chem., 2017,15, 1686-1699

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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