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Issue 14, 2015

Functionalized triazolopeptoids – a novel class for mitochondrial targeted delivery

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Abstract

Here we introduce linear 1,4-triazolopeptoids as a novel class of cell penetrating peptidomimetics suitable as organ targeting molecular transporters of bioactive cargo. Repetitive triazole moieties with up to three residues were assembled on solid supports using copper-catalyzed alkyne–azide cycloadditions (CuAAC) in a submonomer approach. Depending on the lipophilicity of their side chain appendages the 1,4-triazolopeptoids showed either endosomal localization or a strong colocalization with the mitochondria of HeLa cells with moderate toxicity. While the basic triazolopeptoids mainly target the neuromast cells in zebrafish embryos, the lipophilic ones colocalize with either cartilage in the jaws and the blood vessel system.

Graphical abstract: Functionalized triazolopeptoids – a novel class for mitochondrial targeted delivery

Supplementary files

Article information


Submitted
04 Feb 2015
Accepted
20 Feb 2015
First published
20 Feb 2015

Org. Biomol. Chem., 2015,13, 4226-4230
Article type
Paper

Functionalized triazolopeptoids – a novel class for mitochondrial targeted delivery

D. Althuon, F. Rönicke, D. Fürniss, J. Quan, I. Wellhöfer, N. Jung, U. Schepers and S. Bräse, Org. Biomol. Chem., 2015, 13, 4226 DOI: 10.1039/C5OB00250H

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