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Scientific result | Chemistry | Methodologies for life sciences
Researchers from the CEA-IBITECS in collaboration
with a team from the University of Strasbourg (UDS) have developed new
reagents known as “chelating azides”, which can rapidly and selectively
couple to any compound equipped with an alkyne group. The reaction can
take place in any environment, including within a cell. These results
were published as a VIP (Very Important Paper) on the website of
Angewandte Chemie International Edition.
Bio-orthogonal chemistry refers to a set of artificial reactions that can take
place in a living organism, without interfering with its own biochemical
activity. This allows, for example, following the fate of a substrate of
interest (a metabolite, enzyme inhibitor, drug, etc.) inside the cell. The first
step of the procedure is to modify the substrate by grafting to it a functional
chemical group that does not affect its biological activity, before introducing
it into the cell. Next, a probe complementary to the functional group is
introduced that will react in situ with the latter and thus label the substrate
that is to be followed. The coupling between an azide (on the probe) and an
alkyne (on the substrate), two non-natural chemical functions, is one of the
most commonly used bio-orthogonal reactions. However, this poses a problem since
the reaction is catalyzed by copper, a cytotoxic metal, which limits its use in
Chemists from the CEA-IBITECS, with their colleagues from the UDS, have resolved
this problem by creating a family of compounds combining a copper chelator1
agent (enclosing a single metal atom) with an azide function. Provided with a
marker, such a compound can be used as a probe for binding to any substrate of
interest to which an alkyne group has been grafted. Thanks to these “chelating
azides” the reaction can proceed in the blood or within a cell, in a non-toxic
manner and as fast as in a simple environment (the coupling occurs in less than
thirty seconds).The scope is immense, ranging from medicinal chemistry (assembly
of drugs for therapeutic antibodies, etc.) to imagery (tracers based on 64Cu) to
pharmacology (drug monitoring).
 A ligand capable of binding a metal ion, in the manner of a pliers
Copper-Chelating Azides for Efficient Click Conjugations in Complex Media, Angewandte Chemie International Edition
CEA is a French government-funded technological research organisation in four main areas: low-carbon energies, defense and security, information technologies and health technologies. A prominent player in the European Research Area, it is involved in setting up collaborative projects with many partners around the world.