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Press release | Health ＆ life sciences | Pharmacology
A team of CEA researchers, in collaboration with two laboratories associating INSA Toulouse, CNRS and Université Paul Sabatier (Toulouse), has developed a new labeling process that will make it possible to speed up in vivo studies of candidate drugs. This original and pioneering process is based on a reaction mechanism discovered using computer modeling.
The results were published in Angewandte Chemie on August 13, 2015.
than one "candidate drug" in ten that reaches the stage of clinical trials goes on to
be made available on the market. This figure is even lower in the case of
candidates for certain central nervous system pathologies. This makes the
time-to-market increasingly lengthy and, in particular, implies higher
development costs. Now, however, this trend could be reversed thanks to the
early identification of the most effective and least harmful candidate drugs by
assessing their behavior in vivo (in animals and also in humans) right
from the initial stages of development. To achieve this, we need to
"stick" a label on such molecules, without altering their nature,
which will allow them to be accurately detected and traced within the organism.
One technique consists in replacing certain atoms (H, C, F, etc.) of the
molecule with their (stable or radioactive) isotopes. This gives us a labeled
molecule. Hydrogen (H), present in all organic molecules used in human health
science, can be replaced with deuterium (stable) or tritium (radioactive).
One of the
major challenges in isotope chemistry is to find a way to synthesize labeled
molecules quickly, cheaply and using environment-friendly techniques.
Incorporating deuterium or tritium at a defined position on a molecule with
pharmacological potential generally requires the use of chemical precursors and
there are several stages involved in its construction.
A team from CEA,
in collaboration with the Laboratoire de Physique et Chimie de Nano-Objets (CNRS/INSA Toulouse/Université Paul Sabatier) and
the Laboratoire de Chimie et Coordination (CNRS)
based in Toulouse, has developed a labeling method using "C-H
activation". This method, which can be performed under mild conditions, is
therefore applicable to complex and fragile molecules and uses ruthenium
nanoparticles with a deuterium-impregnated surface. The researchers worked on
the isotopic exchange in a C-H bond, in the case where the carbon atom is
chiral, i.e. it has four different groups of atoms bonded to it. A chiral
carbon atom cannot be superimposed upon its mirror image (as is the case for
our two hands). The huge majority of drugs and potential drug molecules contain
this type of carbon. The researchers have successfully demonstrated the
exceptional potential of ruthenium nanoparticles with a deuterium-impregnated
surface in activating an isotopic exchange on chiral carbon without altering
the initial three-dimensional structure of the molecule. Associated with these
results, the research teams in Toulouse carried out a computational chemistry study which revealed the extremely novel reaction mechanism
involved in this process. This opens up new possibilities in chemistry and
biology and paves the way toward new developments in labeling that may be find
applications in fundamental research and drug chemistry or even materials
 Institut National des Sciences Appliquées in Toulouse
 A "candidate drug" is a compound
(or small molecule) with good therapeutic potential and whose activity and
specific characteristics have been tested and optimized.
 The so-called "C-H activation"
process makes it possible to replace a hydrogen atom bonded to a carbon atom
with other atoms. However, this requires reagents which can be complex and
expensive as well as extreme reaction conditions that can alter the structure
of molecules and, therefore, their chemical and biological properties.
known as numerical
chemistry or computer chemistry, this is a branch of chemistry and/or physical chemistry which applies the
laws of theoretical chemistry used in computer programs
to calculate the structures and
properties of chemical objects such as molecules, solids, etc.
Enantiospecific C‒H Activation using Ruthenium Nanocatalysts
Céline Taglang, Luis Miguel Martínez-Prieto, Iker del Rosal, Laurent Maron, Romuald Poteau,
Karine Philippot, Bruno Chaudret, Serge Perato, Anaïs Sam Lone, Céline Puente, Christophe
Dugave, Bernard Rousseau, Grégory Pieters
Angewandte Chemie – August 2015
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.