Nuclear Magnetic Resonance Spectroscopy

From left to right: Mosbah El Hayek, Gildas Bertho, Fatiha Kateb, Mathieu Baudin, Arthur Roux, Cédric Caradeuc, Nicolas Giraud, Léa Gutierrez.

Team Description

We develop original concepts that aim at enhancing resolution and sensitivity in NMR spectra of complex samples, to a point where their analysis becomes a faster, easier, and a more accurate process. 

The research group on NMR of Biological Substances is part of the team Bio-Spectroscopies. We develop methods that combine advanced NMR-based approaches with other physical chemical techniques including simulation tools to study complex molecular and supramolecular systems in the field of Health Sciences, targeting their dynamic and structural features. Over the last decade, we have contributed to exploring fundamental research issues at the frontier of chemistry and biology, ranging from the study of supramolecular interactions involving proteins, to the metabolic profiling of biofluids and the hyperpolarization of biological samples. These projects are carried out in the frame of several collaborations with  laboratories working in the fields of organic chemistry, biochemistry, structural biology or medical research.

 

Research Themes

Methodological developments for ultra-high resolution NMR

We design novel pulse sequences that exceed the resolution limits of traditional NMR analyzes on complex samples. We are also working on the development of modelling and data analysis tools to make the best use of the information obtained on the biological systems under study.

In this context, we have carried out methodological developments to acquire Pure Shift spectra with efficient suppression of the water signal on chalenging biofluids. We ahave shown how the analysis of the resulting metabolic profiles allows for getting a unique insight into the metabolic pathways that are key to Lymphoma cells and for addressing the mechanisms of action of a combination of antimetabolic drugs. [1] We have also demonstrated the robustness of a new analytical workflow based on the use of a library of reference Pure Shift spectra to fit the fingerprint of each metabolite of interest and determine its concentration. [2]

[1] J Proteome Res 21 (4), 1041-1051, 2022.
[2] Anal. Chem. 94, 43, 14974–14984, 2022

Dynamic and structural study of biomolecular interactions

Describing and understanding supramolecular interactions in large biological or bio-mimetic systems has become a major stake over the recent years. However, despite the considerable progress that have been achieved in this field, probing at an atomic scale protein-protein, protein-nucleic acid, protein-lipid, protein-carbohydrate interactions, or the interactions with small molecules, enzyme substrates and regulators, still constitutes a critical challenge for chemists and biochemists.

We are carrying out several collaborations with the groups of Dr. Olivier Maury (Ecole Normale Supérieure de Lyon), Pr. Elise Dumont (Université Côte d’Azur, Nice) and Dr. Christelle Hureau (Laboratoire de Chimie de Coordination, Toulouse) to understand the supramolecular properties of molecules that can be used as crystallization agents of proteins, as modulators of the aggregation process of amyloid peptides, or as non-covalent paramagnetic tags to probe the structure of proteins and peptides by NMR, both in solution and in the solid state. We notably develop an original approach combining paramagnetic NMR and molecular dynamics to probe the dynamic interaction processes between biomolecules and lanthanide complexes. [1] We have recently shown that this hybrid approach makes it possible to capture the detail of these interactions on time scales which are complementary, and to propose a global vision of the dynamic process which reconciles the points of view of the two techniques.

[1] Physical Chemistry Chemical Physics, 23, 11224-11232 (2021) DOI: 10.1039/D0CP06570F

Metabolomics in the field of Health Sciences

We provide medical researchers with a better understanding, based on metabolomics by NMR, of the complex interplay between the different factors that contribute to the development of diseases. Recent progress in metabolomics has improved our understanding of the system-levels effect of metabolites in biofluids, cells and tissues, using either Mass Spectrometry and/or NMR as complementary detection techniques.
NMR is a highly versatile tool for obtaining metabolic profiles. It allows for analysing all the small metabolites simultaneously, with a high reproducibility. This technique is also non-destructive, robust and quantitative.
Over the last decade, we have developed an expertise in deciphering the complex metabolic pathways that are involved in the evolution of diseases at every step of biological and medical research projects, from preliminary in vitro studies to clinical trials. [1]
Our goal is notably to bring another vision that is complementary to transcriptomics or genomics and can contribute to establish pertinent biomarkers that will help to develop new diagnosis and prognosis approaches. We can help medical researchers to better understand the mechanism of action of new therapeutic approaches, by exploring how the metabolism is correlated to the response of patients to a given treatment. In this context, our group is also developing new analytical tools for boosting resolution and sensitivity of NMR analyses and thus paving the way for new therapeutic options. [2]

[1] NMR in Biomedicine. 2023; 36(11):e5006. DOI:10.1002/nbm.5006
[2] Magn Reson Chem 2023, 1. DOI: 10.1002/mrc.5356

Dissolution Dynamic Nuclear Polarization (D-DNP) of bio-samples.

Our research activity on hyperpolarization, using dissolution dynamic nuclear polarization (D-DNP), is in line with the study of biological samples, which is a strong theme in our team. By exploiting the high signal enhancements of several orders of magnitude allowed by DNP, we seek to push the limits in terms of temporal resolution for the study of cellular processes in real time, but also to analyse complex biological samples containing low concentrations of metabolites. The starting point of our studies is the cellular metabolism of glutamine and its deregulation in the presence of certain pathologies such as cancer or cardiovascular dysfunction. [1] Initially focused on the study of enzymatic reactions in vitro and on cell extracts, our experiments aim at working in real time on living cells or during ex vivo MRI experiments, as well as on biological samples such as blood, urine or serum, while developing synergies with other thematics and methodological developments of the team, such as high-resolution detection sequences.

[1] ChemPhysChem 2023, 24, e202300151. DOI: 10.1002/cphc.202300151

 

NMR Facility at UMR 8601

Our group is hosting the NMR facility of our Research Unit, including 3 NMR spectrometers (500 MHz to 600 MHz) and a prototype polarizer for Dissolution Dynamic Nuclear Polarization (D-DNP), to improve the sensitivity of solution NMR of bio-samples.

We are members of the Equipex program “CACSICE” (Center for the Analysis of Complex Systems in Complex Environments), and the Equipex program “Paris en resonance”, which provides access to DNP enhanced NMR equipment for users from both academic and industrial laboratories. We have also recently implemented the first NMR facility in France dedicated to metabolomic analyses for Health Sciences “Metabo Paris Santé”.

Publications

2024

1. Lipoproteome dysregulation precedes conversion to psychosis in ultra-high-risk subjects,
M.T. Avella, G. Bertho, O. Kébir, C. Caradeuc, M.O. Krebs, N. Giraud, B. Chaumette, A. Frajerman,
Neuroscience Applied, Volume 3, Supplement 1, (2024),103948
DOI: 10.1016/j.nsa.2024.103948

2. One touch is all it takes: the supramolecular interaction between ubiquitin and lanthanide complexes revisited by paramagnetic NMR and molecular dynamics,
K. Dos Santos,  A. Bartocci, N. Gillet, S. Denis-Quanquin, A. Roux, E. Lin, Z. Xu, R. Finizola,P. Chedozeau,X. Chen, C. Caradeuc, M. Baudin, G. Bertho, F. Riobé, O. Maury, E. Dumont* and N. Giraud* ,
Physical Chemistry Chemical Physics (2024)
DOI: 10.1039/D4CP00463A

2023

4. Guest exchange in a biomimetic ZnII cavity-complex: kinetic control by a catalytic water, through pore selection, 2nd sphere assistance, and induced-fit processes
Nyssen, N., Giraud, N., Wouters, J., Jabin, I., Leherte, L. & Reinaud, O.*
Inorganic Chemistry Frontiers, in Press (2023) DOI : 10.1039/D3QI01271A

3. NMR metabolomics study of the chronic low-dose exposure to a cocktail of Persistent Organic Pollutants
Lucas-Torres, C., Caradeuc, C., Prieur, L., Djemai, H., Layale, Y., Noirez, P., Coumoul, X., Audouze, K., Giraud, N., & Bertho, G.*
NMR in Biomedicine, in Press (2023) DOI : 10.1002/nbm.5006

2. Present and Future of Pure Shift NMR in Metabolomics
Chen, X., Bertho, G., Caradeuc, C., Giraud, N.* and Lucas-Torres, C.*,
Magnetic Resonance in Chemistry Metabolomics Special Issue: Frontiers in NMR Metabolomics, invited review (2023) DOI: 10.1002/mrc.5356

1. A Toolbox For Glutamine Use In Dissolution Dynamic Nuclear Polarization: From Enzymatic Reaction Monitoring To The Study Of Cellular Metabolic Pathways And Imaging.
Dos Santos, K, Bertho, G., Caradeuc, C., Baud, V., Montagne, A., Abergel, D., Giraud, N.* & Baudin, M.*
ChemPhysChem (2023) DOI: 10.1002/cphc.202300151

2022

5. Absolute Metabolite Quantification Using Pure Shift NMR: Towards Quantitative Metabolic Profiling of Aqueous Biological Samples
Chen, X., Caradeuc, C., Montagne, A., Baud, V., Bertho, G., Lucas-Torres, C.*, Giraud, N.*
Anal. Chem. 94, 43, 14974–14984 (2022) DOI: 10.1021/acs.analchem.2c02823

4. Synthesis and Characterization of Novel Conformers of (E)-2-(3-nitro-H-imidazo[1,2-a]pyridin-2-ylthio)-N’-benzylideneacetohydrazide Derivatives
Evrard, A., Coulibaly, S.*, Coulibali, S *, Kouassi, S., Achi, P.A., Giraud, N. and Bertho, G.
Magnetic Resonance in Chemistry, 60, 1157-1170 (2022) DOI: 10.1002/mrc.5308

3. Lanthanide tris-dipicolinate: a do-it-all complex?
Denis Quanquin, S., D’Aléo, A., Balogh, C., N’Dala Louika, I., Salaam, J., le Guennic, B., Thieuleux, C., Camp, C., Veyre, L., Costuas, K., Rigaut, S., Le Bozec, H., Andraud, C., Dumont, E., Gilet, N., Chapelle, C., Girard, E., Giraud, N., Pilet, G., Riobé, F., Maury, O*
Actualité Chimique, 475, 12 (2022)

2. Ultrahigh-Resolution NMR with Water Signal Suppression for a Deeper Understanding of the Action of Antimetabolic Drugs on Dif-fuse Large B-Cell Lymphoma
Bertho, G., Lordello, L., Chen, X., Lucas-Torres, C., Oumezziane, I.E., Caradeuc, C., Baudin, M., Nuan-Aliman, S., Thieblemont, C., Baud, V.* and Giraud, N.*
Journal of Proteome Research, 21, 4, 1041-1051 (2022) DOI: https://doi.org/10.1021/acs.jproteome.1c00914

1. Structural Analysis of Unstable Norbixin Isomers Guided by Pure Shift Nuclear Magnetic Resonance.
Bertho, G.* Oumezziane, I.E., Caradeuc, C., Guibout, L., Balducci, C., Dinan, L., Dilda, P.J., Camelo, S., Lafont, R., and Giraud, N.*
Magnetic Resonance in Chemistry, 60, 504-514 (2022) DOI: https://doi.org/10.1002/mrc.5252

2021

10. Spin Thermometry: A Straightforward Measure of Millikelvin Deuterium Spin Temperatures Achieved by Dynamic Nuclear Polarization,
B. Aghelnejad, S. Marhabaie, M. Baudin, G. Bodenhausen, and D. Carnevale
The Journal of Physical Chemistry Letters 11 (9), 3219-3225 (2020)
https://doi.org/10.1021/acs.jpclett.0c00713

9. Effects of Microwave Gating on Nuclear Spin Echoes in Dynamic Nuclear Polarization.
D. Guarin, D. Carnevale, M. Baudin, P. Pelupessy, D. Abergel, and G. Bodenhausen.
J. Phys. Chem. Lett., 2021, 13, 175-182 (2021).
https://doi.org/10.1021/acs.jpclett.1c03436

8. On the Supra-LUMO Interaction: Case Study of a Sudden Change of Electronic Structure as a Functional Emergence.
Lainé, P.*, Gosset, A., Lachmanová, S.N.,  Cherraben, S., Bertho, G., Forté, J., Perruchot, C., Jacquot de Rouville, H.P., Pospíšil, L., Hromadová, M., Brémond, E.
Chemistry – A European Journal, 27, 17889-17899 (2021)
https://doi.org/10.1002/chem.202103136

7. Loss of prion protein control of glucose metabolism promotes neurodegeneration in model of prion diseases.
Arnould, H., Baudouin, V., Baudry, A., Ribeiro, L.W., Ardila-Osorio, H., Pietri, M., Caradeuc, C., Soultawi, C., Williams, D., Alvarez, M., Crozet, C., Djouadi, F., Laforge, M., Bertho, G., Kellermann, O., Launay, J.M., Schmitt-Ulms, G., Schneider, B.*
PLoS Pathogens 17(10): e1009991.
https://doi.org/10.1371/journal.ppat.1009991

6. Distinction between 2’- and 3’ – phosphate isomers of a fluorescent NADPH analogue led to strong inhibition of cancer cells proliferation and migration..
Lima, M., Dilly, S., Daunay, S., Abbe, P., Solier, S., Guillaumond, F., Tubiana, S.S., Escargueil, A.E., Henriques, J.A.P., Ferrand, N., Erdelmeier, I., Boucher, J.L., Bertho, G., Agranat, I., Rocchi, S., Sabbah, M., Slama-Schwok, A.*
Antioxydants, 10 (5), 723 (2021)
https://doi.org/10.3390/antiox10050723

5. The complex metabolism of poststerone in male rats.
Balducci, C., Dinan, L., Guibout, L., Foucault, A.S., Carbonne, C., Durand, J.D., Caradeuc, C., Bertho, G., Girault, J.P., Lafont, R.
The Journal of Steroid Biochemistry and Molecular Biology, 212, 105897, (2021)
https://doi.org/10.1016/j.jsbmb.2021.105897

4. Adenomyosis is associated with specific proton nuclear magnetic resonance (1H-NMR) serum metabolic profiles.
Bourdon, M., Santulli, P., Kateb, F., Pocate-Cheriet, K., Batteux, F., Maignien, C., Chouzenoux, S., Bordonne, C., Marcellin, L., Bertho, G.*, Chapron, C.*
Fertility and Sterility, 116 (1), 243-254 (2021)
https://doi.org/10.1016/j.fertnstert.2021.02.031

3. Book Chapter: Analyse Métabolomique par Résonance Magnétique Nucléaire : Application aux Maladies Porphyriques
G. Bertho
in La Révolution Biotechnologique et la médecine de demain
Ducancel F., Schneider, B.
Doin Ed., ISBN: 978-2-7040-1620-4 (2021)

2. Capturing The Dynamic Association Between A Tris-Dipicolinate Lanthanide Complex And A Decapeptide: A Combined Paramagnetic NMR And Molecular Dynamics Exploration.
Denis-Quanquin, S., Bartocci, A., Szczepaniak, F., Riobé, F., Maury, O., Dumont, E.*, Giraud, N.*
Physical Chemistry Chemical Physics. 23, 11224-11232 (2021)
https://doi.org/10.1039/D0CP06570F

1. Solid-State versus Solution Investigation of a Luminescent Chiral BINOL-Derived Bisphosphate Single-Molecule Magnet
Mattei C.A., Montigaud, V., Gendron F., Denis-Quanquin S., Dorcet V., Giraud N., Riobé F., Argouarch G., Maury O., Le Guennic B.,* Cador O., Lalli C., Pointillart F.*
Inorg. Chem. Front., 8, 947-962 (2021)
https://doi.org/10.1039/D0QI01192D

2020

4. Mn(I) Complex Redox Potential Tunability by Remote Lewis Acid Interaction.
Srinivasan, A. Campos, J., Giraud, N., Robert M. and Rivada-Wheelaghan O.* Dalton Trans., 2020,49, 16623-16626 (2020https://dx.doi.org/10.1039/D0DT02467H

3. The Follicular fluid metabolome differs according to the endometriosis phenotype.
Pocate-Cheriet, K., Santulli, P., Kateb, F., Bourdon, M., Maignien, C., Batteux, F., Chouzenoux, S., Patrat, C., Wolf, J.P., Bertho, G. & Chapron, C., Reproductive BioMedicine Online, 41, 1023-1037 (2020) https://doi.org/10.1016/j.rbmo.2020.09.002

2. Endometriosis Phenotypes Are Associated With Specific Serum Metabolic Profiles Determined By Proton-Nuclear Magnetic Resonance.
Maignien, C., Santulli, P., Kateb, F., Caradeuc, C., Marcellin, L., Pocate-Cheriet, K., Bourdon, M., Chouzenoux, S., Batteux, F., Bertho, G. & Chapron, C., Reproductive BioMedicine Online, 41, 640-652 (2020https://doi.org/10.1016/j.rbmo.2020.06.019

1. Multinuclear NMR in Polypeptide Liquid Crystals: Three Fertile Decades of Methodological Developments and Analytical Challenges.
Lesot, P.*, Aroulanda, C., Berdagué, P., Meddour, A., J., Merlet, D., Farjon, J., Giraud, N., & Lafon, O. Progress in Nuclear Magnetic Resonance Spectroscopy, 116, 85-154 (2019) https://dx.doi.org/10.1016/j.pnmrs.2019.10.001

2019

1. Monitoring Conformational Changes in an Enzyme Conversion Inhibitor Using Pure Shift Exchange NMR Spectroscopy. Aloui, G., Bouabdallah, S., Baltaze, J.P., Herbert Pucheta, J.E., Touil, S., Farjon, J. & Giraud, N.* ChemPhysChem, 20, 1738-1746 (2019) https://dx.doi.org/10.1002/cphc.201900244

2. A biomimetic strategy for the selective recognition of organophosphates in 100% water: synergies of electrostatic interactions, cavity embedment and metal coordination. Collin, S., Giraud, N., Dumont, E., & Reinaud, O.* Organic Chemistry Frontiers, 6, 1627-1636 (2019) https://dx.doi.org/10.1039/c9qo00263d

2018

1. Combining pure shift and J‐edited spectroscopies: A strategy for extracting chemical shifts and scalar couplings from highly crowded proton spectra of oligomeric saccharides. Pitoux, D., Hu, Z., Plainchont, B., Merlet, D., Farjon, J., Bonnaffé, D. & Giraud, N.* Magnetic Resonance in Chemistry, 56, 954-962 (2018) https://dx.doi.org/10.1002/mrc.4715

2. Highly Accurate Quantitative Analysis Of Enantiomeric Mixtures From Spatially Frequency Encoded 1H NMR Spectra. Plainchont, B., Pitoux, D., Cyrille, M. & Giraud, N.* Analytical Chemistry, 90, 1595-1600 (2018) https://dx.doi.org/10.1021/acs.analchem.7b02411

3. 1H NMR analyses of enantiomeric mixtures using chiral liquid crystals (invited paper). Farjon, J. & Giraud, N.* Current Opinion in Colloid and Interface Science, 33, 1-8 (2018) https://dx.doi.org/10.1016/j.cocis.2017.11.001

4. Real-time and non-invasive monitoring of renal endoplasmic reticulum stress in individuals with a hemodynamic impairment.
B. Fohlen, Q. Tavernier, T. Huynh, C. Caradeuc, D. Le Corre, G. Bertho, B. Cholley, N. Pallet
EBioMedicine, 27, 284-292 (2018). https://doi.org/10.1016/j.ebiom.2017.12.023

5. Urinary metabolic profiling of asymptomatic Acute Intermittent Porphyria using a rule-mining-based algorithm.
M. Luck, C. Schmitt, N. Talbi, L. Gouya, C. Caradeuc, H. Puy, G. Bertho*, N. Pallet*
Metabolomics, 14, 10 (2018). https://doi.org/10.1007/s11306-017-1305-9

6. Bacterial Transferase MraY, a Source of Inspiration towards New Antibiotics, Mickaël J. Fer, Laurent Le Corre, Nicolas Pietrancosta, Nathalie Evrard-Todeschi, Samir Olatunji, Ahmed Bouhss, Sandrine Calvet-Vitale*,  Christine Gravier-Pelletier*. Current Medicinal Chemistry, 2018, 25 , Issue 42 , 2018 https://doi.org/10.2174/0929867325666180330095154

Till 2017
2017 

M Sarkis, MA Miteva, M Chiara Dasso Lang, M Jaouen, M-A Sari, M-O Galcéra, M Ethève-Quelquejeu, C Garbay, G Bertho*, E Braud* Insights into the interaction of high potency inhibitor IRC-083864 with phosphatase CDC25 : Binding model of CDC25 inhibitor IRC-083864 Proteins, 2017, Jan 5 doi: 101002/prot25236

M Melikian, B Eluard, G Bertho, V Baud, N Evrard-Todeschi Model of the Interaction between the NF-κB Inhibitory protein p100 and the E3 ubiquitin ligase β-TrCP based on NMR and Docking Experiments J Chem Inf Model, 2017 Jan 13 doi: 101021/acsjcim5b00409

Yurenko YP, Bazzi S, Marek R, Kozelka J Anion-π Interactions in Flavoproteins Involve a Substantial Charge-Transfer Component Chemistry 2017, 23 3246-3250

Kozelka J Lone pair-π interactions in biological systems: occurrence, function, and physical origin, Eur Biophys J 2017 May 2 doi: 101007/s00249-017-1210-1

R Balzan, L Fernandes, L Pidial, A Comment, B Tavitian, PR Vasos Pyruvate cellular uptake and enzymatic conversion probed by dissolution DNP‐NMR: the impact of overexpressed membrane transporters Magn Reson Chem, 2017, 55:579-583

 

2016

R Balzan, L Fernandes, A Comment, L Pidial, B Tavitian, PR Vasos Dissolution Dynamic Nuclear Polarization Instrumentation for Real-time Enzymatic Reaction Rate Measurements by NMR JoVE, 2016, e53548-e53548

M Luck, G Bertho, M Bateson, A Karras, A Yartseva, E Thervet, C Damon, N Pallet* Rule-Mining for the Early Prediction of Chronic Kidney Disease Based on Metabolomics and Multi-Source Data PLoS One 2016 Nov 18;11(11):e0166905

J-W Chiao, M Melikian, L Han, A Tsao, S K Mencher, J Fallon, G Bertho* & L G Wang* Interaction of a small molecule and STAT3-SH2 domain to block Y705 phosphorylation and inhibit lupus nephritis Biochem Pharmacol, 2016, 99, 123-131

Novotný J, Bazzi S, Marek R, Kozelka J Lone-pair-π interactions: analysis of the physical origin and biological implications Phys Chem Chem Phys 2016 Jul 28;18(28):19472-81

 

2015

I Anosova, S Melnik, K Tripsianes, F Kateb, I Grummt, M Sattler A novel RNA binding surface of the TAM domain of TIP5/BAZ2A mediates epigenetic regulation of rRNA genes Nucleic Acids Res 2015, 43, 5208-5220

Badri Z, Foroutan-Nejad C, Kozelka J, Marek R On the non-classical contribution in lone-pair-π interaction: IQA perspective Phys Chem Chem Phys 2015 Oct 21;17(39):26183-9

M Luck*, A Yartseva, G Bertho, E Thervet, P Beaune, N Pallet, C Damon Metabolic profiling of 1H NMR spectra in Chronic Kidney Disease with local predictive modeling Proc Int Conf Mach Learn Appl, 2015, 176-181

L Ducassou, F André, B Ramassamy, Y Xu-Li, M-A Loriot, P Beaune, G Bertho, M Lombard, D Mansuy, J-L Boucher Expression in Yeast and Discovery of New Substrates of Human Orphan Cytochrome P450 2U1: Interpretation of their Hydroxylation Regioselectivity from Docking Studies on a Protein 3D Model Biochim Biophys Acta 2015 ; 1850(7), 1426-37

 

2014

N Pallet, E Thervet, P Beaune, A Karras, G Bertho* The urinary metabolome of chronic kidney disease Kidney Int, 2014, 85, 1239–1240

M Carichon, N Pallet, C Schmitt, T Lefebvre, L Gouya, N Talbi, J-C Deybach, P Beaune, P Vasos, H Puy, G Bertho* The urinary metabolic fingerprint of Acute Intermittent Porphyria analyzed by 1H-NMR spectroscopy Anal Chem, 2014, 86, 2166−2174

S Téletchéa, V Stresing, S Hervouet, M Baud’huin, M-F Heymann, G Bertho, C Charrier, K Ando, D Heymann Novel RANK antagonists for the treatment of bone resorptive disease: Theoretical predictions and experimental validation J Bone Miner Res 2014, 29, 1466-1477

A Sadet, L Fernandes, F Kateb, R Balzan, PR Vasos Long-lived coherences: Improved dispersion in the frequency domain using continuous-wave and reduced-power windowed sustaining irradiation J Chem Phys 2014, 141 (5), 054203

 

2013

F Kateb, H Perrin, K Tripsianes, P Zou, R Spadaccini, M Bottomley, TM Franzmann, J Buchner,S Ansieau, M Sattler Structural and Functional Analysis of the DEAF-1 and BS69 MYND Domains PLoS One 2013, 8: e54715

L Fernandes, C Guerniou, I Marín‐Montesinos, M Pons, F Kateb, PR Vasos Long‐lived states in an intrinsically disordered protein domain Magn Reson Chem 2013, 51 (11), 729-733

C Decroos, V Balland, J-L Boucher, G Bertho, Y Xu, D Mansuy Towards Stable Electron Paramagnetic Resonance Oximetry Probes Synthesis, Characterization and Metabolic Evaluation of New Ester Derivatives of a Tris-(para-carboxyltetrathiaaryl)methyl (TAM) RadicalChem Res Toxicol, 2013, 26, 1561–1569

P Dansette, D Levent, A Hessani, G Bertho, D Mansuy Thiolactone Sulfoxides as New Reactive Metabolites Acting as Bis-Electrophiles: Implication in Clopidogrel and Prasugrel Bioactivation Chem Res Toxicol, 2013, 26, :794-802

C Charrier, G Bertho, O Petigny, P Moneton, R Azerad A new derivative detected in accelerated ageing of artesunate-amodiaquine fixed dose combination tablets J Pharm Biomed Anal 2013, 81-82:20-26

M Hamel, M Lecinq, M Gulea, J Kozelka Ortho-(methylsulfanyl) phenylphosphonates and derivatives: Synthesis and applications as mono-or bidentate ligands for the preparation of platinum complexes J Org Chem, 2013, Vol 745–746, 206–213

Bergès J, Fourré I, Pilmé J, Kozelka J Quantum chemical topology study of the water-platinum(II) interaction Inorg Chem 2013 Feb 4;52(3):1217-27

 

2012

T Suchánková, K Kubíček, J Kašpárková, V Brabec, J Kozelka Platinum–DNA interstrand crosslinks: Molecular determinants of bending and unwinding of the double helix J Inorg Biochem 2012 Mar;108:69-79

Monnet J, Kozelka J Cisplatin GG-crosslinks within single-stranded DNA: origin of the preference for left-handed helicity J Inorg Biochem 2012 Oct;115:106-12

A Mantsyzov, G Bouvier, N Evrard-Todeschi, G Bertho* Contact-based ligand-clustering approach for the identification of active compounds in virtual screening Adv Appl Bioinform Chem, 2012, doi:102147/AABCS30881

Fougeray, I Mami, G Bertho, C Legendre, P Beaune, E Thervet, N Pallet Tryptophan depletion and the kinase GCN2 mediate interferon γ-induced autophagy J Immunol, 2012, 189, 2954-2964

P Rada, A I Rojo, N Evrard-Todeschi, N G Innamorato, A Cotte, T Jaworski, J C Tobón-Velasco, H Devijver, M Flor García-Mayoral, F Van Leuven, J D Hayes, G Bertho*, A Cuadrado* Structural and functional characterization of Nrf2 degradation by the GSK-3/β-TrCP axis Mol Cell Biol, 2012, 32, 3486-3499

P Dansette, J Rosi, J Debernardi, G Bertho, D Mansuy Metabolic Activation of Prasugrel : Nature of the two Competitive Pathways Resulting in the Opening of its Thiophene RingChem Res Toxicol, 2012, 25, 1058–1065

C Chopard, T Prangé, G Bertho Naphthalene-dioxygenase catalysed cis-dihydroxylation of bicyclic azaarenes RSC Adv, 2012, 2, 605-615

PM Dansette, J Rosi, G Bertho, D Mansuy Cytochromes P450 Catalyze Both Steps of the Major Pathway of Clopidogrel Bioactivation Whereas Paraoxonase Catalyzes the Formation of a Minor Thiol Metabolite Isomer Chem Res Toxicol, 2012, 25, 348-356

 

2011

Kozelka, J* Evaluation of dissociation constants from competition binding experiments based on the relative binding ratio Anal Biochem, 2011,409, 66‐73

Kumpun, S ; Maria, A ; Crouzet, S ; Evrard‐Todeschi, N ; Girault, JP ; Lafont, R* Ecdysteroids from Chenopodium quinoa Willd, an ancient Andean crop of high nutritional value Food Chem, 2011, 125, 1226‐123

Kumpun, S ; Girault, JP ; Dinan, L ; Blais, C ; Maria, A ; Dauphin‐Villemant, C ; Yingyongnarongkul, B ; Suksamrarn, A ; Lafont, R* The metabolism of 20‐hydroxyecdysone in mice: relevance to pharmacological effects and gene switch applications of ecdysteroids. J Steroid Biochem Mol Biol, 2011, 126, 1‐9

Pons, J ; Tanchou, V ; Girault, JP ; Bertho, G ; Evrard‐Todeschi, N* NMR applications for identifying β‐TrCP protein‐ligand interactions Mini Rev Med Chem, 2011, 11, 283‐297

Sarkar, R ; Ahuja, P *; Vasos, PR ; Bornet, A ; Wagnieres, O ; Bodenhausen, G Long‐lived coherences for line‐narrowing in high‐field NMR Progr Nucl Magn Res Spectrosc, 2011, 59, 83‐9

Segawa, TF *; Bornet, A ; Salvi, N ; Mieville, P ; Vitzthum, V ; Carnevale, D ; Jannin, S ; Caporini, MA ; Ulzega, S ; Vasos, PR ; Rey, M ; Bodenhausen, G* Extending Timescales and Narrowing Linewidths in NMR Chimia, 2011, 65, 652‐655

Bornet, A ; Ahuja, P ; Sarkar, R ; Fernandes, L ; Hadji, S ; Lee, SY ; Haririnia, A ; Fushman, D ; Bodenhausen, G ; Vasos, PR* Long‐lived states to monitor protein unfolding by proton NMR Chem. Phys. Chem., 2011, 12, 2729‐2734

 

2010

Rizzato, S ; Bergès, J ; Mason, SA ; Albinati, A ; Kozelka, J* Dispersion‐driven hydrogen bonding: predicted hydrogen bond between water and platinum(II) identified by neutron diffraction Angew Chem Int Ed, 2010,49, 7440‐7443

Ahuja, P ; Sarkar, R ; Jannin, S ; Vasos, PR *; Bodenhausen, G  Proton hyperpolarisation preserved in long‐lived states  Chem Commun, 2010, 46, 8192‐8194

Mamadalieva, NZ ; Janibekov, AA ; Girault, JP ; Lafont, R*  Two minor phytoecdysteroids of the plant Silene viridiflora.  Nat Prod Commun, 2010, 5, 1579‐1582

Bouvier, G ; Evrard‐Todeschi, N ; Girault, JP ; Bertho, G* Automatic clustering of docking poses in virtual screening process using self‐organising map Bioinformatics, 2010, 26, 53‐60

 

2009

Kozelka, J*  Molecular origin of the sequence‐dependent kinetics of reactions between cisplatin derivatives and  DNA  Inorg Chim Acta, 2009,362, 651–668

Téletchéa, S ; Skauge, T ; Sletten, E ; Kozelka, J* Cisplatin Adducts on a GGG Sequence within a DNA Duplex Studied by NMR Spectroscopy and Molecular Dynamics Simulations Chem. Eur. J., 2009,15, 12320 – 12337

Crouzet, S ; Maria, A ; Dinan, L ; Lafont, R ; Girault, JP* Ecdysteroids from Cyanotis longifolia Benth. (Commelinaceae). Arch Insect Biochem Physiol, 2009, 72, 194‐209

Zibareva, L ; Yeriomina, VI ; Munkhjargal, N ; Girault, JP ; Dinan, L ; Lafont, R. * The phytoecdysteroid profiles of 7 species of Silene (Caryophyllaceae). Arch Insect Biochem Physiol, 2009, 72, 234‐248

 

2008

Ho, R ; Girault, JP ; Cousteau, PY ; Bianchini, JP ; Raharivelomanana, P ; Lafont, R* Isolation of a new class of ecdysteroid conjugates (glucosyl‐ferulates) using a combination of liquid chromatographic methods. J Chromatogr Sci, 2008, 46, 102‐110

Bertho, G *;. Bouvier, G ; Hui Bon Hoa, G ; Girault, JP* The key‐role of tyrosine 155 in the mechanism of prion transconformation as highlighted by a study of sheep mutant peptides. Peptides, 2008, 29, 1073‐1084

Pons, J ; Evrard‐Todeschi, N ; Bertho, G ; Gharbi‐Benarous, J ; Tanchou, V ; Benarous, R ; Girault, JP* Transfer‐NMR and Docking Studies Identify the Binding of the Peptide Derived from Activating Transcription Factor 4 to Protein Ubiquitin Ligase beta‐TrCP. Competition STD‐NMR with beta‐Catenin Biochemistry, 2008, 47, 14‐29 (Hot article)

Evrard‐Todeschi, N ; Pons, J ; Gharbi‐Benarous, J ; Bertho, G ; Benarous, R ; Girault, JP* Structure of the Complex between Phosphorylated Substrates and the beta‐TrCP Ubiquitine Ligase Receptor: A combined NMR, Molecular Modelling and Docking Approach J Chem Inf Model, 2008, 48, 2350‐2361

 

2007

Pons, J ; Evrard‐Todeschi, N ; Bertho, G ; Gharbi‐Benarous, J ; Sonois, V ; Benarous, R ; Girault, JP* Structural studies on 24P‐IkBa peptide derived from a human IkB‐a protein‐related with the inhibition of the transcription factor nuclear NFkB activity Biochemistry, 2007, 46, 2958‐2972

Pons, J ; Evrard‐Todeschi, N ; Bertho, G ; Gharbi‐Benarous, J ; Benarous, R ; Girault, JP* Phosphorylation‐Dependent Structure of ATF4 Peptides derived from a Human ATF4 Protein, a Member of the Family of Transcription Factors Peptides, 2007, 28, 2253‐2267

Snogan, E ; Vahirua‐Lechat, I ; Ho, R ; Bertho, G ; Girault, JP ; Ortiga, S ; Maria, A ; Lafont R* Ecdysteroids from the Medicinal Fern Microsorum scolopendria (Burm. f.) Phytochem Anal., 2007, 18, 441‐450

Aitken, DJ ; Albinati, A ; Gutier, A ; Husson, H‐P ; Morgant, G ; Nguyen‐Huy, D ; Kozelka, J *; Lemoine, P ; Ongeri, S ; Rizzato, S ; Viossat, B Platinum(II) and Palladium(II) Complexes with N‐Aminoguanidine Eur J Inorg Chem, 2007, 3327 ‐ 3334

Hamel, M ; Rizzato, S ; Lecinq, M ; Sene, A ; Vazeux, M ; Gulea, M ; Albinati, A ; Kozelka, J* Study of Intramolecular Competition between Carboxylate and Phosphonate for PtII with the Aid of a Novel Tridentate Carboxylato‐Thioether‐Phosphonato Ligand Chem. Eur. J., 2007,13, 5441‐5449

Nuclear Magnetic Resonance Spectroscopy

Team Description

We develop original concepts that aim at enhancing resolution in spectra of complex samples, to a point where their analysis becomes a faster, easier, and a more accurate process. 

The research group on NMR of Biological Substances is part of the team Bio-Spectroscopies. We develop original approaches that combine advanced NMR methods with other physical chemical techniques including simulation tools to study molecular and supramolecular systems in the field of Health Sciences, targeting their dynamic and structural features. Over the last decade, we have contributed to exploring fundamental research issues at the frontier of chemistry and biology, ranging from the study of supramolecular interactions involving proteins, to the metabolic profiling of biofluids and the hyperpolarization of biological samples. These projects are carried out in the frame of several collaborations with  laboratories working in the fields of organic chemistry, biochemistry, structural biology or medical research.

 

Research Themes

Methodological developments for ultra-high resolution NMR

We design novel pulse sequences that exceed the resolution limits of traditional NMR analyzes on complex samples. We are also working on the development of modelling and data analysis tools to make the best use of the information obtained on the biological systems under study.

In this context, we have carried out methodological developments to acquire Pure Shift spectra with efficient suppression of the water signal on chalenging biofluids. We ahave shown how the analysis of the resulting metabolic profiles allows for getting a unique insight into the metabolic pathways that are key to Lymphoma cells and for addressing the mechanisms of action of a combination of antimetabolic drugs. [1] We have also demonstrated the robustness of a new analytical workflow based on the use of a library of reference Pure Shift spectra to fit the fingerprint of each metabolite of interest and determine its concentration. [2]

[1] J Proteome Res 21 (4), 1041-1051, 2022.
[2] Anal. Chem. 94, 43, 14974–14984, 2022

Dynamic and structural study of biomolecular interactions

Describing and understanding supramolecular interactions in large biological or bio-mimetic systems has become a major stake over the recent years. However, despite the considerable progress that have been achieved in this field, probing at an atomic scale protein-protein, protein-nucleic acid, protein-lipid, protein-carbohydrate interactions, or the interactions with small molecules, enzyme substrates and regulators, still constitutes a critical challenge for chemists and biochemists.

We are carrying out several collaborations with the groups of Dr. Olivier Maury (Ecole Normale Supérieure de Lyon), Pr. Elise Dumont (Université Côte d’Azur, Nice) and Dr. Christelle Hureau (Laboratoire de Chimie de Coordination, Toulouse) to understand the supramolecular properties of molecules that can be used as crystallization agents of proteins, as modulators of the aggregation process of amyloid peptides, or as non-covalent paramagnetic tags to probe the structure of proteins and peptides by NMR, both in solution and in the solid state. We notably develop an original approach combining paramagnetic NMR and molecular dynamics to probe the dynamic interaction processes between biomolecules and lanthanide complexes. [1] We have recently shown that this hybrid approach makes it possible to capture the detail of these interactions on time scales which are complementary, and to propose a global vision of the dynamic process which reconciles the points of view of the two techniques.

[1] Physical Chemistry Chemical Physics, 23, 11224-11232 (2021) DOI: 10.1039/D0CP06570F

Metabolomics in the field of Health Sciences

We provide medical researchers with a better understanding, based on metabolomics by NMR, of the complex interplay between the different factors that contribute to the development of diseases. Recent progress in metabolomics has improved our understanding of the system-levels effect of metabolites in biofluids, cells and tissues, using either Mass Spectrometry and/or NMR as complementary detection techniques.
NMR is a highly versatile tool for obtaining metabolic profiles. It allows for analysing all the small metabolites simultaneously, with a high reproducibility. This technique is also non-destructive, robust and quantitative.
Over the last decade, we have developed an expertise in deciphering the complex metabolic pathways that are involved in the evolution of diseases at every step of biological and medical research projects, from preliminary in vitro studies to clinical trials. [1]
Our goal is notably to bring another vision that is complementary to transcriptomics or genomics and can contribute to establish pertinent biomarkers that will help to develop new diagnosis and prognosis approaches. We can help medical researchers to better understand the mechanism of action of new therapeutic approaches, by exploring how the metabolism is correlated to the response of patients to a given treatment. In this context, our group is also developing new analytical tools for boosting resolution and sensitivity of NMR analyses and thus paving the way for new therapeutic options. [2]

[1] NMR in Biomedicine. 2023; 36(11):e5006. DOI:10.1002/nbm.5006
[2] Magn Reson Chem 2023, 1. DOI: 10.1002/mrc.5356

Dissolution Dynamic Nuclear Polarization (D-DNP) of bio-samples.

Our research activity on hyperpolarization, using dissolution dynamic nuclear polarization (D-DNP), is in line with the study of biological samples, which is a strong theme in our team. By exploiting the high signal enhancements of several orders of magnitude allowed by DNP, we seek to push the limits in terms of temporal resolution for the study of cellular processes in real time, but also to analyse complex biological samples containing low concentrations of metabolites. The starting point of our studies is the cellular metabolism of glutamine and its deregulation in the presence of certain pathologies such as cancer or cardiovascular dysfunction. [1] Initially focused on the study of enzymatic reactions in vitro and on cell extracts, our experiments aim at working in real time on living cells or during ex vivo MRI experiments, as well as on biological samples such as blood, urine or serum, while developing synergies with other thematics and methodological developments of the team, such as high-resolution detection sequences.

[1] ChemPhysChem 2023, 24, e202300151. DOI: 10.1002/cphc.202300151

NMR Facility at UMR 8601

Our group is hosting the NMR facility of our Research Unit, including 3 NMR spectrometers (500 MHz to 600 MHz) and a prototype polarizer for Dissolution Dynamic Nuclear Polarization (D-DNP), to improve the sensitivity of solution NMR of bio-samples.

We are members of the Equipex program “CACSICE” (Center for the Analysis of Complex Systems in Complex Environments), and the Equipex program “Paris en resonance”, which provides access to DNP enhanced NMR equipment for users from both academic and industrial laboratories. We have also recently implemented the first NMR facility in France dedicated to metabolomic analyses for Health Sciences “Metabo Paris Santé”.

2024

1. Lipoproteome dysregulation precedes conversion to psychosis in ultra-high-risk subjects,
M.T. Avella, G. Bertho, O. Kébir, C. Caradeuc, M.O. Krebs, N. Giraud, B. Chaumette, A. Frajerman,
Neuroscience Applied, Volume 3, Supplement 1, (2024),103948
DOI: 10.1016/j.nsa.2024.103948

2. One touch is all it takes: the supramolecular interaction between ubiquitin and lanthanide complexes revisited by paramagnetic NMR and molecular dynamics,
K. Dos Santos,  A. Bartocci, N. Gillet, S. Denis-Quanquin, A. Roux, E. Lin, Z. Xu, R. Finizola,P. Chedozeau,X. Chen, C. Caradeuc, M. Baudin, G. Bertho, F. Riobé, O. Maury, E. Dumont* and N. Giraud* ,
Physical Chemistry Chemical Physics (2024)
DOI: 10.1039/D4CP00463A

2023

4. Guest exchange in a biomimetic ZnII cavity-complex: kinetic control by a catalytic water, through pore selection, 2nd sphere assistance, and induced-fit processes
Nyssen, N., Giraud, N., Wouters, J., Jabin, I., Leherte, L. & Reinaud, O.*
Inorganic Chemistry Frontiers, in Press (2023) DOI : 10.1039/D3QI01271A

3. NMR metabolomics study of the chronic low-dose exposure to a cocktail of Persistent Organic Pollutants
Lucas-Torres, C., Caradeuc, C., Prieur, L., Djemai, H., Layale, Y., Noirez, P., Coumoul, X., Audouze, K., Giraud, N., & Bertho, G.*
NMR in Biomedicine, in Press (2023) DOI : 10.1002/nbm.5006

2. Present and Future of Pure Shift NMR in Metabolomics
Chen, X., Bertho, G., Caradeuc, C., Giraud, N.* and Lucas-Torres, C.*,
Magnetic Resonance in Chemistry Metabolomics Special Issue: Frontiers in NMR Metabolomics, invited review (2023) DOI: 10.1002/mrc.5356

1. A Toolbox For Glutamine Use In Dissolution Dynamic Nuclear Polarization: From Enzymatic Reaction Monitoring To The Study Of Cellular Metabolic Pathways And Imaging.
Dos Santos, K, Bertho, G., Caradeuc, C., Baud, V., Montagne, A., Abergel, D., Giraud, N.* & Baudin, M.*
ChemPhysChem (2023) DOI: 10.1002/cphc.202300151

 

2022

5. Absolute Metabolite Quantification Using Pure Shift NMR: Towards Quantitative Metabolic Profiling of Aqueous Biological Samples
Chen, X., Caradeuc, C., Montagne, A., Baud, V., Bertho, G., Lucas-Torres, C.*, Giraud, N.*
Anal. Chem. 94, 43, 14974–14984 (2022) DOI: 10.1021/acs.analchem.2c02823

4. Synthesis and Characterization of Novel Conformers of (E)-2-(3-nitro-H-imidazo[1,2-a]pyridin-2-ylthio)-N’-benzylideneacetohydrazide Derivatives
Evrard, A., Coulibaly, S.*, Coulibali, S *, Kouassi, S., Achi, P.A., Giraud, N. and Bertho, G.
Magnetic Resonance in Chemistry, 60, 1157-1170 (2022) DOI: 10.1002/mrc.5308

3. Lanthanide tris-dipicolinate: a do-it-all complex?
Denis Quanquin, S., D’Aléo, A., Balogh, C., N’Dala Louika, I., Salaam, J., le Guennic, B., Thieuleux, C., Camp, C., Veyre, L., Costuas, K., Rigaut, S., Le Bozec, H., Andraud, C., Dumont, E., Gilet, N., Chapelle, C., Girard, E., Giraud, N., Pilet, G., Riobé, F., Maury, O*
Actualité Chimique, 475, 12 (2022)

2. Ultrahigh-Resolution NMR with Water Signal Suppression for a Deeper Understanding of the Action of Antimetabolic Drugs on Dif-fuse Large B-Cell Lymphoma
Bertho, G., Lordello, L., Chen, X., Lucas-Torres, C., Oumezziane, I.E., Caradeuc, C., Baudin, M., Nuan-Aliman, S., Thieblemont, C., Baud, V.* and Giraud, N.*
Journal of Proteome Research, 21, 4, 1041-1051 (2022) DOI: https://doi.org/10.1021/acs.jproteome.1c00914

1. Structural Analysis of Unstable Norbixin Isomers Guided by Pure Shift Nuclear Magnetic Resonance.
Bertho, G.* Oumezziane, I.E., Caradeuc, C., Guibout, L., Balducci, C., Dinan, L., Dilda, P.J., Camelo, S., Lafont, R., and Giraud, N.*
Magnetic Resonance in Chemistry, 60, 504-514 (2022) DOI: https://doi.org/10.1002/mrc.5252

 

2021

10. Spin Thermometry: A Straightforward Measure of Millikelvin Deuterium Spin Temperatures Achieved by Dynamic Nuclear Polarization,
B. Aghelnejad, S. Marhabaie, M. Baudin, G. Bodenhausen, and D. Carnevale
The Journal of Physical Chemistry Letters 11 (9), 3219-3225 (2020)
https://doi.org/10.1021/acs.jpclett.0c00713

9. Effects of Microwave Gating on Nuclear Spin Echoes in Dynamic Nuclear Polarization.
D. Guarin, D. Carnevale, M. Baudin, P. Pelupessy, D. Abergel, and G. Bodenhausen.
J. Phys. Chem. Lett., 2021, 13, 175-182 (2021).
https://doi.org/10.1021/acs.jpclett.1c03436

8. On the Supra-LUMO Interaction: Case Study of a Sudden Change of Electronic Structure as a Functional Emergence.
Lainé, P.*, Gosset, A., Lachmanová, S.N.,  Cherraben, S., Bertho, G., Forté, J., Perruchot, C., Jacquot de Rouville, H.P., Pospíšil, L., Hromadová, M., Brémond, E.
Chemistry – A European Journal, Accepted Article (2021)
https://doi.org/10.1002/chem.202103136

7. Loss of prion protein control of glucose metabolism promotes neurodegeneration in model of prion diseases.
Arnould, H., Baudouin, V., Baudry, A., Ribeiro, L.W., Ardila-Osorio, H., Pietri, M., Caradeuc, C., Soultawi, C., Williams, D., Alvarez, M., Crozet, C., Djouadi, F., Laforge, M., Bertho, G., Kellermann, O., Launay, J.M., Schmitt-Ulms, G., Schneider, B.*
PLoS Pathogens 17(10): e1009991.
https://doi.org/10.1371/journal.ppat.1009991

6. Distinction between 2’- and 3’ – phosphate isomers of a fluorescent NADPH analogue led to strong inhibition of cancer cells proliferation and migration..
Lima, M., Dilly, S., Daunay, S., Abbe, P., Solier, S., Guillaumond, F., Tubiana, S.S., Escargueil, A.E., Henriques, J.A.P., Ferrand, N., Erdelmeier, I., Boucher, J.L., Bertho, G., Agranat, I., Rocchi, S., Sabbah, M., Slama-Schwok, A.*
Antioxydants, 10 (5), 723 (2021)
https://doi.org/10.3390/antiox10050723

5. The complex metabolism of poststerone in male rats.
Balducci, C., Dinan, L., Guibout, L., Foucault, A.S., Carbonne, C., Durand, J.D., Caradeuc, C., Bertho, G., Girault, J.P., Lafont, R.
The Journal of Steroid Biochemistry and Molecular Biology, 212, 105897, (2021)
https://doi.org/10.1016/j.jsbmb.2021.105897

4. Adenomyosis is associated with specific proton nuclear magnetic resonance (1H-NMR) serum metabolic profiles.
Bourdon, M., Santulli, P., Kateb, F., Pocate-Cheriet, K., Batteux, F., Maignien, C., Chouzenoux, S., Bordonne, C., Marcellin, L., Bertho, G.*, Chapron, C.*
Fertility and Sterility, 116 (1), 243-254 (2021)
https://doi.org/10.1016/j.fertnstert.2021.02.031

3. Book Chapter: Analyse Métabolomique par Résonance Magnétique Nucléaire : Application aux Maladies Porphyriques
G. Bertho
in La Révolution Biotechnologique et la médecine de demain
Ducancel F., Schneider, B.
Doin Ed., ISBN: 978-2-7040-1620-4 (2021)

2. Capturing The Dynamic Association Between A Tris-Dipicolinate Lanthanide Complex And A Decapeptide: A Combined Paramagnetic NMR And Molecular Dynamics Exploration.
Denis-Quanquin, S., Bartocci, A., Szczepaniak, F., Riobé, F., Maury, O., Dumont, E.*, Giraud, N.*
Physical Chemistry Chemical Physics. 23, 11224-11232 (2021)
https://doi.org/10.1039/D0CP06570F

1. Solid-State versus Solution Investigation of a Luminescent Chiral BINOL-Derived Bisphosphate Single-Molecule Magnet
Mattei C.A., Montigaud, V., Gendron F., Denis-Quanquin S., Dorcet V., Giraud N., Riobé F., Argouarch G., Maury O., Le Guennic B.,* Cador O., Lalli C., Pointillart F.*
Inorg. Chem. Front., 8, 947-962 (2021)
https://doi.org/10.1039/D0QI01192D

2020

4. Mn(I) Complex Redox Potential Tunability by Remote Lewis Acid Interaction.
Srinivasan, A. Campos, J., Giraud, N., Robert M. and Rivada-Wheelaghan O.* Dalton Trans., 2020,49, 16623-16626 (2020https://dx.doi.org/10.1039/D0DT02467H

3. The Follicular fluid metabolome differs according to the endometriosis phenotype.
Pocate-Cheriet, K., Santulli, P., Kateb, F., Bourdon, M., Maignien, C., Batteux, F., Chouzenoux, S., Patrat, C., Wolf, J.P., Bertho, G. & Chapron, C., Reproductive BioMedicine Online, 41, 1023-1037 (2020) https://doi.org/10.1016/j.rbmo.2020.09.002

2. Endometriosis Phenotypes Are Associated With Specific Serum Metabolic Profiles Determined By Proton-Nuclear Magnetic Resonance.
Maignien, C., Santulli, P., Kateb, F., Caradeuc, C., Marcellin, L., Pocate-Cheriet, K., Bourdon, M., Chouzenoux, S., Batteux, F., Bertho, G. & Chapron, C., Reproductive BioMedicine Online, 41, 640-652 (2020https://doi.org/10.1016/j.rbmo.2020.06.019

1. Multinuclear NMR in Polypeptide Liquid Crystals: Three Fertile Decades of Methodological Developments and Analytical Challenges.
Lesot, P.*, Aroulanda, C., Berdagué, P., Meddour, A., J., Merlet, D., Farjon, J., Giraud, N., & Lafon, O. Progress in Nuclear Magnetic Resonance Spectroscopy, 116, 85-154 (2019) https://dx.doi.org/10.1016/j.pnmrs.2019.10.001

2019

1. Monitoring Conformational Changes in an Enzyme Conversion Inhibitor Using Pure Shift Exchange NMR Spectroscopy. Aloui, G., Bouabdallah, S., Baltaze, J.P., Herbert Pucheta, J.E., Touil, S., Farjon, J. & Giraud, N.* ChemPhysChem, 20, 1738-1746 (2019) https://dx.doi.org/10.1002/cphc.201900244

2. A biomimetic strategy for the selective recognition of organophosphates in 100% water: synergies of electrostatic interactions, cavity embedment and metal coordination. Collin, S., Giraud, N., Dumont, E., & Reinaud, O.* Organic Chemistry Frontiers, 6, 1627-1636 (2019) https://dx.doi.org/10.1039/c9qo00263d

2018

1. Combining pure shift and J‐edited spectroscopies: A strategy for extracting chemical shifts and scalar couplings from highly crowded proton spectra of oligomeric saccharides. Pitoux, D., Hu, Z., Plainchont, B., Merlet, D., Farjon, J., Bonnaffé, D. & Giraud, N.* Magnetic Resonance in Chemistry, 56, 954-962 (2018) https://dx.doi.org/10.1002/mrc.4715

2. Highly Accurate Quantitative Analysis Of Enantiomeric Mixtures From Spatially Frequency Encoded 1H NMR Spectra. Plainchont, B., Pitoux, D., Cyrille, M. & Giraud, N.* Analytical Chemistry, 90, 1595-1600 (2018) https://dx.doi.org/10.1021/acs.analchem.7b02411

3. 1H NMR analyses of enantiomeric mixtures using chiral liquid crystals (invited paper). Farjon, J. & Giraud, N.* Current Opinion in Colloid and Interface Science, 33, 1-8 (2018) https://dx.doi.org/10.1016/j.cocis.2017.11.001

4. Real-time and non-invasive monitoring of renal endoplasmic reticulum stress in individuals with a hemodynamic impairment.
B. Fohlen, Q. Tavernier, T. Huynh, C. Caradeuc, D. Le Corre, G. Bertho, B. Cholley, N. Pallet
EBioMedicine, 27, 284-292 (2018). https://doi.org/10.1016/j.ebiom.2017.12.023

5. Urinary metabolic profiling of asymptomatic Acute Intermittent Porphyria using a rule-mining-based algorithm.
M. Luck, C. Schmitt, N. Talbi, L. Gouya, C. Caradeuc, H. Puy, G. Bertho*, N. Pallet*
Metabolomics, 14, 10 (2018). https://doi.org/10.1007/s11306-017-1305-9

6. Bacterial Transferase MraY, a Source of Inspiration towards New Antibiotics, Mickaël J. Fer, Laurent Le Corre, Nicolas Pietrancosta, Nathalie Evrard-Todeschi, Samir Olatunji, Ahmed Bouhss, Sandrine Calvet-Vitale*,  Christine Gravier-Pelletier*. Current Medicinal Chemistry, 2018, 25 , Issue 42 , 2018 https://doi.org/10.2174/0929867325666180330095154

Till 2017
2017 

M Sarkis, MA Miteva, M Chiara Dasso Lang, M Jaouen, M-A Sari, M-O Galcéra, M Ethève-Quelquejeu, C Garbay, G Bertho*, E Braud* Insights into the interaction of high potency inhibitor IRC-083864 with phosphatase CDC25 : Binding model of CDC25 inhibitor IRC-083864 Proteins, 2017, Jan 5 doi: 101002/prot25236

M Melikian, B Eluard, G Bertho, V Baud, N Evrard-Todeschi Model of the Interaction between the NF-κB Inhibitory protein p100 and the E3 ubiquitin ligase β-TrCP based on NMR and Docking Experiments J Chem Inf Model, 2017 Jan 13 doi: 101021/acsjcim5b00409

Yurenko YP, Bazzi S, Marek R, Kozelka J Anion-π Interactions in Flavoproteins Involve a Substantial Charge-Transfer Component Chemistry 2017, 23 3246-3250

Kozelka J Lone pair-π interactions in biological systems: occurrence, function, and physical origin, Eur Biophys J 2017 May 2 doi: 101007/s00249-017-1210-1

R Balzan, L Fernandes, L Pidial, A Comment, B Tavitian, PR Vasos Pyruvate cellular uptake and enzymatic conversion probed by dissolution DNP‐NMR: the impact of overexpressed membrane transporters Magn Reson Chem, 2017, 55:579-583

 

2016

R Balzan, L Fernandes, A Comment, L Pidial, B Tavitian, PR Vasos Dissolution Dynamic Nuclear Polarization Instrumentation for Real-time Enzymatic Reaction Rate Measurements by NMR JoVE, 2016, e53548-e53548

M Luck, G Bertho, M Bateson, A Karras, A Yartseva, E Thervet, C Damon, N Pallet* Rule-Mining for the Early Prediction of Chronic Kidney Disease Based on Metabolomics and Multi-Source Data PLoS One 2016 Nov 18;11(11):e0166905

J-W Chiao, M Melikian, L Han, A Tsao, S K Mencher, J Fallon, G Bertho* & L G Wang* Interaction of a small molecule and STAT3-SH2 domain to block Y705 phosphorylation and inhibit lupus nephritis Biochem Pharmacol, 2016, 99, 123-131

Novotný J, Bazzi S, Marek R, Kozelka J Lone-pair-π interactions: analysis of the physical origin and biological implications Phys Chem Chem Phys 2016 Jul 28;18(28):19472-81

 

2015

I Anosova, S Melnik, K Tripsianes, F Kateb, I Grummt, M Sattler A novel RNA binding surface of the TAM domain of TIP5/BAZ2A mediates epigenetic regulation of rRNA genes Nucleic Acids Res 2015, 43, 5208-5220

Badri Z, Foroutan-Nejad C, Kozelka J, Marek R On the non-classical contribution in lone-pair-π interaction: IQA perspective Phys Chem Chem Phys 2015 Oct 21;17(39):26183-9

M Luck*, A Yartseva, G Bertho, E Thervet, P Beaune, N Pallet, C Damon Metabolic profiling of 1H NMR spectra in Chronic Kidney Disease with local predictive modeling Proc Int Conf Mach Learn Appl, 2015, 176-181

L Ducassou, F André, B Ramassamy, Y Xu-Li, M-A Loriot, P Beaune, G Bertho, M Lombard, D Mansuy, J-L Boucher Expression in Yeast and Discovery of New Substrates of Human Orphan Cytochrome P450 2U1: Interpretation of their Hydroxylation Regioselectivity from Docking Studies on a Protein 3D Model Biochim Biophys Acta 2015 ; 1850(7), 1426-37

 

2014

N Pallet, E Thervet, P Beaune, A Karras, G Bertho* The urinary metabolome of chronic kidney disease Kidney Int, 2014, 85, 1239–1240

M Carichon, N Pallet, C Schmitt, T Lefebvre, L Gouya, N Talbi, J-C Deybach, P Beaune, P Vasos, H Puy, G Bertho* The urinary metabolic fingerprint of Acute Intermittent Porphyria analyzed by 1H-NMR spectroscopy Anal Chem, 2014, 86, 2166−2174

S Téletchéa, V Stresing, S Hervouet, M Baud’huin, M-F Heymann, G Bertho, C Charrier, K Ando, D Heymann Novel RANK antagonists for the treatment of bone resorptive disease: Theoretical predictions and experimental validation J Bone Miner Res 2014, 29, 1466-1477

A Sadet, L Fernandes, F Kateb, R Balzan, PR Vasos Long-lived coherences: Improved dispersion in the frequency domain using continuous-wave and reduced-power windowed sustaining irradiation J Chem Phys 2014, 141 (5), 054203

 

2013

F Kateb, H Perrin, K Tripsianes, P Zou, R Spadaccini, M Bottomley, TM Franzmann, J Buchner,S Ansieau, M Sattler Structural and Functional Analysis of the DEAF-1 and BS69 MYND Domains PLoS One 2013, 8: e54715

L Fernandes, C Guerniou, I Marín‐Montesinos, M Pons, F Kateb, PR Vasos Long‐lived states in an intrinsically disordered protein domain Magn Reson Chem 2013, 51 (11), 729-733

C Decroos, V Balland, J-L Boucher, G Bertho, Y Xu, D Mansuy Towards Stable Electron Paramagnetic Resonance Oximetry Probes Synthesis, Characterization and Metabolic Evaluation of New Ester Derivatives of a Tris-(para-carboxyltetrathiaaryl)methyl (TAM) RadicalChem Res Toxicol, 2013, 26, 1561–1569

P Dansette, D Levent, A Hessani, G Bertho, D Mansuy Thiolactone Sulfoxides as New Reactive Metabolites Acting as Bis-Electrophiles: Implication in Clopidogrel and Prasugrel Bioactivation Chem Res Toxicol, 2013, 26, :794-802

C Charrier, G Bertho, O Petigny, P Moneton, R Azerad A new derivative detected in accelerated ageing of artesunate-amodiaquine fixed dose combination tablets J Pharm Biomed Anal 2013, 81-82:20-26

M Hamel, M Lecinq, M Gulea, J Kozelka Ortho-(methylsulfanyl) phenylphosphonates and derivatives: Synthesis and applications as mono-or bidentate ligands for the preparation of platinum complexes J Org Chem, 2013, Vol 745–746, 206–213

Bergès J, Fourré I, Pilmé J, Kozelka J Quantum chemical topology study of the water-platinum(II) interaction Inorg Chem 2013 Feb 4;52(3):1217-27

 

2012

T Suchánková, K Kubíček, J Kašpárková, V Brabec, J Kozelka Platinum–DNA interstrand crosslinks: Molecular determinants of bending and unwinding of the double helix J Inorg Biochem 2012 Mar;108:69-79

Monnet J, Kozelka J Cisplatin GG-crosslinks within single-stranded DNA: origin of the preference for left-handed helicity J Inorg Biochem 2012 Oct;115:106-12

A Mantsyzov, G Bouvier, N Evrard-Todeschi, G Bertho* Contact-based ligand-clustering approach for the identification of active compounds in virtual screening Adv Appl Bioinform Chem, 2012, doi:102147/AABCS30881

Fougeray, I Mami, G Bertho, C Legendre, P Beaune, E Thervet, N Pallet Tryptophan depletion and the kinase GCN2 mediate interferon γ-induced autophagy J Immunol, 2012, 189, 2954-2964

P Rada, A I Rojo, N Evrard-Todeschi, N G Innamorato, A Cotte, T Jaworski, J C Tobón-Velasco, H Devijver, M Flor García-Mayoral, F Van Leuven, J D Hayes, G Bertho*, A Cuadrado* Structural and functional characterization of Nrf2 degradation by the GSK-3/β-TrCP axis Mol Cell Biol, 2012, 32, 3486-3499

P Dansette, J Rosi, J Debernardi, G Bertho, D Mansuy Metabolic Activation of Prasugrel : Nature of the two Competitive Pathways Resulting in the Opening of its Thiophene RingChem Res Toxicol, 2012, 25, 1058–1065

C Chopard, T Prangé, G Bertho Naphthalene-dioxygenase catalysed cis-dihydroxylation of bicyclic azaarenes RSC Adv, 2012, 2, 605-615

PM Dansette, J Rosi, G Bertho, D Mansuy Cytochromes P450 Catalyze Both Steps of the Major Pathway of Clopidogrel Bioactivation Whereas Paraoxonase Catalyzes the Formation of a Minor Thiol Metabolite Isomer Chem Res Toxicol, 2012, 25, 348-356

 

2011

Kozelka, J* Evaluation of dissociation constants from competition binding experiments based on the relative binding ratio Anal Biochem, 2011,409, 66‐73

Kumpun, S ; Maria, A ; Crouzet, S ; Evrard‐Todeschi, N ; Girault, JP ; Lafont, R* Ecdysteroids from Chenopodium quinoa Willd, an ancient Andean crop of high nutritional value Food Chem, 2011, 125, 1226‐123

Kumpun, S ; Girault, JP ; Dinan, L ; Blais, C ; Maria, A ; Dauphin‐Villemant, C ; Yingyongnarongkul, B ; Suksamrarn, A ; Lafont, R* The metabolism of 20‐hydroxyecdysone in mice: relevance to pharmacological effects and gene switch applications of ecdysteroids. J Steroid Biochem Mol Biol, 2011, 126, 1‐9

Pons, J ; Tanchou, V ; Girault, JP ; Bertho, G ; Evrard‐Todeschi, N* NMR applications for identifying β‐TrCP protein‐ligand interactions Mini Rev Med Chem, 2011, 11, 283‐297

Sarkar, R ; Ahuja, P *; Vasos, PR ; Bornet, A ; Wagnieres, O ; Bodenhausen, G Long‐lived coherences for line‐narrowing in high‐field NMR Progr Nucl Magn Res Spectrosc, 2011, 59, 83‐9

Segawa, TF *; Bornet, A ; Salvi, N ; Mieville, P ; Vitzthum, V ; Carnevale, D ; Jannin, S ; Caporini, MA ; Ulzega, S ; Vasos, PR ; Rey, M ; Bodenhausen, G* Extending Timescales and Narrowing Linewidths in NMR Chimia, 2011, 65, 652‐655

Bornet, A ; Ahuja, P ; Sarkar, R ; Fernandes, L ; Hadji, S ; Lee, SY ; Haririnia, A ; Fushman, D ; Bodenhausen, G ; Vasos, PR* Long‐lived states to monitor protein unfolding by proton NMR Chem. Phys. Chem., 2011, 12, 2729‐2734

 

2010

Rizzato, S ; Bergès, J ; Mason, SA ; Albinati, A ; Kozelka, J* Dispersion‐driven hydrogen bonding: predicted hydrogen bond between water and platinum(II) identified by neutron diffraction Angew Chem Int Ed, 2010,49, 7440‐7443

Ahuja, P ; Sarkar, R ; Jannin, S ; Vasos, PR *; Bodenhausen, G  Proton hyperpolarisation preserved in long‐lived states  Chem Commun, 2010, 46, 8192‐8194

Mamadalieva, NZ ; Janibekov, AA ; Girault, JP ; Lafont, R*  Two minor phytoecdysteroids of the plant Silene viridiflora.  Nat Prod Commun, 2010, 5, 1579‐1582

Bouvier, G ; Evrard‐Todeschi, N ; Girault, JP ; Bertho, G* Automatic clustering of docking poses in virtual screening process using self‐organising map Bioinformatics, 2010, 26, 53‐60

 

2009

Kozelka, J*  Molecular origin of the sequence‐dependent kinetics of reactions between cisplatin derivatives and  DNA  Inorg Chim Acta, 2009,362, 651–668

Téletchéa, S ; Skauge, T ; Sletten, E ; Kozelka, J* Cisplatin Adducts on a GGG Sequence within a DNA Duplex Studied by NMR Spectroscopy and Molecular Dynamics Simulations Chem. Eur. J., 2009,15, 12320 – 12337

Crouzet, S ; Maria, A ; Dinan, L ; Lafont, R ; Girault, JP* Ecdysteroids from Cyanotis longifolia Benth. (Commelinaceae). Arch Insect Biochem Physiol, 2009, 72, 194‐209

Zibareva, L ; Yeriomina, VI ; Munkhjargal, N ; Girault, JP ; Dinan, L ; Lafont, R. * The phytoecdysteroid profiles of 7 species of Silene (Caryophyllaceae). Arch Insect Biochem Physiol, 2009, 72, 234‐248

 

2008

Ho, R ; Girault, JP ; Cousteau, PY ; Bianchini, JP ; Raharivelomanana, P ; Lafont, R* Isolation of a new class of ecdysteroid conjugates (glucosyl‐ferulates) using a combination of liquid chromatographic methods. J Chromatogr Sci, 2008, 46, 102‐110

Bertho, G *;. Bouvier, G ; Hui Bon Hoa, G ; Girault, JP* The key‐role of tyrosine 155 in the mechanism of prion transconformation as highlighted by a study of sheep mutant peptides. Peptides, 2008, 29, 1073‐1084

Pons, J ; Evrard‐Todeschi, N ; Bertho, G ; Gharbi‐Benarous, J ; Tanchou, V ; Benarous, R ; Girault, JP* Transfer‐NMR and Docking Studies Identify the Binding of the Peptide Derived from Activating Transcription Factor 4 to Protein Ubiquitin Ligase beta‐TrCP. Competition STD‐NMR with beta‐Catenin Biochemistry, 2008, 47, 14‐29 (Hot article)

Evrard‐Todeschi, N ; Pons, J ; Gharbi‐Benarous, J ; Bertho, G ; Benarous, R ; Girault, JP* Structure of the Complex between Phosphorylated Substrates and the beta‐TrCP Ubiquitine Ligase Receptor: A combined NMR, Molecular Modelling and Docking Approach J Chem Inf Model, 2008, 48, 2350‐2361

 

2007

Pons, J ; Evrard‐Todeschi, N ; Bertho, G ; Gharbi‐Benarous, J ; Sonois, V ; Benarous, R ; Girault, JP* Structural studies on 24P‐IkBa peptide derived from a human IkB‐a protein‐related with the inhibition of the transcription factor nuclear NFkB activity Biochemistry, 2007, 46, 2958‐2972

Pons, J ; Evrard‐Todeschi, N ; Bertho, G ; Gharbi‐Benarous, J ; Benarous, R ; Girault, JP* Phosphorylation‐Dependent Structure of ATF4 Peptides derived from a Human ATF4 Protein, a Member of the Family of Transcription Factors Peptides, 2007, 28, 2253‐2267

Snogan, E ; Vahirua‐Lechat, I ; Ho, R ; Bertho, G ; Girault, JP ; Ortiga, S ; Maria, A ; Lafont R* Ecdysteroids from the Medicinal Fern Microsorum scolopendria (Burm. f.) Phytochem Anal., 2007, 18, 441‐450

Aitken, DJ ; Albinati, A ; Gutier, A ; Husson, H‐P ; Morgant, G ; Nguyen‐Huy, D ; Kozelka, J *; Lemoine, P ; Ongeri, S ; Rizzato, S ; Viossat, B Platinum(II) and Palladium(II) Complexes with N‐Aminoguanidine Eur J Inorg Chem, 2007, 3327 ‐ 3334

Hamel, M ; Rizzato, S ; Lecinq, M ; Sene, A ; Vazeux, M ; Gulea, M ; Albinati, A ; Kozelka, J* Study of Intramolecular Competition between Carboxylate and Phosphonate for PtII with the Aid of a Novel Tridentate Carboxylato‐Thioether‐Phosphonato Ligand Chem. Eur. J., 2007,13, 5441‐5449