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3. Crystal Structure of Bis(1-butyl-1-methypyrrolidinium) Perthiodicarbonate Complex.

Author

Pinaud, Noël, Danten, Yann, Marchivie, Mathieu, Besnard, Marcel, Cabaço, Isabel, and Guillon, Jean

Subjects
*CARBON disulfide, *X-ray diffraction, *SPACE groups, *CRYSTAL structure, *IONIC liquids
Abstract

Bis(1-butyl-1-methypyrrolidinium) perthiodicarbonate was obtained by the reaction of carbon disulfide with 1-butyl-1-methypyrrolidinium acetate ([BmPyrro][Ac]) in the liquid phase. Structural characterization of this original complex was achieved by single-crystal X-ray diffraction (SCXRD) analysis. The asymmetric unit of the title compound, C2S6·2C9H20N, consisted of two crystallographically 1-methyl-1-butyl pyrrolidinium cations and one perthiodicarbonate anion. The complex C2S6·2C9H20N crystallized in the monoclinic space group, C 2/c, and possessed the following cell parameters: a = 16.0970(10) Å, b = 14.7140(9) Å, c = 12.3280(8) Å, α = 90°, β = 112.3730(12)°, γ = 90°, V = 2700.11 Å3, and Z = 8, Z' = 0.5. [ABSTRACT FROM AUTHOR]

Published
2024
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4. Design, Synthesis, and In Vitro Antimalarial Evaluation of New 1,3,5- Tris [(4-(Substituted-Aminomethyl)Phenoxy)Methyl]Benzenes.

Author

Albenque-Rubio, Sandra, Guillon, Jean, Agnamey, Patrice, Damiani, Céline, Savrimoutou, Solène, Mustière, Romain, Pinaud, Noël, Moreau, Stéphane, Mergny, Jean-Louis, Ronga, Luisa, Kanavos, Ioannis, Marchivie, Mathieu, Moukha, Serge, Dozolme, Pascale, Sonnet, Pascal, and Cohen, Anita

Subjects
BENZENE compounds, BENZENE derivatives, NITROGEN compounds, CYTOTOXINS, PLASMODIUM falciparum, QUADRUPLEX nucleic acids
Abstract

By taking into account our previously described series of 1,3,5-tris[(4-(substituted-aminomethyl)phenyl)methyl]benzene compounds, we have now designed, prepared, and evaluated in vitro against Plasmodium falciparum a novel series of structural analogues of these molecules, i.e., the 1,3,5-tris[(4-(substituted-aminomethyl)phenoxy)methyl]benzene derivatives. The pharmacological data showed antimalarial activity with IC50 values in the sub and μM range. The in vitro cytotoxicity of these new nitrogen polyphenoxymethylbenzene compounds was also evaluated on human HepG2 cells. The 1,3,5-tris[(4-(substituted-aminomethyl)phenoxy)methyl]benzene derivative 1m was found as one of the most potent and promising antimalarial candidates with favorable cytotoxic to antiprotozoal properties in the P. falciparum strains W2 and 3D7. In conclusion, this 1,3,5-tris[(4-(pyridin-3-ylmethylaminomethyl)phenoxyl)methyl]benzene 1m (IC50 = 0.07 μM on W2, 0.06 μM on 3D7, and 62.11 μM on HepG2) was identified as the most promising antimalarial derivative with selectivity indexes (SI) of 887.29 on the W2 P. falciparum chloroquine-resistant strain, and of 1035.17 on the chloroquine-sensitive and mefloquine decreased sensitivity strain 3D7. It has been previously described that the telomeres of P. falciparum could represent potential targets for these types of polyaromatic compounds; therefore, the capacity of our novel derivatives to stabilize the parasitic telomeric G-quadruplexes was assessed using a FRET melting assay. However, with regard to the stabilization of the protozoal G-quadruplex, we observed that the best substituted derivatives 1, which exhibited some interesting stabilization profiles, were not the most active antimalarial compounds against the two Plasmodium strains. Thus, there were no correlations between their antimalarial activities and selectivities of their respective binding to G-quadruplexes. [ABSTRACT FROM AUTHOR]

Published
2024
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5. New 2,4-bis[(substituted-aminomethyl)phenyl]phenylquinazoline and 2,4-bis[(substituted-aminomethyl)phenyl]phenylquinoline Derivatives: Synthesis and Biological Evaluation as Novel Anticancer Agents by Targeting G-Quadruplex

Author

Guillon, Jean, primary, Le Borgne, Marc, additional, Milano, Vittoria, additional, Guédin-Beaurepaire, Aurore, additional, Moreau, Stéphane, additional, Pinaud, Noël, additional, Ronga, Luisa, additional, Savrimoutou, Solène, additional, Albenque-Rubio, Sandra, additional, Marchivie, Mathieu, additional, Kalout, Haouraa, additional, Walker, Charley, additional, Chevallier, Louise, additional, Buré, Corinne, additional, Largy, Eric, additional, Gabelica, Valérie, additional, Mergny, Jean-Louis, additional, Baylot, Virginie, additional, Ferrer, Jacky, additional, Idrissi, Yamina, additional, Chevret, Edith, additional, Cappellen, David, additional, Desplat, Vanessa, additional, Schelz, Zsuzsanna, additional, and Zupkó, István, additional

Published
2023
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9. New 2,4-bis[(substituted-aminomethyl)phenyl]phenylquinazoline and 2,4-bis[(substituted-aminomethyl)phenyl]phenylquinoline Derivatives: Synthesis and Biological Evaluation as Novel Anticancer Agents by Targeting G-Quadruplex.

Author

Guillon, Jean, Le Borgne, Marc, Milano, Vittoria, Guédin-Beaurepaire, Aurore, Moreau, Stéphane, Pinaud, Noël, Ronga, Luisa, Savrimoutou, Solène, Albenque-Rubio, Sandra, Marchivie, Mathieu, Kalout, Haouraa, Walker, Charley, Chevallier, Louise, Buré, Corinne, Largy, Eric, Gabelica, Valérie, Mergny, Jean-Louis, Baylot, Virginie, Ferrer, Jacky, and Idrissi, Yamina

Subjects
BIOSYNTHESIS, ANTINEOPLASTIC agents, NUCLEIC acids, QUINOLINE derivatives, CIRCULAR dichroism
Abstract

The syntheses of novel 2,4-bis[(substituted-aminomethyl)phenyl]phenylquinazolines 12 and 2,4-bis[(substituted-aminomethyl)phenyl]phenylquinolines 13 are reported here in six steps starting from various halogeno-quinazoline-2,4-(1H,3H)-diones or substituted anilines. The antiproliferative activities of the products were determined in vitro against a panel of breast (MCF-7 and MDA-MB-231), human adherent cervical (HeLa and SiHa), and ovarian (A2780) cell lines. Disubstituted 6- and 7-phenyl-bis(3-dimethylaminopropyl)aminomethylphenyl-quinazolines 12b, 12f, and 12i displayed the most interesting antiproliferative activities against six human cancer cell lines. In the series of quinoline derivatives, 6-phenyl-bis(3-dimethylaminopropyl)aminomethylphenylquinoline 13a proved to be the most active. G-quadruplexes (G4) stacked non-canonical nucleic acid structures found in specific G-rich DNA, or RNA sequences in the human genome are considered as potential targets for the development of anticancer agents. Then, as small aza-organic heterocyclic derivatives are well known to target and stabilize G4 structures, their ability to bind G4 structures have been determined through FRET melting, circular dichroism, and native mass spectrometry assays. Finally, telomerase inhibition ability has been also assessed using the MCF-7 cell line. [ABSTRACT FROM AUTHOR]

Published
2024
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10. Potassium 6-Oxo-7,13,16,22-tetraazatetracyclo[12.6.2.1 8,12.0 17,21 ]tricosa-1(20),8(23),9,11,14,16,18,21-octaen-2-yne-15-carboxylate.

Author

Blouet, Camille, Letast, Stéphanie, Robert, Thomas, Bach, Stéphane, Pinaud, Noël, Joubert, Nicolas, Viaud-Massuard, Marie-Claude, Guillon, Jean, Logé, Cédric, and Denevault-Sabourin, Caroline

Subjects
QUINOXALINE compounds, POTASSIUM, MACROCYCLIC compounds, KINASES
Abstract

Potassium 6-oxo-7,13,16,22-tetraazatetracyclo[12.6.2.18,12.017,21]tricosa-1(20),8(23),9,11,14,16,18,21-octaen-2-yne-15-carboxylate was synthesized through a multi-step pathway, starting from commercially available 3-iodo-1,2-phenylenediamine. Structure characterization of this new substituted macrocyclic quinoxaline compound was achieved using 1H NMR, 13C NMR, and HRMS spectral analysis. This new macrocyclic derivative demonstrated submicromolar potency on both Pim-1 and Pim-2 isoforms, with an interesting selectivity profile against a selected panel of human kinases. [ABSTRACT FROM AUTHOR]

Published
2023
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11. Synthesis, Crystal Structure and Anti-Leukemic Activity of (E)-Pyrrolo[1,2- a ]quinoxalin-4-yl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one.

Author

Guillon, Jean, Savrimoutou, Solène, Albenque-Rubio, Sandra, Pinaud, Noël, Fillová, Nina, Moreau, Stéphane, Baylot, Virginie, and Desplat, Vanessa

Subjects
CRYSTAL structure, QUINOXALINE compounds, CELL lines, LEUKEMIA
Abstract

(E)-Pyrrolo[1,2-a]quinoxalin-4-yl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one was designed then synthesized using a multi-step pathway starting from commercially available 2-nitroaniline. Structure characterization of this original substituted pyrrolo[1,2-a]quinoxaline compound was achieved by using FT-IR, 1H-NMR, 13C-NMR, X-Ray and HRMS spectral analysis. This new pyrroloquinoxaline shows interesting cytotoxic potential against different human leukemia cell lines (MV4-11, K562, MOLM14 and Jurkat cells). [ABSTRACT FROM AUTHOR]

Published
2023
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12. T 1Mapping From MPRAGE Acquisitions: Application to the Measurement of the Concentration of Nanoparticles in Tumors for Theranostic Use

Author

Lavielle, Audrey, primary, Boux, Fabien, additional, Deborne, Justine, additional, Pinaud, Noël, additional, Dufort, Sandrine, additional, Verry, Camille, additional, Grand, Sylvie, additional, Troprès, Irène, additional, Vecco‐Garda, Clément, additional, Le Duc, Géraldine, additional, Mornet, Stéphane, additional, and Crémillieux, Yannick, additional

Published
2022
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15. T1 Mapping From MPRAGE Acquisitions: Application to the Measurement of the Concentration of Nanoparticles in Tumors for Theranostic Use.

Author

Lavielle, Audrey, Boux, Fabien, Deborne, Justine, Pinaud, Noël, Dufort, Sandrine, Verry, Camille, Grand, Sylvie, Troprès, Irène, Vecco‐Garda, Clément, Le Duc, Géraldine, Mornet, Stéphane, and Crémillieux, Yannick

Subjects
IN vivo studies, GRAY matter (Nerve tissue), LINEAR statistical models, LABORATORY rats, WHITE matter (Nerve tissue), CONTRAST media
Abstract

Background: The measurement of the concentration of theranostic agents in vivo is essential for the assessment of their therapeutic efficacy and their safety regarding healthy tissue. To this end, there is a need for quantitative T1 measurements that can be obtained as part of a standard clinical imaging protocol applied to tumor patients. Purpose: To generate T1 maps from MR images obtained with the magnetization‐prepared rapid gradient echo (MPRAGE) sequence. To evaluate the feasibility of the proposed approach on phantoms, animal and patients with brain metastases. Study Type: Pilot. Phantom/Animal model/Population: Solutions containing contrast agents (chelated Gd3+ and iron nanoparticles), male rat of Wistar strain, three patients with brain metastases. Field Strength/Sequence: A 3‐T and 7‐T, saturation recovery (SR), and MPRAGE sequences. Assessment: The MPRAGE T1 measurement was compared to the reference SR method on phantoms and rat brain at 7‐T. The robustness of the in vivo method was evaluated by studying the impact of misestimates of tissue proton density. Concentrations of Gd‐based theranostic agents were measured at 3‐T in gray matter and metastases in patients recruited in NanoRad clinical trial. Statistical Tests: A linear model was used to characterize the relation between T1 measurements from the MPRAGE and the SR acquisitions obtained in vitro at 7‐T. Results: The slope of the linear model was 0.966 (R2 = 0.9934). MPRAGE‐based T1 values measured in the rat brain were 1723 msec in the thalamus. MPRAGE‐based T1 values measured in patients in white matter and gray matter amounted to 747 msec and 1690 msec. Mean concentration values of Gd3+ in metastases were 61.47 μmol. Data Conclusion: The T1 values obtained in vitro and in vivo support the validity of the proposed approach. The concentrations of Gd‐based theranostic agents may be assessed in patients with metastases within a standard clinical imaging protocol using the MPRAGE sequence. Evidence Level: 2. Technical Efficacy: Stage 1. [ABSTRACT FROM AUTHOR]

Published
2023
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24. Minimally invasive implantable NMR microcoils for in vivo metabolic profiling of microliter volumes

Author

Deborne, Justine, Pinaud, Noël, Ciobanu, Luisa, Wong, Alan, Crémillieux, Yannick, Institut des Sciences Moléculaires (ISM), Université Montesquieu - Bordeaux 4-Université Sciences et Technologies - Bordeaux 1 (UB)-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Service NEUROSPIN (NEUROSPIN), Université Paris-Saclay-Direction de Recherche Fondamentale (CEA) (DRF (CEA)), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA), Laboratoire Structure et Dynamique par Résonance Magnétique (LCF) (LSDRM), Nanosciences et Innovation pour les Matériaux, la Biomédecine et l'Energie (ex SIS2M) (NIMBE UMR 3685), Institut Rayonnement Matière de Saclay (IRAMIS), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut Rayonnement Matière de Saclay (IRAMIS), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), ANR-10-LABX-0057,TRAIL,Translational Research and Advanced Imaging Laboratory(2010), Université Montesquieu - Bordeaux 4-Université Sciences et Technologies - Bordeaux 1-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Direction de Recherche Fondamentale (CEA) (DRF (CEA)), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay, Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Institut Rayonnement Matière de Saclay (IRAMIS), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Palacin, Serge, and Translational Research and Advanced Imaging Laboratory - - TRAIL2010 - ANR-10-LABX-0057 - LABX - VALID

Subjects
[CHIM.ANAL] Chemical Sciences/Analytical chemistry, [CHIM.ANAL]Chemical Sciences/Analytical chemistry
Abstract

International audience; IntroductionThe use of implanted NMR microcoils still remains a relatively unexploited research area, without emerging or significant biomedical applications. The limitations inherent to implanted NMR coils derive obviously from the relatively weak detection sensitivity of NMR, hindering great challenges for nano-volume analyses. In addition, the necessity to preserve tissue during microprobe implantation imposes severe constraints on the geometry and structure of the NMR microcoil. In this study, we present in vitro and in vivo results obtained with innovative and minimally invasive microcoils.MethodsAn example of implantable NMR microprobe is shown in Figure 1. This filar-type architecture is based on the use of twisted copper microwires (diameter of 150 μm). The twisted wires are inserted inside a polyamide tubing (outer diameter of 380 μm). A biocompatible glue is used to seal the polyamide tube, while tuning and matching capacitors are connected to the two sides of the wire. For in vivo experiments, cannulae were stereotaxically positionned the day before the insertion of the NMR microcoils in the brain of male wistar rats. Experiments were performed at 7 T and 17.2 T. NMR spectra were acquired using a PRESS sequence. 3D MRI acquisitions were performed using a ZTE (zero echo time) sequence.Results/DiscussionThe quality factor of the loaded coils was ranging between 100 and 120. The full width at half maximum of water peak were measured to 6 Hz. In vivo results are illustrated in Figure 2 with a PRESS NMR spectrum obtained in the rat brain with a twisted microcoil (a volume coil was used for selective excitation). In this particular example of water-suppressed acquisition (240 averages, 10-minutes acquisition) at 7 Tesla, main peaks of brain metabolites (NAA, glu, gln, pCr, Cr, etc) can be easily identified and quantified. The ZTE MRI image (right side of Figure 1) shows the sensitive detection zone of the microprobe (volume evaluated to 500 nL) extending to about 200 μm away from the wire.ConclusionsThe MRS/MRI results obtained in vitro and in vivo illustrate the relevance of the microcoil design with respect to spectral resolution, detection sensitivity, spatial selectivity and limited invasiveness. Foreseen applications include the investigation of metabolism in microliter volumes in physiological conditions and in diseases with metabolic dysfunctions (tumoral environement, neurodegenerative pathologies, etc).

Published
2020

25. 1-Phenyl-8-[[4-(pyrrolo[1,2-a]quinoxalin-4-yl)phenyl]methyl]-1,3,8-triazaspiro[4.5]decan-4-one: Synthesis, Crystal Structure and Anti-Leukemic Activity

Author

Guillon, Jean, Savrimoutou, Solène, Rubio, Sandra, Moreau, Stéphane, Pinaud, Noël, Marchivie, Mathieu, Desplat, Vanessa, Toulin, Stéphane, Acides Nucléiques : Régulations Naturelle et Artificielle (ARNA), Université de Bordeaux (UB)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut des Sciences Moléculaires (ISM), Université Montesquieu - Bordeaux 4-Université Sciences et Technologies - Bordeaux 1 (UB)-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie de la Matière Condensée de Bordeaux (ICMCB), Université de Bordeaux (UB)-Institut Polytechnique de Bordeaux-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Biothérapies des maladies génétiques et cancers, Université Bordeaux Segalen - Bordeaux 2-Institut National de la Santé et de la Recherche Médicale (INSERM), and Université Montesquieu - Bordeaux 4-Université Sciences et Technologies - Bordeaux 1-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
antiproliferative activity, [CHIM.THER] Chemical Sciences/Medicinal Chemistry, pyrrolo[1,2-a]quinoxaline derivative, [CHIM.CRIS]Chemical Sciences/Cristallography, leukemia, lcsh:Inorganic chemistry, pyrrolo[1 2-a]quinoxaline derivative, [CHIM.THER]Chemical Sciences/Medicinal Chemistry, [CHIM.CRIS] Chemical Sciences/Cristallography, lcsh:QD146-197
Abstract

1-Phenyl-8-[[4-(pyrrolo[1,2-a]quinoxalin-4-yl)phenyl]methyl]-1,3,8-triazaspiro[4.5]decan-4-one has been successfully synthesized via a multi-step pathway starting from 2-nitroaniline. Structure characterization of this original pyrrolo[1,2-a]quinoxaline derivative was achieved by FT-IR, 1H-NMR, 13C-NMR, X-Ray and HRMS spectral analysis. This title compound shows interesting cytotoxic potential against several human leukemia cell lines (K562, HL60, and U937 cells).

Published
2020

26. New Quinoxaline Derivatives as Dual Pim-1/2 Kinase Inhibitors: Design, Synthesis and Biological Evaluation

Author

Oyallon, Bruno, primary, Brachet-Botineau, Marie, additional, Logé, Cédric, additional, Robert, Thomas, additional, Bach, Stéphane, additional, Ibrahim, Sajida, additional, Raoul, William, additional, Croix, Cécile, additional, Berthelot, Pascal, additional, Guillon, Jean, additional, Pinaud, Noël, additional, Gouilleux, Fabrice, additional, Viaud-Massuard, Marie-Claude, additional, and Denevault-Sabourin, Caroline, additional

Published
2021
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27. Synthesis, Crystal Structure and Anti-Leukemic Activity of 1,3-Dihydro-1-{1-[4-(4-phenylpyrrolo[1,2- a ]quinoxalin-3-yl)benzyl]piperidin-4-yl}-2 H -benzimidazol-2-one.

Author

Guillon, Jean, Savrimoutou, Solène, Albenque-Rubio, Sandra, Pinaud, Noël, Moreau, Stéphane, and Desplat, Vanessa

Subjects
CRYSTAL structure, QUINOXALINE compounds, CELL lines, LEUKEMIA
Abstract

1,3-Dihydro-1-{1-[4-(4-phenylpyrrolo[1,2-a]quinoxalin-3-yl)benzyl]piperidin-4-yl}-2H-benzimidazol-2-one has been synthesized through a multi-step pathway starting from commercially available 2-nitroaniline. A structure characterization of this new substituted pyrrolo[1,2-a]quinoxaline compound was achieved by using FT-IR, 1H-NMR, 13C-NMR, X-Ray and HRMS spectral analysis. This new pyrroloquinoxaline derivative shows an interesting cytotoxic potential against several human leukemia cell lines (HL60, K562 and U937 cells). [ABSTRACT FROM AUTHOR]

Published
2022
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28. Indeno[1,2-b]indole scaffold in drug discovery: An effective template in kinase inhibitor medicinal chemistry

Author

Jose, Joachim, primary, Le Borgne, Marc, primary, Birus, Robin, additional, Marminon, Christelle, additional, Aichele, Dagmar, additional, Haidar, Samer, additional, Ousset, Marine, additional, Ettouati, Laurent, additional, Alchab, Faten, additional, Audebert, Solène, additional, Rolland de Ravel, Marc, additional, Pinaud, Noël, additional, Bouaziz, Zouhair, additional, and Guillon, Jean, additional

Published
2020
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29. Nebulised Gadolinium-Based Nanoparticles for a Multimodal Approach: Quantitative and Qualitative Lung Distribution Using Magnetic Resonance and Scintigraphy Imaging in Isolated Ventilated Porcine Lungs

Author

Montigaud, Yoann, primary, Pourchez, Jérémie, additional, Leclerc, Lara, additional, Tillement, Olivier, additional, Clotagatide, Anthony, additional, Bal, Clémence, additional, Pinaud, Noël, additional, Ichinose, Nobuyasu, additional, Zhang, Bei, additional, Perinel, Sophie, additional, Lux, François, additional, Crémillieux, Yannick, additional, and Prevot, Nathalie, additional

Published
2020
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32. Online Quantification of Lactate Concentration in Microdialysate During Cerebral Activation Using 1H-MRS and Sensitive NMR Microcoil

Author

Crémillieux, Yannick, Dumont, Ursule, Mazuel, Leslie, Salvati, Roberto, Zhendre, Vanessa, Rizzitelli, Silvia, Blanc, Jordy, ROUMES, Hélène, Pinaud, Noël, Bouzier-Sore, Anne-Karine, Chezal, Jean-Michel, Institut des Sciences Moléculaires (ISM), Université Montesquieu - Bordeaux 4-Université Sciences et Technologies - Bordeaux 1 (UB)-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Imagerie Moléculaire et Stratégies Théranostiques (IMoST), Institut National de la Santé et de la Recherche Médicale (INSERM)-Université Clermont Auvergne [2017-2020] (UCA [2017-2020]), Biologie du fruit et pathologie (BFP), Université Bordeaux Segalen - Bordeaux 2-Institut National de la Recherche Agronomique (INRA)-Université Sciences et Technologies - Bordeaux 1 (UB), Centre de résonance magnétique des systèmes biologiques (CRMSB), Université de Bordeaux (UB)-Centre National de la Recherche Scientifique (CNRS), Nutrition et Neurobiologie intégrée (NutriNeuro), Université Bordeaux Segalen - Bordeaux 2-Institut National de la Recherche Agronomique (INRA)-Université Sciences et Technologies - Bordeaux 1 (UB)-Institut Polytechnique de Bordeaux-Ecole nationale supérieure de chimie, biologie et physique, Université Montesquieu - Bordeaux 4-Université Sciences et Technologies - Bordeaux 1-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Centre National de la Recherche Scientifique (CNRS), Imagerie Moléculaire et Stratégies Théranostiques - Clermont Auvergne (IMoST), Institut National de la Santé et de la Recherche Médicale (INSERM)-Université Clermont Auvergne (UCA), Chimie et Biologie des Membranes et des Nanoobjets (CBMN), Université Sciences et Technologies - Bordeaux 1-École Nationale d'Ingénieurs des Travaux Agricoles - Bordeaux (ENITAB)-Centre National de la Recherche Scientifique (CNRS), Résonance magnétique des systèmes biologiques (RMSB), Université Bordeaux Segalen - Bordeaux 2-Centre National de la Recherche Scientifique (CNRS), Nutrition et Neurobiologie intégrée (NutriNeur0), Ecole nationale supérieure de chimie, biologie et physique-Institut Polytechnique de Bordeaux-Université Sciences et Technologies - Bordeaux 1-Institut National de la Recherche Agronomique (INRA)-Université Bordeaux Segalen - Bordeaux 2, Université Montesquieu - Bordeaux 4-Université Sciences et Technologies - Bordeaux 1-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Clermont Auvergne [2017-2020] (UCA [2017-2020])-Institut National de la Santé et de la Recherche Médicale (INSERM), Université Bordeaux Segalen - Bordeaux 2-Institut National de la Recherche Agronomique (INRA)-Université Sciences et Technologies - Bordeaux 1, Centre National de la Recherche Scientifique (CNRS)-Université de Bordeaux (UB), Université Bordeaux Segalen - Bordeaux 2-Institut National de la Recherche Agronomique (INRA)-Université Sciences et Technologies - Bordeaux 1-Institut Polytechnique de Bordeaux-Ecole nationale supérieure de chimie, biologie et physique, and Université Clermont Auvergne (UCA)-Institut National de la Santé et de la Recherche Médicale (INSERM)

Subjects
1H-MRS, lactate, [SDV.IB.IMA] Life Sciences [q-bio]/Bioengineering/Imaging, microdialysis, [SDV.IB.IMA]Life Sciences [q-bio]/Bioengineering/Imaging, [SDV.NEU.NB]Life Sciences [q-bio]/Neurons and Cognition [q-bio.NC]/Neurobiology, barrel cortex, [SDV.NEU]Life Sciences [q-bio]/Neurons and Cognition [q-bio.NC], [SDV.NEU] Life Sciences [q-bio]/Neurons and Cognition [q-bio.NC], 1 H-MRS, NMR microcoil, Neuroscience, Original Research
Abstract

International audience; The dynamic in vivo profiling of lactate is of uppermost importance in both neuroenergetics and neuroprotection fields, considering its central suspected role as a metabolic and signaling molecule. For this purpose, we implemented proton magnetic resonance spectroscopy (1 H-MRS) directly on brain microdialysate to monitor online the fluctuation of lactate contents during neuronal stimulation. Brain activation was obtained by right whisker stimulation of rats, which leads to the activation of the left barrel cortex area in which the microdialysis probe was implanted. The experimental protocol relies on the use of dedicated and sensitive home-made NMR microcoil able to perform lactate NMR profiling at submillimolar concentration. The MRS measurements of extracellular lactate concentration were performed inside a pre-clinical MRI scanner allowing simultaneous visualization of the correct location of the microprobe by MRI and detection of metabolites contained in the microdialysis by MRS. A 40% increase in lactate concentration was measured during whisker stimulation in the corresponding barrel cortex. This combination of microdialysis with online MRS/MRI provides a new approach to follow in vivo lactate fluctuations, and can be further implemented in physio-pathological conditions to get new insights on the role of lactate in brain metabolism and signaling.

Published
2019

35. Synthesis and antiproliferative effect of new ethyl 4-(4-substitutedpiperidin-1-yl)]benzylpyrrolo[1,2-a]quinoxaline-carboxylate derivatives on human leukemic cells

Author

Desplat, Vanessa, Vincenzi, Marian, Lucas, Romain, Moreau, Stéphane, Savrimoutou, Solène, Rubio, Sandra, Pinaud, Noël, Bigat, David, Enriquez, Elodie, Marchivie, Mathieu, Routier, Sylvain, Sonnet, Pascal, ROSSI, FILOMENA, Ronga, Luisa, Guillon, Jean, Desplat, Vanessa, Vincenzi, Marian, Lucas, Romain, Moreau, Stéphane, Savrimoutou, Solène, Rubio, Sandra, Pinaud, Noël, Bigat, David, Enriquez, Elodie, Marchivie, Mathieu, Routier, Sylvain, Sonnet, Pascal, Rossi, Filomena, Ronga, Luisa, and Guillon, Jean

Subjects
pyrrolo[1,2-a]quinoxaline • synthesis • cytotoxic activity • cancer • leukemia
Abstract

Acute leukemia is a hematological malignancy with high incidence and recurrence rates, and is characterized by an accumulation of blasts in bone marrow due to proliferation of immature lymphoid or myeloid cells associated with a blockade of differentiation. The heterogeneity of leukemia led to look for new specific molecules for leukemia subtypes or even for therapyresistant cases. Among heterocyclic derivatives that attracted attention due to their large spread biological activities, we have focused our interest towards the pyrrolo[1,2-a]quinoxaline heterocyclic framework that has been previously identified as an interesting scaffold for antiproliferative activities against various human cancer cell lines. In this work, new ethyl 4-[4-(4-substitutedpiperidin-1-yl)]benzylpyrrolo[1,2-a]quinoxaline-carboxylate derivatives 1a-o have been designed, synthesized and evaluated against five different leukemia cell lines, including Jurkat and U266 (lymphoid cell lines), and K562, U937, HL60 (myeloid cell lines), and also on normal human peripheral blood mononuclear cells (PBMNCs). These new pyrrolo[1,2-a]quinoxaline series showed interesting cytotoxic potential against all tested leukemia cell lines. In particular, pyrroloquinoxalines 1a and 1m-n seem to be interesting due to their high ctivity against leukemia and their low activity against normal hematopoietic cells leading to high index of selectivity.

Published
2017

36. Three‐dimensional quantitative MRI of aerosolized gadolinium‐based nanoparticles and contrast agents in isolated ventilated porcine lungs

Author

Crémillieux, Yannick, primary, Montigaud, Yoann, additional, Bal, Clémence, additional, Pinaud, Noël, additional, Pham, Vi, additional, Perinel, Sophie, additional, Natuzzi, Marco, additional, Lux, François, additional, Tillement, Olivier, additional, Ichinose, Nobuyasu, additional, Zhang, Bei, additional, and Pourchez, Jérémie, additional

Published
2019
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38. Understanding chemical reactions of CO2 and its isoelectronic molecules with 1-butyl-3-methylimidazolium acetate by changing the nature of the cation: The case of CS2 in 1-butyl-1-methylpyrrolidinium acetate studied by NMR spectroscopy and density functional theory calculations

Author

Cabaço, M. Isabel, Besnard, Marcel, Vaca Chávez, Fabián, Pinaud, Noël, Sebastião, Pedro J., Coutinho, João A. P., and Danten, Yann

Subjects
CHEMICAL reactions, ISOELECTRONIC sequences, ACETATES, METHYLPYRIDINE, DENSITY functional theory, NUCLEAR magnetic resonance spectroscopy
Abstract

NMR spectroscopy (¹H, 13C, 15N) shows that carbon disulfide reacts spontaneously with 1-butyl-1- methylpyrrolidinium acetate ([BmPyrro][Ac]) in the liquid phase. It is found that the acetate anions play an important role in conditioning chemical reactions with CS2 leading, via coupled complex reactions, to the degradation of this molecule to form thioacetate anion (CH3COS-), CO2, OCS, and trithiocarbonate (CS32-). In marked contrast, the cation does not lead to the formation of any adducts allowing to conclude that, at most, its role consists in assisting indirectly these reactions. The choice of the [BmPyrro]+ cation in the present study allows disentangling the role of the anion and the cation in the reactions. As a consequence, the ensemble of results already reported on CS2-[Bmim][Ac] (1), OCS-[Bmim][Ac] (2), and CO2-[Bmim][Ac] (3) systems can be consistently rationalized. It is argued that in system (1) both anion and cation play a role. The CS2 reacts with the acetate anion leading to the formation of CH3COS-, CO2, and OCS. After these reactions have proceeded the nascent CO2 and OCS interact with the cation to form imidazolium-carboxylate ([Bmim] CO2) and imidazoliumthiocarboxylate ([Bmim] COS). The same scenario also applies to system (2). In contrast, in the CO2-[Bmim] [Ac] system a concerted cooperative process between the cation, the anion, and the CO2 molecule takes place. A carbene issued from the cation reacts to form the [Bmim] CO2, whereas the proton released by the ring interacts with the anion to produce acetic acid. In all these systems, the formation of adduct resulting from the reaction between the solute molecule and the carbene species originating from the cation is expected. However, this species was only observed in systems (2) and (3). The absence of such an adduct in system (1) has been theoretically investigated using DFT calculations. The values of the energetic barrier of the reactions show that the formation of [Bmim] CS2 is unfavoured and that the anion offers a competitive reactive channel via an oxygensulphur exchange mechanism with the solute in systems (1) and (2). [ABSTRACT FROM AUTHOR]

Published
2014
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39. Three‐dimensional quantitative MRI of aerosolized gadolinium‐based nanoparticles and contrast agents in isolated ventilated porcine lungs.

Author

Crémillieux, Yannick, Montigaud, Yoann, Bal, Clémence, Pinaud, Noël, Pham, Vi, Perinel, Sophie, Natuzzi, Marco, Lux, François, Tillement, Olivier, Ichinose, Nobuyasu, Zhang, Bei, and Pourchez, Jérémie

Subjects
LUNGS, NANOPARTICLES, IONIZING radiation, BRONCHI, MAGNETIC resonance imaging
Abstract

Purpose: The objective of this study is to evaluate the suitability and performance of ultra‐short echo time (UTE) sequences for imaging and quantifying the deposition of nebulized MRI contrast agents in human‐sized lungs. Methods: Nebulization of clinically used contrast agent or gadolinium‐based nanoparticles were performed using a commercial jet nebulizer in isolated and ventilated porcine lungs connected to a 3D‐printed human upper airways replica. MR images of isolated lungs were acquired on a 3T clinical MR scanner using 3D UTE sequences at different flip angles. Results: 3D acquisitions with isotropic millimetric resolution were obtained in less than 4 min. Images exhibit homogeneous and large MR signal enhancement (above 200%) following nebulization of both types of aerosols. Deposition of aerosol down to the level of the bronchi of secondary lobules was visualized. T1 values and the concentration of nanoparticles obtained by MRI were found to correlate with the amount of nebulized gadolinium3+ ions. Conclusion: The distribution of aerosolized gadolinium‐based contrast agent or nanoparticles can be visualized and quantified using UTE MRI in large animal ventilated lung model on a clinical MRI scanner. This protocol can be used for assessing and quantifying aerosol regional deposition with high spatial resolution (1 mm 3D isotropic) without ionizing radiation and could be applied in the future for diagnostic or therapeutic applications in patients. [ABSTRACT FROM AUTHOR]

Published
2020
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40. Synthesis and evaluation of the cytotoxic activity of novel ethyl 4-[4-(4-substitutedpiperidin-1-yl)]benzyl-phenylpyrrolo[1,2-a]quinoxaline-carboxylate derivatives in myeloid and lymphoid leukemia cell lines

Author

Desplat, Vanessa, Vincenzi, Marian, Lucas, Romain, Moreau, Stéphane, Savrimoutou, Solène, Pinaud, Noël, Lesbordes, Jordi, Peyrilles, Elodie, Marchivie, Mathieu, Routier, Sylvain, Sonnet, Pascal, Rossi, Filomena, Ronga, Luisa, and Guillon, Jean

Published
2016
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41. Synthesis, Crystal Structure and Anti-leukemic Activity of 4-{4-[(4-(2-Oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl)benzyl]}-3-phenyl-3H-pyrrolo[2,3-c]quinoline

Author

Guillon, Jean, primary, Moreau, Stéphane, additional, Desplat, Vanessa, additional, Vincenzi, Marian, additional, Pinaud, Noël, additional, Savrimoutou, Solène, additional, Rubio, Sandra, additional, Ronga, Luisa, additional, Rossi, Filomena, additional, and Marchivie, Mathieu, additional

Published
2018
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42. In vivo online magnetic resonance quantification of absolute metabolite concentrations in microdialysate

Author

GLÖGGLER, Stefan, RIZZITELLI, Silvia, PINAUD, Noël, RAFFARD, Gérard, ZHENDRE, Vanessa, BOUCHAUD, Véronique, SANCHEZ, Stephane, RADECKI, Guillaume, CIOBANU, Luisa, WONG, Alan, CREMILLIEUX, Yannick, Institut des Sciences Moléculaires (ISM), Centre National de la Recherche Scientifique (CNRS)-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Université Sciences et Technologies - Bordeaux 1-Université Montesquieu - Bordeaux 4-Institut de Chimie du CNRS (INC), Centre de résonance magnétique des systèmes biologiques (CRMSB), Centre National de la Recherche Scientifique (CNRS)-Université de Bordeaux (UB), Service NEUROSPIN (NEUROSPIN), Université Paris-Saclay-Direction de Recherche Fondamentale (CEA) (DRF (CEA)), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA), Laboratoire Structure et Dynamique par Résonance Magnétique (LCF) (LSDRM), Nanosciences et Innovation pour les Matériaux, la Biomédecine et l'Energie (ex SIS2M) (NIMBE UMR 3685), Institut Rayonnement Matière de Saclay (IRAMIS), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Institut Rayonnement Matière de Saclay (IRAMIS), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), ANR-10-IDEX-0003,IDEX BORDEAUX,Initiative d'excellence de l'Université de Bordeaux(2010), ANR-12-JSV5-0005,HRMACS,Développement et exploration de nouveaux micro-détecteurs RMN tournants pour des analyses métabolomiques de biopsies de petite masse(2012), Université Montesquieu - Bordeaux 4-Université Sciences et Technologies - Bordeaux 1 (UB)-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université de Bordeaux (UB)-Centre National de la Recherche Scientifique (CNRS), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut Rayonnement Matière de Saclay (IRAMIS), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Chimie et Biologie des Membranes et des Nanoobjets (CBMN), École Nationale d'Ingénieurs des Travaux Agricoles - Bordeaux (ENITAB)-Institut de Chimie du CNRS (INC)-Université de Bordeaux (UB)-Centre National de la Recherche Scientifique (CNRS), Institut de recherche en informatique de Toulouse (IRIT), Université Toulouse 1 Capitole (UT1), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse - Jean Jaurès (UT2J)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées, Centre de Recherche en Acquisition et Traitement de l'Image pour la Santé (CREATIS), Université Jean Monnet [Saint-Étienne] (UJM)-Hospices Civils de Lyon (HCL)-Institut National des Sciences Appliquées de Lyon (INSA Lyon), Université de Lyon-Institut National des Sciences Appliquées (INSA)-Université de Lyon-Institut National des Sciences Appliquées (INSA)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Centre National de la Recherche Scientifique (CNRS)-Institut National de la Santé et de la Recherche Médicale (INSERM), Université de Bordeaux (UB)-École Nationale d'Ingénieurs des Travaux Agricoles - Bordeaux (ENITAB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Toulouse Capitole (UT Capitole), Université de Toulouse (UT)-Université de Toulouse (UT)-Université Toulouse - Jean Jaurès (UT2J), Université de Toulouse (UT)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Toulouse Mind & Brain Institut (TMBI), Université Toulouse - Jean Jaurès (UT2J), Université de Toulouse (UT)-Université de Toulouse (UT)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT), Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Institut National des Sciences Appliquées de Lyon (INSA Lyon), and Université de Lyon-Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Université Jean Monnet - Saint-Étienne (UJM)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Magnetic Resonance Spectroscopy, Brain Neoplasms, [SDV]Life Sciences [q-bio], Microdialysis, Brain, [CHIM.MATE]Chemical Sciences/Material chemistry, Equipment Design, Magnetic Resonance Imaging, Online Systems, Article, Rats, Cell Line, Tumor, Animals, Humans, Female, Rats, Wistar, Glioblastoma
Abstract

International audience; In order to study metabolic processes in animal models of diseases and in patients, microdialysis probes have evolved as powerful tools that are minimally invasive. However, analyses of microdialysate, performed remotely, do not provide real-time monitoring of microdialysate composition. Microdialysate solutions can theoretically be analyzed online inside a preclicinal or clinical MRI scanner using MRS techniques. Due to low NMR sensitivity, acquisitions of real-time NMR spectra on very small solution volumes (μL) with low metabolite concentrations (mM range) represent a major issue. To address this challenge we introduce the approach of combining a microdialysis probe with a custom-built magnetic resonance microprobe that allows for online metabolic analysis (1 H and 13 C) with high sensitivity under continuous flow conditions. This system is mounted inside an MRI scanner and allows performing simultaneously MRI experiments and rapid MRS metabolic analysis of the microdialysate. The feasibility of this approach is demonstrated by analyzing extracellular brain cancer cells (glioma) in vitro and brain metabolites in an animal model in vivo. We expect that our approach is readily translatable into clinical settings and can be used for a better and precise understanding of diseases linked to metabolic dysfunction.

Published
2016
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43. Synthesis and crystal structure of 3-{4-[(4-(2-Oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl)benzyl]}-2-phenylindole

Author

Guillon, Jean, Vincenzi, Marian, Pinaud, Noël, ronga, luisa, rossi, filomena, Savrimoutou, Solène, Moreau, Stéphane, Desplat, Vanessa, Marchivie, Mathieu, Régulations Naturelles et Artificielles (ARNA), Institut National de la Santé et de la Recherche Médicale (INSERM)-Université de Bordeaux Ségalen [Bordeaux 2], Department of Pharmacy and CIRPeB, University of Naples Federico II, Institut des Sciences Moléculaires (ISM), Centre National de la Recherche Scientifique (CNRS)-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Université Sciences et Technologies - Bordeaux 1-Université Montesquieu - Bordeaux 4-Institut de Chimie du CNRS (INC), Biothérapies des maladies génétiques et cancers, Université Bordeaux Segalen - Bordeaux 2-Institut National de la Santé et de la Recherche Médicale (INSERM), Institut de Chimie de la Matière Condensée de Bordeaux (ICMCB), and Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut Polytechnique de Bordeaux-Université de Bordeaux (UB)

Subjects
Single-crystal x-ray study, [CHIM.CRIS]Chemical Sciences/Cristallography, Indole derivative, R factor, Antiproliferative activity, [CHIM.THER]Chemical Sciences/Medicinal Chemistry
Abstract

International audience; The X-ray crystal structure of 3-{4-[(4-(2-oxo-2,3-dihydro-1H-benzimidazol- 1-yl)piperidin-1-yl)benzyl]}-2-phenylindole, a compound that showed high cytotoxic potential against various leukemia cell lines, was established. The 3D spatial determination confirmed the structure in the solid state. It crystallizes in the triclinic space group P-1 with cell parameters a=9.572(7) Å, b=11.091(2) Å, c=15.976(4) Å, α=92.53(2), β=105.45(3), γ=94.65(3), V=1625.6(13) Å3 and Z=2. The crystal structure was refined to final values of R1=0.0638 and wR2=0.1800. The crystal packing is controlled by intermolecular hydrogen bonding and C-H π interactions. In addition, these new data could be further used to clarify the mechanism of action, implicating the antiproliferative effect of this new synthetic indole derivative on human leukemic cells.

Published
2016

45. Synthesis and Antiproliferative Effect of Ethyl 4-[4-(4-Substituted Piperidin-1-yl)]benzylpyrrolo[1,2-a ]quinoxalinecarboxylate Derivatives on Human Leukemia Cells

Author

Desplat, Vanessa, primary, Vincenzi, Marian, additional, Lucas, Romain, additional, Moreau, Stéphane, additional, Savrimoutou, Solène, additional, Rubio, Sandra, additional, Pinaud, Noël, additional, Bigat, David, additional, Enriquez, Elodie, additional, Marchivie, Mathieu, additional, Routier, Sylvain, additional, Sonnet, Pascal, additional, Rossi, Filomena, additional, Ronga, Luisa, additional, and Guillon, Jean, additional

Published
2017
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46. Crystal structure of a fluoro analogue of 3,4-(methylenedioxy)

Author

Guillon, Jean, Pinaud, Noël, Marchivie, Mathieu, ronga, luisa, Benazzouz, Abdelhamid, Moreau, Stéphane, Régulations Naturelles et Artificielles (ARNA), Institut National de la Santé et de la Recherche Médicale (INSERM)-Université de Bordeaux Ségalen [Bordeaux 2], Institut des Sciences Moléculaires (ISM), Centre National de la Recherche Scientifique (CNRS)-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Université Sciences et Technologies - Bordeaux 1-Université Montesquieu - Bordeaux 4-Institut de Chimie du CNRS (INC), Institut de Chimie de la Matière Condensée de Bordeaux (ICMCB), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut Polytechnique de Bordeaux-Université de Bordeaux (UB), Institut des Maladies Neurodégénératives [Bordeaux] (IMN), and Université de Bordeaux (UB)-Centre National de la Recherche Scientifique (CNRS)

Subjects
[CHIM.MATE]Chemical Sciences/Material chemistry
Abstract

International audience; The X-ray crystal structure of 6-fluoro-3,4-methylenedioxyamphetamine hydrochloride, a fluoro analogue of 3,4-(methylenedioxy)amphetamine, was established. It crystallizes in the orthorhombic space group Pbac with cell parameters a = 24.679(4)Å, b = 9.873(4)Å, c = 9.253(5)Å, V = 2254.5(16)Å3 and Z = 8. The crystal structure was refined to final values of R1 = 0.0601 and wR2 = 0.1479. An X-ray crystal structure analysis revealed that each molecule features strong intermolecular N-H…Cl hydrogen bonds.

Published
2015

47. Online Quantification of Lactate Concentration in Microdialysate During Cerebral Activation Using 1H-MRS and Sensitive NMR Microcoil.

Author

Crémillieux, Yannick, Dumont, Ursule, Mazuel, Leslie, Salvati, Roberto, Zhendre, Vanessa, Rizzitelli, Silvia, Blanc, Jordy, Roumes, Hélène, Pinaud, Noël, and Bouzier-Sore, Anne-Karine

Subjects
LACTATES, PROTON magnetic resonance spectroscopy
Abstract

The dynamic in vivo profiling of lactate is of uppermost importance in both neuroenergetics and neuroprotection fields, considering its central suspected role as a metabolic and signaling molecule. For this purpose, we implemented proton magnetic resonance spectroscopy (1H-MRS) directly on brain microdialysate to monitor online the fluctuation of lactate contents during neuronal stimulation. Brain activation was obtained by right whisker stimulation of rats, which leads to the activation of the left barrel cortex area in which the microdialysis probe was implanted. The experimental protocol relies on the use of dedicated and sensitive home-made NMR microcoil able to perform lactate NMR profiling at submillimolar concentration. The MRS measurements of extracellular lactate concentration were performed inside a pre-clinical MRI scanner allowing simultaneous visualization of the correct location of the microprobe by MRI and detection of metabolites contained in the microdialysis by MRS. A 40% increase in lactate concentration was measured during whisker stimulation in the corresponding barrel cortex. This combination of microdialysis with online MRS/MRI provides a new approach to follow in vivo lactate fluctuations, and can be further implemented in physio-pathological conditions to get new insights on the role of lactate in brain metabolism and signaling. [ABSTRACT FROM AUTHOR]

Published
2019
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48. 1H and 13C NMR assignments of bioactive indeno[1,2-b]indole-10-one derivatives

Author

Al Chab, Faten, Fenet, Bernard, Le Borgne, Marc, Jose, Joachim, Pinaud, Noël, Guillon, Jean, Ettouati, Laurent, Biomolécules Cancer et Chimiorésistances (B2C), Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon, Université de Lyon, Centre Commun de Résonance Magnétique Nucléaire, Université Lyon1 (CCRMN), Institut für Pharmazeutische und Medizinische Chemie, Westfälische Wilhelms-Universität Münster (WWU), Institut des Sciences Moléculaires (ISM), Centre National de la Recherche Scientifique (CNRS)-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Université Sciences et Technologies - Bordeaux 1-Université Montesquieu - Bordeaux 4-Institut de Chimie du CNRS (INC), Pharmacochimie (CNRS FRE 3396), and Université de Bordeaux (UB)

Subjects
[CHIM.THEO]Chemical Sciences/Theoretical and/or physical chemistry, [SDV.SP.MED]Life Sciences [q-bio]/Pharmaceutical sciences/Medication, [CHIM.THER]Chemical Sciences/Medicinal Chemistry, ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2013

50. Online 1H‐MRS measurements of time‐varying lactate production in an animal model of glioma during administration of an anti‐tumoral drug.

Author

Crémillieux, Yannick, Salvati, Roberto, Dumont, Ursule, Pinaud, Noël, Bouchaud, Véronique, Sanchez, Stéphane, Glöggler, Stefan, and Wong, Alan

Abstract

The aims of this study were to implement a magnetic resonance spectroscopy (MRS) protocol for the online profiling of subnanomolar quantities of metabolites sampled from the extracellular fluid using implanted microdialysis and to apply this protocol in glioma‐bearing rats for the quantification of lactate concentration and the measurement of time‐varying lactate concentration during drug administration. MRS acquisitions on the brain microdialysate were performed using a home‐built, proton‐tuned, microsolenoid with an active volume of 2 μL. The microcoil was placed at the outlet of the microdialysis probe inside a preclinical magnetic resonance imaging (MRI) scanner. C6‐bearing rats were implanted with microdialysis probes perfused with artificial cerebrospinal fluid solution and the lactate dehydrogenase (LDH) inhibitor oxamate. Microcoil magnetic resonance spectra were continuously updated using a single‐pulse sequence. Localized in vivo spectra and high‐resolution spectra on the dialysate were also acquired. The limit of detection and limit of quantification per unit time of the lactate methyl peak were determined as 0.37 nmol/ √min and 1.23 nmol/ √min, respectively. Signal‐to‐noise ratios (SNRs) of the lactate methyl peak above 120 were obtained from brain tumor microdialysate in an acquisition time of 4 min. On average, the lactate methyl peak amplitude measured in vivo using the nuclear magnetic resonance (NMR) microcoil was 193 ± 46% higher in tumor dialysate relative to healthy brain dialysate. A similar ratio was obtained from high‐resolution NMR spectra performed on the collected dialysate. Following oxamate addition in the perfusate, a monotonic decrease in the lactate peaks was observed in all animals with an average time constant of 4.6 min. In the absence of overlapping NMR peaks, robust profiling of extracellular lactate can be obtained online using a dedicated sensitive NMR microcoil. MRS measurements of the dynamic changes in lactate production induced by anti‐tumoral drugs can be assessed accurately with temporal resolutions on the order of minutes. The MRS protocol can be readily transferred to the clinical environment with the use of suitable clinical microdialysis probes. [ABSTRACT FROM AUTHOR]

Published
2018
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