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2 results on '"MESH: alpha-Cyclodextrins"'

1. Supramolecular Assemblies of Histidinylated α-Cyclodextrin in the Presence of DNA Scaffold during CDplexes Formation

Author

Olivier R. Martin, Patrick Midoux, Véronique Bennevault-Celton, Chantal Pichon, Philippe Guégan, Allan Urbach, Laboratoire Matériaux Polymères aux Interfaces (MPI), Université d'Évry-Val-d'Essonne (UEVE), Institut de Chimie Organique et Analytique (ICOA), Centre National de la Recherche Scientifique (CNRS)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Université d'Orléans (UO)-Institut de Chimie du CNRS (INC), Centre de biophysique moléculaire (CBM), Université d'Orléans (UO)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), and Université d'Orléans (UO)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
alpha-Cyclodextrins, Stereochemistry, Static Electricity, Biomedical Engineering, Supramolecular chemistry, Pharmaceutical Science, Bioengineering, 02 engineering and technology, Transfection, 010402 general chemistry, DNA condensation, 01 natural sciences, MESH: Histidine, chemistry.chemical_compound, MESH: Plasmids, Humans, Imidazole, Histidine, [SDV.BBM]Life Sciences [q-bio]/Biochemistry, Molecular Biology, A-DNA, MESH: Static Electricity, Pharmacology, MESH: Humans, MESH: Transfection, Organic Chemistry, MESH: DNA, MESH: alpha-Cyclodextrins, DNA, 021001 nanoscience & nanotechnology, 0104 chemical sciences, HEK293 Cells, chemistry, MESH: HEK293 Cells, Polylysine, 0210 nano-technology, Plasmids, Biotechnology
Abstract

International audience; α-Cyclodextrin was transformed in a cationic unit after per substitution with histidine (His-α-CD) and lysine (Lys-α-CD) molecules on the primary face. His-α-CD and Lys-α-CD were used to form electrostatic complexes (CDplexes) with a plasmid DNA encoding luciferase gene, and the ability of CDplexes to transfect mammalian cells was examined using HEK293-T7 cells. The luciferase activity in cells transfected with His-α-CDplexes was 8-fold higher than that obtained Lys-α-CDplexes. When the transfection was carried out in the presence of chloroquine, the luciferase activity with His-α-CDplexes and Lys-α-CDplexes increased 6 and 25 times, respectively. The lower enhancement with His-α-CDplexes confirmed that histidine induced a proton sponge effect inside endosomes upon imidazole protonation, favoring DNA delivery in the cytosol. At the same time, we found that the condensation of DNA with His-α-CD was unexpectedly stronger than that obtained with the lysyl-α-CD counterpart. Moreover, it was as strong as that observed with high molecular weight polylysine. NMR (ROESY and DOSY) investigations in the absence of DNA showed that an inclusion complex is formed between the imidazole ring of histidine and the hydrophobic cavity of CD but no His-α-CD polymers can be formed by intermolecular interactions. These results suggest that intermolecular interactions between imidazole and His-α-CD cavity could be involved to form supramolecular assemblies in the presence of a DNA scaffold leading to DNA condensation into low diameter particles.

Published
2011
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2. Cerebral Blood Volume Quantification in a C6 Tumor Model Using Gadolinium per (3,6-Anhydro) α-Cyclodextrin as a New Magnetic Resonance Imaging Preclinical Contrast Agent

Author

Jean-François Le Bas, Soâd Aous, Hana Lahrech, Adriana-Teodora Perles-Barbacaru, Andrée Gadelle, Jean-Claude Debouzy, Pascal H. Fries, Grenoble Institut des Neurosciences (GIN), Université Joseph Fourier - Grenoble 1 (UJF)-Institut National de la Santé et de la Recherche Médicale (INSERM), Centre de Recherches du Service de Santé des Armées (CRSSA), Service de Santé des Armées, RMN biomédicale : de la cellule à l'homme (RBCH), Université Pierre Mendès France - Grenoble 2 (UPMF)-Université Joseph Fourier - Grenoble 1 (UJF)-CHU Grenoble-DIR CENTRALE DU SSA-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS), Reconnaissance Ionique et Chimie de Coordination (RICC), SYstèmes Moléculaires et nanoMatériaux pour l’Energie et la Santé (SYMMES), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Grenoble Alpes [2016-2019] (UGA [2016-2019])-Institut de Recherche Interdisciplinaire de Grenoble (IRIG), 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)-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)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Grenoble Alpes [2016-2019] (UGA [2016-2019])-Institut de Recherche Interdisciplinaire de Grenoble (IRIG), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA), This work was supported by the Canceropôle Lyon Auvergne Rhône-Alpes (CLARA), the EC COST Action D-38 Metal-Based Systems for Molecular Imaging Applications and the European Molecular Imaging Laboratories (EMIL) network, the Nuclear Energy Division of the Atomic Energy Commission (CEA), the GdR PARIS, the Association for the Research on Cancer (ARC) for postgraduate research grant., Collaboration, Issartel, Jean-Paul, Institut de Chimie du CNRS (INC)-Université Grenoble Alpes [2016-2019] (UGA [2016-2019])-Institut de Recherche Interdisciplinaire de Grenoble (IRIG), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université Grenoble Alpes [2016-2019] (UGA [2016-2019])-Institut de Recherche Interdisciplinaire de Grenoble (IRIG), and Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Centre National de la Recherche Scientifique (CNRS)

Subjects
MESH: Models, Cardiovascular, MESH: Blood Volume, Magnetic Resonance Spectroscopy, Gadolinium, Contrast Media, Blood volume, blood–brain barrier, MESH: Magnetic Resonance Imaging, 030218 nuclear medicine & medical imaging, MESH: Blood-Brain Barrier, MESH: Glioma, Mice, 0302 clinical medicine, MESH: Animals, Blood Volume, medicine.diagnostic_test, Brain Neoplasms, MESH: alpha-Cyclodextrins, Models, Cardiovascular, cerebral blood volume, MESH: Cerebrovascular Circulation, Glioma, contrast agent, Magnetic Resonance Imaging, Extravasation, medicine.anatomical_structure, Neurology, Blood-Brain Barrier, relaxivity, Cerebrovascular Circulation, MESH: Brain Neoplasms, [SDV.NEU]Life Sciences [q-bio]/Neurons and Cognition [q-bio.NC], Cardiology and Cardiovascular Medicine, brain tumor, alpha-Cyclodextrins, Brain tumor, chemistry.chemical_element, Mice, Inbred Strains, Blood–brain barrier, MESH: Mice, Inbred Strains, Nephrotoxicity, 03 medical and health sciences, In vivo, MESH: Contrast Media, Organometallic Compounds, medicine, Animals, [SDV.NEU] Life Sciences [q-bio]/Neurons and Cognition [q-bio.NC], MESH: Mice, MESH: Magnetic Resonance Spectroscopy, business.industry, MESH: Organometallic Compounds, Magnetic resonance imaging, medicine.disease, cyclodextrin, chemistry, Neurology (clinical), MESH: Gadolinium, Nuclear medicine, business, 030217 neurology & neurosurgery
Abstract

In magnetic resonance imaging (MRI), cerebral blood volume (CBV) quantification is dependent on the MRI sequence and on the properties of the contrast agents (CAs). By using the rapid steady-state T1 method, we show the potential of gadolinium per (3,6-anhydro) α-cyclodextrin (Gd-ACX), a new MRI paramagnetic CA (inclusion complex of Gd3+ with per (3,6-anhydro)-α-cyclodextrin), for the CBV quantification in the presence of blood—brain barrier lesions. After biocompatibility and relaxivity experiments, in vivo experiments on rats were performed on a C6 tumor model with 0.05 mmol Gd-ACX/kg (1-weighted images, a signal enhancement of 170% appeared in vessels after injection, but not in the tumor (during the 1 h of observation), in contrast to the 90% signal enhancement obtained with Gd-DOTA (a clinical MRI CA) injected at a T1 isoefficient dose. This result shows the absence of Gd-ACX extravasation into the tumor tissue and its confinement to the vascular space. Fractional CBV values were found similar to Gd-ACX and Gd-DOTA in healthy brain tissue and in the contralateral hemisphere of tumor-bearing rats, whereas only Gd-ACX was appropriate for CBV quantification in tumor regions.

Published
2008
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