A new water-soluble xenon host system with great promise for the Xe NMR-based biosensing approach is presented: the -cryptophane-222-hexacarboxylate. It compares favorably with its already known diastereomer, on the one hand, and with cucurbit[6]uril, on the other hand, in particular in terms of xenon binding constant and xenon in-out exchange, a key parameter for the efficiency of the most sensitive HyperCEST method.
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http://dx.doi.org/10.1039/d2cp03714a | DOI Listing |
Phys Chem Chem Phys
October 2022
NIMBE, CEA, CNRS, Université de Paris Saclay, CEA Saclay, 91191 Gif-sur-Yvette, France.
A new water-soluble xenon host system with great promise for the Xe NMR-based biosensing approach is presented: the -cryptophane-222-hexacarboxylate. It compares favorably with its already known diastereomer, on the one hand, and with cucurbit[6]uril, on the other hand, in particular in terms of xenon binding constant and xenon in-out exchange, a key parameter for the efficiency of the most sensitive HyperCEST method.
View Article and Find Full Text PDFChirality
October 2021
Laboratoire de Chimie, Ens de Lyon, CNRS UMR 5182, Lyon, France.
This review addresses the synthesis of enantiopure cryptophane and the study of their chiroptical properties. Cryptophane derivatives represent an important class of macrocyclic compounds that can bind a large range of species in solution under different conditions. The overwhelming majority of these host molecules is chiral, and their chiroptical properties have been thoroughly investigated.
View Article and Find Full Text PDFAdvancement of hyperpolarized Xe MRI technology toward clinical settings demonstrates the considerable interest in this modality for diagnostic imaging. The number of contrast agents, termed biosensors, for Xe MRI that respond to specific biological targets, has grown and diversified. Directly functionalized xenon-carrying macrocycles, such as the large family of cryptophane-based biosensors, are good for localization-based imaging and provide contrast before and after binding events occur.
View Article and Find Full Text PDFOrg Lett
January 2019
Aix Marseille Univ, CNRS, Centrale Marseille , iSm2 , Marseille , France.
Cyclotriveratrylene (CTV) is a macrocyclic cyclophane presenting a bowl-shaped conformation, used as building block to construct cryptophane and hemicryptophane capsules. A method to synthesize new enantiopure CTV derivatives with an unprecedented spatial arrangement of their substituents, exhibiting C symmetry, is described. The absolute configuration was assigned by ECD spectroscopy coupled with modeling.
View Article and Find Full Text PDFChemphyschem
January 2019
Molecular Imaging, Leibniz-Forschungsinstitut für Molekulare Pharmakologie (FMP), Robert-Rössle-Str. 10, 13125, Berlin, Germany.
Macrocyclic host structures for generating transiently bound Xe have been used in various ultra-sensitive NMR and MRI applications for molecular sensing of biochemical analytes. They are based on hyperpolarized nuclei chemical exchange saturation transfer (Hyper-CEST). Here, we tested a set of water-soluble pillar[5]arenes with different counterions in order to compare their potential contrast agent abilities with that of cryptophane-A (CrA), the most widely used host for such purposes.
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