title: Mechanostereoselective One-Pot Synthesis of Functionalized Head-to-Head Cyclodextrin [3]Rotaxanes and Their Application as Magnetic Resonance Imaging Contrast Agents.
abstract: A versatile, five-component, one-pot synthesis of cyclodextrin (CD) [3]rotaxanes using copper-catalyzed azide-alkyne cycloaddition has been developed. Head-to-head [3]rotaxanes of α-CD selectively functionalized by one or two gadolinium 1,4,7,10-tetraazacyclododecane-1,4,7-triacetic acid monoamide complexes were obtained mechanostereoselectively. The magnetic resonance imaging efficiency, expressed by the longitudinal proton relaxivity of the rotaxanes, was significantly improved as compared to the functionalized CD. In vitro and in vivo preclinical studies showed a higher contrast and retention in the kidney than gadolinium 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid complex, demonstrating the potential of these rotaxanes as MRI contrast agent.
authors.affiliation: Sorbonne Universités , UPMC Univ Paris 06, CNRS, Institut Parisien de Chimie Moléculaire UMR 8232, 4 place Jussieu, 75005 Paris, France.
authors.forename: Jean Wilfried
authors.initials: JW
authors.lastname: Fredy
authors.affiliation: Sorbonne Universités , UPMC Univ Paris 06, CNRS, Institut Parisien de Chimie Moléculaire UMR 8232, 4 place Jussieu, 75005 Paris, France.
authors.forename: Jérémy
authors.initials: J
authors.lastname: Scelle
authors.affiliation: Chimie ParisTech , CNRS, UMR8258 INSERM U1022 Unité de Technologies Chimiques et Biologiques pour la Santé, 11 rue Pierre & Marie Curie, 75005 Paris, France.
authors.forename: Gregory
authors.initials: G
authors.lastname: Ramniceanu
authors.affiliation: Chimie ParisTech , CNRS, UMR8258 INSERM U1022 Unité de Technologies Chimiques et Biologiques pour la Santé, 11 rue Pierre & Marie Curie, 75005 Paris, France.
authors.forename: Bich-Thuy
authors.initials: BT
authors.lastname: Doan
authors.affiliation: Centre de Biophysique Moléculaire, CNRS UPR4301, Université d'Orléans , Rue Charles Sadron, 45071 Cedex 2 Orléans, France.
authors.forename: Célia S
authors.initials: CS
authors.lastname: Bonnet
authors.affiliation: Centre de Biophysique Moléculaire, CNRS UPR4301, Université d'Orléans , Rue Charles Sadron, 45071 Cedex 2 Orléans, France.
authors.forename: Éva
authors.initials: É
authors.lastname: Tóth
authors.affiliation: Sorbonne Universités , UPMC Univ Paris 06, CNRS, Institut Parisien de Chimie Moléculaire UMR 8232, 4 place Jussieu, 75005 Paris, France.
authors.forename: Mickaël
authors.initials: M
authors.lastname: Ménand
authors.affiliation: Sorbonne Universités , UPMC Univ Paris 06, CNRS, Institut Parisien de Chimie Moléculaire UMR 8232, 4 place Jussieu, 75005 Paris, France.
authors.forename: Matthieu
authors.initials: M
authors.lastname: Sollogoub
authors.affiliation: Sorbonne Universités , UPMC Univ Paris 06, CNRS, Institut Parisien de Chimie Moléculaire UMR 8232, 4 place Jussieu, 75005 Paris, France.
authors.forename: Guillaume
authors.initials: G
authors.lastname: Vives
authors.affiliation: Sorbonne Universités , UPMC Univ Paris 06, CNRS, Institut Parisien de Chimie Moléculaire UMR 8232, 4 place Jussieu, 75005 Paris, France.
authors.forename: Bernold
authors.identifier: 0000-0002-2518-1405
authors.initials: B
authors.lastname: Hasenknopf