Skip to Main content Skip to Navigation
Journal articles

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.
Document type :
Journal articles
Complete list of metadata

Cited literature [14 references]  Display  Hide  Download

https://hal.sorbonne-universite.fr/hal-01480341
Contributor : Gestionnaire Hal-Upmc <>
Submitted on : Wednesday, March 1, 2017 - 1:02:39 PM
Last modification on : Tuesday, December 8, 2020 - 3:35:20 AM
Long-term archiving on: : Tuesday, May 30, 2017 - 5:27:35 PM

Identifiers

Citation

Jean Wilfried Fredy, Jérémy Scelle, Gregory Ramniceanu, Bich-Thuy Doan, Célia S. Bonnet, et al.. Mechanostereoselective One-Pot Synthesis of Functionalized Head-to-Head Cyclodextrin [3]Rotaxanes and Their Application as Magnetic Resonance Imaging Contrast Agents. Organic Letters, American Chemical Society, 2017, 19 (5), pp.1136-1139. ⟨10.1021/acs.orglett.7b00153⟩. ⟨hal-01480341⟩

Share

Metrics

Record views

1049

Files downloads

1254