Skip to Main content Skip to Navigation
Theses

Dually Functionalized Cryptophane-[223] Derivatives : Elaboration of Hydrosoluble 129-Xe Biosensors and Chiroptical Aspects

Abstract : Cryptophanes are a family of molecular containers, characterized by their lipophilic internal cavity. The ability of cryptophanes to encapsulate hyperpolarized xenon has opened a great opportunity to develop highly sensitive 129-Xe-based MRI molecular tracers. A large number of 129-Xe-cryptophane biosensors have been developed for targeting various biological events. Although this concept is catchy, many challenges have been encountered, specifically in the elaboration of water soluble and easy functionalizable cryptophane derivatives. The work presented in this thesis aims at developing a new straightforward approach to synthesize water soluble cryptophane sensors. These cages are based on cryptophane-[223] derivatives that bear a central carboxylic acid function to selectively graft a sensing unit, and six water soluble precursors on the cryptophanes’ rims. Using these platforms, three different water soluble sensors have been elaborated. These sensors have been characterized by 129Xe NMR spectroscopy to assess their binding properties and responsiveness. An additional aspect of these derivatives is their ability to undergo a solvent-dependent “self-encapsulation” phenomenon. This is characterized by the inclusion of the central functionality grafted on the propelendioxy linker towards the inner cavity of cryptophanes. This phenomenon has been clearly proved by 1H NMR and IR spectroscopy. The effect on the overall chiroptical properties was also investigated by polarimetry, VCD and ECD spectroscopy.
Document type :
Theses
Complete list of metadatas

Cited literature [248 references]  Display  Hide  Download

https://tel.archives-ouvertes.fr/tel-02463838
Contributor : Abes Star :  Contact
Submitted on : Sunday, February 2, 2020 - 1:07:23 AM
Last modification on : Monday, February 3, 2020 - 1:31:19 PM
Long-term archiving on: : Sunday, May 3, 2020 - 12:38:25 PM

File

BAYDOUN_Orsola_2019LYSEN064_Th...
Version validated by the jury (STAR)

Identifiers

  • HAL Id : tel-02463838, version 1

Citation

Orsola Baydoun. Dually Functionalized Cryptophane-[223] Derivatives : Elaboration of Hydrosoluble 129-Xe Biosensors and Chiroptical Aspects. Organic chemistry. Université de Lyon, 2019. English. ⟨NNT : 2019LYSEN064⟩. ⟨tel-02463838⟩

Share

Metrics

Record views

321

Files downloads

178