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Place Amphi Dorothy Hodgkin
Title
Synthesis and studies of photoswitchable glycosides
Abstract
Photoswitchable glycoconjugates bearing molecular photoswitch linked to glycoside represent a new type of photosensitive molecules which could find applications for light-controllable biological applications and photopharmacology. Rapid access to these compounds with unprotected sugars in aqueous media is highly desirable. Through DMC-mediated glycosylation of dihydroxyazobenzene with unprotected sugars, we have developed a one-pot synthesis of water-soluble glycosyl azobenzenes which displayed excellent photoswitching properites, thermal and photostability in aqueous media.
As applications for photopharmacology, we have designed and synthesized a series of amphiliphic photoswitchable glycosides (APGs) containing different linkers between azobenzene and amphiphilic sugar units, as well as sugar backbone and ammonium moieties in order to reversibly control the self-assembly with nucleic acids and gene delivery via light illumination. Photophysical investigations have revealed that the synthesized APGs show excellent photoswitching behavior in aqueous media. Preliminary self-assembling results demonstrated that all studied APGs vector/pDNA formulations achieve fully pDNA complexation, compaction, and protection at protonatable nitrogen/anionic phosphate (N/P) ratios of 5, 10 and 20, with a relatively uniform particle size distribution and a high potential for forming the stable nanocomplexes.
PhD supervision
- Director: Joanne Xie - Professor, ENS Paris-Saclay
Members of the jury
- Prof. Florence DJÉDAÏNI-PILARD, Université de Picardie Jules Vernes (Laboratoire LG2A, UMR CNRS 7378), Rapportrice
- Dr. Jean-Maurice MALLET, ENS-Paris (Département de chimie, CNRS URA 1686/ UMR 8642), Rapporteur
- Prof. Mélanie ETHEVE-QUELQUEJEU, Université Paris Descartes (Laboratoire LCBPT, CNRS UMR 8601), Examinatrice
- Dr. Sebastien VIDAL Université Paris-Saclay (Laboratoire ICSN, CNRS UPR 2301), Examinateur