Design, synthesis and biological studies of sugar-based ester surfactants

Sugar-based esters represent a class of non-ionic amphiphilic surfactants characterized by a sugar polar head linked to a hydrophobic chain. In the last years, they were highly demanded in different fields due to their numerous biological activites and applications associated to their biodegradable and biocompatible profiles. Even though the increased research on this topic, there is still a lack of information concerning the synthesis and innovative applications of less studied sugar-based esters, such as those with lactose polar heads or bearing aromatic moieties. Therefore, the purpose of this thesis was focused on the design and synthesis of several sugar-based monoester surfactants with different sugar heads and hydrophobic moieties, using enzymatic or chemical methods. To start with, a small series of 6' -O-lactose-based esters was designed and synthesized with the aim to investigate their following properties: (i) antimicrobial activity, (ii) antibiofilm inhibition, (iii) anti-inflammatory activity, (iv) antioxidant activity (v) the in vivo wound healing promotion. Consecutively, a modified Mitsunobu procedure was adopted for the synthesis of the 6-O-sucrose-based monoesters with different hydrophobic chains to analyse their influence on antibacterial and antifungal activities. The best compound was also selected for the anti-inflammatory studies. Then, a novel study focused on the permeability enhancer activity of 6-O-sucrose-based aryl(alkyl) esters was conducted using 6' -O-lactose-based esters analogues as reference compounds. Another research was focused on multistep syntheses design of new mannose-type esters through glycosylation and esterification steps. These compounds were synthesized with the aim to develop a drug delivery method based on mannose-decorated liposomes able to target infected macrophages by leishmania pathogen, improving the drawbacks of current treatments. Finally, an innovative palladium-catalyzed oxidative alkoxycarbonylation of substituted styrenes was applied for the synthesis of different sugar-based trans-cinnamic esters.