Trehalose-based Janus cyclooligosaccharides: the “Click” synthesis and DNA-directed assembly into pH-sensitive transfectious nanoparticles

Abstract

The convergent preparation of Janus molecular nanoparticles by thiourea-“clicking” of α,α′-trehalose halves has been implemented; the strategy allows access to macrocyclic derivatives with seggregated cationic and lipophilic domains that in the presence of DNA undergo pH-dependent self-assembly into lamellar superstructures, as established by electrochemical, structural (SAXS), microscopical (TEM) and computational techniques, that mediate transfection in vitro and in vivo.