Phosphonodithioester-amine coupling in water: a fast reaction to modify the surface of liposomes

Abstract

The incorporation of lipophilic phosphonodithioesters in phospholipid formulations generates clickable liposomes that react with amines. The kinetics of this metal free phosphonodithioester-amine coupling (PAC) on liposomes in water is reported and can be classified as a fast reaction with a second order rate constant of k ≈ 8 × 10² M⁻¹ s⁻¹. The PAC reaction represents a versatile strategy to functionalize liposomes.