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.
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Phosphonodithioester-Amine Coupling as a Key Reaction Step for the Design of Cationic Amphiphiles Used for Gene Delivery.
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Univ Brest, CNRS, CEMCA UMR 6521, 6 Avenue Victor Le Gorgeu, 29238 Brest, France.
A convergent synthesis of cationic amphiphilic compounds is reported here with the use of the phosphonodithioester-amine coupling (PAC) reaction. This versatile reaction occurs at room temperature without any catalyst, allowing binding of the lipid moiety to a polar head group. This strategy is illustrated with the use of two lipid units featuring either two oleyl chains or two-branched saturated lipid chains.
View Article and Find Full Text PDFPhosphonodithioester-amine coupling in water: a fast reaction to modify the surface of liposomes.
Org Biomol Chem
July 2021
Univ Brest, CNRS, CEMCA UMR 6521, 6 Avenue Victor Le Gorgeu, F-29238 Brest, France.
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.
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