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

Montassar Khalil (1) , Dany Jeanne Dit Fouque (1) , Mathieu Berchel (1) , Aurore Fraix (2) , Aurélien Dupont (3) , Salvatore Sortino (2) , Antony Memboeuf (1) , Paul-Alain Jaffres (1)

1 CEMCA - Chimie, Electrochimie Moléculaires et Chimie Analytique
2 Unict - Università degli studi di Catania = University of Catania
3 SFR UMS CNRS 3480 - INSERM 018 - Biosit : biologie, santé, innovation technologique

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.

Mots clés: click chemistry; no metal; reaction in water

Mots clés: amphiphiles; réaction click; sans métal; réaction dans l’eau; liposomes

Domaines: Sciences du Vivant [q-bio]; Chimie

Montassar Khalil, Dany Jeanne Dit Fouque, Mathieu Berchel, Aurore Fraix, Aurélien Dupont, et al.. Phosphonodithioester-amine coupling in water: a fast reaction to modify the surface of liposomes. Organic & Biomolecular Chemistry, 2021, ⟨10.1039/d1ob01078f⟩. ⟨hal-03282994⟩