Functionalized Phospholipid Molecular Platform: Use for Production of Cationic Fluorescent Lipids. Issue 5 (5th December 2013)

• Record Type: Journal Article
• Authors: Berchel, Mathieu; Haelters, Jean‐Pierre; Afonso, Damien; Maroto, Alicia; Deschamps, Laure; Giamarchi, Philippe; Jaffrès, Paul‐Alain
• Is Part Of: European journal of organic chemistry. Issue 5(2014)
• Page Start: 1076
• Page End: 1083
• Publication Date: 2013-12-05
• Subjects: Amphiphiles -- Lipids -- Phospholipids -- Fluorescence -- Click chemistry; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201301416
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: Fluorescent amphiphilic phospholipids (neutral or cationic) in which fluorescent probes are contained in the lipid domain were synthesized via phosphoramide intermediates possessing two distinct lipid chains. One of these lipid chains is ω‐functionalized with an azide or alkyne group, and this is subsequently used to introduce a fluorescent probe by Huisgen cycloaddition. Five different fluorescent probes (naphthalimide, dansyl, fluoresceine, Nile red, and coumarin) were considered in this study. These neutral and cationic fluorescent lipids were included at a 1 % molar ratio with a selected cationic lipid (KLN47) to produce liposomal solutions that were characterized by dynamic light scattering and zeta potential measurements. Abstract : Neutral lipophosphoramides, each containing a clickable functional group (alkyne, azide) located in the lipid domain and a dimethylamine unit, were synthesized from POCl3 in one‐pot fashion. This molecular platform, of great interest for vectorization purposes, is readily functionalized with fluorescent groups, whereas the amine could be alkylated to afford a series of cationic fluorescent lipids.