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Functionalized Phospholipid Molecular Platform: Use for Production of Cationic Fluorescent Lipids
Author(s) -
Berchel Mathieu,
Haelters JeanPierre,
Afonso Damien,
Maroto Alicia,
Deschamps Laure,
Giamarchi Philippe,
Jaffrès PaulAlain
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301416
Subject(s) - cationic polymerization , chemistry , nile red , fluorescence , amphiphile , phospholipid , liposome , cycloaddition , zeta potential , lipid bilayer , alkyne , combinatorial chemistry , photochemistry , organic chemistry , membrane , biochemistry , copolymer , nanotechnology , polymer , catalysis , physics , materials science , quantum mechanics , nanoparticle
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.