77638-27-8Relevant articles and documents
Cationic trialkylphosphates: Synthesis and transfection efficacies compared to phosphoramidate analogues
Le Corre, Stphanie S.,Berchel, Mathieu,Le Gall, Tony,Haelters, Jean-Pierre,Lehn, Pierre,Montier, Tristan,Jaffrs, Paul-Alain
, p. 8041 - 8048 (2014)
We report herein the synthesis of a novel family of cationic lipids, characterized by a trimethylammonium headgroup linked through a phosphate function to either two identical or two different lipid chains. The novelty of this study arises from the use of a trialkyl phosphate group to associate the hydrophobic domain to the cationic polar head. The structure of these new cationic lipids, which differs from that of previously reported lipophosphoramidates, is closer to the phospholipids encountered in the plasma membrane, and possesses a phosphocholine polar head. Evaluation of the transfection activity allowed us to compare the efficacy of cationic lipophosphates with that of lipophosphoramidates. These results demonstrate that cationic lipophosphates and lipophosphoramidates having otherwise identical chemical structures exhibit similar transfection efficacies. The second conclusion is that the structure of the lipid domain is a much more important parameter in governing transfection efficacy than the composition of the linker moiety. The best results were obtained with cationic lipophosphates or lipophosphoramidates possessing two different lipid chains, for example one oleyl chain with one phytanyl chain. These nonsymmetric cationic lipids exhibited transfection efficacies that were 10-to 200-fold better than those obtained with Lipofectamine used as a commercial standard.
Cationic lipophosphoramidates with two different lipid chains: Synthesis and evaluation as gene carriers
Le Corre, Stephanie S.,Berchel, Mathieu,Belmadi, Nawal,Denis, Caroline,Haelters, Jean-Pierre,Le Gall, Tony,Lehn, Pierre,Montier, Tristan,Jaffres, Paul-Alain
, p. 1463 - 1474 (2014/03/21)
Cationic lipids constitute a family of synthetic vectors commonly used for nucleic acids delivery. We herein report the results of a systematic study that aimed to compare the transfection efficacies of cationic lipophosphoramidates possessing either two identical lipid chains (termed symmetric cationic lipids) or two different lipid chains (non-symmetric cationic lipids). In addition, we also compared the transfection results of such a 'molecular approach' (the two different lipid chains being included in the same molecule) with those of a 'supramolecular approach' in which two types of symmetrical cationic lipids were mixed in one liposomal formulation. Thus, the present work allowed us first to optimize the methods used to synthesize non-symmetric cationic lipophosphoramidates. In addition, we could also identify two non-symmetric cationic lipids exhibiting high transfection efficiencies with a series of mammalian cell lines, both vectors being characterized by a single phytanyl chain and either an oleyl or a lauryl lipid chain.
Synthesis and biological activity of dialkylphosphocholines
Lukac, Milos,Mrva, Martin,Fischer-Fodor, Eva,Lacko, Ivan,Bukovsky, Marian,Miklasova, Natalia,Ondriska, Frantisek,Devinsky, Ferdinand
scheme or table, p. 6346 - 6349 (2010/06/11)
A series of dialkylphosphocholines were prepared and evaluated for their biological activity. The antiprotozoal activity was determined against Acanthamoeba lugdunensis. Compound 15 exhibited excellent trophocidal activity. None of the tested dialkylphosphocholines exhibited better fungicidal activity against Candida albicans than miltefosine. The antineoplastic activity was determined against HeLa. The most cytotoxic was compound 10, which was more active against tumor cells as against normal cells.
