Lipophosphonate/lipophosphoramidates: A family of synthetic vectors efficient for gene delivery

Atherton–Todd reaction: mechanism, scope and applications

“…The nature of the cationic polar head is one of the molecular features of the cationic lipids which directly influence the stability of lipoplexes by acting on the strength of the ionic interactions with the anion charge of the phosphate groups from the nucleic acids. The replacement of trimethylammonium with either trimethylphosphonium or trimethylarsonium offers better transfection efficacies probably owing to a better compromise between the stability and the instability of lipoplexes [120]. The synthesis of trimethylarsonium-based phosphoramidate was also achieved by using the AT reaction which proved to be an efficient tool to link the lipid part with the polar head region of the cationic lipid as exemplified in Scheme 37.…”

“…The synthesis of trimethylarsonium-based phosphoramidate was also achieved by using the AT reaction which proved to be an efficient tool to link the lipid part with the polar head region of the cationic lipid as exemplified in Scheme 37. With the same synthetic scheme, guanidinum-based lipophosphoramidates [121] obtained from natural amino acids, methylimidazolium [122], spermine-based amphiphile [123], dicationic lipophosphoramides [119] and arsonium or phosphonium [120] cationic lipids were synthesized.…”

Physicochemical and biological characterization of 1,2-dialkoylamidopropane-based lipoplexes for gene delivery

“…To overcome these limitations, different structures of cationic lipids were synthesized and evaluated for lipofection effectiveness in the past two decades [6,7,18,20,23,42,43]. Moreover, the physicochemical properties of these lipids and their complexes with nucleic acids (DNA, oligonucleotides, and siRNA) were investigated in an attempt to derive a structure activity relationship [4,27,38].…”

Oxime Ether Lipids Containing Hydroxylated Head Groups are More Superior siRNA Delivery Agents than their Nonhydroxylated Counterparts

“…Modifications in the chemical structure of DOTAP and DOTMA have been extensively studied to determine structure–function relationships for optimal transfection efficiency. Delivery of nucleic acids using cationic lipids as carriers is reliant on various factors such as the type of cationic head group [13], length and degree of unsaturation of the hydrophobic domain chains [14], and lipid backbone functionality [15]. The nature of the anionic counterion [16,17], and the nucleic acid-to-cationic lipid charge ratio [18] also play a role in the overall transfection efficiency [14,19].…”