Sunfish Amphiphiles: Conceptually New Carriers for DNA Delivery

Abstract

A conceptually new class of cationic amphiphiles, Sunfish amphiphiles, designed for the delivery of genes into cells is introduced. Sunfish amphiphiles have two hydrophobic tails, connected at the 4-and the N-position to the cationic pyridinium headgroup. Two extreme morphologies visualised by backfolding and combining of both tails at one site (matching situation) or unfolding of the tails at distinct interaction sites at biological membranes will lead to considerable differences in morphological behaviour. The underlying rationale allows controlled release by using this morphological alteration of

Novel Gemini cationic lipids with carbamate groups for gene delivery

“…In some cases, an excess of cationic liposomes to DNA leads to entrapment of DNA molecules between the lamellae in clusters of aggregated multilamellar structures. 31 In other studies, the lamellar structure, 32 a highly ordered tubular structure, the multilamellar structure L C α , and inverted hexagonal structures H C II and H I have also been found. 29 In this study, when N/P ratios were over 6, DNA was highly condensed, giving smaller particle sizes and PDI (Fig.…”

Structural and transfection properties of amine‐substituted gemini surfactant‐based nanoparticles

“…In an attempt to address the issue of low efficiencies, structure-activity and rational design approaches [7][8][9] are being used to synthesize new cationic agents designed to improve transfection efficiencies. Gemini surfactants are one such family of novel compounds now being studied for gene therapeutic applications with structures ranging from simple (such as the m-s-m type) [10][11][12] to more complex peptide [13] and carbohydrate [14][15][16][17][18][19][20] based structures.…”

Synthesis, antifungal, haemolytic and cytotoxic activities of a series of bis(alkylpyridinium)alkanes

“…These were either commercially available or were prepared using literature methods by deprotonation of 2-, 3-or 4-picoline followed by alkylation. 15,16 Headgroups 1-4 were prepared from 3,4-dimethylpyridine 5 upon treatment with 2.5 equiv of LDA, followed by addition of 1-bromobutane. Separation of the resulting mixture provided pure samples of 1, 2, 3 and 4 with an overall yield of 86% (Scheme 1).…”

“…. 1,12-Bis[4 0 -(1 00 -pentenyl)pyridinium]dodecane dichloride(15) 1,12-Dibromododecane 6 (0.20 g, 0.61 mmol) and 4-(1 0 -pentenyl)pyridine (0.21 g, 1.40 mmol) were reacted according to the general procedure. The residue was triturated with Et 2 O (8 Â 10 mL), then purified by chromatography on neutral Al 2 O 3 (activity II-III), (98:2 CHCl 3 /MeOH?90:10 CHCl 3 /MeOH).…”

“…MS: m/z ESI (positive ion) 275 [MÀ2Cl À ] 2+ (100%), 549 [MÀ2Cl À -H + ] + (35), 585 [MÀ37 Cl À ] +(15), 587 [MÀ35 Cl À ] +(5).Found [MÀ2Cl À ] 2+ 275.2609, mmol) were reacted according to the general procedure. The residue was triturated with Et 2 O (8 Â 10 mL), then purified by chromatography on neutral Al 2 O 3 (activity II-III), (98:2 CHCl 3 / MeOH?90:10 CHCl 3 /MeOH).…”