Search results for "Amphiphile"

Studies of the physicochemical and structural properties of self-assembling cationic pyridine derivatives as gene delivery agents.

2015

New amphiphilic pyridine derivatives containing dodecyloxycarbonyl substituents at positions 3 and 5 and cationic moieties at positions 2 and 6 have been designed and synthesised. Compounds of this type can be considered as synthetic lipids. The corresponding 1,4-dihydropyridine (1,4-DHP) derivatives have earlier been proposed as a promising tool for plasmid DNA (pDNA) delivery in vitro. In this work studies of the self-assembling properties of amphiphilic pyridine derivatives leading to the formation of liposomes, determination of particle size, zeta-potential and critical micelle concentration (CMC) with dynamic light scattering (DLS) measurements are described. Furthermore, thermal analy…

Synthesis and self-assembly of novel fluorous cationic amphiphiles with a 3,4-dihydro-2(1H)-pyridone spacer

2011

Abstract The synthesis of fluorous (highly fluorinated) 3,4-dihydro-2(1 H )-pyridone-5-carboxylate cationic amphiphiles have been described, where the dihydropyridone serves as a spacer and either a pyridinium bromide or a triphenylphosphonium bromide form the polar cationic head group. The in water self-assembled aggregates have been observed by atomic force microscopy (AFM) and dynamic light scattering (DLS).

High-Generation Amphiphilic Janus-Dendrimers as Stabilizing Agents for Drug Suspensions

2018

Pharmaceutical nanosuspensions are formed when drug crystals are suspended in aqueous media in the presence of stabilizers. This technology offers a convenient way to enhance the dissolution of poorly water-soluble drug compounds. The stabilizers exert their action through electrostatic or steric interactions, however, the molecular requirements of stabilizing agents have not been studied extensively. Here, four structurally related amphiphilic Janus-dendrimers were synthesized and screened to determine the roles of different macromolecular domains on the stabilization of drug crystals. Physical interaction and nanomilling experiments have substantiated that Janus-dendrimers with fourth gen…

High-performance liquid chromatographic separation of modified and native melittin following transglutaminase-mediated derivatization with a dansyl f…

1991

Abstract The 26-amino acid linear, amphiphilic peptide melittin was enzymatically modified with the fluorescent probe monodansylcadaverine using guinea pig liver transglutaminase and a fluorescent derivative of stoichiometry 1:1 was obtained. Reversed-phase and size-exclusion high-performance liquid chromatographic modes were tested in order to resolve the labelled peptide and native species. The influence of several operational variables was analysed and the elution conditions were optimized so that a satisfactory resolution could be achieved in both instances in a rapid, easy manner. Both chromatographic modes offer the possibility of accurate monitoring of the time course of the enzyme-m…

A head-to-head comparison of poly(sarcosine) and poly(ethylene glycol) in peptidic, amphiphilic block copolymers

2015

Abstract In this work we compare chemical and solution properties, like critical aggregate concentrations (CAC) and hydrodynamic radii of aggregates based on either poly(ethylene glycol) or poly(sarcosine) block copolymers in aqueous solution. The amine functionalized, hydrophilic polymers poly(sarcosine) (degree of polymerization, X n  = 100 and 200) and PEG (X n  = 121 and 242) of comparable hydrodynamic volume were used to initiate the ring opening polymerization of α-amino acid- N -carboxyanhydrides based on ɣ-benzyl- l -glutamate (Glu(OBn)) or e-carboxybenzyl- l -lysine (Lys(Z)). The second, hydrophobic block was kept at a degree of polymerization of 25 and 50 to enable a direct compar…

Tetraethynylethene molecular scaffolding: Nonlinear optical, redox, and amphiphilic properties of donor functionalized polytriacetylene and expanded …

1997

Dissolution of nitrones in alkylphosphates: A structural study

2022

Nitrones are chemical compounds with well-established anti-oxidant and spin-trapping properties. Their low solubility in water for many of them limits their applications, so opportune solvents must be found. In this study, two recently synthetized oxindole nitrones with proven antiproliferative and antioxidant activity have been dissolved in several liquid amphiphiles, chosen as model solvents. The effect of the polar head nature and the alkyl chain length/type have been investigated by a combined experimental (solubility, UV–vis spectroscopy) / computational (molecular dynamics) approach. The different chemical structures of the various solvents offer different chemical environments to the…

Staphylococcal alpha-toxin: formation of the heptameric pore is partially cooperative and proceeds through multiple intermediate stages.

1997

Staphylococcal alpha-toxin is a 293 residue polypeptide that assembles into pore-forming heptamers, residues 118-140, thereby inserting to form an amphipathic beta-barrel in the lipid bilayer. Fluorometric analyses were here conducted using cysteine-substitution mutants site-specifically-labeled at positions 35 or 130 with the environmentally-sensitive fluorophore acrylodan. In conjunction with functional assays, three conformational states of the heptamer were defined, which may represent transitional configurations of the toxin molecule along its way to membrane insertion and pore formation. The first was the freshly assembled, SDS-sensitive heptamer alpha7*a, where a minor alteration in …

Micelles formed from photochemically active amphiphiles: structural characterization by small-angle neutron scattering

1996

Abstract A novel class of photochemically active amphiphiles has been synthesized containing a ketone moiety as a biradical or radical pair precursor on the hydrophobic tail of sodium sulfate surfactants. Alteration of the molecular structure of each ketone-containing surfactant allows for the systematic and predictable manipulation of the micellar size and shape, both of which are important in determining the coupling between the unpaired electrons confined within the micelle and the intraradical dynamics. The structure of the resulting aggregates has been analyzed by small-angle neutron scattering (SANS). The results show that the amphiphiles form ellipsoidal micelles with aggregation num…

Tuning the Self-Assembly of Rectangular Amphiphilic Cruciforms

2014

The self-assembly of a series of nonionic amphiphilic cruciforms based on the 1,2,4,5-tetrakis(phenylethynyl)benzene (TPEB) skeleton, in which the peripheral substituents have been modified to modulate the morphology of the supramolecular structures, is reported. The presence of linear paraffinic and hydrophilic chains in TPEBs 1 and 2 gives rise to two-dimensional structures of high aspect ratio. In contrast, the incorporation of dendronized hydrophilic chains results in the formation of twisted ribbons in amphiphile 3 and impedes the organized self-assembly of TPEB 4. Theoretical calculations show that the self-assembly of these amphiphiles might be initiated with the formation of π-stack…