Synthesis of Triazole-Based Nonionic Surfactants for Nanostructured Drug Delivery: Investigation of Their Physicochemical and Biological Aspects

Synthesis of novel nonionic surfactants has attracted attention of synthetic chemists due to the issues of the currently used commercial surfactants. The synthesis of three biocompatible triazole-based nonionic surfactants is reported for nanovesicular drug loading. The surfactants were synthesized in a three-step reaction and characterized using ¹HNMR and mass spectroscopy techniques. They were investigated for their critical micelle concentration (CMC) using a UV–Visible spectrophotometer. Their biocompatibility was investigated against cell culture and in blood. All the synthesized nonionic surfactants were further explored for their nanovesicular drug loading using clarithromycin as a model hydrophobic drug. Nonionic surfactants revealed lower CMC in 35–45 μM and were less hemolytic and cytotoxic. They were capable of self-assembling in nanosize niosomal vesicles encapsulating increased amounts of drug. The results suggest the synthesized nonionic surfactants as biocompatible nanotechnology-based drug-delivery vehicles.     

Understanding and Modeling the Effect of Surfactants in Enhanced Particle Removal from Surfaces in Aqueous Media

The removal of particulate contamination is a critical issue for many manufacturing processes. It is particularly critical to the electronics industry in which small pieces of microscopic debris remaining after chemical mechanical planarization (cmp) using submicron polishing particles can cause device failure. One way to enhance particle removal following the cmp process is to utilize surfactants. Recent research has shown ways to model the effect of surfactants on enhanced particle removal. However, previous research has not demonstrated the effect of ionic strength on enhanced particle removal associated with surfactant use. Past research has also not shown the combined effects of ionic strength and surfactant concentration on enhanced particle removal using surfactants. This article summarizes the parameters affecting particle removal, and it provides data and analysis on the effect of ionic strength as well as the combined effects of ionic strength and surfactant concentration on particle removal following cmp processing.     

Stimulatory effects of tannins and cholic acid on tryptic hydrolysis of proteins: Ecological implications

The biochemical basis for considering tannins as digestion inhibitors has been reexamined. Both stimulatory and inhibitory effects of tannins on tryptic hydrolysis are reported. We show how stimulation may result from tannin-induced structural changes in the substrate protein, effectively denaturing it. The surfactant and bile constituent cholic acid also produced similar stimulatory effects. These results have considerable implications for normal digestive physiology as well as for the impact of tannins on argicultural and natural herbivore populations.     

Effect of surfactants on phenol removal by the method of polymerization and precipitation catalysed by Coprinus cinereus peroxidase

The removal of phenol by peroxidase‐catalysed polymerization was examined using Coprinus cinereus peroxidase in the presence of surfactants. The non‐ionic surfactants with poly(oxyethene) residues, Triton X‐100, Triton X‐405 and Tween 20, enhanced the phenol removal efficiency at a level similar to high relative molecular mass poly(ethylene glycol) (relative molecular mass 3000). Although the improvement in the removal efficiency was less than that of Triton X‐100, Span 20, sodium lauryl sulfate (SDS) and lauryl trimethylammonium bromide (DTAB) also enhanced the removal efficiency. The requirement of the enzyme for almost 100% removal of 100 mg dm^?3 phenol decreased to one‐fourth by the addition of 30 mg dm^?3 Triton X‐100. Triton X‐100, Triton X‐405, Tween 20 and DTAB could reactivate the enzyme precipitated with the phenol polymer, leading to the restarting of the phenol removal reaction. Copyright © 2003 Society of Chemical Industry     

Some concepts on design of surfactant gels and vesicles

It is conjectured that anionic-cationic surfactant combination can be regarded as equivalent to a double chain surfactant and using molecular packing considerations it is shown that vesicles, viscoelastic solutions and liquid crystals can be designed by the proper choice of chain lengths of the pair. Using these concepts new systems are designed, from mixtures of cetyltrimethyl ammonium bromide and sodium alkyl sulfonates, to produce both viscoelastic gels and vesicles.     

An Insight View on Synthetic Protocol,Surface Activity,and Biological Aspects of Novel Biocompatible Quaternary Ammonium Cationic Gemini Surfactants

In this study, we prepared a novel series of diester-functionalized cationic gemini surfactants (C_m-E2O2-C_m) containing ethylene oxide as a spacer with varying alkyl chain lengths and characterized by ¹H NMR, FT-IR, elemental analysis, and ESI-MS. The physicochemical properties of the geminis were explored by tensiometry, fluorescence, dye solubilization, and Krafft point. These geminis acquire superior surface activity than the conventional surfactants. Fluorescence spectroscopy analysis affirmed that the micropolarity and aggregation number of micelles diminished with increase in the alkyl chain length. These geminis represent a new group of amphiphiles of considerably high biodegradability, better cleavability, and low toxicity as assessed by BOD test, FT-IR analysis, and HC₅₀ analysis, respectively. They also showed significant level of antimicrobial activity toward some specified bacterial strains of Gram-positive and Gram-negative by using agar well diffusion method. Furthermore, the thermogravimetric analysis provided information regarding thermal stabilities of the newly synthesized gemini surfactants.     

Effects of surfactant and particle size on the microstructure and strength of Si3N4 foams with high porosity

The highly porous Si₃N₄ ceramic foams were prepared by direct foaming with mixed surfactants. The surface tension and viscosity of slurries were tailored by different carbon chain length of surfactants and different mean Si₃N₄ particle size to achieve the pore size controlling. The nearly linear relationship between the pore size and the ratio of surface tension to viscosity was observed, which indicates that the pore size could be precisely tailored by the slurry properties. Si₃N₄ ceramic foams with porosity of nearly 94%, mean pore size of 110–230 µm, and compressive strength of 1.24–3.51 MPa were obtained.     

Chemo-enzymatic synthesis of amino acid-based surfactants

The application of lipases to the synthesis of amino acid-based surfactants was investigated. Low yields (2–9%) were obtained in the acylation of free amino acids, such as l-serine and l-lysine, as well as their ethyl esters and amides with fatty acids, owing in part to low miscibility of the reactants. When the N-carbobenzyloxy (Cbz)-l-amino acids were used in an effort to improve miscibility of the amino acid derivatives with the acyl donor, a dramatic improvement was observed for N-Cbz-l-serine (92% yield) but not for N _α-Cbz- or N _ζ-Cbz-l-lysine (7 and 2% yield, respectively). As an alternative, and efficient synthesis of N _ζ-acyl-l-lysines was developed, based on the regiospecific chemical acylation of copper(II) lysinate. In pursuit of a general route to amino acid-fatty acid surfactants, the utility of a polyol linker was investigated. Thus, the glycerol ester of N _α′ N _ζ-di-Cbz-l-lysine was prepared and evaluated as a substrate for acylation. As expected, this and other glycer-1-yl esters of N-protected amino acids were excellent substrates for lipase-catalyzed acylation. Their reaction with myristic acid in the presence of Novozyme resulted in the regioselective acylation of the primary hydroxyl group of the glycerol moiety to afford the corresponding 1-O-(N-Cbz-l-aminoacyl)-3-O-myris-toylglycerols with conversions of 50–90%. These were readily deprotected to give a range of 1-O-(aminoacyl)-3-O-myristoyl-glycerols with overall yields of 27–71%.