Synthesis, micellization properties, and cytotoxicity trends of N-hydroxyethyl-3-alkyloxypyridinium surfactants (original) (raw)
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INTERACTION OF 3-HYDROXY PYRIDINE AND SURFACTANT MICELLES: A FLUORESCENCE STUDIES
Asian Journal of Pharmaceutical and Clinical Research Journal, 2021
Objective: Micellar solubilization is a powerful alternative for dissolving hydrophobic compound in aqueous environment. 3-hydroxy pyridine (3-HP) derivatives are the potential endogenous photosensitizers. 3-HP derivatives show protective effect in clinical extreme condition such as hypoxia, hyperthermia, hypokinesia. Micellization of 3-HP followed by solubilization would catalyze its pharmaceutical activities which may serve better results in medicinal and analytical fields. Methods: Fluorescence and absorption spectroscopy techniques are used to monitor the micellar solubilization studies of 3-HP. Solubilization studies of 3-HP with various anionic, cationic and nonionic surfactants have been performed in aqueous medium around 23-25°C temperature. The solubilization action of the surfactant has also been determined by theoretical calculated spectral parameters such as empirical fluorescence coefficient, quantum yield, stokes, shift and molar absorption coefficient. Results: 3-HP shows fluorescence excitation peak at 315 nm and emission peak at 390 nm respectively while the absorbance of 3-HP has been found to be maximum at 305 nm. The fluorescence as well as the theoretically calculated spectral data has been used to characterize the hetero environment of the micelles in terms of their polarity, probe solubilization site and critical micelle concentration. Conclusion: This article briefly discusses the importance of surfactants in biological system model as well as the use of micelles in pharmacy as an important tool that finds numerous applications.
Journal of colloid and interface science, 2014
Four new amide functionalized N-methylpiperazinium amphiphiles having tetradecyl, hexadecyl alkyl chain lengths and counterions; chloride or bromide have been synthesized and characterized by various spectroscopic techniques. These new surfactants have been investigated in detail for their self-assembling behavior by surface tension, conductivity and fluorescence measurements. The thermodynamic parameters of these surfactants indicate that micellization is exothermic and entropy-driven. The dynamic light scattering (DLS) and transmission electron microscopy (TEM) experiments have been performed to insight the aggregate size of these cationics. Thermal degradation of these new surfactants has also been evaluated by thermal gravimetric analysis (TGA). These new surfactants form stable complexes with DNA as acknowledged by agarose gel electrophoresis, ethidium bromide exclusion and zeta potential measurements. They have also been found to have low cytotoxicity by MTT (3-(4,5-dimethylth...
Micellar properties of nicotinamide-based surfactants
Journal of Colloid and Interface Science, 1989
Data on the critical micellar concentration (CMC) and critical micellar temperature (CMT) are reported for various 1-alkyl-3-carbamoylpyridinium halide surfactants (N-alkylnicotinamides) R -N A + X -(R = C4, C8, Cm, C~2, C14, and C16, X = C1, Br, and I) in aqueous solution. Nicotinamide-based surfactants have critical micelle concentrations similar to that of corresponding alkylpyridinium halide surfactants though the critical micellar temperatures of the former are significantly higher (15-25°C).
Langmuir, 2009
New pyridinium gemini amphiphiles having ethane-1,2-dithiol spacer have been synthesized by regioselective electrophilic cobromination of R-olefins. Ethane-1,2-dithiol (1) and N-bromosuccinimide (6) on reaction with R-olefins (dodecene (2), tetradecene (3), hexadecene (4), and octadecene (5)) gave the respective 1,2-bis(2-bromoalkylthio)ethane (7-10). The bromoalkylthio ethers when reacted with pyridine (11) gave the respective gemini bispyridinium bromide (12-15). The surface properties of new geminis were evaluated by surface tension and conductivity measurements. These gemini surfactants have also been found to be having low cytotoxicity by MTT (3-(4,5-dimethylthiazol-2-yl)-2,5diphenyltetrazolium bromide) assay on C6 glioma cells. The DNA binding capabilities of these amphiphiles have been determined below as well as above critical micelle concentration. The preliminary studies by agarose gel electrophoresis indicated chain length dependent DNA binding abilities which has further been proved by ethidium bromide exclusion experiments and transmission electron microscopy (TEM).
2020
Surfactants are amphiphilic compounds that are widely used in various technological fields and biological systems. In many of these applications, mixtures of amphiphiles in organic solvents are employed for better performance The work aims at establishing the extent of ideality or otherwise in the mixed micelles of n-alkyl trimethylammonium bromide, (n = 14 and 16 for TTABr and CTABr respectively), in water (AQ) and water-monoethanolamine (AQ-MEA) at different mole fractions (0.1 to 0.6) and temperatures by Conductance measurement.: The values of the critical micelle concentration (Cmx) obtained in AQ, and AQ-MEA were lower than that obtained assuming an ideal mixing system. Substantial deviation from ideality was observed in the presence of AQ-MEA at all temperatures, suggestive of more favourable association of the surfactants in MEA solvent. The composition (χ1) of the mixed micelles obtained in the context of Rubingh’s model showed that the micelles of CTABr were dominant, and t...
Micellization of mixtures of amphiphilic drugs and cationic surfactants: A detailed study
Colloids and Surfaces B-biointerfaces
The micellization behaviors of two amphiphilic drugs ((amitriptyline hydrochloride (AMT) and imipramine hydrochloride (IMP)) in presence of cationic surfactants (conventional as well as gemini) have been investigated conductometrically at four mole fractions and four temperatures. The critical micelle concentration (cmc) values come out to be lower than cmcid values (cmcid is the cmc value at ideal mixing state) indicating attractive interactions between the two components in mixed micelles. Micellar mole fractions of surfactants (X1 and X1M), calculated by Rubingh and Motomura models, are always greater than X1id (micellar mole fraction at ideal mixing). The rigid structure of drugs decreases their contribution in mixed micelles as compared to that predicted by X1id values. Although α1 (mole fraction of surfactant) is higher for DTAB than that of 12-4-12, the contribution of 12-4-12 is almost equal to that of DTAB. The interaction parameter (β) is negative at all temperatures and at all compositions indicating attractive interactions. Activity coefficients (f1 and f2) are always less than unity suggesting nonideality in the systems. Thermodynamic parameters suggest dehydration of hydrophobic part of the drug at or above certain temperature which is different for the two drugs.► Micellization of amphiphilic drug–cationic surfactant systems have been analyzed. ► Rubingh and Motomura models show higher contribution of surfactants in mixed micelles. ► The negative β values suggest attractive interactions between the components. ► For drug/drug–surfactant systems, ΔHm° values change from negative to positive with temperature.
Carbohydrate Research, 2001
The following sequence of reactions has been employed to synthesize the title anionic surfactants: where R=C 7 H 15 ; C 11 H 23 ; and C 15 H 31 , respectively, and Py refers to pyridine. Aggregation of the surfactants synthesized (predominantly a anomers) in water was studied at 40°C by conductivity measurements. Increasing the chain length of R decreases the critical micelle concentration (CMC) and the degree of counter-ion dissociation. The dependence of the Gibbs free energy of micellization and CMC on the length of R is similar to other ionic surfactants, but the head-group, i.e., the sulfated sugar moiety is less hydrophilic than the structurally related group (OCH 2 CH 2) 2 OSO 3 − Na + , most probably because of intermolecular H-bonding in the micellar pseudo-phase
Russian journal of …, 2002
1-Cetyl-3-(2-hydroxyiminopropyl)imidazolium chloride and bromide were synthesized for the first time. These compounds are functionalized zwitterionic surfactants which give rise to micelle formation in aqueous solution. Kinetic and thermodynamic analysis of nucleophilic cleavage of p-nitrophenyl p-toluenesulfonate, diethyl p-nitrophenyl phosphate, and ethyl p-nitrophenyl ethylphosphonate in the presence of 1-cetyl-3-(2-hydroxyiminopropyl)imidazolium halide micelles showed that the latter are powerful nucleophilic reagents whose kinetic behavior can be described in terms of a simple pseudophase distribution model. The efficiency of substrate solubilization with zwitterionic surfactant micelles and the reactivity of the oximate fragment in the micelle phase were estimated on a quantitative level. The observed acceleration of S N 2 reactions with the examined p-nitrophenyl esters relative to analogous reactions of zwitterionic 1-methyl-3-(2-hydroxyiminopropyl)imidazolium halides is, respectively, 12 800, 550, and 900 times; it is explained mainly by increased concentration of the reactants in micelles.