LIQUID–LIQUID INTERFACE STUDY OF HYDROCARBONS, ALCOHOLS, AND CATIONIC SURFACTANTS WITH WATER

2009 ◽  
Vol 16 (04) ◽  
pp. 599-608 ◽  
Author(s):  
MAN SINGH ◽  
HIDEKI MATSUOKA
Keyword(s):  
Cationic Surfactants ◽  
Nonionic Surfactants ◽  
Alkyl Chain ◽  
Hydrophobic Interactions ◽  
Liquid Interface ◽  
Saturated Hydrocarbons ◽  
Inductive Effects ◽  
Interface Study ◽  
Similar Decrease ◽  
Sigma Bond

Molecular interaction dynamics at liquid–liquid interface (LLI), involved nondispersive solution as compared with the interaction in bulk phase. Thereby, interfacial tension (IFT, mN/m) of LLI for four saturated hydrocarbons, six alcohols, and three cationic surfactants are reported at 298.15 K. The pentane, hexane, heptane, octane hydrocarbons and pentanol, hexanol, heptanol, 1-octanol, 2-octanol, and 1-decanol alcohols were used and IFT data were compared with 4 mm kg-1 dodecyltrimethylammoniumbromide (DTAB), trimethylsulfoxoniumiodide (TMSOI), methyltrioctylammoniumchloride (MTOAC) surfactants studied in benzene–water LLI. The IFT data are noted as hydrocarbons > DTAB > TMSOI > alcohols > MTOAC. The hydrocarbons and alcohols decreased IFT within 16 to 49% and 87 to 92%, respectively, whereas the surfactants within 78.3 to 95.9%. The alcohols developed interaction similar to surfactants and are denoted as nonionic surfactants for making mixtures of low IFT with hydrophilic and hydrophobic interactions to the level of the surfactants. The pentanol and MTOAC caused similar decrease in IFT so the pentanol developed the hydrophilic and hydrophobic interactions of the strength of MTOAC. Comparatively, the hydrocarbons showed lower decrease but the octane showed 49% decrease in IFT. Thus, the hydrocarbon with longer alkyl chain and the alcohol with shorter behave as good surfactants. The hydrocarbons with inductive effect on sigma bond between carbon atoms in alkyl chain also weakened the IFT and influenced the hydrophobic interactions. The MTOAC with four octyl units reduced 96% IFT so inductive effects monitor LLI dynamics.

Micellization Behaviour of Cationic Surfactants in the Presence of Food Additives: Conductance and Spectroscopic Investigations

2020 ◽  
Vol 10 ◽  
Author(s):  
Sonika Arti ◽  
Neha Aggarwal
Keyword(s):  
Glutamic Acid ◽  
Cationic Surfactants ◽  
Hydrophobic Interactions ◽  
Food Additives ◽  
Specific Conductance ◽  
Food Additive ◽  
Nmr Studies ◽  
Degree Of Ionization ◽  
Increase With Increase ◽  
Micellization Process

Aim: The micellization behavior of cationic surfactants have been studied in the presence of food additives. Objectives: Micellization behaviour of cationic surfactants, cetyltrimethylammonium bromide (CTAB) and tetradecyltrimethylammonium bromide (TTAB) has been studied in water and in various concentrations of salts (food additives) L-glutamic acid, sodium propionate, sodium citrate tribasic dihydrate and disodium tartrate dihydrate at (298.15, 308.15 and 318.15) K. Methods: Two methods used in the present study are specific conductance measurements and spectroscopy (NMR) studies. Results: From the specific conductance(κ), various parameters such as critical micelle concentration (CMC), degree of ionization of micelle (α), standard Gibbs free energy (ΔGom), enthalpy (ΔHom), and entropy (ΔSom) of micellization have also been calculated. Thermodynamic parameters related to the micellization process were also analyzed through NMR studies. Conclusion: The CMC values are influenced by the presence of food additive. The magnitude of CMC values increase with increase in concentration of food additive. In all the cases, enthalpy of micellization, ∆Hom values are found to be negative whereas entropy of micellization, ∆S om values are positive which indicate that hydrophobic interactions play a major role in the micellization process. Also, NMR studies reveal that tartrate and citrate are more hydrated than glutamic acid and propionate, resulting in more downfield shift.

scholarly journals Contribution of Molecular Structure to Self-Assembling and Biological Properties of Bifunctional Lipid-Like 4-(N-Alkylpyridinium)-1,4-Dihydropyridines

Pharmaceutics ◽  
2019 ◽  
Vol 11 (3) ◽  
pp. 115 ◽  
Author(s):  
Martins Rucins ◽  
Pavels Dimitrijevs ◽  
Klavs Pajuste ◽  
Oksana Petrichenko ◽  
Ludmila Jackevica ◽  
...  
Keyword(s):  
Chain Length ◽  
Alkyl Chain ◽  
Hydrophobic Interactions ◽  
Biological Activities ◽  
Biological Properties ◽  
Alkyl Chain Length ◽  
Critical Aggregation Concentration ◽  
Self Assembling ◽  
Basal Cytotoxicity

The design of nanoparticle delivery materials possessing biological activities is an attractive strategy for the development of various therapies. In this study, 11 cationic amphiphilic 4-(N-alkylpyridinium)-1,4-dihydropyridine (1,4-DHP) derivatives differing in alkyl chain length and propargyl moiety/ties number and position were selected for the study of their self-assembling properties, evaluation of their cytotoxicity in vitro and toxicity on microorganisms, and the characterisation of their interaction with phospholipids. These lipid-like 1,4-DHPs have been earlier proposed as promising nanocarriers for DNA delivery. We have revealed that the mean diameter of freshly prepared nanoparticles varied from 58 to 513 nm, depending upon the 4-(N-alkylpyridinium)-1,4-DHP structure. Additionally, we have confirmed that only nanoparticles formed by 4-(N-dodecylpyridinium)-1,4-DHP derivatives 3 and 6, and by 4-(N-hexadecylpyridinium)-1,4-DHP derivatives 10 and 11 were stable after two weeks of storage. The nanoparticles of these compounds were found to be homogenous in size distribution, ranging from 124 to 221 nm. The polydispersity index (PDI) values of 1,4-DHPs samples 3, 6, 10, and 11 were in the range of 0.10 to 0.37. We also demonstrated that the nanoparticles formed by 4-(N-dodecylpyridinium)-1,4-DHP derivatives 3, 6, and 9, and 4-(N-hexadecylpyridinium)-1,4-DHP derivatives 10 and 11 had zeta-potentials from +26.07 mV (compound 6) to +62.80 mV (compound 11), indicating a strongly positive surface charge and confirming the relative electrostatic stability of these nanoparticle solutions. Transmission electron microscopy (TEM) images of nanoaggregates formed by 1,4-DHPs 3 and 11 confirmed liposome-like structures with diameters around 70 to 170 nm. The critical aggregation concentration (CAC) value interval for 4-(N-alkylpyridinium)-1,4-DHP was from 7.6 µM (compound 11) to 43.3 µM (compound 6). The tested 4-(N-alkylpyridinium)-1,4-DHP derivatives were able to quench the fluorescence of the binary 1,6-diphenyl-1,3,5-hexatriene (DPH)—1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) system, demonstrating hydrophobic interactions of 1,4-DHPs with phospholipids. Thus, 4-(N-dodecylpyridinium)-1,4-DHP derivative 3 quenched the fluorescence of the DPH–DPPC system more efficiently than the other 4-(N-alkylpyridinium)-1,4-DHP derivatives. Likewise the compound 3, also 4-(N-dodecylpyridinium)-1,4-DHP derivative 9 interacted with the phospholipids. Moreover, we have established that increasing the length of the alkyl chain at the quaternised nitrogen of the 4-(N-alkylpyridinium)-1,4-DHP molecule or the introduction of propargyl moieties in the 1,4-DHP molecule significantly influences the cytotoxicity on HT-1080 (human fibrosarcoma) and MH-22A (mouse hepatocarcinoma) cell lines, as well as the estimated basal cytotoxicity. Additionally, it was demonstrated that the toxicity of the 4-(N-alkylpyridinium)-1,4-DHP derivatives on the Gram-positive and Gram-negative bacteria species and eukaryotic microorganism depended on the presence of the alkyl chain length at the N-alkyl pyridinium moiety, as well as the number of propargyl groups. These lipid-like compounds may be proposed for the further development of drug formulations to be used in cancer treatment.

Intermolecular interactions between a dye and cationic surfactants: Effects of alkyl chain, head group, and counterion

2011 ◽  
Vol 380 (1-3) ◽  
pp. 119-127 ◽  
Author(s):  
Mohammad Rashidi-Alavijeh ◽  
Soheila Javadian ◽  
Hussein Gharibi ◽  
Morteza Moradi ◽  
Ali Reza Tehrani-Bagha ◽  
...  
Keyword(s):  
Intermolecular Interactions ◽  
Cationic Surfactants ◽  
Alkyl Chain ◽  
Head Group

scholarly journals Influence of Asphaltenes in the Properties of Liquid–Liquid Interface between Water and Linear Saturated Hydrocarbons

ACS Omega ◽  
2018 ◽  
Vol 3 (4) ◽  
pp. 3851-3856 ◽  
Author(s):  
Dheiver Santos ◽  
Walisson Souza ◽  
Cesar Santana ◽  
Everton Lourenço ◽  
Alexandre Santos ◽  
...  
Keyword(s):  
Liquid Interface ◽  
Saturated Hydrocarbons

scholarly journals Strategy for Designing Selective Lysosomal Acid α-Glucosidase Inhibitors: Binding Orientation and Influence on Selectivity

Molecules ◽  
2020 ◽  
Vol 25 (12) ◽  
pp. 2843 ◽  
Author(s):  
Atsushi Kato ◽  
Izumi Nakagome ◽  
Mizuki Hata ◽  
Robert J. Nash ◽  
George W. J. Fleet ◽  
...  
Keyword(s):  
Alkyl Chain ◽  
Hydrophobic Interactions ◽  
Antiviral Agents ◽  
Design Strategy ◽  
Docking Study ◽  
Piperidine Ring ◽  
Hydroxyl Groups ◽  
Storage Site ◽  
Molecular Docking Study ◽  
Lysosomal Acid

Deoxynojirimycin (DNJ) is the archetypal iminosugar, in which the configuration of the hydroxyl groups in the piperidine ring truly mimic those of d-glucopyranose; DNJ and derivatives have beneficial effects as therapeutic agents, such as anti-diabetic and antiviral agents, and pharmacological chaperones for genetic disorders, because they have been shown to inhibit α-glucosidases from various sources. However, attempts to design a better molecule based solely on structural similarity cannot produce selectivity between α-glucosidases that are localized in multiple organs and tissues, because the differences of each sugar-recognition site are very subtle. In this study, we provide the first example of a design strategy for selective lysosomal acid α-glucosidase (GAA) inhibitors focusing on the alkyl chain storage site. Our design of α-1-C-heptyl-1,4-dideoxy-1,4-imino-l-arabinitol (LAB) produced a potent inhibitor of the GAA, with an IC50 value of 0.44 µM. It displayed a remarkable selectivity toward GAA (selectivity index value of 168.2). A molecular dynamic simulation study revealed that the ligand-binding conformation stability gradually improved with increasing length of the α-1-C-alkyl chain. It is noteworthy that α-1-C-heptyl-LAB formed clearly different interactions from DNJ and had favored hydrophobic interactions with Trp481, Phe525, and Met519 at the alkyl chain storage pocket of GAA. Moreover, a molecular docking study revealed that endoplasmic reticulum (ER) α-glucosidase II does not have enough space to accommodate these alkyl chains. Therefore, the design strategy focusing on the shape and acceptability of long alkyl chain at each α-glucosidase may lead to the creation of more selective and practically useful inhibitors.

NMR studies of hydrocarbons solubilized in aqueous micellar solutions

1991 ◽  
Vol 69 (5) ◽  
pp. 822-833 ◽  
Author(s):  
Roderick E. Wasylishen ◽  
Jan C. T. Kwak ◽  
Zhisheng Gao ◽  
Elisabeth Verpoorte ◽  
J. Bruce MacDonald ◽  
...  
Keyword(s):  
Alkyl Chain ◽  
Chemical Shifts ◽  
Nmr Relaxation ◽  
Spin Lattice Relaxation ◽  
Ionic Surfactant ◽  
Nmr Studies ◽  
Unsaturated Hydrocarbons ◽  
Saturated Hydrocarbons ◽  
Surfactant Micelle ◽  
H Nmr

Information concerning the solubilization of hydrocarbons in ionic surfactant micelles was obtained from 2H NMR relaxation, 1H NMR chemical shifts, and 1H NMR paramagnetic relaxation measurements. The rotational motion of deuterated hydrocarbons, which is related to the micellar microviscosity at the location of the hydrocarbons, was probed by 2H NMR relaxation. The relaxation data are interpreted using both the two-step and the single-step models, and the results are discussed in terms of the micellar microviscosity and the location of the hydrocarbons in micelles. The location of the hydrocarbons in micelles was further investigated by determining the aromatic ring current-induced 1H chemical shifts along the surfactant alkyl chain and by comparing the 1H spin-lattice relaxation enhancement of the hydrocarbons and the surfactant alkyl chain, induced by Mn2+ on the micellar surface. The hydrocarbons used include benzene, naphthalene, acenaphthalene, triphenylene, cyclohexane, cyclododecane, and tert-butylcyclohexane and the surfactants studied are hexadecyl-, tetradecyl-, and dodecyltrimethylammonium bromide; hexadecyl-, tetradecyl-, and dodecylpyridinium halide; and sodium dodecyl sulfate. The results indicate that the micellar microviscosity at the location of saturated hydrocarbons is approximately 5 cP for both the cationic and anionic micelles, whereas the micellar microviscosity at the location of unsaturated hydrocarbons is much higher. The unsaturated hydrocarbons are found to reside primarily near the surfactant headgroup in the cationic micelles, but are distributed evenly throughout the anionic SDS micelles. The saturated hydrocarbons appear to be located in the interior of the micelles. Key words: NMR, relaxation, solubilization, surfactant, micelle.

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