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Journal of Advanced Pharmaceutical... 2023Drug excipient compatibility studies are considered important in successful formulation of drug products. Suggested methods for this purpose are thermal techniques under...
Drug excipient compatibility studies are considered important in successful formulation of drug products. Suggested methods for this purpose are thermal techniques under isothermal or nonisothermal conditions. In this study, modafinil, a wakefulness-promoting drug, was investigated under nonisothermal conditions using differential scanning calorimetry. Four different heating rates, 5, 10, 15, and 20°C/min, were performed for modafinil pure material and its physical mixtures with magnesium stearate (MgSt) or Gelucire 48/16. Activation energy (Ea) was calculated from the straight line of plotting a function of heating rate versus temperature and found that modafinil-Gelucire physical mixture increased Ea. This indicates drug-excipient interaction, supported by evidence from Fourier transform infrared spectroscopy and nuclear magnetic resonance spectroscopy. No significant interaction was detected with MgSt.
PubMed: 37255876
DOI: 10.4103/japtr.japtr_663_22 -
Journal of Oleo Science 2011Hydroxyl fatty acids and their derivatives are of high value due to their wide range of industrial application, including cosmetic, food, personal care and... (Review)
Review
Hydroxyl fatty acids and their derivatives are of high value due to their wide range of industrial application, including cosmetic, food, personal care and pharmaceutical products. Realizing the importance of hydroxyl fatty acids, and yet due to the absence of the conventional starting raw materials, Malaysia has developed 9,10-dihydroxystearic acid (9,10-DHSA) and its derivatives from locally abundant palm based oils. The aim of this article is to provide a general description of the works that have thus far being done on palm based 9,10-DHSA: starting from its conception and production from commercial grade palm based crude oleic acid via epoxidation and hydrolysis, purification through solvent crystallization and characterization through wet and analytical chemistry, moving on to developmental works done on producing its derivatives through blending, esterification, amidation and polymerization, and completing with applications of 9,10-DHSA and its derivatives, e.g. DHSA-stearates and DHSA-estolides, in commercial products such as soaps, deodorant sticks and shampoos. This article incorporates some of the patent filed technological knowhow on 9,10-DHSA and its derivatives, and will also point out some of the shortcomings in previously published documents and provide some recommendations for future research works in mitigating these shortcomings.
Topics: Particle Size; Plant Oils; Stearic Acids; Surface Properties
PubMed: 21502724
DOI: 10.5650/jos.60.237 -
Scientific Reports Dec 2023Food emulsifier are mostly prepared from a lipophilic lipid tail with a hydrophilic sugar head. In this study, the lipophilic tail was obtained from apricot kernels,...
Food emulsifier are mostly prepared from a lipophilic lipid tail with a hydrophilic sugar head. In this study, the lipophilic tail was obtained from apricot kernels, which are food waste, and the hydrophilic head was gluconic acid instead of sugar, in order to draw attention to the non-cyclic poly hydroxyl compounds. Thus, oleic acid of apricot kernel was used as the lipophilic moiety of the prepared surfactant. So, apricot kernel was grinned and dried, oil was extracted using soxhlet apparatus, Physical and chemical parameters and fatty acids composition of the extracted oil had been determined. The extracted oil was then hydrolyzed into glycerol and a mixture of free fatty acids. The fatty acids mixture was separated. Then, oleic acid was extracted individually in pure form using supercritical CO extractor, it was then confirmed according to its melting point, Gas chromatography-mass spectrometry (GC-MS) after esterification, elemental analysis, Proton nuclear magnetic resonance (HNMR), and mass spectrometry (MS) to detect the corresponding molecular ion peak. The pure individual oleic acid was converted to hydroxy stearic acid, which was then converted to an amphiphilic compound (surfactant) via esterification reaction with the hydrophilic gluconic acid, and afforded a new surfactant known as 2,3,4,5-tetrahydroxy-6-((9-((-2,3,4,5,6-pentahydroxyhexanoyl) oxy)octadecanoyl) oxy)hexanoic acid or stearyl gluconate for simplification. The structures elucidation of all synthesized compound was established according to elemental analysis and spectral data (Fourier transform infrared IR, H NMR, C NMR and MS). Moreover, the prepared compound was tasted for its antibacterial activity, and showed good activities against some types of bacteria. The surface-active properties, foamability, foaming stability and emulsion stability of stearyl gluconate were studied and compared with the properties of the well-known surfactant sucrose stearate, and it was clear that, the activity of stearyl gluconate as a surfactant was higher than that of sucrose stearate. Moreover, establishment of safety of this compound was performed using albino rats by acute oral toxicity and kidney and liver functions of these mice. On the other hand, the prepared surfactant was used in the production of low fat-free cholesterol mayonnaise as egg replacer. Texture properties and the sensory evaluation of the prepared mayonnaise showed that the properties were improved by using the new prepared surfactant. Thus, the prepared gluconyl stearate can be used as a safe food additive.
Topics: Rats; Mice; Animals; Prunus armeniaca; Surface-Active Agents; Food; Refuse Disposal; Plant Oils; Fatty Acids; Gluconates; Anti-Bacterial Agents; Sugars; Oleic Acids
PubMed: 38057365
DOI: 10.1038/s41598-023-48404-x -
ACS Omega Jul 2022This article presents new possibilities of using thin films of lanthanide stearates as sorbent materials. Modification of the Q-sense device resonator with monolayers of...
This article presents new possibilities of using thin films of lanthanide stearates as sorbent materials. Modification of the Q-sense device resonator with monolayers of lanthanide stearates by the Langmuir-Schaeffer method made it possible to study the process of insulin protein adsorption on the surface of new thin-film sorbents. The resulting films were also characterized by compression isotherms, chemical analysis, scanning electron microscopy, and mass spectrometry. The transition of stearic acid to salt was recorded by IR spectroscopy. Using the LDI MS method, the main component of thin films, lanthanide distearate, was established. The presence of Eu in thin films was revealed. In the case of europium stearate, the maximum value of insulin adsorption was obtained, -1.67·10 mole/cm. The findings suggest the possibility of using thin films of lanthanide stearates as a sorption material for the proteomics determination of the quantitative protein content in complex fluid systems by specific adsorption on modified surfaces and isolation of such proteins from complex mixtures.
PubMed: 35910105
DOI: 10.1021/acsomega.1c07300 -
Materials (Basel, Switzerland) Jul 2023The common, commercial reversible thermochromic (RT) melamine-formaldehyde resin microcapsules containing formaldehyde are very harmful to human health. To address this...
The common, commercial reversible thermochromic (RT) melamine-formaldehyde resin microcapsules containing formaldehyde are very harmful to human health. To address this issue, we successfully prepared a novel formaldehyde-free microcapsule via interfacial polymerization using RT compositions as the core and poly(urethane-urea) (PUU) as the shell. The core material consisted of a color former (crystal violet lactone), a developer (bisphenol AF), and a solvent (methyl stearate). To optimize the synthesis of the microcapsules, an L (3) orthogonal design and single-factor experiments were employed to analyze the effects of four factors (N3300-to-L75 shell material mass ratio, core-to-shell material mass ratio, emulsifier concentration, and shear rate during emulsification) on the encapsulation efficiency. The results showed that the optimal parameter values were as follows: a shear rate of 2500 rpm, N3300-to-L75 shell material mass ratio of 1:4, core-to-shell material mass ratio of 11:5, and emulsifier concentration of 3.5%. The influence of the shear rate on the particle size and distribution, surface morphology, dispersibility, and reversible thermochromic properties of the microcapsules was investigated. Furthermore, analyses on the phase-change characteristics, thermal stability, ultraviolet aging, and solvent and acid-base resistances of the microcapsules were conducted systematically. Finally, a reversible thermochromic mark containing the RTPUU microcapsules was designed and fabricated, which could be used against falsification. Moreover, these RTPUU microcapsules can be potentially used for anticounterfeiting applications.
PubMed: 37512425
DOI: 10.3390/ma16145150 -
The EMBO Journal Sep 2023
PubMed: 37496466
DOI: 10.15252/embj.2023114802 -
Journal of Lipid Research Sep 2022The spike protein of severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) and other coronaviruses mediates host cell entry and is S-acylated on multiple...
The spike protein of severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) and other coronaviruses mediates host cell entry and is S-acylated on multiple phylogenetically conserved cysteine residues. Multiple protein acyltransferase enzymes have been reported to post-translationally modify spike proteins; however, strategies to exploit this modification are lacking. Using resin-assisted capture MS, we demonstrate that the spike protein is S-acylated in SARS-CoV-2-infected human and monkey epithelial cells. We further show that increased abundance of the acyltransferase ZDHHC5 associates with increased S-acylation of the spike protein, whereas ZDHHC5 knockout cells had a 40% reduction in the incorporation of an alkynyl-palmitate using click chemistry detection. We also found that the S-acylation of the spike protein is not limited to palmitate, as clickable versions of myristate and stearate were also labelled the protein. Yet, we observed that ZDHHC5 was only modified when incubated with alkyne-palmitate, suggesting it has specificity for this acyl-CoA, and that other ZDHHC enzymes may use additional fatty acids to modify the spike protein. Since multiple ZDHHC isoforms may modify the spike protein, we also examined the ability of the FASN inhibitor TVB-3166 to prevent S-acylation of the spike proteins of SARS-CoV-2 and human CoV-229E. We show that treating cells with TVB-3166 inhibited S-acylation of expressed spike proteins and attenuated the ability of SARS-CoV-2 and human CoV-229E to spread in vitro. Our findings further substantiate the necessity of CoV spike protein S-acylation and demonstrate that de novo fatty acid synthesis is critical for the proper S-acylation of the spike protein.
Topics: Acylation; Acyltransferases; Alkynes; Azetidines; COVID-19; Coenzyme A; Cysteine; Fatty Acid Synthase, Type I; Humans; Myristates; Nitriles; Palmitates; Pyrazoles; SARS-CoV-2; Spike Glycoprotein, Coronavirus; Stearates
PubMed: 35921881
DOI: 10.1016/j.jlr.2022.100256 -
PloS One 2017Lipid nanocapsules (LNCs) are biomimetic nanocarriers used for the encapsulation of a broad variety of active ingredients. Similar to surface active compounds, LNCs...
Lipid nanocapsules (LNCs) are biomimetic nanocarriers used for the encapsulation of a broad variety of active ingredients. Similar to surface active compounds, LNCs contain both hydrophilic and hydrophobic parts in their structure. Moreover, the components of LNCs, macrogol 15 hydroxystearate (MHS) and lecithin, are known for their surface active properties. Therefore, the aim of this paper was to investigate the capability of the LNCs to decrease surface tension using two techniques: drop tensiometry and the Wilhelmy plate method. LNCs with diameters ranging from 30 to 100 nm were successfully obtained using a phase inversion technique. The LNCs' properties, such as size and zeta potential, depend on the composition. LNCs exhibit a lower limiting surface tension compared to MHS (34.8-35.0 mN/m and 37.7-38.8 mN/m, respectively), as confirmed by both drop tensiometry and the Wilhelmy plate method. LNCs have exhibited a saturated interfacial concentration (SIC) that was 10-fold higher than the critical micellar concentration (CMC) of MHS or the SIC of binary and ternary mixtures of LNC ingredients. The SIC of the LNC formulations depended on the mass mixing ratio of the MHS/triglycerides but not on the presence of lecithin. The CMC/SIC values measured by the Wilhelmy plate method were higher than those obtained using drop tensiometry because of the longer duration of the tensiometry measurement. In conclusion, the surfactant-like properties of the LNCs offer new possibilities for medical and pharmaceutical applications.
Topics: Lecithins; Lipids; Micelles; Nanocapsules; Polyethylene Glycols; Glycine max; Stearates; Surface Properties; Surface Tension
PubMed: 28796777
DOI: 10.1371/journal.pone.0179211 -
The Journal of Clinical Investigation Oct 2019Palmitic acid esters of hydroxy stearic acids (PAHSAs) are bioactive lipids with antiinflammatory and antidiabetic effects. PAHSAs reduce ambient glycemia and improve...
Palmitic acid esters of hydroxy stearic acids (PAHSAs) are bioactive lipids with antiinflammatory and antidiabetic effects. PAHSAs reduce ambient glycemia and improve glucose tolerance and insulin sensitivity in insulin-resistant aged chow- and high-fat diet-fed (HFD-fed) mice. Here, we aimed to determine the mechanisms by which PAHSAs improve insulin sensitivity. Both acute and chronic PAHSA treatment enhanced the action of insulin to suppress endogenous glucose production (EGP) in chow- and HFD-fed mice. Moreover, chronic PAHSA treatment augmented insulin-stimulated glucose uptake in glycolytic muscle and heart in HFD-fed mice. The mechanisms by which PAHSAs enhanced hepatic insulin sensitivity included direct and indirect actions involving intertissue communication between adipose tissue and liver. PAHSAs inhibited lipolysis directly in WAT explants and enhanced the action of insulin to suppress lipolysis during the clamp in vivo. Preventing the reduction of free fatty acids during the clamp with Intralipid infusion reduced PAHSAs' effects on EGP in HFD-fed mice but not in chow-fed mice. Direct hepatic actions of PAHSAs may also be important, as PAHSAs inhibited basal and glucagon-stimulated EGP directly in isolated hepatocytes through a cAMP-dependent pathway involving Gαi protein-coupled receptors. Thus, this study advances our understanding of PAHSA biology and the physiologic mechanisms by which PAHSAs exert beneficial metabolic effects.
Topics: Adipose Tissue, White; Animals; Cyclic AMP; Diet, High-Fat; Glucagon; In Vitro Techniques; Insulin Resistance; Lipolysis; Liver; Male; Mice; Mice, Inbred C57BL; Models, Biological; Receptors, G-Protein-Coupled; Signal Transduction; Stearates
PubMed: 31449056
DOI: 10.1172/JCI127092 -
CNS Neuroscience & Therapeutics Jun 2023In recent years, the ability of neural stem cells (NSCs) transplantation to treat Parkinson's disease (PD) has attracted attention. However, it is still a challenge to...
BACKGROUND
In recent years, the ability of neural stem cells (NSCs) transplantation to treat Parkinson's disease (PD) has attracted attention. However, it is still a challenge to promote the migration of NSCs to the lesion site and their directional differentiation into dopaminergic neurons in PD. C-C motif chemokine ligand 5 (CCL5) and C-C motif chemokine receptor 5 (CCR5) are expressed in the brain and are important regulators of cell migration. It has been reported that ethyl stearate (PubChem CID: 8122) has a protective effect in 6-OHDA-induced PD rats.
METHODS
Parkinson's disease rats were injected with 6-hydroxydopamine (6-OHDA) into the right substantia nigra, and striatum followed by 8 μL of an NSC cell suspension containing 100 μM ethyl stearate and 8 × 10 cells in the right striatum. The effect of transplantation NSCs combined with ethyl stearate was assessed by evaluating apomorphine (APO)-induced turning behavior and performance in the pole test. Quantitative real-time reverse transcription-polymerase chain reaction (qRT-PCR), Western blotting (WB), and immunofluorescence staining were also performed.
RESULTS
NSCs transplantation combined with ethyl stearate ameliorated the behavioral deficits of PD rats. PD rats that received transplantation NSCs combined with ethyl stearate exhibited increased expression of tyrosine hydroxylase (TH) and an increased number of green fluorescent protein (GFP)-positive cells. Furthermore, GFP-positive cells migrated into the substantia nigra and differentiated into dopaminergic neurons. The expression of CCL5 and CCR5 was significantly increased after transplantation NSCs combined with ethyl stearate.
CONCLUSIONS
These findings suggest that NSCs transplantation combined with ethyl stearate can improve the motor behavioral performance of PD rats by promoting NSCs migration from the striatum to the substantia nigra via CCL5/CCR5 and promoting the differentiation of NSCs into dopaminergic neurons.
Topics: Rats; Animals; Parkinson Disease; Oxidopamine; Rats, Sprague-Dawley; Neural Stem Cells; Cell Differentiation; Substantia Nigra; Dopaminergic Neurons; Disease Models, Animal
PubMed: 36924304
DOI: 10.1111/cns.14119