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1.
Soft Matter ; 20(25): 4935-4949, 2024 Jun 26.
Article in English | MEDLINE | ID: mdl-38873752

ABSTRACT

Deformation of the cell membrane is well understood from the viewpoint of protein interactions and free energy balance. However, the various dynamic properties of the membrane, such as lipid packing and hydrophobicity, and their relationship with cell membrane deformation are unknown. Therefore, the deformation of 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) and oleic acid (OA) giant unilamellar vesicles (GUVs) was induced by heating and cooling cycles, and time-lapse analysis was conducted based on the membrane hydrophobicity and physical parameters of "single-parent" and "daughter" vesicles. Fluorescence ratiometric analysis by simultaneous dual-wavelength detection revealed the variation of different hydrophilic GUVs and enabled inferences of the "daughter" vesicle composition and the "parent" membrane's local composition during deformation; the "daughter" vesicle composition of OA was lower than that of the "parents", and lateral movement of OA was the primary contributor to the formation of the "daughter" vesicles. Thus, our findings and the newly developed methodology, named in situ quantitative membrane property-morphology relation (QmPMR) analysis, would provide new insights into cell deformation and accelerate research on both deformation and its related events, such as budding and birthing.


Subject(s)
1,2-Dipalmitoylphosphatidylcholine , Cell Membrane , Hydrophobic and Hydrophilic Interactions , Oleic Acid , Unilamellar Liposomes , Unilamellar Liposomes/chemistry , Unilamellar Liposomes/metabolism , Oleic Acid/chemistry , 1,2-Dipalmitoylphosphatidylcholine/chemistry , Cell Membrane/chemistry
2.
J Oleo Sci ; 73(6): 847-855, 2024.
Article in English | MEDLINE | ID: mdl-38825538

ABSTRACT

Unsaturated fatty acids, such as oleic and linoleic acids, are easily oxidized by exposure to temperature and light in the presence of air to form unsaturated fatty acid hydroperoxides as primary oxidation products. However, the catabolic rates of unsaturated fatty acid hydroperoxides in the human body remain unknown. In this study, ethyl esters of 13C-labeled linoleic acid (*C18:2-EE) and oleic acid (*C18:1-EE) and their hydroperoxides (*C18:2-EE-OOH and *C18:1-EE-OOH, respectively) prepared by the photo-oxidation of *C18:2-EE and *C18:1-EE, respectively, were administered to mice and their catabolic rates were determined by measuring the expired 13CO2 levels. *C18:2-EE-OOH and *C18:1-EE-OOH were ß-oxidized faster than *C18:2-EE and *C18:1-EE, respectively. Notably, rapid ß-oxidation of *C18:2-EE-OOH and *C18:1-EE-OOH was similar to that of medium-chain fatty acids, such as octanoic acid. Then, degradation products of C18:2-EE-OOH and C18:1-EE-OOH were analyzed under gastric conditions by gas chromatography/mass spectrometry. Major decomposition products of C18:2-EE-OOH and C18:1-EE-OOH were medium-chain compounds, such as octanoic acid ethyl ester, 9-oxo-nonanoic acid ethyl ester, and 10-oxo-8-decenoic acid ethyl esters, indicating that C18:2-EE-OOH and C18:1-EE-OOH isomers formed during photo-oxidation were decomposed under acidic conditions. These findings support previous reports that dietary lipid hydroperoxides are not absorbed into the intestine as lipid hydroperoxides but as degradation products. This is the first study to suggest that dietary lipid hydroperoxides decompose during gastric digestion to form medium-chain compounds that are directly absorbed into the liver via the portal vein and rapidly catabolized via ß-oxidation.


Subject(s)
Carbon Dioxide , Carbon Isotopes , Linoleic Acid , Oleic Acid , Oxidation-Reduction , Animals , Oleic Acid/metabolism , Oleic Acid/chemistry , Linoleic Acid/metabolism , Linoleic Acid/chemistry , Carbon Dioxide/metabolism , Carbon Dioxide/chemistry , Mice , Male , Hydrogen Peroxide/metabolism
3.
AAPS PharmSciTech ; 25(6): 144, 2024 Jun 25.
Article in English | MEDLINE | ID: mdl-38918282

ABSTRACT

The current treatment for oral inflammatory ulcerative diseases has limitations. In situ forming hydrogels have shown great potential to deliver therapeutic substances for drug delivery to the buccal cavity. This study aimed to prepare and characterize lipid- and surfactant-based mixed micelle in situ gel (MIG) and evaluate whether it can offer more favorable properties than the in situ gel for effective treatment of the disease. Dexamethasone was incorporated into the MIGs particles, based on Poloxamer 407 and chitosan. The lower gelation time at 37 ℃ was considered a criterion to select superior formulations among the different lipid- and surfactant-based candidates. Further characterization was performed to evaluate the opted formulations regarding morphology, physical stability, rheology, texture, and release profile. All formulations were thermoresponsive and had a shorter gelation time as the temperature increased. Dexamethasone was released in a highly controlled manner, and morphological evaluation revealed that the mixed micelle in situ gels had spherical nanoparticles. Thixotropic behavior was observed in all MIGs, indicating a prolonged retention time of the formulation after oral administration. This study has shown that among different MIGs, the one with oleic acid is a more promising candidate than the in situ gel and other MIGs for drug delivery to the buccal cavity.


Subject(s)
Chitosan , Dexamethasone , Drug Delivery Systems , Drug Liberation , Gels , Micelles , Poloxamer , Dexamethasone/administration & dosage , Dexamethasone/chemistry , Chitosan/chemistry , Gels/chemistry , Drug Delivery Systems/methods , Poloxamer/chemistry , Surface-Active Agents/chemistry , Chemistry, Pharmaceutical/methods , Hydrogels/chemistry , Anti-Inflammatory Agents/administration & dosage , Anti-Inflammatory Agents/chemistry , Nanoparticles/chemistry , Drug Carriers/chemistry , Rheology/methods , Oral Ulcer/drug therapy , Administration, Oral , Lipids/chemistry , Oleic Acid/chemistry
4.
Int J Biol Macromol ; 269(Pt 2): 132136, 2024 Jun.
Article in English | MEDLINE | ID: mdl-38718999

ABSTRACT

In this work, shellac plasticized with oleic acid was solvent cast to prepare the flexible and water-resistant film for packaging applications. The films were prepared with varying amounts of oleic acid and studied in detail for appearance, surface morphology, thermal, chemical, barrier, mechanical, and robustness. The surface morphology confirmed the smooth surface of films up to SH-OA20 (100:20 w/w; shellac: oleic acid). Fourier-transform infrared spectroscopy confirmed that oleic acid reduced the hydrogen bonding of the shellac matrix to provide a plasticization effect. Also, the thermal analysis showed a reduction in the melting enthalpy. Moreover, the plasticized films had a better barrier to water vapor due to increased smoothness and reduction in brittleness. Adding oleic acid also increased the elongation at break up to 40 % without any changes in tensile strength. The flexibility of the films increased with the oleic acid content, making them resistant to burst, crumbling, bending, rolling, and stretching. Oleic acid also showed the retardation of aging and thermal aging of shellac. In the future, the long-term stability and migration of the films can be investigated.


Subject(s)
Oleic Acid , Tensile Strength , Water , Oleic Acid/chemistry , Water/chemistry , Edible Films , Chemical Phenomena , Temperature , Spectroscopy, Fourier Transform Infrared , Steam , Resins, Plant
5.
ACS Nano ; 18(23): 15249-15260, 2024 Jun 11.
Article in English | MEDLINE | ID: mdl-38818704

ABSTRACT

Bimetallic iron-noble metal alloy nanoparticles have emerged as promising contrast agents for magnetic resonance imaging (MRI) due to their biocompatibility and facile control over the element distribution. However, the inherent surface energy discrepancy between iron and noble metal often leads to Fe atom segregation within the nanoparticle, resulting in limited iron-water molecule interactions and, consequently, diminished relaxometric performance. In this study, we present the development of a class of ligand-induced atomically segregation-tunable alloy nanoprobes (STAN) composed of bimetallic iron-gold nanoparticles. By manipulating the oxidation state of Fe on the particle surface through varying molar ratios of oleic acid and oleylamine ligands, we successfully achieve surface Fe enrichment. Under the application of a 9 T MRI system, the optimized STAN formulation, characterized by a surface Fe content of 60.1 at %, exhibits an impressive r1 value of 2.28 mM-1·s-1, along with a low r2/r1 ratio of 6.2. This exceptional performance allows for the clear visualization of hepatic tumors as small as 0.7 mm in diameter in vivo, highlighting the immense potential of STAN as a next-generation contrast agent for highly sensitive MR imaging.


Subject(s)
Alloys , Contrast Media , Gold , Magnetic Resonance Imaging , Metal Nanoparticles , Alloys/chemistry , Ligands , Gold/chemistry , Animals , Contrast Media/chemistry , Metal Nanoparticles/chemistry , Humans , Mice , Iron/chemistry , Surface Properties , Particle Size , Liver Neoplasms/diagnostic imaging , Oleic Acid/chemistry
6.
Int J Pharm ; 659: 124284, 2024 Jun 25.
Article in English | MEDLINE | ID: mdl-38810934

ABSTRACT

The study aimed to create a low loading, high retention, easier to apply O/W mometasone furoate (MF) cream using a chemical enhancer (CE) approach to provide more options for patients with atopic dermatitis (AD) and to investigate molecular mechanisms of its increased release and retention. A Box-Behnken design determined the optimal formulation based on stability and in vitro skin retention. Evaluations included appearance, rheological properties, irritation, in vivo tissue distribution and pharmacodynamics. Molecular mechanisms of enhanced release were studied using high-speed centrifugation, molecular dynamics and rheology. The interaction between the CE, MF and skin was studied by tape stripping, CLSM, ATR-FTIR and SAXS. The formulation was optimized to contain 0.05% MF and used 10% polyglyceryl-3 oleate (POCC) as the CE. There was no significant difference from Elocon® cream in in vivo retention and pharmacodynamics but increased in vivo retention by 3.14-fold and in vitro release by 1.77-fold compared to the basic formulation. POCC reduced oil phase cohesive energy density, enhancing drug mobility and release. It disrupted skin lipid phases, aiding drug entry and formed hydrogen bonds, prolonging retention. This study highlights POCC as a CE in the cream, offering insights for semi-solid formulation development.


Subject(s)
Drug Liberation , Mometasone Furoate , Skin Cream , Skin , Mometasone Furoate/administration & dosage , Mometasone Furoate/pharmacokinetics , Mometasone Furoate/chemistry , Animals , Skin Cream/administration & dosage , Skin Cream/chemistry , Skin/metabolism , Skin/drug effects , Administration, Cutaneous , Male , Skin Absorption/drug effects , Chemistry, Pharmaceutical/methods , Glycerol/chemistry , Glycerol/analogs & derivatives , Dermatitis, Atopic/drug therapy , Female , Excipients/chemistry , Anti-Inflammatory Agents/administration & dosage , Anti-Inflammatory Agents/chemistry , Anti-Inflammatory Agents/pharmacology , Anti-Inflammatory Agents/pharmacokinetics , Drug Compounding/methods , Oleic Acid/chemistry , Polymers/chemistry
7.
Chem Res Toxicol ; 37(6): 968-980, 2024 Jun 17.
Article in English | MEDLINE | ID: mdl-38743843

ABSTRACT

The widespread use of silver nanoparticles (AgNPs) in various applications and industries has brought to light the need for understanding the complex relationship between the physicochemical properties (shape, size, charge, and surface chemistry) of AgNPs that affect their ability to enter cells and cause toxicity. To evaluate their toxicological outcomes, this study systematically analyzed a series of homogeneous hybrid lipid-coated AgNPs spanning sizes from 5 to 100 nm with diverse shapes (spheres, triangles, and cubes). The hybrid lipid membrane comprises hydrogenated phosphatidylcholine (HPC), sodium oleate (SOA), and hexanethiol (HT), which shield the AgNP surface from surface oxidation and toxic Ag+ ion release to minimize its contribution to toxicity. To reduce any significant effects by surface chemistry, the HPC, SOA, and HT membrane composition ratio was kept constant, and the AgNPs were assessed using embryonic zebrafish (Danio rerio). While a direct comparison cannot be drawn due to the lack of complementary sizes below 40 nm for triangular plates and cubes due to synthetic challenges, significant mortality was observed for spherical AgNPs (AgNSs) of 5, 20, 40, and 60 nm at 120 h postfertilization at concentrations ≥6 mg Ag/L. In contrast, the 10, 80, and 100 nm AgNSs, 40, 70, and 100 nm triangular plate AgNPs (AgNPLs), and 55, 75, and 100 nm cubic AgNPs (AgNCs) showed no significant mortality at 5 days postfertilization following exposure to AgNPs at concentrations up to 12 mg Ag/L. With constant surface chemistry on the AgNPs, size is the dominant factor driving toxicological responses, with smaller nanoparticles (5 to 60 nm) being the most toxic. Larger AgNSs, AgNCs, and AgNPLs from 75 to 100 nm do not show any evidence of toxicity. However, when closely examining sizes between 40 and 60 nm for AgNSs, AgNCs, and AgNPLs, there is evidence that discriminates shape as a driver of toxicity since sublethal responses generally were observed to follow a pattern, suggesting toxicity is most significant for AgNSs followed by AgNPLs and then AgNCs, which is the least toxic. Sum frequency generation vibrational spectroscopy showed that irrespective of size or shape, all hybrid lipid-coated AgNPs interact with membrane surfaces and "snorkel" between phases into the lipid monolayer with minimal energetic cost. These findings decisively demonstrate that not only smaller AgNPs but also the shape of the AgNPs influences their biological compatibility.


Subject(s)
Cell Membrane , Metal Nanoparticles , Particle Size , Silver , Zebrafish , Silver/chemistry , Metal Nanoparticles/chemistry , Metal Nanoparticles/toxicity , Animals , Cell Membrane/drug effects , Cell Membrane/chemistry , Surface Properties , Oleic Acid/chemistry , Phosphatidylcholines/chemistry , Lipids/chemistry
8.
J Mater Chem B ; 12(22): 5479-5495, 2024 Jun 05.
Article in English | MEDLINE | ID: mdl-38742683

ABSTRACT

The non-invasive nature and potential for sustained release make transdermal drug administration an appealing treatment option for cancer therapy. However, the strong barrier of the stratum corneum (SC) poses a challenge for the penetration of hydrophilic chemotherapy drugs such as 5-fluorouracil (5-FU). Due to its biocompatibility and capacity to increase drug solubility and permeability, especially when paired with chemical enhancers, such as oleic acid (OA), which is used in this work, choline glycinate ([Cho][Gly]) has emerged as a potential substance for transdermal drug delivery. In this work, we examined the possibility of transdermal delivery of 5-FU for the treatment of breast cancer using an ionic hydrogel formulation consisting of [Cho][Gly] with OA. Small angle neutron scattering, rheological analysis, field emission scanning electron microscopy, and dynamic light scattering analysis were used to characterize the ionic hydrogel. The non-covalent interactions present between [Cho][Gly] and OA were investigated by computational simulations and FTIR spectroscopy methods. When subjected to in vitro drug permeation using goat skin in a Franz diffusion cell, the hydrogel demonstrated sustained release of 5-FU and effective permeability in the order: [Cho][Gly]-OA gel > [Cho][Gly] > PBS (control). The hydrogel also demonstrated 92% cell viability after 48 hours for the human keratinocyte cell line (HaCaT cells) as well as the normal human cell line L-132. The breast cancer cell line MCF-7 and the cervical cancer cell line HeLa were used to study in vitro cytotoxicity that was considerably affected by the 5-FU-loaded hydrogel. These results indicate the potential of the hydrogel as a transdermal drug delivery vehicle for the treatment of breast cancer.


Subject(s)
Administration, Cutaneous , Fluorouracil , Hydrogels , Hydrogels/chemistry , Humans , Fluorouracil/chemistry , Fluorouracil/pharmacology , Fluorouracil/administration & dosage , Animals , Drug Delivery Systems , Cell Survival/drug effects , Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Antineoplastic Agents/administration & dosage , Goats , Drug Liberation , Skin Absorption/drug effects , Oleic Acid/chemistry , Skin/metabolism , Choline/chemistry , Glycine/chemistry , Glycine/administration & dosage , Adhesives/chemistry , Drug Carriers/chemistry
9.
Molecules ; 29(9)2024 May 01.
Article in English | MEDLINE | ID: mdl-38731587

ABSTRACT

We aimed to obtain the optimal formula for human milk fat substitute (HMFS) through a combination of software and an evaluation model and further verify its practicability through an animal experiment. The results showed that a total of 33 fatty acid (FA) and 63 triglyceride (TAG) molecular species were detected in vegetable oils. Palmitic acid, oleic acid, linoleic acid, 18:1/16:0/18:1, 18:2/16:0/18:2, 18:1/18:1/18:1 and 18:1/18:2/18:1, were the main molecular species among the FAs and TAGs in the vegetable oils. Based on the HMFS evaluation model, the optimal mixed vegetable oil formula was blended with 21.3% palm oil, 2.8% linseed oil, 2.6% soybean oil, 29.9% rapeseed oil and 43.4% maize oil, with the highest score of 83.146. Moreover, there was no difference in the weight, blood routine indices or calcium and magnesium concentrations in the feces of the mice between the homemade mixed vegetable oil (HMVO) group and the commercial mixed vegetable oil (CMVO) group, while nervonic acid (C24:1) and octanoic acid (C8:0) were absorbed easily in the HMVO group. Therefore, these results demonstrate that the mixing of the different vegetable oils was feasible via a combination of computer software and an evaluation model and provided a new way to produce HMFS.


Subject(s)
Fat Substitutes , Fatty Acids , Milk, Human , Plant Oils , Software , Triglycerides , Humans , Animals , Plant Oils/chemistry , Fatty Acids/chemistry , Milk, Human/chemistry , Mice , Triglycerides/chemistry , Fat Substitutes/chemistry , Palm Oil/chemistry , Soybean Oil/chemistry , Linseed Oil/chemistry , Rapeseed Oil/chemistry , Corn Oil/chemistry , Caprylates/chemistry , Palmitic Acid/chemistry , Oleic Acid/chemistry
10.
Carbohydr Polym ; 337: 122187, 2024 Aug 01.
Article in English | MEDLINE | ID: mdl-38710543

ABSTRACT

The effects of different electron beam irradiation doses (2, 4, 8 KGy) and various types of fatty acids (lauric acid, stearic acid, and oleic acid) on the formation, structure, physicochemical properties, and digestibility of starch-lipid complex were investigated. The complexing index of the complexes was higher than 85 %, indicating that the three fatty acids could easily form complexes with starch. With the increase of electron beam irradiation dose, the complexing index increased first and then decreased. The highest complexing index was lauric acid (97.12 %), stearic acid (96.80 %), and oleic acid (97.51 %) at 2 KGy radiation dose, respectively. Moreover, the microstructure, crystal structure, thermal stability, rheological properties, and starch solubility were analyzed. In vitro digestibility tests showed that adding fatty acids could reduce the content of hydrolyzed starch, among which the resistant starch content of the starch-oleic acid complex was the highest (54.26 %). The lower dose of electron beam irradiation could decrease the digestibility of starch and increase the content of resistant starch.


Subject(s)
Electrons , Fatty Acids , Solubility , Starch , Starch/chemistry , Fatty Acids/chemistry , Lauric Acids/chemistry , Rheology , Hydrolysis , Oleic Acid/chemistry , Lipids/chemistry
11.
Food Res Int ; 186: 114355, 2024 Jun.
Article in English | MEDLINE | ID: mdl-38729701

ABSTRACT

In this study, five C18 fatty acids (FA) with different numbers of double bonds and configurations including stearic acid (SA), oleic acid (OA), elaidic acid (EA), linoleic acid (LA), and α-linolenic acid (ALA), were selected to prepare highland barely starch (HBS)-FA complexes to modulate digestibility and elaborate the underlying mechanism. The results showed that HBS-SA had the highest complex index (34.18 %), relative crystallinity (17.62 %) and single helix content (25.78 %). Furthermore, the HBS-C18 FA complexes were formed by EA (C18 FA with monounsaturated bonds) that had the highest R1047/1022 (1.0509) and lowest full width at half-maximum (FWHM, 20.85), suggesting good short-range ordered structure. Moreover, all C18 FAs could form two kinds of V-type complexes with HBS, which can be confirmed by the results of CLSM and DSC measurements, and all of them showed significantly lower digestibility. HBS-EA possessed the highest resistant starch content (20.17 %), while HBS-SA had the highest slowly digestible starch content (26.61 %). In addition, the inhibition of HBS retrogradation by fatty acid addition was further proven, where HBS-SA gel firmness (37.80 g) and aging enthalpy value were the lowest, indicating the most effective. Overall, compounding with fatty acids, especially SA, could be used as a novel way to make functional foods based on HBS.


Subject(s)
Digestion , Fatty Acids , Hordeum , Oleic Acid , Starch , Starch/chemistry , Fatty Acids/analysis , Fatty Acids/chemistry , Hordeum/chemistry , Oleic Acid/chemistry , Stearic Acids/chemistry , Linoleic Acid/chemistry , alpha-Linolenic Acid/chemistry , Oleic Acids
12.
ACS Appl Mater Interfaces ; 16(21): 27087-27101, 2024 May 29.
Article in English | MEDLINE | ID: mdl-38752799

ABSTRACT

An ideal vehicle with a high transfection efficiency is crucial for gene delivery. In this study, a type of cationic carbon dot (CCD) known as APCDs were first prepared with arginine (Arg) and pentaethylenehexamine (PEHA) as precursors and conjugated with oleic acid (OA) for gene delivery. By tuning the mass ratio of APCDs to OA, APCDs-OA conjugates, namely, APCDs-0.5OA, APCDs-1.0OA, and APCDs-1.5OA were synthesized. All three amphiphilic APCDs-OA conjugates show high affinity to DNA through electrostatic interactions. APCDs-0.5OA exhibit strong binding with small interfering RNA (siRNA). After being internalized by Human Embryonic Kidney (HEK 293) and osteosarcoma (U2OS) cells, they could distribute in both the cytoplasm and the nucleus. With APCDs-OA conjugates as gene delivery vehicles, plasmid DNA (pDNA) that encodes the gene for the green fluorescence protein (GFP) can be successfully delivered in both HEK 293 and U2OS cells. The GFP expression levels mediated by APCDs-0.5OA and APCDs-1.0OA are ten times greater than that of PEI in HEK 293 cells. Furthermore, APCDs-0.5OA show prominent siRNA transfection efficiency, which is proven by the significantly downregulated expression of FANCA and FANCD2 proteins upon delivery of FANCA siRNA and FANCD2 siRNA into U2OS cells. In conclusion, our work demonstrates that conjugation of CCDs with a lipid structure such as OA significantly improves the gene transfection efficiency, providing a new idea about the designation of nonviral carriers in gene delivery systems.


Subject(s)
Carbon , RNA, Small Interfering , Transfection , Humans , HEK293 Cells , Carbon/chemistry , Transfection/methods , RNA, Small Interfering/chemistry , RNA, Small Interfering/metabolism , Lipids/chemistry , Cations/chemistry , DNA/chemistry , Quantum Dots/chemistry , Gene Transfer Techniques , Oleic Acid/chemistry , Green Fluorescent Proteins/metabolism , Green Fluorescent Proteins/genetics , Cell Line, Tumor
13.
Pak J Pharm Sci ; 37(1): 43-52, 2024 Jan.
Article in English | MEDLINE | ID: mdl-38741399

ABSTRACT

Drug-resistant malaria is a global risk to the modern world. Artremisinin (ART) is one of the drugs of choice against drug-resistant (malaria) which is practically insoluble in water. The objective of our study was to improve the solubility of artemisinin (ART) via development of binary complexes of ART with sulfobutylether ß-cyclodextrins (SBE7 ß-CD), sulfobutylether ß-cyclodextrins (SBE7 ß-CD) and oleic acid (ternary complexes). These are prepared in various drugs to excipients ratios by physical mixing (PM) and solvent evaporation (SE) methods. Characterizations were achieved by powder X-ray diffraction (PXRD), scanning electron microscopy (SEM) and attenuated total reflectance Fourier Transform Infrared (ATR-FTIR) spectroscopy. The aqueous-solubility in binary complexes was 12-folds enhanced than ternary complexes. Dissolution of binary and ternary complexes of artemisinin in simulated gastric fluid (pH 1.6) was found highest and 35 times higher for ternary SECx. The crystallinity of artemisinin was decreased in physical mixtures (PMs) while SECx exhibited displaced angles. The attenuated-intensity of SECx showed least peak numbers with more displaced-angles. SEM images of PMs and SECx showed reduced particle size in binary and ternary systems as compared to pure drug-particles. ATR-FTIR spectra of binary and ternary complexes revealed bonding interactions among artemisinin, SBE7 ß-CD and oleic acid.


Subject(s)
Artemisinins , Oleic Acid , Solubility , X-Ray Diffraction , beta-Cyclodextrins , beta-Cyclodextrins/chemistry , Artemisinins/chemistry , Oleic Acid/chemistry , Spectroscopy, Fourier Transform Infrared , Microscopy, Electron, Scanning , Antimalarials/chemistry , Excipients/chemistry , Drug Compounding
14.
Molecules ; 29(8)2024 Apr 12.
Article in English | MEDLINE | ID: mdl-38675571

ABSTRACT

Phyllanthus emblica is a natural medicinal herb with diverse bioactivities. Certain extracts from this herb have been confirmed to possess anti-glycolipid metabolic disorder activity. To further develop its utility value and explore its potential in combating glycolipid metabolic disorders, we designed a series of experiments to investigate the structure, antioxidant activity, and anti-glycolipid metabolic disorder activity of Phyllanthus emblica polysaccharides. In this study, we extracted and purified polysaccharides from Phyllanthus emblica and thoroughly analyzed their structure using various techniques, including NMR, methylation analysis, and surface-enhanced Raman spectroscopy. We investigated the hypolipidemic and anti-glycolipid metabolism disorder activity of Phyllanthus emblica polysaccharides for the first time utilizing oleic acid (OA) and advanced glycation end products (AGEs) as inducers. Additionally, the antioxidant activity of Phyllanthus emblica polysaccharides was assessed in vitro. These findings lay the groundwork for future investigations into the potential application of Phyllanthus emblica polysaccharides as an intervention for preventing and treating diabetes.


Subject(s)
Antioxidants , Phyllanthus emblica , Polysaccharides , Phyllanthus emblica/chemistry , Polysaccharides/pharmacology , Polysaccharides/chemistry , Polysaccharides/isolation & purification , Antioxidants/pharmacology , Antioxidants/chemistry , Antioxidants/isolation & purification , Glycolipids/chemistry , Glycolipids/pharmacology , Glycolipids/isolation & purification , Glycation End Products, Advanced/metabolism , Plant Extracts/pharmacology , Plant Extracts/chemistry , Animals , Oleic Acid/chemistry , Oleic Acid/pharmacology , Humans
15.
Int J Pharm ; 658: 124176, 2024 Jun 10.
Article in English | MEDLINE | ID: mdl-38688427

ABSTRACT

The aim of this study was to evaluate the enhanced thermal stability and physicochemical properties of fattigated vaccine antigens. High molecular weight influenza hemagglutinin (Heg) was used as a model antigen because of low heat stability requiring cold chamber. Heg was conjugated with long-chain oleic acid (C18) and short-chain 3-decenoic acid (C10) to prepare fattigated Heg. Circular dichroism analysis revealed no significant changes in the three-dimensional structure post-conjugation. In the liquid state, the fattigated Heg was self-assembled into nanoparticles (NPs) due to its amphiphilic nature, with sizes of 136.27 ± 12.78 nm for oleic acid-conjugated Heg (HOC) and 88.73 ± 3.27 nm for 3-decenoic acid-conjugated Heg (HDC). Accelerated thermal stability studies at 60 °C for 7 days demonstrated that fattigated Heg exhibited higher thermal stability than Heg in various liquid or solid states. The longer-chained HOC showed better thermal stability than HDC in the liquid state, attributed to increased hydrophobic interactions during self-assembly. In bio-mimicking liquid states at 37 °C, HOC exhibited higher thermal stability than Heg. Furthermore, solid-state HOC with cryoprotectants (trehalose, mannitol, and Tween® 80) had significantly increased thermal stability due to reduced exposure of protein surface area via nanonization behavior. The current fattigation platform could be a promising strategy for developing thermostable nano vaccines of heat-labile vaccine antigens.


Subject(s)
Drug Stability , Hemagglutinin Glycoproteins, Influenza Virus , Nanoparticles , Nanoparticles/chemistry , Hemagglutinin Glycoproteins, Influenza Virus/chemistry , Hemagglutinin Glycoproteins, Influenza Virus/immunology , Influenza Vaccines/chemistry , Influenza Vaccines/administration & dosage , Oleic Acid/chemistry , Vaccines, Conjugate/chemistry , Fatty Acids/chemistry , Hot Temperature , Particle Size , Polysorbates/chemistry , Hydrophobic and Hydrophilic Interactions , Fatty Acids, Monounsaturated/chemistry , Antigens/chemistry , Antigens/immunology
16.
Biomater Adv ; 160: 213865, 2024 Jun.
Article in English | MEDLINE | ID: mdl-38643693

ABSTRACT

Microneedle technology offers a minimally invasive treatment strategy to deliver chemotherapeutics to localized tumors. Amalgamating the surface functionalized nanoparticles with microneedle technology can potentially deliver drugs directly to tumors and subsequently target cancer cells via, overexpressed receptors on the cell surface, thereby enhancing the treatment efficacy while reducing side effects. Here, we report cetuximab anchored hyaluronic acid-oleylamine and chitosan-oleic acid-based hybrid nanoparticle (HA-OA/CS-OA NPT)-loaded dissolving microneedles (MN) for targeted delivery of cabazitaxel (CBT) in localized breast cancer tumor. The HA-OA/CS-OA NPT was characterized for their size, surface charge, morphology, physicochemical characteristics, drug release behavior, and in vitro anti-cancer efficacy. The HA-OA/CS-OA NPT were of ~125 nm size, showed enhanced cytotoxicity and cellular uptake, and elicited a superior apoptotic response against MDA-MB-231 cells. Subsequently, the morphology and physicochemical characteristics of HA-OA/CS-OA NPT-loaded MN were also evaluated. The fabricated microneedles were of ~550 µm height and showed loading of nanoparticles equivalent to ~250 µg of CBT. The ex vivo skin permeation study revealed fast dissolution of microneedles upon hydration, while the drug permeation across the skin exhibited ~4-fold improvement in comparison to free drug-loaded MN. In vivo studies performed on DMBA-induced breast cancer in female SD rats showed a marked reduction in tumor volume after administration of drug and nanoparticle-loaded microneedles in comparison to intravenous administration of free drug. However, the HA-OA/CS-OA NPT-MN showed the highest tumor reduction and survival rate, with the lowest body weight reduction in comparison to other treatment groups, indicating its superior efficacy and low systemic toxicity. Overall, the dissolving microneedle-mediated delivery of targeted nanoparticles loaded with chemotherapeutics offers a superior alternative to conventional intravenous chemotherapy.


Subject(s)
Breast Neoplasms , Chitosan , Hyaluronic Acid , Nanoparticles , Needles , Oleic Acid , Hyaluronic Acid/chemistry , Animals , Chitosan/chemistry , Female , Humans , Breast Neoplasms/drug therapy , Breast Neoplasms/pathology , Oleic Acid/chemistry , Cell Line, Tumor , Nanoparticles/chemistry , Nanoparticles/administration & dosage , Rats , Drug Delivery Systems/methods , Antineoplastic Agents/administration & dosage , Antineoplastic Agents/pharmacology , Antineoplastic Agents/pharmacokinetics , Rats, Sprague-Dawley , Drug Liberation
17.
Int J Biol Macromol ; 268(Pt 1): 131672, 2024 May.
Article in English | MEDLINE | ID: mdl-38643912

ABSTRACT

The packaging industry has primarily been dominated by single-use, petrochemical-sourced plastic materials despite their short-term use. Their leakage into the ecosystem after their use poses substantial environmental concerns. As a result, compostable and renewable packaging material alternatives are garnering significant attention. Cellulose acetate is a derivative of cellulose that exhibits excellent tensile properties, transparency, melt processability, and intermediate compostability. However, its application in the food packaging industry is limited due to its hygroscopic behavior and lack of dimensional stability. This study investigated using lignin (pristine and esterified) as a functional additive of cellulose acetate. The effect of varying concentrations of pristine kraft and oleic acid functionalized lignin in the cellulose acetate matrix and its effect on the resulting film's mechanical, morphological, viscoelastic, and water barrier properties were explored. Comprehensive characterization of the thermomechanical processed lignin-cellulose acetate sheets revealed reduced moisture absorption, improved UV and moisture barrier, and enhanced tensile properties with melt processability. Overall, the studied films could have appealing properties for food and other packaging applications, thus, serving as eco-friendly and sustainable alternatives to conventional petroleum-derived packing materials.


Subject(s)
Cellulose , Hydrophobic and Hydrophilic Interactions , Lignin , Oleic Acid , Tensile Strength , Lignin/chemistry , Lignin/analogs & derivatives , Cellulose/chemistry , Cellulose/analogs & derivatives , Oleic Acid/chemistry , Food Packaging/methods , Water/chemistry
18.
J Food Sci ; 89(5): 2857-2866, 2024 May.
Article in English | MEDLINE | ID: mdl-38532702

ABSTRACT

The separation sheets for fruit leather are traditionally made of plastic film or wax paper, which not only leads to environmental issues but also is inconvenience to consumers. This study evaluated edible fruit leather separation sheets using food polymers, including hydroxypropyl methyl cellulose (HPMC) and incorporation of cranberry pomace water extract (CPE) for providing natural fruit pigment, flavor, and phenolics. HPMCCPE film was then further improved by incorporating hydrophobic compound (oleic acid, OA) and vitamin E (VE) via cellulose nanocrystal (CNC) Pickering emulsion (CNCP) for enhancing film hydrophobicity and nutritional benefit, respectively. The CNCP-HPMCCPE film exhibited reduced water vapor permeability (∼0.033 g mm/m2 d Pa) compared to HPMCCPE film (∼0.59 g mm/m2 d Pa) and had the least change in mass and moisture content when wrapping fruit leather for up to 2 weeks of ambient storage. The fruit leather wrapped by CNCP-HPMCCPE film showed lower weight change than those by films without CNCP due to low mass transfer between film and fruit leather. CNCP resulted in controlled release of VE into a food simulating solvent (ethanol). The developed colorful and edible fruit leather separation sheet satisfied the increased market demands on sustainable food packaging. PRACTICAL APPLICATION: Colorful and flavorful edible films made of edible polymers, fruit pomace water extract, and emulsified hydrophobic compounds with vitamin E were created. The films have the satisfactory performance to replace the conventional fruit leather separation sheet made of plastic or wax paper. The edible films can be eaten with packaged fruit leather for not only reducing packaging waste but also providing convenience and nutritional benefit to consumers. These functional edible films may also be utilized to package other food products for promoting packaging sustainability and nutritional benefit.


Subject(s)
Edible Films , Food Packaging , Fruit , Plant Extracts , Vaccinium macrocarpon , Vitamin E , Vaccinium macrocarpon/chemistry , Vitamin E/analysis , Plant Extracts/chemistry , Fruit/chemistry , Food Packaging/methods , Hydrophobic and Hydrophilic Interactions , Permeability , Hypromellose Derivatives/chemistry , Food, Fortified/analysis , Oleic Acid/analysis , Oleic Acid/chemistry
19.
Food Chem ; 448: 139079, 2024 Aug 01.
Article in English | MEDLINE | ID: mdl-38520989

ABSTRACT

Esterification of anthocyanins with saturated fatty acids have been widely investigated, while that with unsaturated fatty acids is little understood. In this study, crude extract (purity âˆ¼ 35 %) of cyanidin-3-O-glucoside (C3G) from black bean seed coat was utilized as reaction substrate, and enzymatically acylated with unsaturated fatty acid (oleic acid). Optimization of various reaction parameters finally resulted in the highest acylation rate of 54.3 %. HPLC-MS/MS and NMR analyses elucidated the structure of cyanidin-3-O-glucoside-oleic acid ester (C3G-OA) to be cyanidin-3-O-(6″-octadecene)-glucoside. Introduction of oleic acid into C3G improved the lipophilicity, antioxidant ability, and antibacterial activity. Further, the color and substance stability analyses showed that the susceptibility of C3G and C3G-OA to different thermal, peroxidative, and illuminant treatments were highly pH dependent, which suggested individual application guidelines. Moreover, C3G-OA showed lower toxicity to normal cell (QSG-7701) and better inhibitory effect on the proliferation of HepG2 cells than C3G, which indicated its potential anti-tumor bioactivity.


Subject(s)
Anthocyanins , Oleic Acid , Anthocyanins/chemistry , Humans , Oleic Acid/chemistry , Esterification , Plant Extracts/chemistry , Antioxidants/chemistry , Antioxidants/pharmacology , Hep G2 Cells , Phaseolus/chemistry , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Molecular Structure
20.
Small ; 20(25): e2309919, 2024 Jun.
Article in English | MEDLINE | ID: mdl-38377304

ABSTRACT

Despite gold-based nanomaterials having a unique role in nanomedicine, among other fields, synthesis limitations relating to reaction scale-up and control result in prohibitively high gold nanoparticle costs. In this work, a new preparation procedure for lipid bilayer-coated gold nanoparticles in water is presented, using sodium oleate as reductant and capping agent. The seed-free synthesis not only allows for size precision (8-30 nm) but also remarkable particle concentration (10 mm Au). These reaction efficiencies allow for multiplexing and reaction standardization in 96-well plates using conventional thermocyclers, in addition to simple particle purification via microcentrifugation. Such a multiplexing approach also enables detailed spectroscopic investigation of the nonlinear growth process and dynamic sodium oleate/oleic acid self-assembly. In addition to scalability (at gram-level), resulting gold nanoparticles are stable at physiological pH, in common cell culture media, and are autoclavable. To demonstrate the versatility and applicability of the reported method, a robust ligand exchange with thiolated polyethylene glycol analogues is also presented.


Subject(s)
Gold , Metal Nanoparticles , Oleic Acid , Gold/chemistry , Metal Nanoparticles/chemistry , Oleic Acid/chemistry , Water/chemistry , Lipid Bilayers/chemistry
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