Hybrid emulsifier systems: Alkyl imidazolium lactoside surfactants derived from natural resources.

A new series of hybrid surfactants comprising an imidazolium as a cation and a disaccharide as a non-ion were synthesized, and their aggregation behavior was also investigated. The synthetic approach used alkylation as an easily accessible route on an imidazole to attempt an economic production followed by coupling with bromoethyl lactoside to form lacto-imidazolium salts surfactants. The coupled surfactants were obtained in almost quantitative yield over several steps. The surfactant surface properties in aqueous media were investigated, including critical micelle concentration (CMC), Krafft temperature, and emulsion stability were studied. The CMC measurements of the alkyl imidazolium lactoside surfactants are significantly lower than normal imidazolium surfactants, while the emulsion investigations encourage the use of alkyl imidazolium lactoside surfactants owing to stabilized assemble behavior as good as APGs.

Development and Evaluation of Biocompatible Topical Petrolatum-liquid Crystal Formulations with Enhanced Skin Permeation Properties.

Transdermal administration represents a major advancement over traditional pharmaceutical dosing methods. However, a frequent issue is inadequate penetration of the active medicinal component through the skin. As a result, in the current research, we assessed the utility of newly developed petrolatum-liquid crystal (LC) ointment formulations and characterized their biocompatibility and function in the transdermal drug delivery system. To begin, we made petrolatum-LC formulations using p-aminobenzoic acid (PABA) as a hydrophilic model molecule. The viscosity, small-angle X-ray scattering (SAXS), particle diameters, and z-potential were measured to assess the physicochemical properties of the formulations. A dialysis release technique was used to evaluate medication release from petrolatum-LC formulations. In vitro testing was performed to determine the potential to enhance skin penetration. The biocompatibility of the produced formulations was further tested using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) assay and single-cell gel electrophoresis. According to the results, the novel petrolatum-LC formulations are biocompatible and effective in forming hexosomes. PABA skin penetration was significantly enhanced by the new petrolatum-LC formulations. According to this study, petroleum-LC formulations are more efficient than commercial petrolatum in terms of skin permeability improvement and PABA skin concentration.

Inhibition of SARS-CoV-2 reproduction using Boswellia carterii: A theoretical study.

This study investigated the possibility of inhibition of the SARS-CoV-2 virus using the compounds alpha-Boswellic acid (ABA) and beta-Boswellic acid (BBA) which are active components in the well-known natural product Boswellia carterii (BC). The SARS-CoV-2 virus reproduces in the body by linking its spike with the cell receptor. At the same time, a pH range (4.5-6) of the cell's lysosomes is considered as a perfect environment to release RNA in the cell cytoplasm. In view of these, docking studies were employed to study the interaction between the spikes of the virus and ABA or BBA using Molecular Graphic Laboratory (MGL) tools and AutoDock Vina application. The binding of the ABA and BBA with the spike of the virus could inhibit its reproduction or provide sufficient time for the immune system to recognize the virus and hence, produce suitable antibodies. In addition, the pKa of ABA, BBA and hydroxychloroquine (HCQ) were calculated using HF/6-311G (d,p) method and then they were compared with the experimental pKa of HCQ. The Lethal Concentrations (LC50) of ABA and BBA were also calculated. In addition, molecular electrostatic potential is reported which indicates the active sites of ABA and BBA.

Shunting microfluidic PCR device for rapid bacterial detection.

Polymerase chain reaction (PCR) is commonly used for the analysis of nucleic acids in a variety of applications including clinical. There is, however, a need for a low cost portable PCR device that allows rapid identification of pathogenic bacteria. We report a shunting PCR microfluidic device comprising: polycarbonate microfluidic PCR chip; shunting thermal cycler and fluorescence detector. The microfluidic PCR chip - fabricated using micro-milling and thermal fusion bonding for sealing of the cover - was shunted between three double side temperature zones for thermal cycling. Rapid amplification was observed with heating and cooling rates of 1.8 °C/s and 2 °C/s respectively. Lock-in photodetector for fluorescence detection of the microfluidic PCR chip achieved at 95% confidence an LOD of 75pM FITC and 0.7 ng µl-1 of dsDNA using a QuantiFluor assay kit. The device was validated using universal primers - based on chromosomal DNA extracted from non-pathogenic K-12 subtype of Escherichia coli (E. coli) - for amplification of fragments of 250, 552 and 1500 bp. PCR amplification was demonstrated, with annealing temperatures ranging between 54 °C and 68 °C, and confirmed using gel electrophoresis. The developed shunting PCR microfluidic device will allow for low cost and portable nucleic acid amplification for the detection of infectious diseases.

Imidazolium-Linked Azido-Functionalized Guerbet Glycosides: Multifunctional Surfactants for Biofunctionalization of Vesicles.

Aiming for glycolipid-based vesicles for targeted drug delivery, cationic Guerbet glycosides with spacered click functionality were designed and synthesized. The cationic charge promoted the distribution of the glycolipids during the formulation, thereby leading to homogeneously small vesicles. The positive surface charge of the vesicles stabilizes them against unwanted fusion and promotes interactions of the drug carriers with typical negative charge-dominated target cells. High bioconjugation potential of the functionalized glycolipids based on the copper-catalyzed azide alkyne cycloaddition makes them highly valuable components for targeted drug delivery systems.

Functionalized glycolipids for potential bioconjugation of vesicles.

Two azide-terminated oligoethylene oxide spacered glycolipids have been synthesized, and their assembly behavior has been studied in comparison to the corresponding base surfactants. The results suggest potential of the Guerbet lactoside-based compound for targeted drug delivery, while a coiling of the ethylene oxide linker disfavors the application of the glucoside.

Renewable resources-based approach to biantennary glycolipids.

A new synthesis approach towards biantennary lipids of Guerbet glycoside type was developed based on oleic acid as sustainable resource. Functionalization of the double bond provided access to primary alcohols with α-branched C19-skeleton. Formulation studies with corresponding lactosides indicated formation of vesicles with high assembly stability. A relatively narrow bimodal size distribution of the latter, which turns into a narrow unimodal distribution of small vesicles upon addition of an ionic cosurfactant, suggests potential for a vesicular drug delivery system.

Synthesis and biological study of acridine-based imidazolium salts.

A new series of acridine based imidazolium salts was synthesized and evaluated for in vitro cytotoxicity against human cancer cell lines by an MTT assay. The synthesis applied a coupling of imidazoles with 9-chloroacridines, which originated from an Ullmann condensation of a 2-chloro-benzoic acid with an aniline. The target compounds were obtained in high yields. The DPPH assay indicated considerable antioxidant activity for target compounds with simple and short alkyl chains on the imidazole, while increasing chain length and the introduction of an additional π-electron system in most cases reduced the activity. All compounds exhibited low biotoxicity against non-cancerous cell lines, whereas a few compounds showed promising anticancer activity. Unlike for the reference drugs Tamoxifen and Paclitaxel, the anticancer activity of acridine imidazolium ions is specific for only selected cancer types. Reasonable fluorescent behaviour of the products provide potential for visualization of the distribution of active drugs in tissue.

Ulcer Prevention Effect Of 3,4,5-Tihydroxy-N0-[(2-Methyl-1H-Indol-3yl)Methylidene]Benzohydrazide In HCl/Ethanol-Induced Gastric Mucosal Damage In Rats.

The newly synthesized, 3,4,5-Trihydroxy-N 0-[(2-methyl-1H-indol-3-yl)-methylidene] benzohydrazide (TIBH), is an indole and gallic acid derivative. The aim of this research investigation was to evaluate the acute toxicity and the ulcer prevention potential of TIBH in HCl/Ethanol-induced gastric ulcer rat model. Six groups of rats were orally received 5ml/kg of vehicle (1 % Carboxy methyl cellulose) for the normal and ulcer control groups each, Omeprazole (20mg/kg) for positive control, 50 mg/kg, 100 mg/kg and 200 mg/kg of TIBH for experimental groups, respectively. After one hour, instead of rats in the normal group which received 5ml/kg of 1% CMC, other groups received 5ml/kg of HCl/Ethanol. All rats were sacrificed after one additional hour. Gastric juice, gastric mucosa, morphologies of gastric ulcers and protein expressions of both control and treatment groups were evaluated. TIBH showed a ulcer prevention potential by increase of the mucus secretion, decrease of the gastric acidity, up-regulation of HSP70 protein, down-regulation of Bax protein, decrease of the lipid peroxidation and the increase of the Superoxide dismutase (SOD) activity in gastric tissue homogenate. Acute toxicity assay exposed valuable information on the safety of this compound. TIBH had a dose dependent ulcer prevention potential against HCl/Ethanol-triggered gastric ulcer.

Alkyl-imidazolium glycosides: non-ionic-cationic hybrid surfactants from renewable resources.

A series of surfactants combining carbohydrate and imidazolium head groups were prepared and investigated on their assembly behavior. The presence of the imidazolium group dominated the interactions of the surfactants, leading to high CMCs and large molecular surface areas, reflected in curved rather than lamellar surfactant assemblies. The carbohydrate, on the other hand, stabilized molecular assemblies slightly and reduced the surface tension of surfactant solutions considerably. A comparative emulsion study discourages the use of pure alkyl imidazolium glycosides owing to reduced assembly stabilities compared with APGs. However, the surfactants are believed to have potential as component in carbohydrate based surfactant mixtures.

Functional glycolipid-crown-ethers by click chemistry.

A series of glycolipid crown ether analogs was prepared by bis-propargylation of lauryl glycoside followed by subsequent click-coupling with ethylene glycol-based diazides. The triazole-linked macrocycles were obtained in remarkable high yields. While the surfactant assembly was affected by presence of sodium ions, suggesting the formation of complexes, no ion-selectivity was observed for the macrocylic ligands. Computational studies suggest a low but significant cation-binding activity of the macrocycle, involving coordination at both oxygen and nitrogen atoms.

Sterically tuned Ag(I)- and Pd(II)-N-heterocyclic carbene complexes of imidazol-2-ylidenes: synthesis, crystal structures, and in vitro antibacterial and anticancer studies.

Unsymmetrically substituted sterically tuned Pd(II)­NHC complexes of the general formula [PdCl2(NHC)2] (NHC = 1-allyl-3-methylimidazolin-2-ylidene, 7; 1-allyl-3-butylimidazol-2-ylidene, 8; 1-benzyl-3-butyl imidazolin-2-ylidene, 9) were prepared through transmetallation from their corresponding Ag(I)­NHC complexes. The Pd complexes were structurally characterized by different spectroscopic and X-ray diffraction methods. Complexes 7 and 9 adopted a trans­anti arrangement of the NHC ligands, whereas complex 8 adopted a cis­syn arrangement. Preliminary antibiogram studies using Gram-negative (Escherichia coli) and Gram-positive (Staphylococcus aureus) bacteria showed that Ag(I)­NHC complexes demonstrate higher activity compared with Pd(I)­NHC complexes. Furthermore, Pd(II)­NHC complexes were evaluated for their anticancer potential using the human colorectal cancer cell line. A higher anticancer activity was observed for complexes 8 and 9, with 26.5 and 6.6 mM IC50 values, respectively.

3-(3-Cyano-benz-yl)-1-methyl-1H-imidazol-3-ium hexa-fluoro-phosphate.

In the title compound, C(12)H(12)N(3) (+)·PF(6) (-), the hexa-fluoro-phosphate anion is disordered over two orientations with refined site occupancies of 0.8071 (17) and 0.1929 (17). The dihedral angle between the imidazole and benzene rings in the cation is 71.26 (7)°. In the crystal, the cations and anions are linked by C-H⋯F and C-H⋯N hydrogen bonds into a three-dimensional network.

Bis(1-benzyl-3-methyl-imidazolium-κC)mercury(II) bis-(hexa-fluoridophosphate).

The asymmetric unit of the title complex, [Hg(C(11)H(12)N(2))(2)](PF(6))(2), consists of one bis-(1-benzyl-3-methyl-imidazolium)mercury(II) cation, one half of the cation and an additional Hg(II) atom, which lies on an inversion centre, and three hexa-fluorido-phosphate anions. The Hg(II) atoms exist in a linear coordination geometry [C-Hg-C = 178.9 (2) and 180°] formed by two carbene C atoms from the imidazole rings. In the crystal, the cations and anions are connected via C-H⋯F hydrogen bonds, forming a three-dimensional network.

2,4-Bis[(3-butyl-imidazol-3-ium-1-yl)meth-yl]-1,3,5-trimethyl-benzene bis-(hexa-fluoro-phosphate).

In the title molecular salt, C(25)H(38)N(4) (2+)·2PF(6) (-), one of the butyl groups and four F atoms in the basal plane of one of the PF(6) (-) octa-hedra are disordered over two sets of sites, with occupancy ratios of 0.704 (5):0.296 (5) and 0.71 (3):0.29 (3), respectively. The central benzene ring makes dihedral angles of 85.17 (12) and 81.97 (12)° with the terminal imidazole rings. In the crystal, cations and anions are linked together via inter-molecular C-H⋯F hydrogen bonds forming a three-dimensional network.

3,3'-Dibenzyl-1,1'-(2,4,6-trimethyl-m-phenyl-enedimethyl-ene)diimidazol-3-ium dibromide.

In the title molecular salt, C(31)H(34)N(4) (2+)·2Br(-), the central benzene ring makes dihedral angles of 80.47 (12) and 82.78 (12)° with the adjacent imidazole rings. The dihedral angle between the two terminal phenyl rings is 79.16 (13)°. In the crystal, the cations and anions are linked via C-H⋯Br hydrogen bonds, forming supra-molecular chains along the c axis.

Potassium bis-[bis-(1-benzyl-3-methyl-imidazolium)silver(I)] tris-(hexa-fluoridophosphate).

In the title compound, K[Ag(C(11)H(12)N(2))(2)](2)(PF(6))(3), the 12-coordinate potassium cation lies on a crystallographic twofold axis and one of the hexa-fluoro-phosphate anions is generated by symmetry. In the complex cation, the Ag(I) ion is coordinated by two C atoms; the two imidazolium rings are orientated at a dihedral angle of 8.14 (14)°. In the 1-benzyl-3-methyl-imidazolium units, the dihedral angles between imidazolium and phenyl rings are 80.47 (15) and 76.53 (14)°. The F atoms of the general-position hexa-fluoro-phosphate anion are disordered over two sets of sites in a 0.767 (17):0.233 (17) ratio. In the crystal, the hexa-fluoro-phosphate anions link the cations into three-dimensional networks via inter-molecular C-H⋯F hydrogen bonds and are further consolidated by π-π stacking [centroid-centroid distances = 3.5518 (15) Å] inter-actions.