betadex and zopiclone

Enantioselective open tubular capillary electrochromatography with carboxymethyl-β-cyclodextrin conjugated gold nanoparticles as stationary phase was developed. This novel open tubular column was fabricated through layer-by-layer self-assembly of gold nanoparticles on a 3-mercaptopropyl-trimethoxysilane-modified fused-silica capillary and subsequent surface functionalization of the gold nanoparticles through self-assembly of 6-mercapto-β-cyclodextrin. The 6-mercapto-β-cyclodextrin was firstly synthesized and determined by extensive spectroscopic data. Scanning electron microscopy, energy dispersive X-ray analysis spectroscopy, and electroosmotic flow experiments were carried out to characterize the prepared open tubular column. Then, the separation effectiveness of the open tubular column was verified by two pairs of ɑ-tetralones derivatives enantiomers and two pairs of basic drug enantiomers (tramadol hydrochloride and zopiclone) as mode analytes. Factors that influence the enantioseparation were optimized, and under the optimized conditions, satisfactory separation results were obtained for the four enantiomers: compound A, compound B, tramadol hydrochloride, and zopiclone with resolutions of 3.79, 1.56, 1.03, 1.60, respectively. For the combination of gold nanoparticles and negatively charged carboxymethyl-β-cyclodextrin, the open tubular column exhibited wider separation range for neutral and basic drugs. Moreover, the repeatability and stability of the column were studied through the run-to-run and day-to-day investigations.

Topics: Azabicyclo Compounds; beta-Cyclodextrins; Capillary Electrochromatography; Gold; Metal Nanoparticles; Molecular Structure; Particle Size; Piperazines; Stereoisomerism; Surface Properties; Tetralones; Tramadol

Inspired by the distinct chemical and physical properties of nanoparticles, here a novel open-tubular capillary electrochromatography column was prepared by electrostatic assembly of poly(diallydimethylammonium chloride) onto the inner surface of a fused-silica capillary, followed by self-adsorption of negatively charged SH-β-cyclodextrin/gold nanoparticles. The formation of the SH-β-cyclodextrin/gold nanoparticles coated capillary was confirmed and characterized by scanning electron microscopy and energy dispersive spectrometry. The results of scanning electron microscopy and energy dispersive spectrometry studies indicated that SH-β-cyclodextrin/gold nanoparticles were successfully coated on the inner wall of the capillary column. The performance of the SH-β-cyclodextrin/gold nanoparticles coated capillary was validated by the analysis of six pairs of chiral drugs, namely zopiclone, carvedilol, salbutamol, terbutaline sulfate, phenoxybenzamine hydrochloride, and ibuprofen. Satisfactory enantioseparation results were achieved, confirming the use of gold nanoparticles as the support could enhance the phase ratio of the open-tubular capillary column. Additionally, the stability and reproducibility of the SH-β-cyclodextrin/gold nanoparticles coated capillary column were also investigated. Then, this proposed method was well validated with good linearity (≥0.999), recovery (90.0-93.5%) and repeatability, and was successfully used for enantioseparation of ibuprofen in spiked plasma samples, which indicated the new column's potential usage in biological analysis.

Topics: Albuterol; Azabicyclo Compounds; beta-Cyclodextrins; Capillary Electrochromatography; Carvedilol; Gold; Ibuprofen; Metal Nanoparticles; Phenoxybenzamine; Piperazines; Stereoisomerism; Terbutaline

The enantioseparation of chiral drugs via CE was first investigated using β-CD as chiral additive and deep eutectic solvents (DESs) as auxiliary additive. The results showed that improved separation of tested chiral drugs was obtained in the presence of DESs and β-CD compared to the single β-CD separation system. With the optimized condition, resolutions of DESs applied β-CD separation system for rac-Zopiclone, rac-Salbutamol, and rac-Amlodipine increased 3-4.2 times as single β-CD separation system. The resolutions reached 4.74, 6.37, and 9.67, respectively. The results demonstrate that DESs are viable additives to CD system in CE for the separation of the chiral drugs.

Topics: Albuterol; Amlodipine; Azabicyclo Compounds; beta-Cyclodextrins; Electrophoresis, Capillary; Piperazines; Solvents; Stereoisomerism

An open-tubular capillary electrochromatography column was prepared by chemically immobilized β-cyclodextrin modified gold nanoparticles onto new surface with the prederivatization of (3-mercaptopropyl)-trimethoxysilane. The synthesized nanoparticles and the prepared column were characterized by transmission electron microscopy, scanning electron microscopy, infrared spectroscopy and ultraviolet visible spectroscopy. When the column was employed as the chiral stationary phase, no enantioselectivity was observed for ten model basic drugs. So β-cyclodextrin was added to the background electrolyte as chiral additive to expect a possible synergistic effect occurring and resulting in a better separation. Fortunately, significant improvement in enantioselectivity was obtained for ten pairs of drug enantiomers. Then, the effects of β-cyclodextrin concentration and background electrolyte pH on the chiral separation were investigated. With the developed separation mode, all the enantiomers (except for venlafaxine) were baseline separated in resolutions of 4.49, 1.68, 1.88, 1.57, 2.52, 2.33, 3.24, 1.63 and 3.90 for zopiclone, chlorphenamine maleate, brompheniramine maleate, dioxopromethazine hydrochloride, carvedilol, homatropine hydrobromide, homatropine methylbromide, venlafaxine, sibutramine hydrochloride and terbutaline sulfate, respectively. Further, the possible separation mechanism involved was discussed.

Topics: Azabicyclo Compounds; beta-Cyclodextrins; Brompheniramine; Capillary Electrochromatography; Carbazoles; Carvedilol; Chemistry Techniques, Analytical; Cyclobutanes; Cyclodextrins; Metal Nanoparticles; Microscopy, Electron, Transmission; Piperazines; Propanolamines; Stereoisomerism; Terbutaline; Tropanes; Venlafaxine Hydrochloride

Enantiomer separation by capillary zone electrophoresis was studied for a set of 34 chiral drugs. Keeping the concentration of beta-cyclodextrin as a chiral solvating agent as constant as possible led to the separation of seven enantiomeric pairs. Carvedilol, Tetryzoline, Tropicamide and Zopiclone gave a baseline separation, Chlorphenamine, Ketamine, and Orciprenaline a partial separation. Statistical analysis revealed that the best separation factors were observed for a medium degree of interaction with the cyclodextrin. A theory explaining this effect provides a helpful guideline for further optimization.

Topics: Azabicyclo Compounds; beta-Cyclodextrins; Carbazoles; Carvedilol; Chemical Phenomena; Chemistry, Physical; Chlorpheniramine; Cyclodextrins; Electrophoresis, Capillary; Imidazoles; Indicators and Reagents; Ketamine; Metaproterenol; Pharmaceutical Preparations; Piperazines; Propanolamines; Stereoisomerism; Tropicamide