Chiral separation of calcium channel antagonists by SFC and HPLC using different immobilized chiral stationary phases

Abstract

Supercritical fluid chromatography and high-performance liquid chromatography techniques are popular for the chiral separations of different drugs and pharmaceuticals. Therefore, this article describes a comparative study of the chiral separation of some calcium channel antagonists such as verapamil, gallopamil, and nisoldipine. The columns used were Chiralpak IG and Chiralpak ID (250 mm  4.6 mm, 5.0 μm). The separation was achieved by using a variety of mobile phases in both techniques. The retention, separation, and resolution factors in SFC were in the range of 1.36-7.30, 1.09-1.72, and 1.16-3.47, while these values in the case of HPLC were 1.03-2.42, 1.12-1.35, and 0.49-2.46. The complete resolution of gallopamil and verapamil was achieved successfully. The chiral recognition was controlled by hydrogen bondings, π-π interactions, dipole induced dipole interactions, van der Waal forces, and steric effects. SFC was found to be a better technique than HPLC because of quick separation, good separation power, economic, environmentfriendly, and green technology.

Recent Advances in Separation and Analysis of Chiral Compounds

“…Polysaccharide derivatives are also promising candidates for HPLC CSPs. − A series of amylose derivatives including amylose tris-[(S)-α-methylbenzylcarbamate], 2,3-bis­(3,5-dimethylphenylcarbamate)-amylose, and amylose tris­(3,5-dimethylphenylcarbamate) were covalently bound on silica particles and further packed into a stainless steel column for HPLC separation of α-lipoic acid/α-dihydrolipoic acid, chiral drugs, and nonsteroidal anti-inflammatory drugs, respectively. − Mixed-mode HPLC shows potential in the separation of complex analytes owing to its multiple separation mechanisms. In this regard, a C18 ionic liquid and cellulose cofunctionalized silica packed column was prepared for mixed-mode (reverse-phase/chiral) HPLC separation of hydrophobic and ionic compounds as well as racemates, including warfarin, 1-phenyl-1-propanol, ketoprofen, and styrene oxide, indicating the great potential of cellulose derivative-based multimode CSPs in chiral separation .…”

Rapid chiral separation of potential antibiotics using supercritical fluid chromatography

“…These chiral columns such as Chiralpak IA and Chiralpak IG are amylose-based chemistry resulting in efficient enantiomeric separation. 7,8 Therefore, some potential antibiotic drugs such as ofloxacin and cefotaxime were selected for the chiral separation using aforesaid chiral stationary phases (CSPs). Ofloxacin belongs to the fluoroquinolones group and is also known as a synthetic anti-microbial agent (Figure 1).…”

“…Among these, polysaccharide‐based immobilized columns are producing remarkable outputs. These chiral columns such as Chiralpak IA and Chiralpak IG are amylose‐based chemistry resulting in efficient enantiomeric separation 7,8 . Therefore, some potential antibiotic drugs such as ofloxacin and cefotaxime were selected for the chiral separation using aforesaid chiral stationary phases (CSPs).…”

Enhancement of separation performance for ofloxacin enantiomers by a biphasic recognition chiral extraction system

“…Diastereoselective crystallization is widely used but tedious and time-consuming. [9][10][11] HPLC and the further developed SMB methods have been shown to be promising and achieved many industrial applications [12][13][14] ; yet, there is still room for improvement due to the expensive equipment and high operational costs. Membrane separation method exhibits excellent separation ability, 15,16 but it is currently only studied in lab-scale applications considering the lower capacity and high-cost issues.…”