Cellulose tris-(3,5-dimethylphenylcarbamate)-based chiral stationary phase for the enantioseparation of drugs in supercritical fluid chromatography: comparison with HPLC.

A cellulose tris-(3,5-dimethylphenylcarbamate)-based chiral stationary phase was studied as a tool for the enantioselective separation of 21 selected analytes with different pharmaceutical and physicochemical properties. The enantioseparations were performed using supercritical fluid chromatography. The effect of the mobile phase composition was studied. Four different additives (diethylamine, triethylamine, isopropylamine, and trifluoroacetic acid) and isopropylamine combined with trifluoroacetic acid were tested and their influence on enantioseparation was compared. The influence of two different mobile phase co-solvents (methanol and propan-2-ol) combined with all the additives was also evaluated. The best mobile phase compositions for the separation of the majority of enantiomers were CO2 /methanol/isopropylamine 80:20:0.1 v/v/v or CO2 /propan-2-ol/isopropylamine/trifluoroacetic acid 80:20:0.05:0.05 v/v/v/v. The best results were obtained from the group of basic β-blockers. A high-performance liquid chromatography separation system composed of the same stationary phase and mobile phase of similar properties prepared as a mixture of hexane/propan-2-ol/additive 80:20:0.1 v/v/v was considered for comparison. Supercritical fluid chromatography was found to yield better results, i.e. better enantioresolution for shorter analysis times than high-performance liquid chromatography. However, examples of enantiomers better resolved under the optimized conditions in high-performance liquid chromatography were also found.

[1]  Christopher J. Welch,et al.  Current challenges and future prospects in chromatographic method development for pharmaceutical research , 2017 .

[2]  M. Kohout,et al.  Consequences of transition from liquid chromatography to supercritical fluid chromatography on the overall performance of a chiral zwitterionic ion-exchanger. , 2017, Journal of chromatography. A.

[3]  L. Nováková,et al.  General screening and optimization strategy for fast chiral separations in modern supercritical fluid chromatography. , 2017, Analytica chimica acta.

[4]  M. Kohout,et al.  Enantioseparation of Chiral Sulfoxides on Amylose-Based Columns: Comparison of Normal Phase Liquid Chromatography and Supercritical Fluid Chromatography , 2017, Chromatographia.

[5]  E. Tesařová,et al.  Enantioselective potential of polysaccharide-based chiral stationary phases in supercritical fluid chromatography. , 2017, Chirality.

[6]  Jun Fan,et al.  Triticonazole enantiomers: Separation by supercritical fluid chromatography and the effect of the chromatographic conditions. , 2016, Journal of separation science.

[7]  E. Francotte,et al.  Comparison of liquid and supercritical fluid chromatography mobile phases for enantioselective separations on polysaccharide stationary phases. , 2016, Journal of chromatography. A.

[8]  E. Tesařová,et al.  Enantioselective separation of biologically active basic compounds in ultra-performance supercritical fluid chromatography. , 2016, Analytica chimica acta.

[9]  Y. Heyden,et al.  Chiral separations of cathinone and amphetamine-derivatives: Comparative study between capillary electrochromatography, supercritical fluid chromatography and three liquid chromatographic modes. , 2016, Journal of pharmaceutical and biomedical analysis.

[10]  Caroline West,et al.  Use and practice of achiral and chiral supercritical fluid chromatography in pharmaceutical analysis and purification. , 2016, Journal of separation science.

[11]  C. Welch,et al.  Pushing the speed limit in enantioselective supercritical fluid chromatography. , 2015, Journal of separation science.

[12]  E. Tesařová,et al.  Evaluation of differences between Chiralpak IA and Chiralpak AD-RH amylose-based chiral stationary phases in reversed-phase high-performance liquid chromatography. , 2015, Journal of separation science.

[13]  Caroline West,et al.  The many faces of packed column supercritical fluid chromatography--a critical review. , 2015, Journal of chromatography. A.

[14]  C. West,et al.  Insights into chiral recognition mechanisms in supercritical fluid chromatography V. Effect of the nature and proportion of alcohol mobile phase modifier with amylose and cellulose tris-(3,5-dimethylphenylcarbamate) stationary phases. , 2014, Journal of chromatography. A.

[15]  Eva Tesařová,et al.  Supercritical fluid chromatography as a tool for enantioselective separation; a review. , 2014, Analytica Chimica Acta.

[16]  B. Chankvetadze Recent developments on polysaccharide-based chiral stationary phases for liquid-phase separation of enantiomers. , 2012, Journal of chromatography. A.

[17]  W. Lindner,et al.  Potential of chiral anion-exchangers operated in various subcritical fluid chromatography modes for resolution of chiral acids. , 2012, Journal of chromatography. A.

[18]  Y. Vander Heyden,et al.  Combined use of isopropylamine and trifluoroacetic acid in methanol-containing mobile phases for chiral supercritical fluid chromatography. , 2012, Journal of chromatography. A.

[19]  L. Morin-Allory,et al.  Insights into chiral recognition mechanisms in supercritical fluid chromatography. I. Non-enantiospecific interactions contributing to the retention on tris-(3,5-dimethylphenylcarbamate) amylose and cellulose stationary phases. , 2011, Journal of chromatography. A.

[20]  L. Morin-Allory,et al.  Insights into chiral recognition mechanisms in supercritical fluid chromatography. II. Factors contributing to enantiomer separation on tris-(3,5-dimethylphenylcarbamate) of amylose and cellulose stationary phases. , 2011, Journal of chromatography. A.

[21]  Y. Vander Heyden,et al.  Comparative enantioseparations of pharmaceuticals in capillary electrochromatography on polysaccharide‐based chiral stationary phases containing selectors with or without chlorinated derivatives , 2010, Electrophoresis.

[22]  C. Eckert,et al.  Spectroscopic Investigation of Alkylcarbonic Acid Formation and Dissociation in CO2-Expanded Alcohols , 2009 .

[23]  G. Webster,et al.  A Comparison of HPLC and SFC Chiral Method Development Screening Approaches for Compounds of Pharmaceutical Interest , 2008 .

[24]  L. T. Taylor,et al.  Elution of Cationic Species with/without Ion Pair Reagents from Polar Stationary Phases via SFC , 2006 .

[25]  P. Sandra,et al.  Rapid method development for chiral separation in drug discovery using sample pooling and supercritical fluid chromatography-mass spectrometry. , 2003, Journal of chromatography. A.