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Cyclodextrins as a chiral mobile phase additive in nano-liquid chromatography: comparison of reversed-phase silica monolithic and particulate capillary columns.
Anal Bioanal Chem. 2012 Mar; 402(9):2935-43.AB

Abstract

Enantioseparations of racemic nonsteroidal anti-inflammatory drugs (naproxen, ibuprofen, ketoprofen, flurbiprofen, suprofen, indoprofen, cicloprofen, and carprofen) were performed by nano-liquid chromatography, employing achiral capillary columns and heptakis(2,3,6-tri-O-methyl)-β-cyclodextrin (TM-β-CD) or hydroxylpropyl-β-cyclodextrin (HP-β-CD) as a chiral mobile phase additive (CMPA). Working under the same experimental conditions (in terms of mobile phase and linear velocity), the performance of a RP-C18 monolithic column was compared with that of a RP-C18 packed column of the same dimensions (100 μm i.d. × 10 cm). Utilizing a mobile phase composed of 30% ACN (v/v) buffered with 50 mM sodium acetate at pH 3, and containing 30 mM TM-β-CD, the monolithic column provided faster analysis but lower resolution than the packed column. This behavior was ascribed to the high permeability of the monolithic column, as well as to its minor selectivity. HP-β-CD was chosen as an alternative to TM-β-CD. Employing the monolithic column, the effects of different parameters such as HP-β-CD concentration, mobile phase composition, and pH on the retention factor and the chiral resolution of the analytes were studied. For the most of the analytes, enantioresolution (which ranged from R(s) = 1.80 for naproxen to R(s) = 0.86 for flurbiprofen) was obtained with a mobile phase consisting of sodium acetate buffer (25 mM, pH 3), 10% MeOH, and 15 mM HP-β-CD. When the same experimental conditions were used with the packed column, no compound eluted within 1 h. Upon increasing the percentage of organic modifier to favor analyte elution, only suprofen eluted within 30 min, with an R(s) value of 1.14 (20% MeOH). Replacing MeOH with ACN resulted in a loss of enantioresolution, except for naproxen (R(s) = 0.89).

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Publisher Full Text (DOI)

Authors+Show Affiliations

Rocco A
Department of Chemistry, Vytautas Magnus University, Kaunas, Lithuania.
Maruška A
No affiliation info available
Fanali S
No affiliation info available

MeSH

AdsorptionAnti-Inflammatory Agents, Non-SteroidalChromatography, High Pressure LiquidChromatography, Reverse-PhaseSilicon Dioxidebeta-Cyclodextrins

Pub Type(s)

Comparative Study
Journal Article

Language

eng

PubMed ID

22349325

Citation

Rocco, Anna, et al. "Cyclodextrins as a Chiral Mobile Phase Additive in Nano-liquid Chromatography: Comparison of Reversed-phase Silica Monolithic and Particulate Capillary Columns." Analytical and Bioanalytical Chemistry, vol. 402, no. 9, 2012, pp. 2935-43.
Rocco A, Maruška A, Fanali S. Cyclodextrins as a chiral mobile phase additive in nano-liquid chromatography: comparison of reversed-phase silica monolithic and particulate capillary columns. Anal Bioanal Chem. 2012;402(9):2935-43.
Rocco, A., Maruška, A., & Fanali, S. (2012). Cyclodextrins as a chiral mobile phase additive in nano-liquid chromatography: comparison of reversed-phase silica monolithic and particulate capillary columns. Analytical and Bioanalytical Chemistry, 402(9), 2935-43. https://doi.org/10.1007/s00216-012-5764-6
Rocco A, Maruška A, Fanali S. Cyclodextrins as a Chiral Mobile Phase Additive in Nano-liquid Chromatography: Comparison of Reversed-phase Silica Monolithic and Particulate Capillary Columns. Anal Bioanal Chem. 2012;402(9):2935-43. PubMed PMID: 22349325.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Cyclodextrins as a chiral mobile phase additive in nano-liquid chromatography: comparison of reversed-phase silica monolithic and particulate capillary columns. AU - Rocco,Anna, AU - Maruška,Audrius, AU - Fanali,Salvatore, Y1 - 2012/02/16/ PY - 2011/10/19/received PY - 2012/01/18/accepted PY - 2012/01/11/revised PY - 2012/2/22/entrez PY - 2012/2/22/pubmed PY - 2012/6/12/medline SP - 2935 EP - 43 JF - Analytical and bioanalytical chemistry JO - Anal Bioanal Chem VL - 402 IS - 9 N2 - Enantioseparations of racemic nonsteroidal anti-inflammatory drugs (naproxen, ibuprofen, ketoprofen, flurbiprofen, suprofen, indoprofen, cicloprofen, and carprofen) were performed by nano-liquid chromatography, employing achiral capillary columns and heptakis(2,3,6-tri-O-methyl)-β-cyclodextrin (TM-β-CD) or hydroxylpropyl-β-cyclodextrin (HP-β-CD) as a chiral mobile phase additive (CMPA). Working under the same experimental conditions (in terms of mobile phase and linear velocity), the performance of a RP-C18 monolithic column was compared with that of a RP-C18 packed column of the same dimensions (100 μm i.d. × 10 cm). Utilizing a mobile phase composed of 30% ACN (v/v) buffered with 50 mM sodium acetate at pH 3, and containing 30 mM TM-β-CD, the monolithic column provided faster analysis but lower resolution than the packed column. This behavior was ascribed to the high permeability of the monolithic column, as well as to its minor selectivity. HP-β-CD was chosen as an alternative to TM-β-CD. Employing the monolithic column, the effects of different parameters such as HP-β-CD concentration, mobile phase composition, and pH on the retention factor and the chiral resolution of the analytes were studied. For the most of the analytes, enantioresolution (which ranged from R(s) = 1.80 for naproxen to R(s) = 0.86 for flurbiprofen) was obtained with a mobile phase consisting of sodium acetate buffer (25 mM, pH 3), 10% MeOH, and 15 mM HP-β-CD. When the same experimental conditions were used with the packed column, no compound eluted within 1 h. Upon increasing the percentage of organic modifier to favor analyte elution, only suprofen eluted within 30 min, with an R(s) value of 1.14 (20% MeOH). Replacing MeOH with ACN resulted in a loss of enantioresolution, except for naproxen (R(s) = 0.89). SN - 1618-2650 UR - https://www.unboundmedicine.com/medline/citation/22349325/Cyclodextrins_as_a_chiral_mobile_phase_additive_in_nano_liquid_chromatography:_comparison_of_reversed_phase_silica_monolithic_and_particulate_capillary_columns_ L2 - https://dx.doi.org/10.1007/s00216-012-5764-6 DB - PRIME DP - Unbound Medicine ER -