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Direct Separation of Clopidogrel Enantiomers by Reverse-Phase Planar Chromatography Method Using beta-Cyclodextrin as a Chiral Mobile Phase Additive

Authorized Users Only
2011
Authors
Antić, Dušan
Filipić, Slavica
Ivković, Branka
Nikolić, Katarina
Agbaba, Danica
Article (Published version)
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Abstract
A simple and rapid TLC method using beta-cyclodextrin as a chiral mobile phase additive (CMPA) was developed for direct separation of S-clopidogrel and its impurity R-clopidogrel. The influence of different factors (stationary phases, organic modifiers, chiral selectors and their concentrations in the mobile phase, and optimal saturation time of the chamber) on enantioseparation was studied. The best resolution of clopidogrel enantiomers was achieved on Polygram (R) cel 300 Ac-10% plates using isopropanol-0.5 mM beta-cyclodextrin (6: 4, v/v) as mobile phase in TLC chamber previously equilibrated with the mobile phase for 20 min. The spots were detected under UV light and using iodine vapours. The method enables rapid separation of clopidogrel enantiomers and can be successfully used in control of stereoselective synthesis of clopidogrel and in control of its purity. Finally, the molecular modelling of the inclusion complexes between the analytes and alpha-, beta-, and gamma-cyclodextri...n was performed to investigate the mechanism of the enantiorecognition.

Keywords:
clopidogrel / enantioseparation / chiral impurity / TLC / beta-cyclodextrin
Source:
Acta Chromatographica, 2011, 23, 2, 235-245
Publisher:
  • Akademiai Kiado Rt, Budapest
Funding / projects:
  • Synthesis, Quantitative Structure and Activity Relationship, Physico-Chemical Characterisation and Analysis of Pharmacologically Active Substances (RS-172033)

DOI: 10.1556/AChrom.23.2011.2.4

ISSN: 1233-2356

WoS: 000291343100004

Scopus: 2-s2.0-79958847889
[ Google Scholar ]
11
8
URI
https://farfar.pharmacy.bg.ac.rs/handle/123456789/1564
Collections
  • Radovi istraživača / Researchers’ publications
Institution/Community
Pharmacy
TY  - JOUR
AU  - Antić, Dušan
AU  - Filipić, Slavica
AU  - Ivković, Branka
AU  - Nikolić, Katarina
AU  - Agbaba, Danica
PY  - 2011
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/1564
AB  - A simple and rapid TLC method using beta-cyclodextrin as a chiral mobile phase additive (CMPA) was developed for direct separation of S-clopidogrel and its impurity R-clopidogrel. The influence of different factors (stationary phases, organic modifiers, chiral selectors and their concentrations in the mobile phase, and optimal saturation time of the chamber) on enantioseparation was studied. The best resolution of clopidogrel enantiomers was achieved on Polygram (R) cel 300 Ac-10% plates using isopropanol-0.5 mM beta-cyclodextrin (6: 4, v/v) as mobile phase in TLC chamber previously equilibrated with the mobile phase for 20 min. The spots were detected under UV light and using iodine vapours. The method enables rapid separation of clopidogrel enantiomers and can be successfully used in control of stereoselective synthesis of clopidogrel and in control of its purity. Finally, the molecular modelling of the inclusion complexes between the analytes and alpha-, beta-, and gamma-cyclodextrin was performed to investigate the mechanism of the enantiorecognition.
PB  - Akademiai Kiado Rt, Budapest
T2  - Acta Chromatographica
T1  - Direct Separation of Clopidogrel Enantiomers by Reverse-Phase Planar Chromatography Method Using beta-Cyclodextrin as a Chiral Mobile Phase Additive
VL  - 23
IS  - 2
SP  - 235
EP  - 245
DO  - 10.1556/AChrom.23.2011.2.4
ER  - 
@article{
author = "Antić, Dušan and Filipić, Slavica and Ivković, Branka and Nikolić, Katarina and Agbaba, Danica",
year = "2011",
abstract = "A simple and rapid TLC method using beta-cyclodextrin as a chiral mobile phase additive (CMPA) was developed for direct separation of S-clopidogrel and its impurity R-clopidogrel. The influence of different factors (stationary phases, organic modifiers, chiral selectors and their concentrations in the mobile phase, and optimal saturation time of the chamber) on enantioseparation was studied. The best resolution of clopidogrel enantiomers was achieved on Polygram (R) cel 300 Ac-10% plates using isopropanol-0.5 mM beta-cyclodextrin (6: 4, v/v) as mobile phase in TLC chamber previously equilibrated with the mobile phase for 20 min. The spots were detected under UV light and using iodine vapours. The method enables rapid separation of clopidogrel enantiomers and can be successfully used in control of stereoselective synthesis of clopidogrel and in control of its purity. Finally, the molecular modelling of the inclusion complexes between the analytes and alpha-, beta-, and gamma-cyclodextrin was performed to investigate the mechanism of the enantiorecognition.",
publisher = "Akademiai Kiado Rt, Budapest",
journal = "Acta Chromatographica",
title = "Direct Separation of Clopidogrel Enantiomers by Reverse-Phase Planar Chromatography Method Using beta-Cyclodextrin as a Chiral Mobile Phase Additive",
volume = "23",
number = "2",
pages = "235-245",
doi = "10.1556/AChrom.23.2011.2.4"
}
Antić, D., Filipić, S., Ivković, B., Nikolić, K.,& Agbaba, D.. (2011). Direct Separation of Clopidogrel Enantiomers by Reverse-Phase Planar Chromatography Method Using beta-Cyclodextrin as a Chiral Mobile Phase Additive. in Acta Chromatographica
Akademiai Kiado Rt, Budapest., 23(2), 235-245.
https://doi.org/10.1556/AChrom.23.2011.2.4
Antić D, Filipić S, Ivković B, Nikolić K, Agbaba D. Direct Separation of Clopidogrel Enantiomers by Reverse-Phase Planar Chromatography Method Using beta-Cyclodextrin as a Chiral Mobile Phase Additive. in Acta Chromatographica. 2011;23(2):235-245.
doi:10.1556/AChrom.23.2011.2.4 .
Antić, Dušan, Filipić, Slavica, Ivković, Branka, Nikolić, Katarina, Agbaba, Danica, "Direct Separation of Clopidogrel Enantiomers by Reverse-Phase Planar Chromatography Method Using beta-Cyclodextrin as a Chiral Mobile Phase Additive" in Acta Chromatographica, 23, no. 2 (2011):235-245,
https://doi.org/10.1556/AChrom.23.2011.2.4 . .

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