Journal : Acta Chromatographica
Article : Study of the oscillatory in-vitro transenantiomerization of the antimers of flurbiprofen and their enantioseparation by thin-layer chromatography (TLC)

Authors :
Bartnik, M.
Department of Pharmacognosy with Medicinal Plant Laboratory, Medical University, 1, Chodźki Str., 20-093 Lublin, Poland,
Kowalski, R.
Subdepartment of Food Quality Assessment and Central Apparatus Laboratory, Agricultural University, 20-950 Lublin, Akademicka 13, Poland,
Polak, B.
Department of Physical Chemistry, Faculty of Pharmacy, Medical University, Lublin, Poland,
Turło, J.
Department of Drug Technology, Medical University of Warsaw, 1, Banacha Street, 02-097 Warsaw, Poland,
Szyrwińska, K.
Department of Inorganic and Analytical Chemistry, Faculty of Pharmacy, Poznań University of Medical Sciences, Grunwaldzka 6, 60-780 Poznań, Poland,
Czauderna, M.
The Kielanowski Institute of Animal Physiology and Nutrition, Polish Academy of Sciences, 05-110 Jabłonna, Poland,
Bączek, T.
Medical University of Gdańsk, Department of Biopharmaceutics and Pharmacodynamics, Gdańsk, Poland,
Chilmonczyk, Z.
National Medicines Institute, 30/34, Chełmska Str., 00-725 Warsaw, Poland,
Hung, Ch. Y.
Department of Biotechnology, National Formosa University, Huwei, Yunlin, 632, Taiwan,
Baboota, S.
Department of Pharmaceutics, Faculty of Pharmacy, Jamia Hamdard, Hamdard Nagar, New Delhi-110062, India,
Sivakumar, T.
Department of Pharmacy, Annamalai University, Annamalai Nagar, Tamil Nadu-608 002, India,
Ivanović, D.
Faculty of Pharmacy, Department of Drug Analysis, Vojvode Stepe 450, 11000 Belgrade, Serbia,
Pavlova, V.
Institute of Chemistry, Faculty of Natural Sciences and Mathematics, Saints Cyril and Methodius University, Arhimedova 5, P.O. Box 162, 1000 Skopje, Macedonia,
Ali, J.
Department of Pharmaceutics, Faculty of Pharmacy, Jamia Hamdard, New Delhi-110062, India,
Nabi, S. A.
Analytical Research Laboratory, Department of Chemistry, Faculty of Science, Aligarh Muslim University, Aligarh-202002, India,
Murray, K. E.
Department of Chemistry, Lafayette College, Easton, PA 18042, USA,
Antić, D.
Institute of Pharmaceutical Chemistry and Drug Analysis, Faculty of Pharmacy, University of Belgrade, Vojvode Stepe 450, 11000 Belgrade, Serbia,
Jóźwiak, G. W.
Department of Inorganic Chemistry, Medical University of Lublin, Staszica 6, 20-081 Lublin, Poland,
Purghazi, K.
Department of Applied Chemistry, Faculty of Chemistry, University of Tarbiat Moallem, 49 Mofatteh Avenue, Tehran 15614, Iran,
Sajewicz, M.
Institute of Chemistry, Silesian University, 9 Szkolna Street, 40-006 Katowice, Poland,
Abstract : In our earlier studies on the spontaneous in-vitro oscillatory transenantiomerization of profens we investigated optically pure S-(+)-ibuprofen and S-(+)-naproxen and the racemic mixtures S,R-(š)-2-phenylpropionic acid and S,R-(š)-ketoprofen, which remained in a state of dynamic equilibrium between the two antimers yet also had the ability to transenantiomerize. In this study we have demonstrated, for the first time, the spontaneous oscillatory in-vitro transenantiomerization of S-(+)-flurbiprofen (an important non-steroidal anti-inflammatory drug, NSAID) and R-(-)-flurbiprofen, as monitored by polarimetry. It is also noteworthy that – as far as we are aware – this is the first report of separation of the enantiomers of flurbiprofen by TLC. This separation was achieved by two-dimensional development using a simple chromatographic system comprising a commercial silica gel layer impregnated with L-arginine as stationary phase and ethanol containing a few drops of glacial acetic acid as mobile phase. Unfortunately, this chromatographic system resulted in catalysis of structural conversion of the optically pure flurbiprofen enantiomer, either S-(+), or R-(-), to the scalemic or racemic mixture of the two antimers. This is an interesting contribution to general knowledge about the reactivity of this particular profen, although the spontaneous and rapid conversion observed prevents use of this TLC system for identification and quantification of individual flurbiprofen enantiomers.

Keywords :
Publishing house : University of Silesia in Katowice
Publication date : 2007
Number : No. 18
Page : 226 – 237

Bibliography
: 1 M. Sajewicz, R. Piętka, A. Pieniak, and T. Kowalska, Acta Chromatogr., 15, 131 (2005)
2 M. Sajewicz, R. Piętka, A. Pieniak, and T. Kowalska, J. Chromatogr. Sci., 43, 542 (2005)
3 M. Sajewicz, R. Piętka, A. Pieniak, and T. Kowalska, J. Liq. Chromatogr. Related Technol., 29, 2059 (2006)
4 M. Sajewicz, M. Gontarska, M. Wróbel, and T. Kowalska, J. Liq. Chromatogr. Related Technol., 30, 2193 (2007)
5 M. Sajewicz, R. Piętka, P. Kuś, and T. Kowalska, Acta Chromatogr., 16, 181 (2006)
6 Aldrich Advancing Science Catalog 2005–2006
7 R. Bhushan and V. Parshad, J. Chromatogr. A, 721, 369 (1996)
DOI :
Qute : Bartnik, M. ,Kowalski, R. ,Polak, B. ,Turło, J. ,Szyrwińska, K. ,Czauderna, M. ,Bączek, T. ,Chilmonczyk, Z. ,Hung, Ch. Y. ,Baboota, S. ,Sivakumar, T. ,Ivanović, D. ,Pavlova, V. ,Ali, J. ,Nabi, S. A. ,Murray, K. E. ,Antić, D. ,Jóźwiak, G. W. ,Purghazi, K. ,Sajewicz, M. ,Sajewicz, M. , Study of the oscillatory in-vitro transenantiomerization of the antimers of flurbiprofen and their enantioseparation by thin-layer chromatography (TLC). Acta Chromatographica No. 18/2007
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