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Application of thin-layer chromatography (TLC) to investigating oscillatory instability of the selected profen enantiomers

Identyfikatory
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
In our earlier studies we intended to evaluate the performance of thin-layer chromatography (TLC) as an analytical tool applied to separation of the selected profen (i.e. 2-arylpropionic acid) enantiomers and we se-lected ibuprofen as a model analyte for this purpose. Surprisingly enough, TLC is relatively seldom used for separation of enantiomers, even though – despite the low number of theoretical plates (N) in this particular techni-que in comparison with fully automated column chromatographic techni-ques (basically GC and HPLC) – it seems very well suited for complete separation of two analytes only (i.e. a pair of enantiomers). Separation of profens can be regarded as a particularly urgent ana-lytical task, because they are among the most widely prescribed synthetic non-steroidal anti-inflammatory drugs and in medicinal chemistry we must be vigilantly aware of possible unpredictable consequences of dispensing medicines as racemic mixtures. In earlier and in more recent studies we have provided enough evi-dence not only to prove that the analytical performance of TLC is suffi-cient for separation of the enantiomers of ibuprofen, but also – even more important – to demonstrate the usefulness of this simple yet very efficient separation technique in physicochemical studies of the oscillatory instability of profens when stored for long periods of time in aqueous media. By use of TLC it was possible to show the oscillatory transenantiomerization of the profens from the S to the R form, and vice versa, during storage. The correctness of our TLC assessment with regard to structural oscillation of enantiomeric profens was later successfully confirmed by means of pola-riemetry.
Słowa kluczowe
Rocznik
Tom
Strony
131--149
Opis fizyczny
Bibliogr. 15 poz., rys., tab.
Twórcy
autor
  • Institute of Chemistry, Silesian University, 9 Szkolna Street, 40-006 Katowice, Poland
autor
  • Institute of Chemistry, Silesian University, 9 Szkolna Street, 40-006 Katowice, Poland
autor
  • Institute of Chemistry, Silesian University, 9 Szkolna Street, 40-006 Katowice, Poland
autor
  • Institute of Chemistry, Silesian University, 9 Szkolna Street, 40-006 Katowice, Poland
Bibliografia
  • [1] R. Bhushan and V. Parshad, J. Chromatogr. A, 721, 369 (1996)
  • [2] M. Sajewicz, R. Piętka, and T. Kowalska, J. Planar Chromatogr., 17, 173 (2004)
  • [3] T. Bando, Y. Namba, and K. Shishido, Tetrahedron: Asymmetry, 8, 2159 (1997)
  • [4] E.J. Ebbers, G.J.A. Ariaans, A. Bruggink, and B. Zwanenburg, Tetrahedron: Asymmetry, 10, 3701 (1999)
  • [5] Z.-L. Wu and Z.-Y. Li, Tetrahedron: Asymmetry, 12, 3305 (2001)
  • [6] X. Yuan, J. Li, Y. Tian, G.-H. Lee, X.-M. Peng, R. Zhu, and X. You, Tetrahedron: Asymmetry, 12, 3015 (2001)
  • [7] V.K. Tandon, Tetrahedron Lett., 42, 5985 (2001)
  • [8] A. Pieniak, K. Kaczmarski, M. Sajewicz, W. Zapała, A. Gołębiowska, R. Tomala, T. Kowalska, Acta Chromatogr., 14, 16 (2004)
  • [9] Y. Xie, H. Liu, and J. Chen, Int. J. Pharmaceutics, 196, 21 (2000)
  • [10] P. Gray and S.K. Scott, “Chemical Oscillations and Instabilities. Non-linear Chemical Kinetics”, Clarendon Press, Oxford, 1994
  • [11] K. Yamamoto, Y. Ueno, K. Otsubo, K. Kawakami, and K. Komatsu, Appl. Environ. Microbiol., 56, 3125 (1990)
  • [12] W. Neupert, R. Brugger, C. Euchenhofer, K. Brune, and G. Geisslinger, Br. J. Pharmacol., 122, 487 (1997)
  • [13] M.F. Landoni and A. Soraci, Current Drug Metabolism, 2, 37 (2001)
  • [14] N.M. Davies, M.R. Wright, A.S. Russell, and F. Jamali, J. Pharm. Sci., 85, 1170 (2000)
  • [15] R.K. Janjikhel, J.D. Bricker, D. Borochovitz, and C.M. Adeyeye, Drug Delivery, 6, 163 (1999)
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BAT3-0028-0074
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