Czasopismo
2012
|
Vol. 24, no. 2
|
145--161
Tytuł artykułu
Autorzy
Wybrane pełne teksty z tego czasopisma
Warianty tytułu
Języki publikacji
Abstrakty
Drug analysis is among the most sensitive areas of chemical analysis, simply because of its relevance to human health. Profens make the most important group of nonsteroidal anti-inflammatory drugs (NSAIDs), and in many countries some of them are freely sold over the counter. The in vitro liquid chromatographic analysis of profen drugs faces certain not commonly recognized yet acute and often impassable problems, due to the specific physicochemical properties of these compounds. In this mini review, we share our experience on the practical failures with the enantioseparation of profen drugs both by means of chiral planar and column chromatography. By use of such analytical techniques as polarimetry, 1H and 13C NMR spectroscopy, and mass spectrometry, we point out objectively the reasons that make liquid chromatographic enantioseparation of profens an almost impossible task. These compounds have an inherent ability (both in aqueous and nonaqueous solutions) to undergo oscillatory chiral conversion and oscillatory condensation, combined with a highly pronounced gelating ability. In our view, the oscillatory chiral conversion of profens questions the credibility of widespread claims on the superiority of the curative potential with the (+)-profens over that of the respective (−)-antimers (although the rightfulness of such claims cannot be dismissed, as the in vivo and in vitro behavior of many drugs are known to sometimes fundamentally differ). Moreover, it seems highly probable that, due to their highly pronounced gelating property, profen drugs can easily clog the blood vessels and thereby jeopardize living organisms.
Czasopismo
Rocznik
Tom
Strony
145--161
Opis fizyczny
Bibliogr. 34 poz., rys., tab.
Twórcy
autor
- University of Silesia Department of General Chemistry and Chromatography 9 Szkolna Street 40-006 Katowice Poland
autor
- University of Silesia Department of General Chemistry and Chromatography 9 Szkolna Street 40-006 Katowice Poland, teresa.kowalska@us.edu.pl
Bibliografia
- [1] J.C. Frölich, Trends Pharmacol. Sci., 18, 30–34 (1997)
- [2] S.J. Baek, L.C. Wilson, C.H. Lee, and T.H. Eling, J. Pharmacol. Exp. Ther., 30, 1126–1131 (2002)
- [3] R.M. Pertusi, J. Am. Osteopath. Assoc., 104, (No.11_suppl), 19–24 (2004)
- [4] K. Yamamoto, Y. Ueno, K. Otsubo, K. Kawakami, and K. Komatsu, Appl. Environ. Microbiol., 56, 3125–3129 (1990)
- [5] W. Neupert, R. Brugger, C. Euchenhofer, K. Brune, and G. Geisslinger, Br. J. Pharmacol., 122, 487–492 (1997)
- [6] R.K. Janjikhel, J.D. Bricker, D. Borochovitz, and C.M. Adeyeye, Drug Deliv., 6, 163–170 (1999)
- [7] N.M. Davies, M.R. Wright, A.S. Russell, and F. Jamali, J. Pharm. Sci., 85, 1170–1179 (1996)
- [8] M.F. Landoni and A. Soraci, Curr. Drug Metab., 2, 37–51 (2001)
- [9] A. Bonabello, M.R. Galmozzi, R. Canaparo, G.C. Isaia, L. Serpe, E. Mutoni, and G.P. Zara, Anesth. Analg., 97, 402–408 (2003)
- [10] V. Wsol, L. Skalova, and B. Szotakova, Curr. Drug Metab., 5, 517–533 (2004)
- [11] T. Kowalska and J. Sherma (Eds), Thin Layer Chromatography in Chiral Separations and Analysis, CRC Press, Boca Raton, FL, 2007
- [12] R. Bhushan and V. Parshad, J. Chromatogr. A, 721, 369–372 (1996)
- [13] M. Sajewicz, R. Piętka, A. Pieniak, and T. Kowalska, Acta Chromatogr., 15, 131–149 (2005)
- [14] M. Sajewicz, R. Piętka, A. Pieniak, and T. Kowalska, J. Chromatogr. Sci., 43, 542–548 (2005)
- [15] M. Sajewicz, R. Piętka, A. Pieniak, and T. Kowalska, J. Liq. Chromatogr. Relat. Technol., 29, 2059–2069 (2006)
- [16] M. Sajewicz, M. Gontarska, D. Kronenbach, and T. Kowalska, J. Planar Chromatogr., 21, 349–353 (2008)
- [17] P. Belanger, J.G. Atkinson, and R.S. Stuart, Chem. J. Chem. Soc. D: Commun., 1067–1068 (1969)
- [18] Y. Xie, H. Liu, and J. Chen, Int. J. Pharm., 196, 21–26 (2000)
- [19] M. Sajewicz, R. Piętka, P. Kuś, and T. Kowalska, Acta Chromatogr., 16, 181–191 (2006)
- [20] G. Nicolis and I. Prigogine, Self-Organization in Non-Equilibrium Systems, Wiley, New York, 1977
- [21] M. Sajewicz, M. Gontarska, Ł. Wojtal, D. Kronenbach, M. Leda, I.R. Epstein, and T. Kowalska, J. Liq. Chromatogr. Relat. Technol., 31, 1986–2005 (2008)
- [22] E. Peacock-Lopez, D.B. Radov, and C.S. Flesner, Biophys. Chem., 65, 171–178 (1997)
- [23] L.L. Tsai, G.R. Hutchinson, and E. Peacock-Lopez, J. Chem. Phys., 113, 2003–2006 (2000)
- [24] M. Sajewicz, R. Wrzalik, M. Gontarska, D. Kronenbach, M. Leda, I.R. Epstein, and T. Kowalska, J. Liq. Chromatogr. Relat. Technol., 32, 1359–1372 (2009)
- [25] M. Sajewicz, M. Matlengiewicz, M. Leda, M. Gontarska, D. Kronenbach, T. Kowalska, and I.R. Epstein, J. Phys. Org. Chem., 23, 1066–1073 (2010)
- [26] M. Sajewicz, M. Gontarska, D. Kronenbach, M. Leda, T. Kowalska, and I.R. Epstein, J. Syst. Chem., 1(7) (2010). DOI:10.1186/1759-2208-1-7
- [27] M. Matlengiewicz, M. Sajewicz, M. Gontarska, D. Kronenbach, and T. Kowalska, Acta Chromatogr., 22, 81–90 (2010)
- [28] M. Sajewicz, M. Matlengiewicz, D. Kronenbach, M. Gontarska, and T. Kowalska, Acta Chromatogr., 21, 259–271 (2009)
- [29] M. Sajewicz, M. Gontarska, D. Kronenbach, and T. Kowalska, Acta Chromatogr., 21, 151–160 (2009)
- [30] P.V. Ivanov, V.I. Maslova, N.G. Bondareva, O.A. Yur’eva, N.V. Kozlova, E.A. Chernyshev, K. Yu. Odintsov, and E.A. Zykunova, Russ. Chem. Bull., 46, 2138–2141 (1997)
- [31] E.A. Chernyshev, P.V. Ivanov, and D.N. Golubykh, Russ. Chem. Bull., 50, 1998–2009 (2001)
- [32] C. Beldie, N. Aelenei, A. Onu, and D. Lazar, Eur. Polym. J., 18, 331–335 (1982)
- [33] M. Sajewicz, M. Gontarska, D. Kronenbach, E. Berry, T. Kowalska, J. Chromatogr. Sci. DOI:10.1093/chromsci/bmr051
- [34] M. Sajewicz, M. Gontarska, D. Kronenbach, E. Berry, T. Kowalska, Acta Chromatogr. DOI:10.1556/AChrom.24.2012.1.1
Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.baztech-9d69a6bd-0185-4d9e-bbe6-7771e7d50fdf