Summary
The use of 1,1′-[ethenylidenebis(sulfonyl)]bis-benzene as a pre-chromatographic reagent for LC analysis of thiol drugs is proposed. The reagent reacts rapidly (2 min) under mild conditions (pH 7.5, ambient) with thiol drugs and the resulting adducts can be chromatographed under reversed-phase conditions (C-18 column). Excess reagent can be removed from the reaction mixture by simple liquid-liquid extraction with chloroform. The HPLC method using UV detection was successfully applied to the analysis of reduced glutathione (GSH), N-acetylcysteine, N-2-mercaptopropionylglycine and captopril in their commercial formulations.
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References
E. F. Reynolds, Ed., Martindale, The Extra Pharmacopoeia, Pharmaceutical Press, London, 29th ed. 1989.
S. Tognella, M. Tedeschi, R. Assereto, O. Tofanetti, E. Cavalletti. U.S. US 4, 871,528; 3 Oct. 1989 (Chem. Abstr. 112, 240543d).
W. R. Baeyens, K. Imai, B. Lin Ling, “Chromatographic Determination of Thiols through Selective Fluorescence Derivatization: A Review”. In Progress in Analitical Luminescence, ASTM STP 1009, D. Eastwood, L. J. Cline Love, Eds., American Society for Testing and Materials, Philadelphia, 1988, p. 83.
H. Lingeman, W. J. M. Underberg. Detection Oriented Derivatization Techniques in Liquid Chromatography. Marcel Dekker, Ed., 1990.
R. A. Winters, J. Zukowsky, N. Ercal, R. H. Matthews, R. Spitz, Anal. Biochem.227, 14 (1995).
K. Nakashima, T. Ishmary, N. Kuroda, S. Akiyama, Biomed. Chromatogr.9, 90 (1995).
A. I. Haj-Yehia, L. Z. Benet, Pharm. Res.12, 155 (1995).
A. I. Haj-Yehia, L. Z. Benet, J. Chromatogr.660, 45 (1995).
V. Cavrini, R. Gatti, A. M. Di Pietra, M. A. Raggi, Chromatographia23, 680 (1987).
A. M. Di Pietra, R. Gotti, D. Bonazzi, V. Andrisano, V. Cavrini, J. Pharm. Biomed. Anal.12, 91 (1994).
R. Gatti, V. Cavrini, P. Roveri, S. Pinzauti, J. Chromatogr.507, 451 (1990).
R. Gotti, V. Andrisano, V. Cavrini, A. Bongini, Chromatographia39, 23 (1994).
R. Gotti, V. Andrisano, R. Gatti, V. Cavrini, S. Candeletti, Biomed. Chromatogr.8, 306 (1994).
H. Kataoka, K. Takagi, M. Makita, Biomed. Chromatogr.9, 85 (1995).
M. Castagnola, D. Di Pierro, R. Scatena, B. Tavazzi, G. Nocca, D. V. Rossetti, B. Giardina, Biomed. Chromatogr.7, 220 (1993).
B. Lin Ling, W. R. G. Baeyens, C. Dewaele, Anal. Chim. Acta.255, 283 (1991).
F. D. Carvalho, F. Remiao, P. Vale, J. A. Timbrell, M. I. Bastos, M. A. Ferreira, Biomed. Chromatogr.8, 134 (1994).
O. De Lucchi, L. Pasquato, G. Modena, Tetrahedron Lett.25, 3643 (1984).
E. Ghigi, Gazz. Chim. Ital.68, 184 (1938).
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Cavrini, V., Gotti, R., Andrisano, V. et al. 1,1′-[Ethenylidenebis(sulfonyl)]bis-benzene: A useful pre-chromatographic derivatization reagent for HPLC analysis of thiol drugs. Chromatographia 42, 515–520 (1996). https://doi.org/10.1007/BF02290285
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DOI: https://doi.org/10.1007/BF02290285