Teicoplanin-based enantioselective, potentiometric membrane electrodes for the determination of R-baclofen in pharmaceutical formulations

Analytical Letters

Volumn 37, Issue 15, 2004, Pages 3161-3173

  Rat'ko, Alexander A ^a   Stefan, Raluca Ioana ^a  

^a UNIVERSITY OF PRETORIA   (South Africa)

Author keywords

Enantioselective; Macrocyclic antibiotics; Potentiometric membrane electrode; R baclofen; Teicoplanin

Indexed keywords

ACETONITRILE; BACLOFEN; NORTON; TEICOPLANIN;

ARTICLE; DRUG DETERMINATION; ELECTRODE; ENANTIOSELECTIVITY; PHARMACEUTICS; POTENTIOMETRY;

EID: 11344277825     PISSN: 00032719     EISSN: None     Source Type: Journal    
DOI: 10.1081/AL-200040315     Document Type: Article

References (44)

1. Ward, T.J.; Ward, K.D. In The Impact of Stereochemistry on Drug Development and Use; Chemical Analysis Series; Aboul-Enein, H.Y., Warner, W.I., Eds.; John Wiley & Sons, Inc., 1997; Vol. 142, 317-332.
2. Stefan, R.I.; van Staden, J.F.; Aboul-Enein, H.Y. Electrochemical Sensors in Bioanalysis; Marcel Dekker Inc.: New York, 2001.
3. Armstrong, D.W. A new class of chiral selectors for enantiomeric separations by LC, TLC, GC, CE and SFC Pittsburg Conference Abstracts. 1994, 572.
4. Armstrong, D.W.; Tang, Y.; Chen, S.; Zhou, Y.; Bagwill, C.; Chen, J. Macrocyclic antibiotics as a new class of chiral selectors for liquid chromatography. Anal. Chem. 1994, 66, 1473-1484.
5. Armstrong, D.W.; Rundlett, K.; Reid, G., III. Use of a macrocyclic antibiotic as the chiral selector for enantiomeric separations by TLC. Anal. Chem. 1994, 66, 1690-1695.
6. Armstrong, D.W.; Zhou, Y. Use of a macrocyclic antibiotic as a chiral selector for enantiomeric separations by TLC. J. Liq. Chromatogr. 1994, 17, 1695-1707.
7. Armstrong, D.W.; Rundlett, K.; Chen, J. Evaluation of the macrocyclic antibiotic vancomycin as a chiral selector for capillary electrophoresis. Chirality 1994, 6, 496-509.
8. Parenti, F.; Beretta, G.; Berti, M.; Arioli, V. Teichomycins: new antibiotics from Actinoplanes teichomyceticus. NOV. SP. J. Antibiot. 1978, XXXI, 276-283.
9. Williams, A.H.; Gruneberg, R.N. Teicoplanin. J. Antimicrobiol. Chemother. 1994, 14, 4412-4445.
10. Hunt, A.H.; Moloy, R.M.; Occolowitz, J.L.; Marconi, G.G.; Debono, M. Structure of the major glycopeptide of the teicoplanin complex. J. Am. Chem. Soc. 1984, 106, 4891-4895.
11. Borghi, A.; Coronelli, C.; Faninolo, L.; Allievi, G.; Pallanza, R.; Gallo, G.G. Teichomycins: new antibiotics from Actinoplanes teichomyceticus. NOV. SP. IV. Separation and characterization of the components of teichomycin (teicoplanin). J. Antibiot. 1984, XXXVII, 615-620.
12. Glupczynski, Y.; Lagast, H.; van der Anwera, P.; Thys, J.P.; Crokaert, J.; Yourassowsky, E.; Meunier-Carpentier, F.; Klastersky, J.; Kans, J.P.; Serruys-Schoutens, E.; Legrand, J.C. Clinical evaluation of teicoplanin for therapy of severe infections caused by Gram-positive bacteria. Antimicrob. Agents Chemother. 1986, 29, 52-56.
13. Wise, R.; Donovan, I.A.; McNulty, C.A.M.; Waldron, R.; Andrews, J.M. Teicoplanin, its pharmacokinetics, blister and peritoneal penetration. J. Hospital Invest. 1986, 7, 47-55.
14. Watana, J.; Kunakorn, C. In-vitro activity of teicoplanin alone and in combination with rifamycin, gentamycin or tobramycin against coagulase-negative staphylococci. J. Antimicrobiol. Chemother. 1987, 19, 439-443.
15. Kato, K.; Tanaka, S.; Fujii, S.; Katayama, M.; Kimoto, H. Preparation of optically active trifluoromethylated (3′-indolyl) thiacarboxylic acids, novel plant growth regulators through lipase catalyzed enantioselective hydrolysis. J. Biosci. Bioeng. 1999, 87, 76-81.
16. Rundlett, K.L.; Gasper, M.P.; Zhou, E.Y.; Armstrong, D.W. Capillary enantiomeric saparations using the glycopeptide antibiotic, teicoplanin. Chirality 1996, 8, 88-107.
17. Corti, A.; Soffientini, A.; Cassani, G. Binding of the glycopeptide antibiotic teicoplanin to D-anlanyl-D-alanine-agarose: The effect of micellar aggregates. J. Applied Biochem. 1985, 7, 133.
18. Gasper, M.; Berthod, A.; Nair, U.B.; Armstrong, D.W. Comparison and modeling study of vancomycin, ristocetin A and teicoplanin for CE enantioseparations. Anal. Chem. 1996, 68, 2501-2508.
19. Aboul-Enein, H.Y.; Ali, I. Macrocyclic antibiotics as effective chiral selectors for enantiomeric resolution by liquid chromatography and capillary electrophoresis. Chromatographia 2000, 52, 679-691.
20. Berthod, A.; Liu, Y.; Bagwill, C.; Armstrong, D.W. Facile liquid chromatographic enantioresolution of native amino acids and peptides using a teicoplanin chiral stationary phase. J. Chromatogr. A 1996, 731, 123-137.
21. Tesařova, E.; Bosakova, Z.; Zuskova, I. Enantioseparation of selected N-tert-butyloxycarbonyl amino acids by high performance liquid chromatography and capillary electrophoresis with a teicoplanin chiral selector. J. Chromatogr. A 2000, 879, 147-156.
22. Rat'ko, A.A.; Stefan, R.I.; van Staden, J.F.; Aboul-Enein, H.Y. Determination of L-carnitine using enantioselective, potentiometric membrane electrodes based on macrocyclic antibiotics. Talanta 2004, 63, 515-519.
23. Rat'ko, A.A.; Stefan, R.I.; van Staden, J.F.; Aboul-Enein, H.Y. Enantioselective, potentiometric membrane electrode based on vancomycin. Its application for the determination of D-pipecolic acid. Sens. Actuators B 2004, 99, 546-550.
24. Rat'ko, A.A.; Stefan, R.I.; van Staden, J.F.; Aboul-Enein, H.Y. Macrocyclic antibiotics as chiral selectors in the design of enantioselective, potentiometric membrane electrodes for the determination of L- and D-enantiomers of methotrexate. Talanta 2004, 64, 145-150.
25. Goodman, A.G.; Gilman, L.S.; Rall, T.W.; Murad, F. (Eds.) Goodman and Gilman's, The Pharmacological Basics of Therapeutics, 7th Ed.; Macmillan: New York, 1985; 487.
26. Bowery, N.G.; Hill, D.R.; Hudson, A.L.; Doble, A.; Middleniss, D.N.; Shaw, J.; Turnhill, M. (-)Baclofen decreases neurotransmitter release in the mammalian CNS by an action at a novel GABA receptor. Nature 1980, 283, 92-94.
27. B receptors. IL Farmaco 2003, 58, 173-183.
28. 2 sites in rat brain. Nature 1981, 290, 149-152.
29. Olpe, H.R.; Demieville, H.; Baltzer, V.; Bencze, W.L.; Koella, W.P.; Wolf, P.; Hass, H.L. The biological activity of d-baclofen (Lioresal®). Eur. J. Pharm. 1978, 52, 133-136.
30. Swahn, C.G.; Beving, H.; Sedvall, G. Mass fragmentographic determination of 4-amino-3-(p-chlorophenyl)butyric acid (baclofen) in cerebrospinal fluid and serum. J. Chromatogr. 1979, 162, 433-438.
31. Knuttson, E.; Lindblom, U.; Martensson, A. Plasma and cerebro-spinal fluid levels of baclofen (Lioresal®) at optimal therapeutic responses in spastic paresis. J. Neurol. Sci. 1974, 23, 473-484.
32. Wuis, E.W.; Beneken Kolmer, E.W.; van Beijsterveld, L.E.C.; Burgers, R.C.M.; Vree, T.B.; van der Kleyn, E. Enantioselective high-performance liquid chromatographic determination of baclofen after derivatization with a chiral adduct of o-phthaldialdehyde. J. Chromatogr. 1987, 415, 419-422.
33. Harrison, P.M.; Tonkin, A.M.; McLean, A.J. Simple and rapid analysis of atenolol and metoprolol in plasma using solid-phase extraction and high-performance liquid chromatography. J. Chromatogr. 1985, 339, 429-433.
34. Rustum, A.M. Simple and rapid reverse-phase high-performance liquid chromatographic determination of baclofen in human plasma with ultraviolet detection/application to a pharmacokinetic study. J. Chromatogr. 1989, 487, 107-115.
35. Zhu, Z.; Neinrick, L. Chiral separation and determination of R-(-) and S-(+)-baclofen in human plasma by high performance liquid chromatography. J. Chromatogr. B 2003, 785, 277-283.
36. Wuis, E.W.; Dirks, R.J.M.; Vrel, T.P.; van der Kleyn, E. High performance liquid chromatographic analysis of baclofen in plasma and urine of man after pre-column extraction and derivatization with phtalaldehyde. J. Chromatogr. 1985, 337, 341-350.
37. Shimada, K.; Mitamura, K.; Morita, M.; Hirakata, K. Separation of the diastereomers of baclofen by high-performance liquid chromatography using cyclodextrin as a mobile phase additive. J. Liq. Chromatogr. 1993, 16, 3311-3320.
38. Tosunoglu, S.; Ersoy, L. Determination of baclofen in human plasma and urine by high-performance liquid chromatography with fluorescence detection. Analyst 1995, 120, 373-375.
39. Wall, G.M.; Baker, J.K.A. Determination of baclofen and alpha-baclofen in rat liver homogenate and human urine using solid-phase extraction, phthalaldehyde-t-butyl thiol derivatization and high-performance liquid chromatography with amperometric detection. J. Chromatogr. A 1989, 491, 151-162.
40. Milleroiux, L.; Brault, M.; Gualano, V.; Mignot, A. High-performance liquid chromatographic determination of baclofen in human plasma. J. Chromatogr. B 1996, 729, 309-314.
41. Flärdth, M.; Jacobson, B.-M. Sensitive method for determination of baclofen in plasma by means of solid-phase extraction and liquid chromatography-hyphen;tandem mass spectrometry. J. Chromatogr. A 1999, 846, 169-173.
42. Chiang, M.-T.; Chang, S.Y.; Whang, C.-W. Analysis of baclofen by capillary electrophoresis with laser induced fluorescence detection. J. Chromatogr. A 2000, 877, 233-237.
43. Gu, Y.-S.; Whang, C.-W. Capillary electrophoresis of baclofen with argon-ion laser-induced fluorescence detection. J. Chromatogr. A 2002, 972, 289-293.
44. Hefnawy, M.M.; Aboul-Enein, H.Y. Enantioselective high-performance liquid chromatographic method for determination of baclofen in human plasma. Talanta 2003, 61, 667-673.