Abstract
Non-covalent complexes between three derivitized cyclodextrins (CD’s) and six local anesthetics were studied using capillary electrophoresis (CE) and electrospray ionization mass spectrometry (ESI-MS). The CE study was performed using the complete filling technique (CFT). A comparison between the migration data from CE and ESI-MS inclusion complex peak abundances was made representing the association between local anesthetics and CD’s in the solution and the gas phase, respectively. The results from this study showed comparable behavior of the complexes in the CE and mass spectrometer, indicating similarity in the parameters controlling the stability of these complexes. Therefore, the formation of specific non-covalent complexes, as shown in this study, could be used to predict the behavior of a complexing agent with a substrate in the solution phase by observing data obtained from ESI-MS.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
Selva, A.; Redenti, E.; Ventura, P.; Zanol, M.; Casetta, B. Study of β-Cyclodextrin-Ketoconazole-Tartaric Acid Multicomponenet Non-covalent Association by Positive and Negative Ionspray Mass Spectrometry. J. Mass Spectrom. 1998, 33, 729–734.
Smith, R. D.; Light-Wahl, K. J. The Observation of Non-Covalent Interactions in Solution by Electrospray Ionization Mass Spectrometry; Promise, Pitfalls, and Prognosis. Biol. Mass Spectrom. 1993, 22, 493–501.
Srinivasan, K.; Bartlett, M. G. Comparison of Cyclodextrin-Barbiturate Non-Covalent Complexes Using Electrospray Ionization Mass Spectrometry and Capillary Electrophoresis. Rapid Commun. Mass Spectrom. 2000, 14, 624–632.
Penn, S. G.; Goodall, D. M.; Moning, C. A.; Loran, J. S. Non-Covalent Complexes Formation of Cyclodextrins Studied by Electro Spray Ionization Mass Spectrometry. Proceedings of the 43rd ASMS Conference on Mass Spectrometry and Allied Topics; Atlanta, GA, 1995; p 236.
Gallagher, R. T.; Ball, C. P.; Gatehouse, D. R.; Gates, P. J.; Lobell, M.; Derrick, P. J. Cyclodextrin-Piroxicam Inclusion Complexes: Analysis by Mass Spectrometry and Molecular Modeling. Anal. Chem. 1997, 165/166, 523–531.
Lu, W.; Cole, R. B. Determination of Chiral Pharmaceutical Compounds, Terbutaline, Ketamine and Propranolol, by On-Line Capillary Electrophoresis-Electrospray Ionization Mass Spectrometry. J. Chromatogr. B. 1998, 714, 69–75.
Cunniff, J. B.; Vouros, P. False Positives in the Detection of Cyclodextrins Inclusion Complexes by Electrospray Mass-Spectrometry. J. Am. Soc. Mass Spectrom. 1995, 6, 437–447.
Cunniff, J. B.; Vouros, P.; Kaplan, D. L.; Fossey, S. A. The Origin and Ion of Non-covalent Peptide Dimers Observed in Liquid Secondary-Ion Mass-Spectometry Explained via First-Order Gas-Phase Kinetics. Biol. Mass Spectrom. 1994, 23, 741–748.
Ramirez, J.; He, F.; Lebrilla, C. B. Gas-Phase Chiral Differentiation of Amino Acid Guests Cyclodextrin Hosts. J. Am. Chem. Soc. 1998, 120, 7387–7388.
Li, Y. T.; Hsieh, Y. L.; Henion, J. D.; O’Cain, T. D.; Sciehser, G. A.; Ganem, B. Analysis of the Energetics of Gas-Phase Immunophilin-Ligand Complexes by Ion Spray Mass Spectrometry. J. Am. Chem. Soc. 1994, 116, 7487–7493.
Ramanathan, R.; Prokai, L. Electrospray Ionization Mass Spectrometric Study of Encapsulation of Amino Acids by Cyclodextrins. J. Am. Soc. Mass Spectrom. 1995, 6, 866–871.
Lorenz, S. A.; Maziarz, E. P., III; Wood, T. D. Using Solution Phase Hydrogen/Deutrium (H/D) Exchange to Determine the Origin of Non-Covalent Complexes Observed by Electrospray Ionization Mass Spectrometry; in Solution or in Vacuo. J. Am. Soc. Mass Spectrom. 2001, 12, 795–804.
Sun, W.; Cui, M.; Liu, S.; Song, F.; Elkin, N. Electrospray Ionization Mass Spectrometry of Incubated Solutions and in Eluates of Gel Permeation Chromatography. Rapid Commun. Mass Spectrom. 1998, 12, 2016–2022.
Amini, A.; Javerfalk, E.; Bastami, S.; Westerlund, D. Simultaneous Separation and Enantioresolution of Racemic Local Anesthetic Drugs by Capillary Zone Electrophoresis with Tween 20 and Methyl-β-Cyclodextrin as Selectors, Employing a Double Plug Technique. Electrophoresis 1999, 20, 204–211.
Valtcheva, L.; Mohammad, J.; Pettersson, G.; Hjerten, S. Chiral Separation of Beta-Blockers by High-Performance Capillary Electrophoresis Based on Non-Immobilized Cellulase as Enantioselective Protein. J. Chromatogr. 1993, 638, 263–267.
Tanaka, Y.; Terabe, S. Partial Separation Zone Technique for the Separation of Enantiomers by Affinity Electrokinetic Chromatography with Proteins as Chiral Pseudo-Stationary Phases. J. Chromatogr. A. 1995, 694, 277–284.
Amini, A.; Paulsen-Sorman, U. Enantioseparation of Local Anesthetic Drugs by Capillary Zone Electrophoresis with Cyclodextrins as Chiral Selector Using a Partial Filling Technique. Electrophoresis 1997, 18, 1019–1025.
Amini, A.; Wiserma, B.; Westerlund, D.; Paulsen-Sorman, U. Determination of the Enantiomeric Purity of S-Ropivacaine by Capillary Electrophoresis with Methyl-β-Cyclodextrin as Chiral Selector Using Conventional and Complete Filling Techniques. Eur. J. Pharm. Sci. 1999, 9, 17–24.
Amini, A.; Petterson, C.; Westerlund, D. Enantioresolution of Disopyramide by Capillary Affinity Electrokinetic Chromatography with Human α1-Acid Glycoprotein (AGP) as Chiral Selector Applying a Partial Filling Technique. Electrophoresis 1997, 18, 950–957.
Timothy, J.; Dann, G, III; Brown, A. P. Separation of Enantiomers Using Vancomycin in a Countercurrent Process by Suppression of Electroosmosis. Chirality 1996, 8, 77–83.
Kuhn, R.; Stoecklin, F.; Erni, F. Chiral Separations by Host-Guest Complexation With Cyclodextrin and Crown Ether in Capillary Zone Electrophoresis. Chromatographia 1992, 33, 32–36.
Camilleri, P. Capillary Electrophoresis Theory and Practice. CRC Press: London, 1993, p 129.
Chang, T. T.; Lay, J. O.; Francel, R. J. Electrokinetic Separations with Miceller Solutions and Open-Tubular Capillaries. Anal. Chem. 1984, 56, 111–113.
Kaneta, K.; Tanaka, S.; Taga, M.; Yoshida, H. Migration Behavior of Inorganic Anions in Micellar Electrokinetic Capillary Chromatography Using a Cationic Surfactant. Anal. Chem. 1992, 64, 798–801.
Haskins, N. J.; Saunders, M. R.; Camilleri, P. The Complexation and Chiral Selectivity of 2-Hydroxypropyl-β-cyclodextrin with Guest Molecules as Studied by Electrospray Mass Spectrometry. Rapid Commun. Mass Spectrom. 1994, 8, 423–426.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Al-nouti, Y., Bartlett, M.G. Comparison of local anesthetic-cyclodextrin non-covalent complexes using capillary electrophoresis and electrospray ionization mass spectrometry. J Am Soc Spectrom 13, 928–935 (2002). https://doi.org/10.1016/S1044-0305(02)00395-1
Received:
Revised:
Accepted:
Issue Date:
DOI: https://doi.org/10.1016/S1044-0305(02)00395-1