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Volumn 25, Issue 2, 2013, Pages 79-88

Comparative enantioseparation of ketoprofen with trimethylated α-, β-, and γ-cyclodextrins in capillary electrophoresis and study of related selector-selectand interactions using nuclear magnetic resonance spectroscopy

Author keywords

1D ROESY; capillary electrophoresis; cyclodextrins; enantiomer affinity pattern; ketoprofen; nuclear magnetic resonance spectroscopy; separation mechanism

Indexed keywords

ALPHA CYCLODEXTRIN; BETA CYCLODEXTRIN; CYCLODEXTRIN; GAMMA CYCLODEXTRIN; HEPTAKIS(2,3,6 O TRIMETHYL) BETA CYCLODEXTRIN; HEXAKIS(2,3,6 TRI O METHYL) ALPHA CYCLODEXTRIN; KETOPROFEN; OCTAKIS(2,3,6 TRI O METHYL) GAMMA CYCLODEXTRIN; PROTON; UNCLASSIFIED DRUG;

EID: 84872863095     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.22111     Document Type: Article
Times cited : (34)

References (30)
  • 1
    • 0035847239 scopus 로고    scopus 로고
    • Enantioseparations in capillary electromigration techniques: Recent developments and future trends
    • Chankvetadze B, Blaschke G,. Enantioseparations in capillary electromigration techniques: recent developments and future trends. J Chromatogr A 2001; 906: 309-363.
    • (2001) J Chromatogr A , vol.906 , pp. 309-363
    • Chankvetadze, B.1    Blaschke, G.2
  • 2
    • 4444353743 scopus 로고    scopus 로고
    • Combined approach using capillary electrophoresis and NMR spectroscopy for an understanding of enantioselective recognition mechanisms by cyclodextrins
    • Chankvetadze B,. Combined approach using capillary electrophoresis and NMR spectroscopy for an understanding of enantioselective recognition mechanisms by cyclodextrins. Rev Chem Soc 2004; 33: 337-347.
    • (2004) Rev Chem Soc , vol.33 , pp. 337-347
    • Chankvetadze, B.1
  • 3
    • 34748924126 scopus 로고    scopus 로고
    • Enantioseparations by using capillary electrophoretic techniques: The story of 20 and a few more years
    • Chankvetadze B,. Enantioseparations by using capillary electrophoretic techniques: the story of 20 and a few more years. J Chromatogr A 2007; 1168: 45-70.
    • (2007) J Chromatogr A , vol.1168 , pp. 45-70
    • Chankvetadze, B.1
  • 4
    • 0033657182 scopus 로고    scopus 로고
    • Enantioseparation of aminoglutethimide with cyclodextrins in capillary electrophoresis and studies of selector-selectand interactions using NMR spectroscopy and electrospray ionization mass spectrometry
    • Chankvetadze B, Fillet M, Burjanadze N, Bergenthal D, Bergander C, Luftmann H, Crommen J, Blaschke G,. Enantioseparation of aminoglutethimide with cyclodextrins in capillary electrophoresis and studies of selector-selectand interactions using NMR spectroscopy and electrospray ionization mass spectrometry. Enantiomer 5; 2000: 313-322.
    • (2000) Enantiomer , vol.5 , pp. 313-322
    • Chankvetadze, B.1    Fillet, M.2    Burjanadze, N.3    Bergenthal, D.4    Bergander, C.5    Luftmann, H.6    Crommen, J.7    Blaschke, G.8
  • 6
    • 0034646951 scopus 로고    scopus 로고
    • Mechanistic study of opposite migration order of dimethindene enantiomers in capillary electrophoresis in the presence of native β-CD and heptakis-(2,3,6-tri-O-methyl)-β-CD
    • Chankvetadze B, Pintore G, Burjanadze N, Bergenthal D, Bergander K, Breitkreutz J, Mühlenbrock C, Blaschke G,. Mechanistic study of opposite migration order of dimethindene enantiomers in capillary electrophoresis in the presence of native β-CD and heptakis-(2,3,6-tri-O-methyl)-β-CD. J Chromatogr A 2000; 875: 455-469.
    • (2000) J Chromatogr A , vol.875 , pp. 455-469
    • Chankvetadze, B.1    Pintore, G.2    Burjanadze, N.3    Bergenthal, D.4    Bergander, K.5    Breitkreutz, J.6    Mühlenbrock, C.7    Blaschke, G.8
  • 7
    • 0034647083 scopus 로고    scopus 로고
    • Separation of brompheniramine enantiomers by capillary electrophoresis and study of chiral recognition mechanisms of cyclodextrins using NMR-spectroscopy, UV-spectrometry, ESI-MS and x-ray crystallography
    • Chankvetadze B, Burjanadze N, Pintore G, Bergenthal D, Bergander K, Mühlenbrock C, Breitkreutz J, Blaschke G,. Separation of brompheniramine enantiomers by capillary electrophoresis and study of chiral recognition mechanisms of cyclodextrins using NMR-spectroscopy, UV-spectrometry, ESI-MS and x-ray crystallography. J Chromatogr A 2000; 875: 471-484.
    • (2000) J Chromatogr A , vol.875 , pp. 471-484
    • Chankvetadze, B.1    Burjanadze, N.2    Pintore, G.3    Bergenthal, D.4    Bergander, K.5    Mühlenbrock, C.6    Breitkreutz, J.7    Blaschke, G.8
  • 8
    • 0034795481 scopus 로고    scopus 로고
    • Mechanistic studies on the opposite migration order of clenbuterol enantiomers in capillary electrophoresis with β-CD and single-isomer heptakis(2,3-diacetyl-6-sulfo)-β-CD
    • Chankvetadze B, Lomsadze K, Bergenthal D, Breitkreutz J, Bergander K, Blaschke G,. Mechanistic studies on the opposite migration order of clenbuterol enantiomers in capillary electrophoresis with β-CD and single-isomer heptakis(2,3-diacetyl-6-sulfo)-β-CD. Electrophoresis 2001; 22: 3178-3184.
    • (2001) Electrophoresis , vol.22 , pp. 3178-3184
    • Chankvetadze, B.1    Lomsadze, K.2    Bergenthal, D.3    Breitkreutz, J.4    Bergander, K.5    Blaschke, G.6
  • 9
    • 77953066002 scopus 로고    scopus 로고
    • Separation of propranolol enantiomers by using capillary electrophoresis with various cyclodextrins: Comparative CE and NMR studies
    • Servais AC, Rousseau A, Fillet M, Lomsadze K, Salgado A, Crommen J, Chankvetadze B,. Separation of propranolol enantiomers by using capillary electrophoresis with various cyclodextrins: comparative CE and NMR studies. J Sep Sci 2010; 33: 1617-1624.
    • (2010) J Sep Sci , vol.33 , pp. 1617-1624
    • Servais, A.C.1    Rousseau, A.2    Fillet, M.3    Lomsadze, K.4    Salgado, A.5    Crommen, J.6    Chankvetadze, B.7
  • 10
    • 0030760710 scopus 로고    scopus 로고
    • Nature and design of enantiomer migration order in chiral capillary electrophoresis
    • Chankvetadze B, Schulte G, Blaschke G,. Nature and design of enantiomer migration order in chiral capillary electrophoresis. Enantiomer 1997; 2: 157-179.
    • (1997) Enantiomer , vol.2 , pp. 157-179
    • Chankvetadze, B.1    Schulte, G.2    Blaschke, G.3
  • 11
    • 0036868789 scopus 로고    scopus 로고
    • Enantiomer migration order in chiral capillary electrophoresis
    • Chankvetadze B,. Enantiomer migration order in chiral capillary electrophoresis. Electrophoresis 2002; 23: 4022-4035.
    • (2002) Electrophoresis , vol.23 , pp. 4022-4035
    • Chankvetadze, B.1
  • 12
    • 70350627333 scopus 로고    scopus 로고
    • Mathematical approach by a selectivity model for rationalization of pH- and selector concentration-dependent reversal of the enantiomer migration order in capillary electrophoresis
    • Hammitzsch-Wiedemann M, Scriba Gke,. Mathematical approach by a selectivity model for rationalization of pH- and selector concentration- dependent reversal of the enantiomer migration order in capillary electrophoresis. Anal Chem 2009; 81: 8765-8773.
    • (2009) Anal Chem , vol.81 , pp. 8765-8773
    • Hammitzsch-Wiedemann, M.1    Scriba, G.2
  • 14
    • 0036191642 scopus 로고    scopus 로고
    • Gastric toxicity of racemic ketoprofen and its enantiomers in rat: Oxygen radical generation and COX-expression
    • Alarcón de la Lastra C, Nieto A, Martin MJ, Cabré F, Herrerías JM, Motilva V,. Gastric toxicity of racemic ketoprofen and its enantiomers in rat: oxygen radical generation and COX-expression. Inflamm Res 2002; 51: 51-57.
    • (2002) Inflamm Res , vol.51 , pp. 51-57
    • Alarcón De La Lastra, C.1    Nieto, A.2    Martin, M.J.3    Cabré, F.4    Herrerías, J.M.5    Motilva, V.6
  • 16
    • 0037327270 scopus 로고    scopus 로고
    • Comparative study of analgesic efficacy and morphine-sparing effect of intramuscular dexketoprofen trometamol with ketoprofen or placebo after major orthopaedic surgery
    • Hanna MH, Elliott KM, Stuart-Taylor ME, Roberts DR, Buggy D, Arthurs GJ,. Comparative study of analgesic efficacy and morphine-sparing effect of intramuscular dexketoprofen trometamol with ketoprofen or placebo after major orthopaedic surgery. Br J Clin Pharmacol 2003; 55: 126-133.
    • (2003) Br J Clin Pharmacol , vol.55 , pp. 126-133
    • Hanna, M.H.1    Elliott, K.M.2    Stuart-Taylor, M.E.3    Roberts, D.R.4    Buggy, D.5    Arthurs, G.J.6
  • 17
    • 0000052374 scopus 로고    scopus 로고
    • Supramolecular photochemistry of 2-(3-benzoylphenyl)propionic acid (Ketoprofen). A study in the β-cyclodextrin cavity
    • Monti S, Sortino S, De Guidi G, Marconi G,. Supramolecular photochemistry of 2-(3-benzoylphenyl)propionic acid (Ketoprofen). A study in the β-cyclodextrin cavity. New J Chem 1998; 22: 599-604.
    • (1998) New J Chem , vol.22 , pp. 599-604
    • Monti, S.1    Sortino, S.2    De Guidi, G.3    Marconi, G.4
  • 18
    • 23044488711 scopus 로고    scopus 로고
    • Study of structural features and thermodynamic parameters, determining the chromatographic behaviour of drug-cyclodextrin complexes
    • Rozou S, Michaleas S, Antoniadou-Vyza E,. Study of structural features and thermodynamic parameters, determining the chromatographic behaviour of drug-cyclodextrin complexes. J Chromatogr A 2005; 1087: 86-94.
    • (2005) J Chromatogr A , vol.1087 , pp. 86-94
    • Rozou, S.1    Michaleas, S.2    Antoniadou-Vyza, E.3
  • 19
    • 78650732037 scopus 로고    scopus 로고
    • Stereoselective interaction of ketoprofen enantiomers with β-cyclodextrin: Ground state binding and photochemistry
    • Marconi G, Mezzina E, Manet I, Manoli F, Zambellic B, Monti S,. Stereoselective interaction of ketoprofen enantiomers with β-cyclodextrin: ground state binding and photochemistry. Photochem Photobiol Sci 2011; 10: 48-59.
    • (2011) Photochem Photobiol Sci , vol.10 , pp. 48-59
    • Marconi, G.1    Mezzina, E.2    Manet, I.3    Manoli, F.4    Zambellic, B.5    Monti, S.6
  • 20
    • 0028951162 scopus 로고
    • Use of cyclodextrins in capillary electrophoresis for the chiral resolution of some 2-arylpropionic acid non-steroidal anti-inflammatory drugs
    • Fanali S, Aturki Z,. Use of cyclodextrins in capillary electrophoresis for the chiral resolution of some 2-arylpropionic acid non-steroidal anti-inflammatory drugs. J Chromatogr A 1995; 694: 297-305.
    • (1995) J Chromatogr A , vol.694 , pp. 297-305
    • Fanali, S.1    Aturki, Z.2
  • 21
    • 0032498170 scopus 로고    scopus 로고
    • Separation of profen enantiomers by capillary electrophoresis using cyclodextrins as chiral selectors
    • Blanco M, Coello J, Iturriaga H, Maspoch S, Pérez-Maseda C,. Separation of profen enantiomers by capillary electrophoresis using cyclodextrins as chiral selectors. J Chromatogr A 1998; 793: 165-175.
    • (1998) J Chromatogr A , vol.793 , pp. 165-175
    • Blanco, M.1    Coello, J.2    Iturriaga, H.3    Maspoch, S.4    Pérez-Maseda, C.5
  • 22
    • 0032513194 scopus 로고    scopus 로고
    • Chiral and nonchiral determination of ketoprofen in pharmaceuticals by capillary zone electrophoresis
    • Blanco M, Coello J, Iturriaga H, Maspoch S, Pérez-Maseda C,. Chiral and nonchiral determination of ketoprofen in pharmaceuticals by capillary zone electrophoresis. J Chromatogr A 1998; 799: 301-307.
    • (1998) J Chromatogr A , vol.799 , pp. 301-307
    • Blanco, M.1    Coello, J.2    Iturriaga, H.3    Maspoch, S.4    Pérez-Maseda, C.5
  • 23
    • 0346372542 scopus 로고    scopus 로고
    • Enantiomeric purity determination of ketoprofen by capillary electrophoresis: Development and validation of the method
    • Blanco M, González JM, Torras E, Valverde I,. Enantiomeric purity determination of ketoprofen by capillary electrophoresis: development and validation of the method. Anal Bioanal Chem 2003; 375: 157-163.
    • (2003) Anal Bioanal Chem , vol.375 , pp. 157-163
    • Blanco, M.1    González, J.M.2    Torras, E.3    Valverde, I.4
  • 24
    • 0036499466 scopus 로고    scopus 로고
    • Prediction of selectivity for enantiomeric separations of uncharged compounds by capillary electrophoresis involving dual cyclodextrin systems
    • Abushoffa AM, Fillet M, Hubert P, Crommen J,. Prediction of selectivity for enantiomeric separations of uncharged compounds by capillary electrophoresis involving dual cyclodextrin systems. J Chromatogr A 2002; 948: 321-329.
    • (2002) J Chromatogr A , vol.948 , pp. 321-329
    • Abushoffa, A.M.1    Fillet, M.2    Hubert, P.3    Crommen, J.4
  • 25
    • 0032928628 scopus 로고    scopus 로고
    • Enantiomeric resolution of some nonsteroidal antiinflammatory and anticoagulant drugs using β-cyclodextrins by capillary electrophoresis
    • Zhu X, Lin B, Epperlein U, Koppenhoefer B,. Enantiomeric resolution of some nonsteroidal antiinflammatory and anticoagulant drugs using β-cyclodextrins by capillary electrophoresis. Chirality 1999; 11: 56-62.
    • (1999) Chirality , vol.11 , pp. 56-62
    • Zhu, X.1    Lin, B.2    Epperlein, U.3    Koppenhoefer, B.4
  • 26
    • 0346504132 scopus 로고    scopus 로고
    • Simultaneous chiral discrimination of multiple profens by cyclodextrin-modified capillary electrophoresis in normal and reversed polarity modes
    • La S, Kim J, Kim JH, Goto J, Kim KR,. Simultaneous chiral discrimination of multiple profens by cyclodextrin-modified capillary electrophoresis in normal and reversed polarity modes. Electrophoresis 2003; 24: 2642-2649.
    • (2003) Electrophoresis , vol.24 , pp. 2642-2649
    • La, S.1    Kim, J.2    Kim, J.H.3    Goto, J.4    Kim, K.R.5
  • 27
    • 4544333142 scopus 로고    scopus 로고
    • Enantiomeric resolution of 2-arylpropionic acid nonsteroidal anti-inflammatory drugs by capillary electrophoresis: Methods and applications
    • Patel BK, Hanna-Brown M, Hadley MR, Hutt AJ,. Enantiomeric resolution of 2-arylpropionic acid nonsteroidal anti-inflammatory drugs by capillary electrophoresis: methods and applications. Electrophoresis 2004; 25: 2625-2656.
    • (2004) Electrophoresis , vol.25 , pp. 2625-2656
    • Patel, B.K.1    Hanna-Brown, M.2    Hadley, M.R.3    Hutt, A.J.4
  • 28
    • 0032080489 scopus 로고    scopus 로고
    • HPLC determination of ketoprofen enantiomers in human serum using a nonporous octadecylsilane 1.5 mm column with hydroxypropyl β-cyclodextrin as mobile phase additive
    • Ameyibor E, Stewart JT,. HPLC determination of ketoprofen enantiomers in human serum using a nonporous octadecylsilane 1.5 mm column with hydroxypropyl β-cyclodextrin as mobile phase additive. J Pharm Biomed Anal 1998; 17: 83-88.
    • (1998) J Pharm Biomed Anal , vol.17 , pp. 83-88
    • Ameyibor, E.1    Stewart, J.T.2
  • 29
    • 5144229966 scopus 로고
    • Practical aspects of two-dimensional transverse NOE spectroscopy
    • Bax A, Davis DG,. Practical aspects of two-dimensional transverse NOE spectroscopy. J Magn Reson 1985; 63: 207-213.
    • (1985) J Magn Reson , vol.63 , pp. 207-213
    • Bax, A.1    Davis, D.G.2
  • 30
    • 0001263889 scopus 로고
    • Cross relaxation without TOCSY: Transverse rotating-frame Overhauser effect spectroscopy
    • Hwang TL, Shaka AJ,. Cross relaxation without TOCSY: transverse rotating-frame Overhauser effect spectroscopy. J Am Chem Soc 1992; 114: 3157-3159.
    • (1992) J Am Chem Soc , vol.114 , pp. 3157-3159
    • Hwang, T.L.1    Shaka, A.J.2


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