Mechanistic study on the opposite migration order of clenbuterol enantiomers in capillary electrophoresis with beta-cyclodextrin and single-isomer heptakis(2,3-diacetyl-6-sulfo)-beta-cyclodextrin.
Opposite migration order was observed for the enantiomers of the chiral beta2-adrenergic drug clenbuterol (CL) in capillary electrophoresis (CE) when resolved with native beta-cyclodextrin (beta-CD) and heptakis (2,3-diacetyl-6-sulfo)-beta-CD (HDAS-beta-CD). The possible mechanisms of the affinity reversal of the CL enantiomers depending on the structure of the CD were studied using 1H-nuclear magnetic resonance (1H-NMR) spectrometry and one-dimensional rotating frame nuclear Overhauser and exchange spectrometry (1-D ROESY). Significant differences were observed between the structure of the (+/-)-CL complexes with beta-CD and HDAS-beta-CD.
Chankvetadze
B
B
Institute of Pharmaceutical Chemistry, University of Münster, Germany.
Lomsadze
K
K
Bergenthal
D
D
Breitkreutz
J
J
Bergander
K
K
Blaschke
G
G
D002976:Clenbuterol / Q000737:chemistry* / Q000302:isolation & purification; D003505:Cyclodextrins / Q000737:chemistry; D019075:Electrophoresis, Capillary / Q000379:methods*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D012996:Solutions; D013237:Stereoisomerism; D047392:beta-Cyclodextrins
D003505:Cyclodextrins; D007202:Indicators and Reagents; D012996:Solutions; D047392:beta-Cyclodextrins; C447200:heptakis(2,3-diacetyl-6-sulfo)-cyclodextrin; C031215:betadex; D002976:Clenbuterol