Study on the separation of ofloxacin enantiomers by hydroxyl-propyl-β-cyclodextrin as a chiral selector in capillary electrophoresis: a computational approach

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• 作者：FakhrEldin O. Suliman ; Abdalla A. Elbashir…
• 关键词：Ofloxacin ; Enantioseparation ; Capillary electrophoresis ; Molecular dynamics ; PM7
• 刊名：Journal of Inclusion Phenomena and Macrocyclic Chemistry
• 出版年：2015
• 出版时间：October 2015
• 年：2015
• 卷：83
• 期：1-2
• 页码：119-129
• 全文大小：2,398 KB
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  24.Li, W., Liu, C., Tan, G.,
• 作者单位：FakhrEldin O. Suliman (1)
  Abdalla A. Elbashir (2)
  Oliver J. Schmitz (3)
  
  1. Department of Chemistry, College of Science, Sultan Qaboos University, Box 36, Al-Khod 123, Muscat, Oman
  2. Department of Chemistry, Faculty of Science, University of Khartoum, Box 321, Khartoum, Sudan
  3. Applied Analytical Chemistry, Faculty of Chemistry, University of Duisburg-Essen, Essen, Germany
  
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Organic Chemistry
  Food Science
  Crystallography
  
• 出版者：Springer Netherlands
• ISSN：1573-1111

文摘

Hydroxypropyl-β-cyclodextrin (HPβCD) has been used successfully as a chiral additive to separate ofloxacin (OFL) enantiomers in a capillary electrophoresis system. Using electrospray-mass spectrometry (ESI–MS) it was revealed that OFL forms an inclusion complex with HPβCD at 1:1 stoichiometry. The interaction of the enantiomers with the host was further investigated by molecular modeling using molecular mechanics dockings, PM7 semiempirical calculations and molecular dynamics simulations. Calculations using PM7 semiempirical methods indicated that the separation is brought about by a large difference in the binding energies (??E) of 15 kcal mol? between R-OFL-HPβCD and S-OFL-HPβCD inclusion complexes. S-OFL was predicted to be eluted first by the PM7 method which corroborates the experimental results. Moreover, the molecular dynamic simulations show that the formation of stable R-OFL-HPβCD is because it is more deeply inserted into the cavity of the host. The study also revealed the absence of the role of strong hydrogen bonding in the enantioseparations. Keywords Ofloxacin Enantioseparation Capillary electrophoresis Molecular dynamics PM7