Enantioselective separation of azole compounds by EKC. Reversal of migration order of enantiomers with CD concentration: research article

Authors
Castro Puyana, MaríaUniversity of Alcalá Author; Crego Navazo, Antonio LuisUniversity of Alcalá Author; Marina Alegre, María LuisaUniversity of Alcalá Author; García Ruiz, CarmenUniversity of Alcalá Author
Identifiers
Permanent link (URI): http://hdl.handle.net/10017/1345
DOI: 10.1002/elps.200600798
ISSN: 0173-0835
Publisher
John Wiley & Sons
Date
2007
Affiliation
Universidad de Alcalá. Departamento de Química Analítica e Ingeniería Química
Funders
The authors thank the Ministerio de Ciencia y Tecnología and the Ministerio de Educación y Ciencia (Spain) for research projects BQU2003-03638 and CTQ2006-03849/BQU, respectively. Authors also thank Johnson & Johnson (Beerse, Belgium) for the kind gift of terconazole racemate and pure 2R,4S-enantiomer of the ketoconazole. Carmen García-Ruiz thanks the Ministerio de Ciencia y Tecnología (Spain) for the Ramón y Cajal program (RYC-2003-001). María CastroPuyana thanks the University of Alcalá for her predoctoral grant
Bibliographic citation
Electrophoresis, 2007, v. 28, p. 2667-2674
Keywords
Apparent binding constants
Azole compounds
Enantioseparation
EKC
Project
BQU2003-03638 (Ministerio de Ciencia y Tecnología)
CTQ2006-03849/BQU (Ministerio de Educación y Ciencia)
RYC-2003-001 (Ministerio de Ciencia y Tecnología)
Document type
info:eu-repo/semantics/article
Version
info:eu-repo/semantics/publishedVersion
Publisher's version
http://dx.doi.org/10.1002/elps.200600798
Rights
© WILEY-VCH, 2007
Access rights
info:eu-repo/semantics/openAccess
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Abstract
The enantioselective separation of a group of six weak base azole compounds was achieved in this work using EKC with three neutral beta-CDs as chiral selectors. The native beta-CD and two other beta-CD derivatives with different types and positions of the substituents on the CD rim ((2-hydroxy)propyl-beta-CD (HP-beta-CD) and heptakis-2,3,6-tri-O-methyl-beta-CD (TM-beta-CD)) were employed. Apparent binding constants for each pair compound-CD were determined in order to study analyte-CD interactions. The best enantiomeric resolutions for miconazole, econazole, and sulconazole were observed with HP-beta-CD whereas for the separation of the enantiomers of ketoconazole, terconazole, and bifonazole, TM-beta-CD was the best chiral selector. The enantioseparations obtained were discussed on the basis of the structure of the compounds taking into account that inclusion into the hydrophobic CD cavity occurred through the phenyl ring closer to the azole group. In addition, a change in the migration order for the enantiomers of two of the compounds studied (ketoconazole and terconazole) with the concentration of HP-beta-CD was observed for the first time.
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