Spectroscopic studies for the inclusion complexation of ketoprofen enantiomers with β-cyclodextrin
Document Type
Article
Publication Date
1-1-2020
Abstract
Inclusion complexes of R-ketoprofen and S-ketoprofen enantiomers with β-cyclodextrin (β-CD) in aqueous solution were studied using various spectroscopic techniques such as Raman, FTIR, UV and fluorescence. The different relative intensities and characteristic band shifts of the two enantiomers from Raman spectra suggests different interaction when complexed with β-CD. Raman experiments revealed a noticeable diminishing of the C[dbnd]C vibration and ring deformation, which indicate the embedding of ketoprofen inside the β-CD cavity. It's revealed that distinct differences between R- and S-ketoprofen in the presence of β-CD at neutral pH. The stoichiometry ratio and binding constant of the inclusion complexes were calculated using Benesi–Hildebrand plot. Both enantiomers showed stoichiometry ratio of 1:1 inclusion complex with β-CD. The binding constant of R-ketoprofen (4088 M−1) is higher than S-ketoprofen (2547 M−1). These values indicated that β-CD formed inclusion complexes more preferentially with R-ketoprofen than S-ketoprofen. Results demonstrated that β-CD can be used as a promising chiral selector for ketoprofen enantiomers. © 2020 Elsevier B.V.
Keywords
Inclusion complexes, Spectrophotometry, β-Cyclodextrin, Ketoprofen enantiomers, Chiral recognition
Divisions
CHEMISTRY
Funders
Fundamental Research Grant Scheme, Ministry of Higher Education ( MOHE ), Malaysia ( FP033-2019A )
Publication Title
Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy
Volume
241
Publisher
Elsevier