Spectroscopic studies for the inclusion complexation of ketoprofen enantiomers with β-cyclodextrin

• Main Authors: Obaid, Asma, Jamil, Arniza Khairani Mohd, Prabu, Samikannu, Saharin, Siti Munirah, Mohamad, Sharifah
• Format: Article
• Published: Elsevier 2020
• Subjects: Q Science (General); QD Chemistry
• Online Access: http://eprints.um.edu.my/25506/; https://doi.org/10.1016/j.saa.2020.118674
• Institution: Universiti Malaya

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.