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Spectroscopic studies for the inclusion complexation of ketoprofen enantiomers with β-cyclodextrin.
Spectrochim Acta A Mol Biomol Spectrosc. 2020 Jul 02; 241:118674.SA

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 CC 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.

Authors+Show Affiliations

Department of Chemistry, Faculty of Science, University of Malaya, Kuala Lumpur 50603, Malaysia; Department of Chemistry, Faculty of Science, Jazan University, Jazan 45142, Saudi Arabia.Department of Chemistry, Faculty of Science, University of Malaya, Kuala Lumpur 50603, Malaysia.Department of Chemistry, Faculty of Science, University of Malaya, Kuala Lumpur 50603, Malaysia.Department of Chemistry, Faculty of Science, University of Malaya, Kuala Lumpur 50603, Malaysia.Department of Chemistry, Faculty of Science, University of Malaya, Kuala Lumpur 50603, Malaysia; Centre for Ionic Liquids, Department of Chemistry, Faculty of Science, University of Malaya, Kuala Lumpur 50603, Malaysia. Electronic address: sharifahm@um.edu.my.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

32652287

Citation

Obaid, Asma, et al. "Spectroscopic Studies for the Inclusion Complexation of Ketoprofen Enantiomers With Β-cyclodextrin." Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy, vol. 241, 2020, p. 118674.
Obaid A, Jamil AKM, Prabu S, et al. Spectroscopic studies for the inclusion complexation of ketoprofen enantiomers with β-cyclodextrin. Spectrochim Acta A Mol Biomol Spectrosc. 2020;241:118674.
Obaid, A., Jamil, A. K. M., Prabu, S., Saharin, S. M., & Mohamad, S. (2020). Spectroscopic studies for the inclusion complexation of ketoprofen enantiomers with β-cyclodextrin. Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy, 241, 118674. https://doi.org/10.1016/j.saa.2020.118674
Obaid A, et al. Spectroscopic Studies for the Inclusion Complexation of Ketoprofen Enantiomers With Β-cyclodextrin. Spectrochim Acta A Mol Biomol Spectrosc. 2020 Jul 2;241:118674. PubMed PMID: 32652287.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Spectroscopic studies for the inclusion complexation of ketoprofen enantiomers with β-cyclodextrin. AU - Obaid,Asma, AU - Jamil,Arniza Khairani Mohd, AU - Prabu,Samikannu, AU - Saharin,Siti Munirah, AU - Mohamad,Sharifah, Y1 - 2020/07/02/ PY - 2020/03/21/received PY - 2020/06/22/revised PY - 2020/06/26/accepted PY - 2020/7/12/pubmed PY - 2020/7/12/medline PY - 2020/7/12/entrez KW - Chiral recognition KW - Inclusion complexes KW - Ketoprofen enantiomers KW - Spectrophotometry KW - β-Cyclodextrin SP - 118674 EP - 118674 JF - Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy JO - Spectrochim Acta A Mol Biomol Spectrosc VL - 241 N2 - 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 CC 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. SN - 1873-3557 UR - https://www.unboundmedicine.com/medline/citation/32652287/Spectroscopic_studies_for_the_inclusion_complexation_of_ketoprofen_enantiomers_with_β-cyclodextrin L2 - https://linkinghub.elsevier.com/retrieve/pii/S1386-1425(20)30653-3 DB - PRIME DP - Unbound Medicine ER -
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