Trajectory of the spectral/structural rearrangements for photo-oxidative reaction of neat ketoprofen and its cyclodextrin complex

• Published in: Journal of inclusion phenomena and macrocyclic chemistry 2022-10, Vol.102 (9-10), p.791-800
• Main Authors: Hiroshige, Ryosuke, Goto, Satoru, Tsunoda, Chihiro, Ichii, Risa, Shimizu, Shota, Otsuka, Yuta, Makino, Kosho, Takahashi, Hideyo, Yokoyama, Hideshi
• Format: Article
• Language: English
• Subjects: Chemistry; Chemistry and Materials Science; Crystallography and Scattering Methods; Cyclodextrins; Decarboxylation; Food Science; Irradiation; Ketoprofen; Organic Chemistry; Original Article; Photodegradation; Photolysis; Photosensitivity; Singular value decomposition; Trajectory analysis; Ultraviolet radiation; Vector spaces
• ISSN: 1388-3127; 1573-1111
• DOI: 10.1007/s10847-022-01160-3

Ketoprofen is a nonsteroidal anti-inflammatory drug used as mohrus tape which causes unwanted photosensitivity due to UV irradiation. In addition, photodegradation of ketoprofen induces its decarboxylation. Here, we aim to determine the effect of cyclodextrin on the photolysis of ketoprofen. Separation technique using HPLC confirmed that UV irradiation of ketoprofen produced multiple products. A unique reaction proceeded in the presence of β-cyclodextrin. Furthermore, characterization by UV spectroscopy was performed, and the obtained spectra were analyzed using singular value decomposition. By analyzing the trajectory of the singular vector space, we were able to reflect the difference in the reaction pathway of ketoprofen with and without cyclodextrin. This study uses a singular value decomposition analysis, which is useful as a novel approach for solutions of radical reactions and a promising technique for analysis of radical reactions in the future. Graphical abstract