Influence of complexation with cyclodextrins on photo-induced free radical production by the common sunscreen agents octyl-dimethylaminobenzoate and octyl-methoxycinnamate
Molinari, A.; Tursilli, R.; Casolari, A.; Maldotti, A.; Scalia, S.
Die Pharmazie 61(1): 41-45
2006
ISSN/ISBN: 0031-7144 PMID: 16454205 Document Number: 601001
The influence of complexation with hydroxypropyl-beta-cyclodextrin (HP-beta-CD) or beta-cyclodextrin (beta-CD) on the photo-induced production of free radicals by the sunscreen agents octyl-dimethylaminobenzoate (ODAB), oxybenzone (OB) and octyl-methoxycinnamate (OMC) was investigated. The formation of radical species during irradiation was detected by spin-trapping electron paramagnetic resonance (EPR) spectroscopy. 2,2,6,6-tetramethylpiperidine-1-oxyl, nitroxide radical (TEMPO) and 5,5-dimethyl-1-pyrroline-N-oxide (DMPO) were used a spin-traps. Following the 4-h illumination with simulated sunlight, OB did not generate radicals. On the other hand, photoexcitation of solutions containing ODAB or OMC produced a marked decrease (> 40%) of the TEMPO signal intensity, demonstrating the formation of carbon-centred radicals. In addition, the results obtained on irradiation of ODAB solutions containing DMPO as spin-trap indicated the generation of oxygen-centred radicals. Complexation of ODAB with HP-beta-CD and OMC with beta-CD markedly inhibited (> 64%) the formation of free radicals generated by the sunscreens on exposure to simulated sunlight. Therefore, inclusion of ODAB and OMC into the cyclodextrin cavities minimizes their photosensitising potential.