Sunscreen-Based Photocages for Topical Drugs: A Photophysical and Photochemical Study of A Diclofenac-Avobenzone Dyad.
Sunscreen-Based Photocages for Topical Drugs: A Photophysical and Photochemical Study of A Diclofenac-Avobenzone Dyad.
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DOI：
10.3390/molecules23030673
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发表时间：
2018-03-16
期刊：
影响因子：
--
通讯作者：
Lhiaubet-Vallet V
中科院分区：
文献类型：
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作者：
Aparici-Espert I;Miranda MA;Lhiaubet-Vallet V
药物光敏化是现代生活中日益重要的问题。这种现象发生在皮肤中的化学物质暴露在阳光下时。据报道，光敏药物会导致严重的皮肤皮炎，事实上，通常建议避免日光浴并涂抹防晒霜。在这种情况下，非甾体抗炎药（NSAID）双氯芬酸是一种光敏药物，特别是以局部形式给药时。在这项工作中，已经努力设计和研究一种创新的前药/前过滤系统，含有双氯芬酸和UVA过滤阿伏苯宗，以开发这种局部药物的更安全的使用。该设计是基于阿伏苯宗结构中存在一个公认的光可去除的苯甲酰甲基。通过紫外可见分光光度法和HPLC监测的二联体在氢供体溶剂中的稳态光解证实了双氯芬酸和阿伏苯宗的同时光释放。激光闪光光解和磷光发射实验使我们能够深入了解二联体的光敏三重激发态性质。最后，它表明，阿伏苯宗提供部分光保护双氯芬酸从光环化咔唑衍生物。
Photosensitization by drugs is a problem of increasing importance in modern life. This phenomenon occurs when a chemical substance in the skin is exposed to sunlight. Photosensitizing drugs are reported to cause severe skin dermatitis, and indeed, it is generally advised to avoid sunbathing and to apply sunscreen. In this context, the nonsteroidal anti-inflammatory drug (NSAID) diclofenac is a photosensitive drug, especially when administered in topical form. In this work, efforts have been made to design and study an innovative pro-drug/pro-filter system containing diclofenac and the UVA filter avobenzone in order to develop a safer use of this topical drug. The design is based on the presence of a well-established photoremovable phenacyl group in the avobenzone structure. Steady-state photolysis of the dyad in hydrogen-donor solvents, monitored by UV-Vis spectrophotometry and HPLC, confirms the simultaneous photorelease of diclofenac and avobenzone. Laser flash photolysis and phosphorescence emission experiments allow us to gain insight into the photoactive triplet excited-state properties of the dyad. Finally, it is shown that avobenzone provides partial photoprotection to diclofenac from photocyclization to carbazole derivatives.