Towards symmetry driven and nature inspired UV filter design
Towards symmetry driven and nature inspired UV filter design
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DOI：
10.1038/s41467-019-12719-z
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发表时间：
2019-10-18
影响因子：
16.6
通讯作者：
Stavros, Vasilios G.
中科院分区：
文献类型：
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作者：
Horbury, Michael D.;Holt, Emily L.;Stavros, Vasilios G.
在植物中，芥子酸酯提供了至关重要的保护，免受紫外线辐射暴露的有害影响。这些酯是设计紫外线过滤剂的有前途的基础，特别是对于UVA区域（400 - 315 nm），其中目前缺乏足够的光保护。虽然芥子酸酯由于顺-反（反之亦然）光异构化而具有高度光稳定性，但顺式异构体可显示出增加的遗传毒性;这是目前基于肉桂酸酯的人类防晒剂的令人担忧的问题。为了消除这种可能性，在这里，我们合成了芥子酯与等效的顺式和反式异构体。我们通过创新的超快光谱学在皮肤模拟物上研究其光稳定性，从而模拟接近防晒配方的真实环境。这些研究通过评估内分泌干扰活性和抗氧化潜力来补充。从我们的研究结果来看，对称官能化芥子酸酯可能在下一代防晒制剂中显示出作为自然启发的UV过滤剂的特殊前景。
In plants, sinapate esters offer crucial protection from the deleterious effects of ultraviolet radiation exposure. These esters are a promising foundation for designing UV filters, particularly for the UVA region (400 - 315 nm), where adequate photoprotection is currently lacking. Whilst sinapate esters are highly photostable due to a cis-trans (and vice versa) photoisomerization, the cis-isomer can display increased genotoxicity; an alarming concern for current cinnamate ester-based human sunscreens. To eliminate this potentiality, here we synthesize a sinapate ester with equivalent cis- and trans-isomers. We investigate its photostability through innovative ultrafast spectroscopy on a skin mimic, thus modelling the as close to true environment of sunscreen formulas. These studies are complemented by assessing endocrine disruption activity and antioxidant potential. We contest, from our results, that symmetrically functionalized sinapate esters may show exceptional promise as nature-inspired UV filters in next generation sunscreen formulations.