González María Teresa Páez, Fumagalli Fernando, Benevenuto Carolina Gomes, da Silva Emery Flavio, Gaspar Lorena Rigo
Department of Pharmaceutical Sciences, School of Pharmaceutical Sciences of Ribeirão Preto, University of São Paulo, 14040-903 Ribeirão Preto, SP, Brazil.
Department of Pharmaceutical Sciences, School of Pharmaceutical Sciences of Ribeirão Preto, University of São Paulo, 14040-903 Ribeirão Preto, SP, Brazil.
Eur J Pharm Sci. 2017 Apr 1;101:200-210. doi: 10.1016/j.ejps.2017.02.014. Epub 2017 Feb 10.
Benzophenone-3 (BP-3) is a UV filter with absorption at the UVB and UVA wavelengths which has not been extensively studied in experiments involving its absorbing effects and toxicity. We synthetized four BP-3 derivatives and characterized their photoprotective potential by UV absorption and photodegradation, their phototoxicity potential by 3T3 Neutral Red Uptake (3T3 NRU PT) and their photoreactivity by the reactive oxygen species (ROS) assay. The UV absorption, photodegradation, phototoxicity and photoreactivity of the four BP-3 derivatives (BP-3 carbonate, BP-3 carbazole, BP-3 phenylamine and BP-3 methoxy-phenylamine) were evaluated and compared to those of BP-3. Results showed that all derivatives were photostable, except BP-3 carbonate, which did not absorb in the UVA range. BP-3 phenylamine and BP-3 methoxy-phenylamine were considered non-phototoxic and weakly photoreactive in the ROS assay, while the carbazole derivative was considered phototoxic and non-photoreactive due to its rigid structure. The UV spectra of BP-3 carbonate, BP-3 phenylamine and BP-3 methoxy-phenylamine showed the influence of hydrogen bonding on their UV absorption. Based on these results, we concluded that BP-3 phenylamine and BP-3 methoxy-phenylamine could be promising UVA filters.
二苯甲酮-3（BP-3）是一种紫外线滤过剂，可在UVB和UVA波长处吸收紫外线，但其吸收效应和毒性在实验中尚未得到广泛研究。我们合成了四种BP-3衍生物，并通过紫外线吸收和光降解来表征它们的光保护潜力，通过3T3中性红摄取试验（3T3 NRU PT）来表征它们的光毒性潜力，通过活性氧（ROS）测定来表征它们的光反应性。对四种BP-3衍生物（BP-3碳酸酯、BP-3咔唑、BP-3苯胺和BP-3甲氧基苯胺）的紫外线吸收、光降解、光毒性和光反应性进行了评估，并与BP-3进行了比较。结果表明，除了在UVA范围内不吸收的BP-3碳酸酯外，所有衍生物都具有光稳定性。在ROS测定中，BP-3苯胺和BP-3甲氧基苯胺被认为无光毒性且光反应性较弱，而咔唑衍生物由于其刚性结构被认为具有光毒性且无光反应性。BP-3碳酸酯、BP-3苯胺和BP-3甲氧基苯胺的紫外光谱显示了氢键对其紫外线吸收的影响。基于这些结果，我们得出结论，BP-3苯胺和BP-3甲氧基苯胺可能是有前景的UVA滤过剂。
