Novel benzophenone-3 derivatives with promising potential as UV filters: Relationship between structure, photoprotective potential and phototoxicity

Autor(es)

Paez Gonzalez, Maria Teresa ; Fumagalli, Fernando ; Benevenuto, Carolina Gomes ; Emery, Flavio da Silva ; Gaspar, Lorena Rigo

• Tipo de documento: Artigo Científico
• Fonte: European Journal of Pharmaceutical Sciences; v. 101, p. 200-210, APR 1 2017.
• Citações Web of Science: 4

Resumo

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 B-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. (C) 2017 Elsevier B.V. All rights reserved. (AU)

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