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

Texto completo
Autor(es):
Paez Gonzalez, Maria Teresa ; Fumagalli, Fernando ; Benevenuto, Carolina Gomes ; Emery, Flavio da Silva ; Gaspar, Lorena Rigo
Número total de Autores: 5
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)

Processo FAPESP: 12/20990-2 - Agentes anti-infecciosos: uma evolução dos estudos químico-medicinais de naftotiazóis leishmanicidas e a busca de novos agentes tuberculostáticos
Beneficiário:Flavio da Silva Emery
Linha de fomento: Auxílio à Pesquisa - Regular
Processo FAPESP: 10/00086-4 - Avaliação do potencial fotoprotetor de novos filtros solares de origem marinha: estudo da fotoestabilidade, fototoxicidade, potencial alergênico e performance
Beneficiário:Lorena Rigo Gaspar Cordeiro
Linha de fomento: Auxílio à Pesquisa - Regular