title: Novel benzophenone-3 derivatives with promising potential as UV filters: Relationship between structure, photoprotective potential and phototoxicity.
abstract: 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.
authors.affiliation: Department of Pharmaceutical Sciences, School of Pharmaceutical Sciences of Ribeirão Preto, University of São Paulo, 14040-903 Ribeirão Preto, SP, Brazil. Electronic address: mtpaezg@gmail.com.
authors.forename: María Teresa Páez
authors.initials: MT
authors.lastname: González
authors.affiliation: Department of Pharmaceutical Sciences, School of Pharmaceutical Sciences of Ribeirão Preto, University of São Paulo, 14040-903 Ribeirão Preto, SP, Brazil.
authors.forename: Fernando
authors.initials: F
authors.lastname: Fumagalli
authors.affiliation: Department of Pharmaceutical Sciences, School of Pharmaceutical Sciences of Ribeirão Preto, University of São Paulo, 14040-903 Ribeirão Preto, SP, Brazil.
authors.forename: Carolina Gomes
authors.initials: CG
authors.lastname: Benevenuto
authors.affiliation: Department of Pharmaceutical Sciences, School of Pharmaceutical Sciences of Ribeirão Preto, University of São Paulo, 14040-903 Ribeirão Preto, SP, Brazil.
authors.forename: Flavio
authors.initials: F
authors.lastname: da Silva Emery
authors.affiliation: Department of Pharmaceutical Sciences, School of Pharmaceutical Sciences of Ribeirão Preto, University of São Paulo, 14040-903 Ribeirão Preto, SP, Brazil. Electronic address: lorena@fcfrp.usp.br.
authors.forename: Lorena Rigo
authors.initials: LR
authors.lastname: Gaspar
mesh_terms: D001577:Benzophenones / Q000737:chemistry*; D001681:Biological Assay / Q000379:methods; D017484:Dermatitis, Phototoxic / Q000209:etiology*; D006860:Hydrogen Bonding; D009499:Neutral Red / Q000737:chemistry; D017382:Reactive Oxygen Species / Q000737:chemistry; D013473:Sunscreening Agents / Q000737:chemistry*; D014466:Ultraviolet Rays
chemical_list: D001577:Benzophenones; D017382:Reactive Oxygen Species; D013473:Sunscreening Agents; D009499:Neutral Red; C005290:oxybenzone
keywords: Benzophenone-3; Photostability; Phototoxicity; UV filters