Planejamento, síntese e avaliação in vitro de derivados triazínicos úteis como filtros solares
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Data
2018-01-26
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Universidade Estadual Paulista (Unesp)
Resumo
O desenvolvimento do câncer de pele e o fotoenvelhecimento estão diretamente associados à exposição dos indivíduos à radiação ultravioleta (UV) de modo excessivo e sem a proteção adequada. Os filtros solares são conhecidamente capazes de proteger a pele contra os efeitos nocivos dessa radiação. Apesar disso, os filtros solares ainda apresentam limitações justificando a pesquisa de substâncias mais efetivas e seguras. Este trabalho teve como objetivo o planejamento, a síntese e a avaliação de novos filtros com capacidade ampliada de proteção contra as radiações UVA e UVB, associado a propriedades antioxidantes, obtidos através da estratégia de triplicação molecular tendo como protótipo as moléculas do resveratrol e ethylhexyl triazone. Foram sintetizados, isolados e caracterizados oito substâncias inéditas (FSN-1 a FSN-8). Todas as substâncias fundiram em temperaturas acima de 218°C, significativamente superior ao padrão ethylhexyl triazone (119,99°C), sendo FSN-2 e FSN-7 as substâncias que apresentaram menor e maior temperatura de decomposição, respectivamente (FSN-2: 236,25°C; FSN-7: 326,22°C). Todas as substâncias apresentaram atividade antioxidante, sendo a substância FSN-8 a mais ativa em relação às demais substâncias sintetizadas e aos padrões de resveratrol e ethylhexyl triazone. Embora todas as substâncias tenham comprimento de onda máximo na região espectral UVB, os resultados obtidos no ensaio in vitro de atividade fotoprotetora demonstraram capacidade protetora também contra radiação UVA para todas as substâncias sintetizadas. A substância mais ativa quanto a capacidade fotoprotetora foi a FSN-3, que exibiu valores de FPS de 17 e FPUVA de 13. As substâncias FSN-7 (FPS 14; FPUVA 7) e FSN-1 (FPS 9; FPUVA 5) também merecem destaque, apresentando capacidade fotoprotetora mais efetiva em relação aos padrões resveratrol (FPS 2; FPUVA 2) e ethylhexyl triazone (FPS 3; FPUVA 3). Estes resultados permitiram identificar novos filtros solares com espectro ampliado de proteção UV, úteis para prevenção do câncer de pele e fotoenvelhecimento.
The development of skin cancer and photoaging are directly associated with exposure to ultraviolet (UV) radiation without adequate protection. Sunscreens are known to be able to protect the skin against the harmful effects of such radiation. Despite this, sunscreen still exhibits limitations justifying the research for more effective and safe compounds. The aim of this work was design, synthesize and evaluate new sunscreens possessing wide protection against UVA and UVB, associated with antioxidant properties, obtained through molecular triplication strategy, using resveratrol and ethylhexyl triazone as prototype molecules. Eight novel substances (FSN-1 - FSN-8) were synthesized, isolated and characterized. All synthesized substances melted at temperatures above 218°C, significantly higher than ethylhexyl triazone (119.99°C). FSN-2 and FSN-7 presented, respectively, the lowest and the highest decomposition temperatures (FSN-2: 236,25°C; FSN-7: 326,22°C). All synthesized substances have exhibited antioxidant effect and FSN-8 has exhibited antioxidant effect superior than resveratrol, ethylhexyl triazone and the other substances. All synthesized substances exhibited maximum wavelength at UVB spectral region, and they also showed a protective activity against UVA radiation in photoprotection in vitro assay. FSN-3 was the most active susncreen (SPF 17; UVAPF 13). FSN-7 (SPF 14, UVAPF 7) and FSN-1 (SPF 9; UVAPF 5) also should be highlighted, presenting more photoprotection ability than resveratrol (SPF 2 and UVAPF 2) and ethylhexyltriazone (SPF 3 and UVAPF 3). All these results allowed the identification of new sunscreens with wide spectra against UV radiation useful to prevent skin cancer and photoaging.
The development of skin cancer and photoaging are directly associated with exposure to ultraviolet (UV) radiation without adequate protection. Sunscreens are known to be able to protect the skin against the harmful effects of such radiation. Despite this, sunscreen still exhibits limitations justifying the research for more effective and safe compounds. The aim of this work was design, synthesize and evaluate new sunscreens possessing wide protection against UVA and UVB, associated with antioxidant properties, obtained through molecular triplication strategy, using resveratrol and ethylhexyl triazone as prototype molecules. Eight novel substances (FSN-1 - FSN-8) were synthesized, isolated and characterized. All synthesized substances melted at temperatures above 218°C, significantly higher than ethylhexyl triazone (119.99°C). FSN-2 and FSN-7 presented, respectively, the lowest and the highest decomposition temperatures (FSN-2: 236,25°C; FSN-7: 326,22°C). All synthesized substances have exhibited antioxidant effect and FSN-8 has exhibited antioxidant effect superior than resveratrol, ethylhexyl triazone and the other substances. All synthesized substances exhibited maximum wavelength at UVB spectral region, and they also showed a protective activity against UVA radiation in photoprotection in vitro assay. FSN-3 was the most active susncreen (SPF 17; UVAPF 13). FSN-7 (SPF 14, UVAPF 7) and FSN-1 (SPF 9; UVAPF 5) also should be highlighted, presenting more photoprotection ability than resveratrol (SPF 2 and UVAPF 2) and ethylhexyltriazone (SPF 3 and UVAPF 3). All these results allowed the identification of new sunscreens with wide spectra against UV radiation useful to prevent skin cancer and photoaging.
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Palavras-chave
Filtros solares, Fotoproteção, Resveratrol, Sunscreen, Photoprotection