Planejamento, síntese, caracterização e avaliação toxicológica de um novo composto candidato a protótipo de fotoprotetor orgânico – LQFM184

• Autor(a) principal: Vinhal, Daniela Cristina
• Data de Publicação: 2016
• Tipo de documento: Tese
• Idioma: por
• Título da fonte: Repositório Institucional da UFG
• Texto Completo: http://repositorio.bc.ufg.br/tede/handle/tede/6394
• topic: Câncer de pele; Radiação ultravioleta; Absorbância; Filtro solar; Triazina; LQFM184; Skin cancer; Ultraviolet radiation; Absorbance; Sunscreen; Triazine; LQFM184; CIENCIAS BIOLOGICAS::FARMACOLOGIA

In Brazil, the estimates for the year 2016 point to approximately 596,000 new cases of skin cancer, being mostly related to exposure to ultraviolet radiation. According to current consensus, such damage can be minimized by prophylactic use of sunscreens. This way, this study proposes the planning, synthesis, structural characterization and toxicological assessment of a new candidate compound to organic sunscreen, LQFM184 (20). The structural planning was based both on molecular similarity in chemical action triazine derivatives (10, 11 and 13), cinnamic (4) and LQFM048 (14), with the starting compound (E)-2-cyano-3-(4-hydroxy-3-methoxyphenyl)acrylamide (18) which was produced from vanillin. In addition, LQFM184 (20) compound has molecular weight 729.65 Daltons and the synthetic route proposal consisted of two stages, 53% overall yield, which were performed under the scope of green chemistry. All the synthesized compounds were characterized by techniques of nuclear magnetic resonance, infrared, mass, ultraviolet and fluorescence. From the spectrophotometric absorption technique it was identified that LQFM184 (20) compound had two peaks of maximum absorption (λmax.) 306 nm in the region of UVB and 344 nm for UVA and molar absorptivity (ε) whose values were above 104 M-1 cm-1. As to the technique of cyclic voltammetry LQFM184 (20) compound was stable considering the applied potential and when under an atmosphere of synthetic air showed a weight loss of ~14% in the range of 250°C, characterized as a stable compound at high temperatures. From the in vitro evaluation by the spectrophotometric method described by Mansur it presented Solar Protection Factor (SPF) equal to 3.69 for the UVB. Moreover, the compound does not promote irritation or serious damage when in contact with rabbit cornea cells SIRC and was classified in category 4 of the GHS system as OECD 423, low toxicity. At the end of this work it is possible to observe that the proposed synthetic route to obtain the LQFM184 (20) compound was effective, given the obtained high yields, laborious and low cost steps as well as promising profile sunscreen.