A study on 2-(2’-hydroxyphenyl) benzoxazoles derivatives as potential organic UV filters, Part I
DOI:
https://doi.org/10.1590/s2175-97902022e20547Palavras-chave:
2-(2’-hydroxyphenyl)benzoxazole, Photoprotector, Photostability, Sunscreen, UV radiationResumo
Damage resulting from the incidence of ultraviolet (UV) radiation on the skin is common nowadays, with UVB (290-320 nm) and UVA (320-400 nm) radiation responsible for photoaging, sunburn and carcinogenesis. For this reason, sunscreens represent products of growing interest to prevent such damage. However, there are few organic filters marketed worldwide with photostability and effectiveness at wavelengths greater than 340 nm (long UVA), which justifies the exploration for new compounds. In this work, we determined the photostability and sun protection factor (SPF) of three 2-(2’-hydroxyphenyl)benzoxazole derivative dyes in order to develop new organic UV filters. UV-vis spectrophotometry has high level of reproducibility when compared with in vivo human clinical methods. Solubility determinations were performed in different solvents. The compounds absorbed UVA and UVB radiation, with maximum absorption wavelengths ranging from 336 to 374 nm. Photostability was evaluated using a solar simulator (3 J.m2.s-1 UVA radiation) for a maximum of 3 h. The 2-(amino-2’-hydroxyphenyl) benzoxazoles showed higher photostability than the acetylated derivative under the evaluated conditions. The three benzoxazoles presented SPF values of around 40 and preliminary results indicate that they show suitable properties to act as good chemical filters in photoprotective formulations.
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Abid AR, Marciniak B, Pedzinski T, Shahid M. Photostability and photosensitizing characterization of selected sunscreens. J Photochem Photobiol A. 2017;332:241-50.
Baker LA, Greenough SE, Stavros VG. A Perspective on the ultrafast photochemistry of solution-phase sunscreen molecules. J Phys Chem Lett. 2016;7(22):4655-65.
Baker LA, Marchetti B, Karsili TNV, Stavros VG, Ashfold MNR. Photoprotection: extending lessons learned from studying natural sunscreens to the design of artificial sunscreen constituents. Chem Soc Rev. 2017;46(12):3770-91.
Brazil, ANVISA, RDC 126/2016.
Brazil, Brazilian Pharmacopeia. 2010;1: 548p.
Campo LF. Sistemas de materiais fotossensíveis baseados em corantes fluorescentes como meio ativo para dispositivos ópticos. [Thesis]. Porto Alegre: Universidade Federal do Rio Grande do Sul, Programa de Pós-Graduação em Química; 2003.
Dutra EA, Oliveira DAGC, Kedor-Hackmann ERM, Santoro MIRM. Determination of sun protection factor (SPF) of sunscreens by ultraviolet spectrophotometry. Braz J Pharm Sci. 2004;40(3):381-85.
Farkas R, Lhiaubet-Vallet V, Corbera J, Törincsi M, Gorchs O, Trullas C, et al. Synthesis of new 2-(2´-hydroxyaryl) benzotriazoles and evaluation of their photochemical behavior as potential UV-filters. Molecules. 2010;15(9):6205-16.
Fonseca AP, Rafaela N. Determination of sun protection factor by UV-Vis spectrophotometry. Health Care Curr Rev 2013;1:1.
Gallardo C, Pinillos MJF, Pazmiño AJD, Munera EA. Characterization of Encapsulation Process of Avobenzone in Solid Lipid Microparticle Using a Factorial Design and its Effect on Photostability. J App Pharm Sci. 2014;4(12):35-43
Gilbert E, Pirot F, Bertholle V, Roussel L, Falson F, Padois K. Commonly used UV filter toxicity on biological functions: review of last decade studies. Int J Cosmet Sci. 2013;35(3):208-19.
Herzog BH, Wehrle M, Quass K. Photostability of UV absorber systems in sunscreens. Photochem Photobiol. 2009;85(4):869-78.
Holler MG, Campo LF, Brandelli A, Stefani V. Synthesis and spectroscopic characterization of 2-(2’-hydroxyphenyl) benzazole isothiocyanates as new fluorescent probes for proteins. J Photochem Photobiol A . 2002;149(1-3):217-25
Ignasiak MT, Houée-Levin C, Kciuk G, Marciniak B, Pedzinski T. A Reevaluation of the photolytic properties of 2-hydroxybenzophenone-based UV sunscreens: Are chemical sunscreens inoffensive? Chem Phys Chem. 2015;16(3):628-33.
Mancebo SE, Hu JY, Wang SQ. Sunscreens: a review of health benefits, regulations, and controversies. Dermatol Clin. 2014;32(3):427-38.
Montagner S, Costa A. Bases biomoleculares do fotoenvelhecimento. An Bras Dermatol. 2009;84(3):263-9.
Mansur JS, Breder MN, Mansur MC, Azulay RD. Determination of sun protection factor by spectrophotometry. An Bras Dermatol . 1986;61:121-24.
Nash JF, Tanner PR. Relevance of UV filter/sunscreen product photostability to human safety. Photodermatol Photoimmunol Photomed. 2014;30(2-3):88-95.
Perdiz D, Gróf P, Mezzina M, Nikaido O, Moustacchi E, Sage E. Distribution and repair of bipyrimidine photoproducts in solar UV-irradiated mammalian cells. Possible role of Dewar photoproducts in solar mutagenesis. J Biol Chem. 2000;275(35):26732-42.
Polonini HC, Dias RM, Souza IO, Gonçalves KM, Gomes TB, Raposo NR, et al. Quinolines derivatives as novel sunscreening agents. Bioorg Med Chem Lett. 2013;23(16):4506-10.
Rastogi SC. UV filters in sunscreen products - a survey. Contact Dermatitis. 2002;46(6):348-51.
Rodembusch FS, Leusin FP, Campo LF, Stefani V. Excited state intramolecular proton transfer in amino 2-(2’-hydroxyphenyl) benzazole derivatives: Effects of the solvent and the amino group position. J Lumin. 2007;126(2):728-34.
Sayre RM, Agin PP, LeVee GJ, Marlowe E. A comparison of in vivo and in vitro testing of sunscreening formulas. Photochem Photobiol . 1979;29(3):559-66.
Schuch AP, Lago JC, Yagural T, Menckl CFM. DNA Dosimetry assessment for sunscreen genotoxic photoprotection. PLoS ONE. 2012;7(6):1-8.
Sohn M, Herzog B, Osterwalder U, Imanidis G. Calculation of the sun protection factor of sunscreens with different vehicles using measured film thickness distribution - Comparison with the SPF in vitro J Photochem Photobiol B. 2016;159:74-81.
Stiefel C, Schwack W. Photoprotection in changing times - UV filter efficacy and safety, sensitization processes and regulatory aspects. Int J Cosmet Sci . 2015;37(1):2-30.
Wang SQ, Tanner PR, Lim HW, Nash JF. The evolution of sunscreen products in the United States - a 12-year cross sectional study. Photochem Photobiol Sci. 2013;12(1):197-202.
Yang SI, Liu S, Brooks GJ, Lanctot Y, Gruber JV. Reliable and simple spectrophotometric determination of sun protection factor: A case study using organic UV filter-based sunscreen products. J Cosmet Dermatol. 2018;17(3):518-22.
Zaratti F, Piacentini RD, Guillén HA, Cabrera SH, Lileye JB, McKenzie RL. Proposal for a modification of the UVI risk scale. Photochem Photobiol Sci. 2014;13(7):980-85.
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