Impact of ferulic acid and resveratrol on the effectiveness and safety of sunscreen
DOI:
https://doi.org/10.1590/Keywords:
Resveratrol, Antioxidants, Permeation, Sunscreen, Ferulic acidAbstract
The combination of avobenzone (AVO) and octyl ρ-methoxycinnamate (OMC) is widely used to ensure broad-spectrum photo-protection because they absorb UVA and UVB, respectively. However, they are thermally and photo unstable because they degrade and undergo photo- tautomerization and trans-cis isomerization, thus reducing their photo-protection efficacy during UV exposure. This study aimed to evaluate the potential use of the antioxidants ferulic acid and resveratrol as stabilizing substances in AVO and OMC mixtures in solution or emulsion. The effects of both antioxidants on the thermal/photo-stability and suppression of the filter singlet state, besides skin permeation, were evaluated. Both antioxidants contributed to preserving OMC and AVO during the thermal stability test, which relates to the maintenance of photo-protection even after storing the formulations at high temperatures. Nevertheless, although resveratrol retained part of the OMC trans isomer and suppressed the AVO singlet state when exposed to UV, no contribution to photo-protection stability was observed, contrary to expectations. Regarding the permeation assay, the addition of both antioxidants was accompanied by a reduction of AVO permeation, while resveratrol increased OMC permeation. Thus, the chemical and physicochemical properties of these antioxidants impacted their efficacy and safety profiles; therefore, further studies are required to establish the real cost-benefit ratio for their use in sunscreens.
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References
Adamson AS, Shinkai K. Systemic Absorption of Sunscreen. JAMA. 2020;323:223. https://doi.org/10.1001/ jama.2019.20143
» https://doi.org/10.1001/ jama.2019.20143
ANVISA. RDC nº 600, de 9 de fevereiro de 2022. Dispõe sobre a lista de filtros ultravioletas permitidos para produtos de higiene pessoal, cosméticos e perfumes e internaliza a Resolução GMC MERCOSUL no 44/2015, alterada pela Resolução GMC MERCOSUL no 14/2021. 2022.
Ates G, Steinmetz FP, Doktorova TY, Madden JC, Rogiers V. Linking existing in vitro dermal absorption data to physicochemical properties: Contribution to the design of a weight-of-evidence approach for the safety evaluation of cosmetic ingredients with low dermal bioavailability. Regul Toxicol Pharmacol. 2016;76:74-8. https://doi.org/10.1016/j. yrtph.2016.01.015
» https://doi.org/10.1016/j. yrtph.2016.01.015
Barresi R, Chen E, Liao I-C, Liu X, Baalbaki N, Lynch S, et al. Alteration to the Skin Barrier Integrity Following Broad- spectrum UV Exposure in an Ex vivo Issue Model. J Drugs Dermatol. 2021;20:23-8.
Batista IASA, Gonçalves MIDA, Singh AK, Hackmann ERK, Santoro MIRM. Quantitative Determination of Dimethylaminoethanol in Cosmetic Formulations by Nuclear Magnetic Resonance Spectroscopy. JAOAC Int. 2008;91:1303-8. https://doi.org/10.1093/jaoac/91.6.1303
» https://doi.org/10.1093/jaoac/91.6.1303
Berenbeim JA, Wong NGK, Cockett MCR, Berden G, Oomens J, Rijs AM, et al. Unravelling the Keto-Enol Tautomer Dependent Photochemistry and Degradation Pathways of the Protonated UVA Filter Avobenzone. J Phys Chem A. 2020;124:2919-30. https://doi.org/10.1021/acs. jpca.0c01295
» https://doi.org/10.1021/acs. jpca.0c01295
Bonda CA. Test method for determining compounds capable of quenching electronic singlet state excitation of photoactive compounds. WO-2009020673-A1, 2009.
Delmas D, Aires V, Limagne E, Dutartre P, Mazué F, Ghiringhelli F, et al. Transport, stability, and biological activity of resveratrol. Ann N Y Acad Sci. 2011;1215:48-59. https://doi.org/10.1111/j.1749-6632.2010.05871.x
» https://doi.org/10.1111/j.1749-6632.2010.05871.x
Ellison CA, Tankersley KO, Obringer CM, Carr GJ, Manwaring J, Rothe H, et al. Partition coefficient and diffusion coefficient determinations of 50 compounds in human intact skin, isolated skin layers and isolated stratum corneum lipids. Toxicol In Vitro. 2020;69:104990. https://doi.org/10.1016/j.tiv.2020.104990
» https://doi.org/10.1016/j.tiv.2020.104990
Freire TB, Lima CRRC, Pinto CASO, Borge LF, Baby AR, Velasco MVR. Evaluation of interaction between natural antioxidantsandchemicalsunscreensaimingthephotoprotective efficacy. J Therm Anal Calorim. 2022;147:7829-36. https://doi.org/10.1007/s10973-021-11111-8
» https://doi.org/10.1007/s10973-021-11111-8
Freire TB, Dario MF, Mendes OG, Oliveira AC, Vetore-Neto A, Faria DLA, et al. Nanoemulsion containing caffeine for cellulite treatment: characterization and in vitro evaluation. Braz J Pharm Sci. 2019;55. https://doi.org/10.1590/s2175-97902019000218236
» https://doi.org/10.1590/s2175-97902019000218236
Freitas JV, Praça FSG, Bentley MVLB, Gaspar LR. Trans- resveratrol and beta-carotene from sunscreens penetrate viable skin layers and reduce cutaneous penetration of UV- filters. Int J Pharm. 2015;484:131-7. https://doi.org/10.1016/j.ijpharm.2015.02.062
» https://doi.org/10.1016/j.ijpharm.2015.02.062
Gadgil VR, Darak A, Patil SJ, Chopada A, Kulkarni RA, Patil SM, et al. Recent developments in chemistry of sunscreens & their photostabilization. J Indian Chem Soc. 2023;100:100858. https://doi.org/10.1016/j.jics.2022.100858
» https://doi.org/10.1016/j.jics.2022.100858
Galdi A, Foltis P, Bodnar B, Moyal D, Oresajo C. Sunscreens. Cosmetic Dermatology, Wiley; 2022, p. 204-11. https://doi.org/10.1002/9781119676881.ch21
» https://doi.org/10.1002/9781119676881.ch21
Herzog B, Amorós-Galicia L, Sohn M, Hofer M, Quass K, Giesinger J. Analysis of photokinetics of 2’-ethylhexyl-4- methoxycinnamate in sunscreens. Photochem Photobiol Sci. 2019;18:1773-81. https://doi.org/10.1039/c9pp00084d
» https://doi.org/10.1039/c9pp00084d
Herzog B, Giesinger J, Settels V. Insights into the stabilization of photolabile UV-absorbers in sunscreens. Photochem Photobiol Sci . 2020;19:1636-49. https://doi.org/10.1039/d0pp00335b
» https://doi.org/10.1039/d0pp00335b
Holt EL, Stavros VG. Applications of ultrafast spectroscopy to sunscreen development, from first principles to complex mixtures. Int Rev Phys Chem. 2019;38:243-85. https://doi.org/10.1080/0144235X.2019.1663062
» https://doi.org/10.1080/0144235X.2019.1663062
Holzgrabe U, Deubner R, Schollmayer C, Waibel B. Quantitative NMR spectroscopy-Applications in drug analysis. J Pharm Biomed Anal. 2005;38:806-12. https://doi.org/10.1016/j.jpba.2005.01.050
» https://doi.org/10.1016/j.jpba.2005.01.050
Iyer A, Vaskuri GSSJ, Agrawal A, Khatri D, Srivastava S, Singh S, et al. Does skin permeation kinetics influence efficacy of topical dermal drug delivery system?: Assessment, prediction, utilization, and integration of chitosan biomacromolecule for augmenting topical dermal drug delivery in skin. J Adv Pharm Technol Res. 2021;12:345. https://doi.org/10.4103/japtr.japtr_82_21
» https://doi.org/10.4103/japtr.japtr_82_21
Jiménez MM, Pelletier J, Bobin MF, Martini MC. Influence of encapsulation on the in vitro percutaneous absorption of octyl methoxycinnamate. Int J Pharm . 2004;272:45-55. https://doi.org/10.1016/j.ijpharm.2003.11.029
» https://doi.org/10.1016/j.ijpharm.2003.11.029
Kitasaka S, Yagi M, Kikuchi A. Suppression of menthyl anthranilate (UV-A sunscreen)-sensitized singlet oxygen generation by Trolox and , α-tocopherol. Photochem Photobiol Sci . 2020;19:913-9. https://doi.org/10.1039/d0pp00023j
» https://doi.org/10.1039/d0pp00023j
Klimová Z, Hojerová J, Beránková M. Skin absorption and human exposure estimation of three widely discussed UV filters in sunscreens - In vitro study mimicking real- life consumer habits. Food Chem Toxicol. 2015;83:237-50. https://doi.org/10.1016/j.fct.2015.06.025
» https://doi.org/10.1016/j.fct.2015.06.025
Kojic M, Petkovic M, Etinski M. Unrevealing mechanism of the thermal tautomerization of avobenzone by means of quantum chemical computations. J Serb Chem Soc. 2016;81:1393-406. https://doi.org/10.2298/JSC160531085K
» https://doi.org/10.2298/JSC160531085K
Montenegro L, Turnaturi R, Parenti C, Pasquinucci L. In vitro evaluation of sunscreen safety: effects of the vehicle and repeated applications on skin permeation from topical formulations. Pharmaceutics. 2018;10:27. https://doi.org/10.3390/pharmaceutics10010027
» https://doi.org/10.3390/pharmaceutics10010027
Moyal D. The development of efficient sunscreens. Indian J Dermatol Venereol Leprol. 2012;78:31. https://doi.org/10.4103/0378-6323.97353
» https://doi.org/10.4103/0378-6323.97353
Munem M, Djuphammar A, Sjölander L, Hagvall L, Malmberg P. Animal-free skin permeation analysis using mass spectrometry imaging. Toxicol in Vitro. 2021;71:105062. https://doi.org/10.1016/j.tiv.2020.105062
» https://doi.org/10.1016/j.tiv.2020.105062
Murphy RB, Staton J, Rawal A, Darwish TA. The effect of deuteration on the keto-enol equilibrium and photostability of the sunscreen agent avobenzone. Photochem Photobiol Sci . 2020;19:1410-22. https://doi.org/10.1039/d0pp00265h
» https://doi.org/10.1039/d0pp00265h
Neupane R, Boddu SHS, Renukuntla J, Babu RJ, Tiwari AK. Alternatives to Biological Skin in Permeation Studies: Current Trends and Possibilities. Pharmaceutics. 2020;12:152. https://doi.org/10.3390/pharmaceutics12020152
» https://doi.org/10.3390/pharmaceutics12020152
Pafili A, Meikopoulos T, Kontogiannidou E, Papageorgiou S, Demiri E, Meimari D, et al. Development and validation of LC-MS/MS method for the determination of UV-filters across human skin in vitro. J Chromatogr B. 2021;1167:122561. https://doi.org/10.1016/j.jchromb.2021.122561
» https://doi.org/10.1016/j.jchromb.2021.122561
Pereira R, Silva SG, Pinheiro M, Reis S, Vale ML. Current status of amino acid-based permeation enhancers in transdermal drug delivery. Membranes (Basel). 2021;11:343. https://doi.org/10.3390/membranes11050343
» https://doi.org/10.3390/membranes11050343
Peres DD, Sarruf FD, Oliveira CA, Velasco MVR, Baby AR. Ferulic acid photoprotective properties in association with UV filters: multifunctional sunscreen with improved SPF and UVA-PF. J Photochem Photobiol B. 2018;185:46-9. https://doi.org/10.1016/j.jphotobiol.2018.05.026
» https://doi.org/10.1016/j.jphotobiol.2018.05.026
Pinto CASO, Gonçalves MIA, Martins TEA, Issa MG, Lima FS, Costa GMD, et al. Rutin as photostabilizer for broad spectrum sunscreens. Braz J Dev. 2021;7:92115-32. https://doi.org/10.34117/bjdv7n9-397
» https://doi.org/10.34117/bjdv7n9-397
Rojas J, Londono C, Ciro Y. The health benefits of natural skin UVA photoprotective compounds found in botanical sources. Int J Pharm Pharm Sci. 2016;8:13-23.
SCCS. Scientific Committee on Consumer Safety. The SCCS’s Notes of Guidance for the Testing of Cosmetic Substances and Their Safety Evaluation. 11th Revision. SCCS/1628/21, p. 31. 2021. https://health.ec.europa.eu/system/files/2022-08/sccs_o_250.pdf (accessed January 26, 2023).
» https://health.ec.europa.eu/system/files/2022-08/sccs_o_250.pdf
Serpone N. Sunscreens and their usefulness: have we made any progress in the last two decades? Photochem Photobiol Sci . 2021;20:189-244. https://doi.org/10.1007/s43630-021-00013-1
» https://doi.org/10.1007/s43630-021-00013-1
Union P. Regulation (EC) nº 1223/2009 of the European Parliament and of the Council. Off J Eur Union. 2009;342:59.
WHO. Radiation: Ultraviolet (UV) radiation and skin cancer 2017. https://www.who.int/news-room/q-a-detail/radiation-ultraviolet-(uv)-radiation-and-skin-cancer (accessed August 1, 2021).
» https://www.who.int/news-room/q-a-detail/radiation-ultraviolet-(uv)-radiation-and-skin-cancer
Zhang Y-Y, Zhang J, Zhang W-X, Wang Y, Wang Y-H, Yang Q-Y, et al. Quantitative 1H Nuclear Magnetic Resonance Method for Assessing the Purity of Dipotassium Glycyrrhizinate. Molecules 2021;26:3549. https://doi.org/10.3390/molecules26123549
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