New model of biological membrane (shed snakeskin) for studies of antioxidant activity in photoprotective formulation/ Novo modelo de membrana biológica (ecdise de pele de cobra) para estudos de atividade antioxidante em formulação fotoprotetora

Authors

  • Thamires Batello Freire Brazilian Journals Publicações de Periódicos, São José dos Pinhais, Paraná
  • Orlando Rodrigues Júnior
  • Claudinéia Aparecida Sales de Oliveira Pinto
  • Cassiano Carlos Escudeiro
  • André Rolim Baby
  • Maria Valéria Robles Velasco

DOI:

https://doi.org/10.34117/bjdv7n4-674

Keywords:

snakeskin, EPR, photoprotective formulation, Ferulic acid, resveratrol.

Abstract

Antioxidants of natural origin are used in medicines and cosmetics with several benefits, such as: photoprotective action, anti-aging, moisturizing and anti-pollutant. The human epidermis has an important barrier effect and limited anti-oxidative capacity, so studies with the epidermis is essential. Shed snakeskin (SS) is composed of the stratum corneum and provide a barrier like human stratum corneum. This alternative does not show a tendency to microbiological degradation and can be considered ecologically correct. This study intends to present, in an innovative way, the Electron Paramagnetic Resonance spectroscopy (EPR) and The Forster Resonance Energy Transfer (FRET) were employed to evaluate the natural antioxidant substances (Resveratrol/ RES 3.0 w/w and Ferulic acid/ FA 1.0 w/w) associated with organic sunscreens ingredients (Ethylhexyl Methoxycinnamate/ EHMC 10.0%w/w and Butyl Methoxydibenzoylmethano/ BMBM 5.0%w/w in a photoprotective emulsion (PB). Furthermore, the use of SS seedlings as a possible alternative to the use of human or animal skin ex-vivo. RES and FA can absorb the energy emitted by the EHMC in FRET, preventing the passage through the triplet state, favoring the photostability of this sunscreen, the same not ocorred with the BMBM. Antioxidant activity of the photoprotective formulations was evaluated in vitro by the percentual inhibition of the radical 2,2-diphenyl-1-picrihydrazyl (DPPH•). The antioxidant activity with RES, 97.0% inhibition of DPPH• in the PB, was higher than PB + FA (91.0%), however the concentration of RES in PB was higher than FA. The sample SS + PB + FA was the one with the lowest number of free radicals after irradiation, which corroborated the high percentage of radical inhibition in vitro and it was the better association with the photoprotective formulation.

 

References

ABDEL-AAL, H. A.; MANSORI, M. E.; ZAHOUANI, H. A comparative study of frictional response of shed snakeskin and human skin. HAL, p. 1-29, 2019.

ALBRECHT, S.; AHLBERG, S.; BECKERS, I., KOCKOTT, D.; LADEMANN J.; PAUL, V.; ZASTROW, L.; MEINKE.M. C. Efeitos na detecção de formação de radicais na pele devi-do à irradiação solar medida por espectroscopia EPR. Methods, v. 109, p. 44-54, 2016.

BABY, A. R. Avaliação in vitro da permeabilidade cutânea da rutina em emulsões cosméticas. 2007. 168. Tese Doutorado – Faculdade de Ciências Farmacêuticas, Universi-dade de São Paulo, São Paulo, 2007.

BABY, A. T.; Haroutiounian-Filho, C. A.; Sarruf, F. D.; Tavante-Júnior, C. R.; Pinto, C. A S. O.; Zague, Z.; Arêas, E. P. G.; Kaneko, T. M.; Velasco, M. V. R. Estabilidade e estudo de penetração cutânea in vitro da rutina veiculada em uma emulsão cosmética através de um modelo de biomembrana alternativo. Revista Brasileira de Ciências Farmacêuticas Brazilian Journal of Pharmaceutical Sciences, v. 44, n. 2, 2008.

BALOGH, T. S. Uso cosmético de extratos glicólicos: avaliação da atividade antioxidante, estudo da estabilidade e potencial fotoprotetor. São Paulo, 2011. 244p. Dissertação de Mestrado - Faculdade de Ciências Farmacêuticas - Universidade de São Paulo.

BALOGH, T. S.; PEDRIALI, C. A.; GAMA, R. M.; PINTO, C. A. S. O.; BEDIN, V.; VILLA, R. T.; KANEKO, T. M.; CONSIGLIERI, V. O.; VELASCO, M. V. R.; BABY, A. R. Study of sunless tanning formulas using molted snakeskin as an alternative membrane model. International Journal of Cosmetic Science, v. 33, 359–365, 2011.

BANDONIENE, D.; MURKOVIC, M.; PFANNHAUSER, W.; VENSKUTONIS, P. R.; GRUZDIENE, D. Detection and activity evaluation of radical scavenging compounds by using DPPH free radical and on-line HPLC-DPPH methods. European Food Research Technology, v. 214, p.143–147, 2002.

BRAND-WILLIAMS, W.; BONDET, V. BERSET, C. Kinetics and mechanisms of antioxidant activity using the DPPH· free radical method. Lebensmittel-Wissenschaf und-Technologie, v. 30, n. 6, p. 609-615, 1997.

CANDIDO, T. M.; OLIVEIRA, C. A.; ARIEDE, C. A.; VELASCO, M. V.; ROSADO, C.; BABY, A. R. Safety and Antioxidant Efficacy Profiles of Rutin-Loaded Ethosomes for Topical Application. Journal of the American Association of Pharmaceutical Sciences, v. 19, p. 1773–1780, 2018.

BONDA, C. Research pathways to photostables sunscreens. Cosmetics & Toiletries, v.123, n.2, p.149-260, 2008.

DARIO, M. F.; PAHL, R.; CASTRO, J. R.; LIMA, F. S. L.; KANEKO, T. M.; PINTO, C. A. S. O.; BABY, A. R.; VELASCO, M. V. R. Efficacy of Punica granatum L. hydroalcoholic extract on properties of dyed hair exposed to UVA radiation. Journal of Photochemistry and Photobiology B: Biology, v. 120, p.142-147, 2013.

DARIO, M. F.; BABY, A. R.; VELASCO, M. V. R. Effects of solar radiation on hair and photo-protection. Journal of Photochemistry and Photobiology B: Biology, v.153,p.240-246, 2015.

DARVIN, M. E.; HAAG, S.; MEINKE, M.; ZASTROW, L.; STERRY, W.; LADEMANN, J. Radical Production by Infrared A Irradiation in Human Tissue. Skin Pharmacology and Physiology, v. 23, p. 40–46, 2010.

GÓMEZ, J. A.; KINOSHITA A.; CHEN F.; GUIDELLI E. J.; RECH A. B.; ALVES G.; BAFFA O. Electron magnetic resonance dosimetry. Revista Brasileira de Física Médica v. 5, n. 3, p. 221-32, 2011.

GULÇIN, I. Antioxidant properties of resveratrol: A structure–activity insight . Innovative Food Science and Emerging Technologies, v. 11, p. 210-218, 2010.

HAIGH, J. M.; BEYSSAC, E.; AIACHE, J. M. Can shed snakeskin be considered to be a 'model' membrane for human stratum corneum? Proc. 2nd World Meeting APGI/APV, p. 1041-1042, 1998.

HARADA, K.; MURAKAMI, T.; KAWASAKI, E.; HIGASHI, Y.; YAMAMOTO, S.; YATA, N. In?vitro Permeability to Salicylic Acid of Human, Rodent, and Shed Snakeskin. Journal of Pharmacy and Pharmacology, v. 45, p. 414-418, 1993.

HERRLING, T.; FUCHS, J.; REHBERG, J.; GROTH, N. UV-Induced free radicals in the skin detected by ESR spectroscopy and imaging using nitroxides. Free Radical Biology & Medicine, v. 35, n. 1, p. 59–67, 2003.

HUBNER, A.; SOBREIRA, F.; NETO, A. V.; PINTO, C. A. S. O.; DARIO, M. F.; DÍAZ, I. E. C.; LOURENÇO, R. F.; ROSADO, C.; BABY, A. R.; BACCI, E. M. The Synergistic Behavior of Antioxidant Phenolic Compounds Obtained from Winemaking Waste’s Valorization, Increased the Efficacy of a Sunscreen System. Antioxidants, v.8, n. 11, p. 530, 2019.

ITOH, T.; XIA, J.; MAGAVI, R.; NISHIHATA, T.; RYTTING, H. Use of Shed Snakeskin as a Model Membrane for in Vitro Percutaneous Penetration Studies: Comparison with Human Skin. Pharmaceutical Research, v. 7, p. 1042–1047, 1990.

JIA, Z., ZHU, H., MISRA, B. R., MAHANEY, J. E., LI, Y., MISRA, H. P. EPR studies on the superoxide-scavenging capacity of the nutraceutical resveratrol. Molecular and Cellular Biochemistry, v. 313, p.187–194, 2008.

KAWAKAMI, Camila Martins et al. Diethylamino hydroxybenzoyl hexyl benzoate (DHHB) as additive to the UV filter avobenzone in cosmetic sunscreen formulations-Evaluation of the photochemical behavior and photostabilizing effect. The European Journal of Pharmaceutical Sciences, v. 99, p. 299-309, 2017.

KOUCHAK, M; HANDALI, S. Effects of Various Penetration Enhancers on Penetration of Aminophylline Through Shed SnakeSkin. Jundishapur Journal of Natural Pharmaceutical Products, v. 9, n. 1, p. 24-29, 2014.

KIKUZAKI, H.; HISAMOTO, M.; HIROSE, K.; AKIYAMA, K.; TANIGUCHI, H. Antioxidant Properties of Ferulic Acid and Its Related Compounds. Journal of Agricultural and Food Chemistry, v. 50, p. 2161?2168, 2002.

KURAMOTO, M.; TANAKA, T.; MAKITA, H.; NAKAMURA, Y.; YATA, N. Characteristics of Shed Snake Skin Permeability to Indomethacin and Fatty Alcohols. Journal of Pharmacy and Pharmacology, v. 48, p. 682-684, 1996

LAKOWICZ, J. R. Principles of Fluorescence Spectroscopy 3rd. Sarat Books, Kolkata, India, v. 1, p. 944, 2006.

LOHAN, S. B.; LAUER, A. C.; ARNDT, S.; FRIEDRICH, A.; TSCHERCH, S.; HAAG, S. F; DARVIN, M. E.; VOLLERT, H.; KLEEMANN, H.; GERSONDE, I.; GROTH, N.; LADEMANN, J.; ROHN, S.; MEINKE, M. C. Determination of the Antioxidant Status of the Skin by In Vivo-Electron Paramagnetic Resonance (EPR) Spectroscopy. Cosmetics, v. 2, n. 3, p. 286-301, 2015.

LUND, L.; LEY, R. D.; FELTON, L. F; TIMMINS, G. S. Determination of Wavelength-Specific UV Protection Factors of Sunscreens in Intact Skin by EPR Measurement of UV-Induced Reactive Melanin Radical. Photochemistry and Photobiology, v. 83, p. 952–957, 2007.

MARTINS, T. E. A.; PINTO, C. A. S. O.; OLIVEIRA, A. C.; VELASCO, M. V. R.; GUITIÉRREZ, A. R. G.; RAFAEL, M. F. C.; TARAZONA, J. P. H.; RETUERTO-FIGUEROA, M. G. Contribution of Topical Antioxidants to Maintain Healthy Skin - A Review, Scientia Pharmaceutica, v. 88, n. 27, p. 1-17, 2020.

MAURYA, D. K.; DEVASAGAYAM, T. P. A. Antioxidant and prooxidant nature of hydroxycinnamic acid derivatives ferulic and caffeic acids. Food and Chemical Toxicology, v. 48, p. 3369-3373, 2010.

MOROCHO-JÁCOME, A.L.; FREIRE, T. B.; OLIVEIRA, A. C.; ALMEIDA, T. S.; ROSADO, VELASCO, M. V. R.; BABY, A. R. In vivo SPF from multifunctional sunscreen systems developed with natural compounds - A review. Journal of Cosmetic Dermatology, v. 00, p. 1-9, 2020.

NGAWHIRUNPAT, T.; PANOMSUK, S.; OPANASOPIT1, P.; ROJANARATA, T.; HATANAKA, T. Comparison of the percutaneous absorption of hydrophilic and lipophilic compounds in shed snakeskin and human skin. Pharmazie, v. 61, n. 4, p. 331-334, 2006.

OGUCHI-FUJIYAMA, N.; MIYAZAWA, K.; KIKUCHIB A.; YAGI, M. Photophysical properties of dioctyl 4-methoxybenzylidenemalonate: UV-B absorber. Photochemical and Photobiological Sciences, v. 11, p. 1528-1535, 2012.

OLIVEIRA, R. V. M.; OHARA, M. T.; VILA, M. M. D. C.; GONÇALVES, M. M. G. In vitro evaluation of copaiba oil as a kojic acid skin enhancer. Brazilian Journal of Pharmaceutical Sciences, v. 46, n. 2, 2010.

PERES, D.D. Ácido ferúlico em protetores solares: desenvolvimento e eficácia multifuncional in vitro, ex vivo e in vivo. São Paulo. 2015. 168p. Tese (Doutorado) – Faculdade de Ciências Farmacêuticas, Universidade de São Paulo, S. Paulo, 2015.

PERES, D. A.; SARRUF, F. D.; OLIVEIRA, C. A.; VELASCO, M. V. R.; BABY, A. R. Ferulic acid photoprotective properties in association with UV filters: multifunctional sunscreen with improved SPF and UVA-PF. Journal of Photochemistry and Photobiology B: Biology, v. 185, p. 46-49, 2018.

PINTO, C.A.S.O. Influência da rutina na fotoestabilização da avobenzona (filtro UVA) e do ?-metoxicinamato de octila (filtro UVB). 2014. 212f. Tese Doutorado – Faculdade de Ciências Farmacêuticas, Universidade de São Paulo, São Paulo, 2014.

PONGJANYAKUL, T.; PRAKONGPAN, S.; PANOMSUK, S.; PUTTIPIPATKHACHORN, S.; PRIPREM, A. Shed king cobra and cobra skins as model membranes for in-vitro nicotine permeation studies. Journal of Pharmacy and Pharmacology, v. 54, n. 10, p. 1345-50, 2002.

POPOV, A. P.; S. HAAG.; MEINKE, M.; LADEMANN J.; PRIEZZHEV A. V, MYLLYLÄ R. Effect of size of TiO2 nanoparticles applied onto glass slide and porcine skin on generation of free radicals under ultraviolet irradiation. Journal of Biomedical Optics, v. 14, n. 2, p. 0210111-0210117, 2009.

PRAÇA, F. G.; MEDINA, W. S. G.; BENTLEY, M. V. L. B. Avaliação de cobra brasileira (Crotalus durisssus terrificus) como modelo substituto de membrana biológica de ensaios in vitro de permeação cutânea de drogas.CuidArt Enfermagem,v.9, n.2, p.122-130, 2015.

RIBEIRO, U. L. A ascensão do consumo ético de produtos vegetarianos e veganos no mercado brasileiro. Observatório de La Economía Latinoamericana, p. 1-12, 2019.

RIGGY, P. C., BARRY, B. W. Shed snakeskin and hairless mouse skin as model membranes for human skin during permeation studies. Journal of Investigative Dermatology, v. 94, n. 2, p. 235-40, 1990.

RINNERTHALER, M.; BISCHOF, J.; STREUBEL, M. K.; TROST, A.; RICHTER, K. Oxidative Stress in Aging Human Skin. Biomolecules, v. 5, p. 545-589; 2015.

SÁNCHEZ-MORENO, C.; LARRAURI, J.A.; SAURA-CALIXTO, F.A. A procedure to measure the antiradical efficiency of polyphenols. Journal of Science of Food and Agriculture, v.76, n.2, p.279-276, 1998.

SCHMOOK, F. P.; MEINGASSNER, J. G.; BILLICH, A. Comparison of human skin or epidermis models with human and animal skin in in-vitro percutaneous absorption. International Journal of Pharmaceutics, v. 215, n. 1–2, p. 51-56, 2001.

SILVA, S. A. M.; MICHNIAK-KOHN B.; LEONARDI, G. R. An overview about oxidation in clinical practice of skin aging. Anais Brasileiros de Dermatologia, v. 92, n. 3, p. 367-74, 2017.

TAKAHASHI, K.; SAKANO, H.; RYTTING, J.H.; NUMATA, N.; KURODA, S.; MIZUNO, N. In-fluence of pH on the Permeability of p-Toluidine and Aminopyrine Through Shed SnakeSkin as a Model Membrane.Drug Development and Industrial Pharmacy, v.27, n.2, p.159–164, 2001.

TAKAOKA, M.S.; BABY, A.R.; PRESTES, P.S.; PINTO, C.A.S.O.; SILVA, V.R.L.; VELASCO, M.V.R.; KAWANO, Y.; KANEKO, T.M. Avaliação da interação de compostos ativos hidratantes com modelo de biomembrana de Crotalus durissus por meio de calorimetria exploratória diferencial e espectroscopia RAMAN. Revista de Ciências Farmacêuticas Básica e Aplicadas, v. 31, n. 1, p.53-58, 2010.

WIDLER, N.; SIGRIST, A.; GAFNER, F. M. Lipid analysis and transepidermal water loss in snakes. IFSCC Magazine, 2002.

YADAV, D. K.; KUMAR, S.; CHOI, E. H.; CHAUDHARY, S.; KIM, M. H. Molecular dynamic simulations of oxidized skin lipid bilayer and permeability of reactive oxygen species. Nature, v. 9, p. 1-10, 2019.

Downloads

Published

2021-04-29

How to Cite

Freire, T. B., Júnior, O. R., Pinto, C. A. S. de O., Escudeiro, C. C., Baby, A. R., & Velasco, M. V. R. (2021). New model of biological membrane (shed snakeskin) for studies of antioxidant activity in photoprotective formulation/ Novo modelo de membrana biológica (ecdise de pele de cobra) para estudos de atividade antioxidante em formulação fotoprotetora. Brazilian Journal of Development, 7(4), 43214–43236. https://doi.org/10.34117/bjdv7n4-674

Issue

Section

Original Papers