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Abstract:

There is still an international need to develop broad-spectrum sunscreen products with an adequate UVB/UVA balance, while the approved filters available in the UVA are scarce. Currently, one of the few UVA filters approved in the United States and Europe is tert-butylmethoxydibenzoylmethane (BMDM, avobenzone). However, this compound is unstable from aphotochemical point of view and cannot be used in combination with certain sunscreens. In this paper, we investigate the photochemical behavior of a set of dibenzoylmethanes and chalcones. In particular, we carry out their absorption and emission spectra, evaluate their photochemical degradation, and study their generation of free radicals and singlet oxygen photoproduction. Two compounds resultedin having the basic properties of UVA filters (2'-hydroxy-4-methoxychalcone and 2'-hydroxy-4-methoxydibenzoylmethane). Further studies are proposed, such as formulating the compounds into emulsions or other common cosmetic presentations, as well as combining them with broadly-used UVB filters. We have also considered the need to establish its toxicological profile. © 2018 by the authors.

Registro:

Documento: Artículo
Título:Absorption and photo-stability of substituted dibenzoylmethanes and chalcones as UVA filters
Autor:Lazópulos, S.Q.; Svarc, F.; Sagrera, G.; Dicelio, L.
Filiación:fabriQUIMICA S.R.L. R and D, Buenos Aires, B1650IJA, Argentina
Facultad de Ciencias Exactas y Naturales UBA, DQIAQF-INQUIMAE, Buenos Aires, C1428EGA, Argentina
Facultad de Química UDELAR, Departamento de Química Orgánica, Montevideo, 11800, Uruguay
BASF Argentina S.A., Buenos Aires, C1049AAA, Uruguay
Palabras clave:Chalcones; Dibenzoylmethanes; Photo-stability; UVA filters
Año:2018
Volumen:5
Número:2
DOI: http://dx.doi.org/10.3390/cosmetics5020033
Título revista:Cosmetics
Título revista abreviado:Cosmetics
ISSN:20799284
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_20799284_v5_n2_p_Lazopulos

Referencias:

  • Hossein-nezhad, A., Holick, M.F., Vitamin D for health: A global perspective (2013) Mayo Clin. Proc, 88, pp. 720-755
  • Papoutsaki, M., Costanzo, A., Treatment of psoriasis and psoriatic arthritis (2013) BioDrugs, 27, pp. 3-12
  • Holick, M.F., Vitamin D and sunlight: Strategies for cancer prevention and other health benefits (2008) Clin. J. Am. Soc. Nephrol, 3, pp. 1548-1554
  • Narayanan, D.L., Saladi, R.N., Fox, J.L., Ultraviolet radiation and skin cancer (2010) Int. J. Dermatol, 49, pp. 979-986
  • Mason, R.S., Reichrath, J., Sunlight, vitamin D and skin cancer (2013) Anti-Cancer Agents Med. Chem, 13, pp. 83-97
  • Pfeifer, G.P., Besaratinia, A., UV wavelength-dependent DNA damage and human non-melanoma and melanoma skin cancer (2012) Photochem. Photobiol. Sci, 11, pp. 90-97
  • Shaat, N.A., Sunscreen evolution (2005) Sunscreens, Regulations and Commercial Development, pp. 4-17. , Shaat, N.A., Ed.; Taylor & Francis: Boca Raton, FL, USA
  • Shaath, N.A., Ultraviolet filters (2010) Photochem. Photobiol. Sci, 9, pp. 464-469
  • Nash, J.F., Tanner, P.R., Relevance of UV filter/sunscreen product photostability to human safety (2014) Photodermatol. Photoimmunol. Photomed, 30, pp. 88-95
  • Dondi, D., Albini, A., Serpone, N., Interactions between different solar UVB/UVA filters contained in commercial sunscreens and consequent loss of UV protection (2006) Photochem. Photobiol. Sci, 5, pp. 835-843
  • Schwack, W., Rudolph, T., Photochemistry of dibenzoylmethane UVA filters, Part I (1995) J. Photochem. Photobiol. B, 28, pp. 229-234
  • Kockler, J., Oelgemöller, M., Robertson, S., Glass, B.D., Influence of titanium dioxide particle size on the photostability of the chemical UV-filters butyl methoxydibenzoylmethane and octocrylene in a microemulsion (2014) Cosmetics, 1, pp. 128-139
  • Svarc, F.E., A brief illustrated history on sunscreens and sun protection (2015) Pure Appl. Chem, 87, pp. 929-936
  • Karlsson, I., Hillerstrom, L., Stenfeldt, A.L., Martensson, J., Borje, A., Photodegradation of dibenzoylmethanes: Potential cause of photocontact allergy to sunscreens (2009) Chem. Res. Toxicol, 22, pp. 1881-1892
  • Sayre, R.M., Dowdy, J.C., Gerwig, A.J., Shields, W.J., Lloyd, R.V., Unexpected photolysis of the sunscreen octinoxate in the presence of the sunscreen avobenzone (2005) Photochem. Photobiol, 81, pp. 452-456
  • Forestier, S., Lang, G., Richard, H., (1992) Cosmetic Use of Dibenzoylmethane Diorganopolysiloxanes and Novel Cosmetic Compositions Containing such Compounds for Protection of Skin and Hair, , 8 September
  • Bonda, C.A., Marinelli, P.J., Hessefort, Y.Z., Trivedi, J., Wentworth, G., (1999) Photostable Sunscreen Compositions Containing Dibenzoylmethane Derivative, e.g, , Parsol®1789, and Diesters or Polyesters of Naphthalene Dicarboxylic Acid Photostabilizers and Enhancers of the Sun Protection Factor (SPF), 30 November
  • Hansenne, I., Josso, M., Method for Providing Dibenzoylmethane Derivatives with Light Stability (2003); Lang, G., Malaval, A., Procedimiento de Preparación de una Composición Cosmética Que contiene un Derivado del Dibenzoilmetano que incluye un Grupo cuaternario (1981); Asero, M., Segal, A., Fotoestabilidad de avobenzona utilizando diferentes antioxidantes (2016) Proceedings of the 4th Argentine Congress of Cosmetic Chemistry (COARQC), , Rosario, Argentina, 16-18 September
  • Zawadiak, J., Mrzyczek, M., Influence of substituent on UV absorption and keto-enol tautomerism equilibrium of dibenzoylmethane derivatives (2012) Spectrochim. Acta A Mol. Biomol. Spectrosc, 96, pp. 815-819
  • Wetz, F., Routaboul, C., Denis, A., Ricco-Lattes, I., A new long-chain UV absorber derived from 4-tert-butyl-40-methoxydibenzoilmethane: Absorbance stability under solar irradiation (2005) J. Cosmet. Sci, 56, pp. 135-148
  • Tarras-Wahlberg, N., Stenhagen, G., Larko, O., Rosen, A., Wenneberg, A.M., Wennerström, O., Changes in ultraviolet absorption of sunscreens after ultraviolet irradiation (1999) J. Investig. Dermatol, 113, pp. 547-553
  • Paris, C., Lhiaubet-Vallet, V., Jiménez, O., Trullas, C., Miranda, M.A., A blocked diketo form of avobenzone: Photostability, photosensitizing properties and triplet quenching by a triazine derived UVB-filter (2009) Photochem. Photobiol, 85, pp. 178-184
  • Gonzenbach, H., Photostability of Cosmetic sunscreens (2006) Pharmaceutical Photostability and Stabilization Technology, pp. 379-396. , Piechocki, J., Thoms, K., Eds.; Informa Healthcare: New York, NY, USA
  • Deflandre, A., Lang, G., Photostability assessment of sunscreens Benzylidene camphor and dibenzoylmethane derivatives (1988) Int. J. Cosm. Sci, 10, pp. 53-62
  • Lhiaubet-Vallet, V., Marin, M., Jimenez, O., Gorchs, O., Trullas, C., Miranda, M.A., Filter-filter interactions Photostabilization, triplet quenching and reactivity with singlet oxygen (2010) Photochem. Photobiol. Sci, 9, pp. 552-558
  • Tovar-Sanchez, A., Sanchez-Quiles, D., Basterretxea, G., Benede, J.L., Chisvert, A., Salvador, A., Moreno-Garrido, I., Blasco, J., Sunscreen products as emerging pollutants to coastal waters (2013) PLoS ONE, 8
  • Danovaro, R., Bongiorni, L., Corinaldesi, C., Giovannelli, D., Damiani, E., Astolfi, P., Greci, L., Pusceddu, A., Sunscreens cause coral bleaching by promoting viral infections (2008) Environ. Health Perspect, 116, pp. 441-447
  • Downs, C.A., Kramarsky-Winter, E., Segal, R., Fauth, J., Knutson, S., Bronstein, O., Ciner, F.R., Woodley, C.M., Toxicopathological effects of the sunscreen UV filter, oxybenzone (benzophenone-3), on coral planulae and cultured primary cells and its environmental contamination in Hawaii and the U.S (2016) Virgin Islands. Arch. Environ. Contam. Toxicol, 70, pp. 265-288
  • Gago-Ferrero, P., Diaz-Cruz, M.S., Barcelo, D., An overview of UV-absorbing compounds (organic UV filters) in aquatic biota (2012) Anal. Bioanal. Chem, 404, pp. 2597-2610
  • Fent, K., Kunz, P., Occurrence, and effects of hormonally active UV filters in the aquatic environment (2009) SOFW, 135, pp. 2-12
  • Poiger, T., Buser, H.R., Balmer, M.E., Bergqvist, P.A., Muller, M.D., Occurrence of UV filter compounds from sunscreens in surface waters: Regional mass balance in two Swiss lakes (2004) Chemosphere, 55, pp. 951-963
  • Giokas, D.L., Salvador, A., Chisvert, A., UV filters: From sunscreens to human body and the environment (2007) Trends Anal. Chem, 26, pp. 360-374
  • Forestier, S., Moire, C., Lang, G., Preparation of Chalcone Derivatives as Sunscreens (1988) Ger. Offen, , DE 3742690 A1 19880630. 30 June
  • Imokawa, G., Takaishi, N., Tejima, T., Nakamura, K., Hattori, M., Masuda, S., Chalcone Derivatives and an Ultraviolet Absorber Containing Them (1995) Ger. Offen, , DE 3441636 A1 19850530, 20 October
  • Fujii, A., Sashita, Y., Mimaki, Y., Matsubara, K., Hara, R., Kitada, Y., Nakajima, T., Myata, Y., 2, 4, 6-Trihydroxychalcone as a UV Absorbing Agent and Cosmetics Containing it (1996) Jpn. KokaiTokkyoKoho, , JP 08113521 A19960507, 7 May
  • Okuya, F., Nishio, H., Kuwamura, S., Deguchi, Y., ChalconeDerivatives and Copolymers Thereof as UV Absorbers (1993) Jpn. KokaiTokkyoKoho, , JP 05263067 A 19931012, 12 October
  • Lahorkar, P.G.R., Vaidya, A.A., Chavan, M.V., Gadgil, V.R., A Photoprotective Personal Care Composition (2014) PCT Int. Appl, , WO 2014191143-A1 20141204, 4 December
  • Sagrera, G., Bertucci, A., Vazquez, A., Seoane, G., Synthesis and antifungal activities of natural and synthetic biflavonoids (2011) Bioorg. Med. Chem, 19, pp. 3060-3073
  • Sagrera, G., Síntesis de nuevos dibenzoilmetanos como potenciales filtros solares (2015) Proceedings of the XXII Latin American and Iberian Congress of Cosmetic Chemists, , Punta del Este, Uruguay, 27-29 October
  • Berger, D., Solar UV simulator skin testing (2003) Cosmetics and Toiletries Manufacture Worldwide, pp. 255-257. , PA 19126-3331; Solar Light Co.: Philadelphia, PA, USA
  • Wilkinson, F., Helman, W.P., Ross, A.B., Rate constant for the decay and reactions of the lowest electronically excited singlet state of molecular oxygen in solution (1995) J. Phys. Chem, 24, pp. 663-1021
  • Calzadilla, P., Sapochnik, D., Cosentino, S., Diz, V., Dicelio, L.E., Calvo, J.C., Guerra, L.N., N-acetylcysteine reduces markers of differentiation in 3T3-L1 adipocytes (2011) Int. J. Mol. Sci, 12, pp. 6936-6951
  • Strassert, C.A., Bilmes, G.M., Awruch, J., Dicelio, L.E., Comparative photophysical investigation of oxygen and sulfur as covalent linkers on octaalkylamino substituted zinc(II) phthalocyanines (2008) Photochem. Photobiol. Sci, 7, pp. 738-747
  • http://www.who.int/uv/publications/globalindex/en/, (accessed on 9 February 2017); Amor, S., Angeli, N.G., Dicelio, L.E., Fotoestabilidad de Filtros Solares (2000) Proceedings of the XXVII Meeting of the Argentine Society of Cosmetic Chemists (AAQC), , Pinamar, Argentina, 3-5 November
  • Kavanaugh, E., (1998) Tentative Final Monograph for OTC Sunscreen Drug Products: Docket No, , 78N0038; The Cosmetic, Toiletry, and Fragrance Association (CTFA): Washington, DC, USA
  • Guideline 2007a (2007) Method for the in vitro Determination of UVA Protection Provided by Sunscreen Products, , The European Cosmetic, Toiletry and Perfumery Association. Bruselles
  • Margarida, S.M., Pinto Silva, L., Esteves da Silva, J.C.G., UV Filter 2-ethylhexyl 4-methoxycinnamate: A structure, energetic and UV-vis spectral analysis based on density functional theory (2014) J. Phys. Org. Chem, 27, pp. 47-56

Citas:

---------- APA ----------
Lazópulos, S.Q., Svarc, F., Sagrera, G. & Dicelio, L. (2018) . Absorption and photo-stability of substituted dibenzoylmethanes and chalcones as UVA filters. Cosmetics, 5(2).
http://dx.doi.org/10.3390/cosmetics5020033
---------- CHICAGO ----------
Lazópulos, S.Q., Svarc, F., Sagrera, G., Dicelio, L. "Absorption and photo-stability of substituted dibenzoylmethanes and chalcones as UVA filters" . Cosmetics 5, no. 2 (2018).
http://dx.doi.org/10.3390/cosmetics5020033
---------- MLA ----------
Lazópulos, S.Q., Svarc, F., Sagrera, G., Dicelio, L. "Absorption and photo-stability of substituted dibenzoylmethanes and chalcones as UVA filters" . Cosmetics, vol. 5, no. 2, 2018.
http://dx.doi.org/10.3390/cosmetics5020033
---------- VANCOUVER ----------
Lazópulos, S.Q., Svarc, F., Sagrera, G., Dicelio, L. Absorption and photo-stability of substituted dibenzoylmethanes and chalcones as UVA filters. Cosmetics. 2018;5(2).
http://dx.doi.org/10.3390/cosmetics5020033