Solar filters, as photostable compounds, are used to protect the human skin against harmful UV radiation. Up until recently, sun protection was limited to the use of sunscreens whose active ingredients are UV filters, which reflect or absorb UV rays depending on their chemical nature. Today there is a trend toward higher sun protection factors and the use of additional ingredients in sunscreens aimed at further protecting against the indirect damage primarily caused by the deeply penetrating UVA rays. In fact, these wavelengths have been shown to generate reactive oxygen species, which become mediators of cellular oxidative damage, leading to oxidative stress and immune suppression in skin.
In this chapter a photoprotection strategy has been described based on the development of sunscreens to minimize light absorption by the photosensitizers, and the use of scavengers to eliminate the reactive oxygen species arising therefrom. Advantage has been taken from the photochemical and photophysical techniques, through the combination of steady-state photolysis, photoproducts isolation and characterization with time-resolved spectroscopy, such as laser flash photolysis.
A broadband UV filter, the bis-ethylhexyloxyphenol methoxyphenyl triazine (Tinosorb S®), which provide protection against direct and indirect UV-induced DNA damage by absorbing solar UV and reducing ROS formation in the skin, has been chosen. Based on its characteristics, it has been considered whether it would be feasible and useful to have a compound which would display in the same molecule both UV-absorbing and antioxidant properties. This type-molecules could find potential applications for reducing skin photo-oxidative damage.
Triplet Excited State Laser Flash Photolysis Sunscreen Agent Intramolecular Hydrogen Transfer Sunscreen Formulation
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.
This is a preview of subscription content, log in to check access.
The author acknowledges M.A. Miranda and N. Duran-Giner for working in this project.
McKenzie RL, Aucamp PJ, Bais AF, Bjorn LO, Ilyas M, Madronich S (2011) Ozone depletion and climate change: impacts on UV radiation. Photochem Photobiol Sci 10:182–198CrossRefGoogle Scholar
Cadet J, Mouret S, Ravanat JL, Douki T (2012) Photoinduced damage to cellular DNA: direct and photosensitized reactions. Photochem Photobiol 88:1048–1065CrossRefGoogle Scholar
Pfeifer GP, Besaratinia A (2012) UV wavelength-dependent DNA damage and human non-melanoma and melanoma skin cancer. Photochem Photobiol Sci 11:90–97CrossRefGoogle Scholar
Sage E, Girard PM, Francesconi S (2012) Unravelling UVA-induced mutagenesis. Photochem Photobiol Sci 11:74–80CrossRefGoogle Scholar
Banyasz A, Vayá I, Changenet-Barret P, Gustavsson T, Douki T, Markovitsi D (2011) Base pairing enhances fluorescence and favors cyclobutane dimer formation induced upon absorption of UVA radiation by DNA. J Am Chem Soc 133:5163–5165CrossRefGoogle Scholar
Mouret S, Baudouin C, Charveron M, Favier A, Cadet J, Douki T (2006) Cyclobutane pyrimidine dimers are predominant DNA lesions in whole human skin exposed to UVA radiation. Proc Natl Acad Sci U S A 103:13765–13770CrossRefGoogle Scholar
Foote CS (1991) Definition of type I and type II photosensitized oxidation. Photochem Photobiol 54:659–660CrossRefGoogle Scholar
Cadet J, Douki T, Ravanat JL, Di Mascio P (2009) Sensitized formation of oxidatively generated damage to cellular DNA by UVA radiation. Photochem Photobiol Sci 8:903–911CrossRefGoogle Scholar
Wauchope OR, Shakya S, Sawwan N, Liebman JF, Greer A (2007) Photocleavage of plasmid DNA by dibenzothiophene S-oxide under anaerobic conditions. J Sulfur Chem 28:11–16CrossRefGoogle Scholar
Orrego JF, Truong TN, Mondragon F (2008) A linear energy relationship between activation energy and absolute hardness: a case study with the O(3P) atom-addition reactions to polyaromatic hydrocarbons. J Phys Chem A 112:8205–8207CrossRefGoogle Scholar
Zhang M, Ravilious GE, Hicks LM, Jez JM, McCulla RD (2012) Redox switching of adenosine-5′-phospho-sulfate kinase with photoactivatable atomic oxygen precursors. J Am Chem Soc 134:16979–16982CrossRefGoogle Scholar
Damiani E, Astolfi P, Greci L (2008) Nitroxide-based UV-filters: a new strategy against UV-damage? Househ Pers Care Today 2:20–23Google Scholar
Herzog B, Wehrle M, Quass K (2009) Photostability of UV absorber systems in sunscreens. Photochem Photobiol 85:869–878CrossRefGoogle Scholar
Sambandan DR, Ratner D (2011) Sunscreens: an overview and update. J Am Acad Dermatol 64:748–758CrossRefGoogle Scholar
Fourtanier A, Moyal D, Seite S (2012) UVA filters in sun-protection products: regulatory and biological aspects. Photochem Photobiol Sci 11:81–89CrossRefGoogle Scholar
Jansen R, Osterwalder U, Wang SQ, Burnett M, Lim HW (2013) Photoprotection Part II. Sunscreen: development, efficacy and controversies. J Am Acad Dermatol 69:1–14CrossRefGoogle Scholar
Moyal DD, Fourtanier AM (2008) Broad-spectrum sunscreens provide better protection from solar ultraviolet-simulated radiation and natural sunlight-induced immunosuppression in human beings. J Am Acad Dermatol 58:149–154CrossRefGoogle Scholar
Chatelain E, Gabard B (2001) Photostabilization of butyl methoxydibenzoylmethane (Avobenzone) and ethylhexyl methoxycinnamate by bis-ethylhexyloxyphenol methoxyphenyl triazine (Tinosorb S), a new UV broadband filter. Photochem Photobiol 74:401–406CrossRefGoogle Scholar
Serpone N, Dondi D, Albini A (2007) Inorganic and organic UV filters: their role and efficacy in sunscreens and suncare products. Inorg Chim Acta 360:794–802CrossRefGoogle Scholar
Paris C, Lhiaubet-Vallet V, Jimenez O, Trullas C, Miranda MA (2009) A blocked diketo form of avobenzone: photostability, photosensitizing properties and triplet quenching by a triazine-derived UVB-filter. Photochem Photobiol 85:178–184CrossRefGoogle Scholar
Maier T, Korting HC (2005) Sunscreens-Which and what for? Skin Pharmacol Physiol 18:253–262CrossRefGoogle Scholar
Inbaraj JJ, Bilski P, Chignell CF (2002) Photophysical and photochemical studies of 2-phenylbenzimidazole and UVB sunscreen 2-phenylbenzimidazole-5-sulfonic acid. Photochem Photobiol 75:107–116CrossRefGoogle Scholar
Bastien N, Millau JF, Rouabhia M, Davies RJH, Drouin R (2010) The sunscreen agent 2-phenylbenzimidazole-5-sulfonic acid photosensitizes the formation of oxidized guanines in cellulo after UV-A or UV-B exposure. J Invest Dermatol 130:2463–2471CrossRefGoogle Scholar
Lhiaubet-Vallet V, Marin M, Jimenez O, Gorchs O, Trullas C, Miranda MA (2010) Filter-filter interactions. Photostabilization, triplet quenching and reactivity with singlet oxygen. Photochem Photobiol Sci 9:552–558CrossRefGoogle Scholar
McGarry PF, Jockusch S, Fujiwara Y, Kaprinidis NA, Turro NJ (1997) DMSO solvent induced photochemistry in highly photostable compounds. The role of intermolecular hydrogen bonding. J Phys Chem A 101:764–767CrossRefGoogle Scholar
Couteau C, Paparis E, Chauvet C, Coiffard L (2015) Tris-biphenyl triazine, a new ultraviolet filter studied in terms of photoprotective efficacy. Int J Pharm 487:120–123CrossRefGoogle Scholar
Venditti E, Brugè F, Astolfi P, Kochevar I, Damiani E (2011) Nitroxides and a nitroxide-based UV filter have the potential to photoprotect UVA-irradiated human skin fibroblasts against oxidative damage. J Dermatol Sci 63:55–61CrossRefGoogle Scholar
Afonso S, Horita K, Sousa e Silva JP, Almeida IF, Amaral MH, Lobao PA, Costa PC, Miranda MS, Esteves da Silva JCG, Sousa Lobo JM (2014) Photodegradation of avobenzone: stabilization effect of antioxidants. J Photochem Photobiol B Biol 140:36–40CrossRefGoogle Scholar
Gaspar LR, Tharmann J, Maia Campos PMBG, Liebsch M (2013) Skin phototoxicity of cosmetic formulations containing photounstable and photostable UV-filters and vitamin A palmitate. Toxicol in Vitro 27:418–425CrossRefGoogle Scholar
Duran-Giner N, Encinas S, Miranda MA (2013) Solar filters as feasible acceptors of atomic oxygen. Photochem Photobiol Sci 12:725–728CrossRefGoogle Scholar
Albini A, Alpegiani M (1984) The photochemistry of the N-oxide function. Chem Rev 84:43–71CrossRefGoogle Scholar
Bucher G, Scaiano JC (1994) Laser flash photolysis of pyridine N-oxide: kinetic studies of atomic oxygen [O(3P)] in solution. J Phys Chem 98:12471–12473CrossRefGoogle Scholar
Ogawa Y, Iwasaki S, Okuda S (1981) A study on the transition state in the photooxygenations by aromatic amine N-oxides. Tetrahedron Lett 22:2277–2280CrossRefGoogle Scholar