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Original

Synthesis and application of a novel sunscreen-antioxidant

, , , &
Pages 485-494 | Received 11 Nov 2005, Published online: 07 Jul 2009

References

  • Clydesdale GJ, Dandie GW, Muller HK. Ultraviolet light induced injury: Immunological and inflammatory effects. Immunol Cell Biol 2001; 79: 547–568
  • Lucas RM, Ponsonby AL. Ultraviolet radiation and health: Friend and foe. Med J Aust 2002; 177: 594–598
  • Elwood JM, Jopson J. Melanoma and sun exposure: An overview of published studies. Int J Cancer 1997; 73: 198–203
  • Wikonai NM, Brash DE. Ultraviolet radiation induced signature mutations in photocarcinogenesis. J Investig Dermatol Symp Proc 1999; 4: 6–10
  • Sliney DH. Epidemiological studies of sunlight and cataract: The critical factor of ultraviolet exposure geometry. Opthalmic Epidemiol 1994; 1: 107–119
  • Gruijl FR. Photocarcinogensis: UVA vs UVB. Meth Enzymol 2000; 319: 359–366
  • Scharffetter-Kochanek K, Wlaschek M, Brenneisen P, Schauen M, Blaudschun R, Wenk J. UV-induced reactive oxygen species in photocarcinogenesis and photoageing. Biol Chem 1997; 378: 1247–1257
  • Phillipson RP, Robi SE, Morris MA, McMillan TJ. UV-A induces persistent genomic instability in human keratinocytes through an oxidative stress mechanism. Free Radic Biol Med 2002; 32: 474–480
  • Packer L. Ultraviolet radiation (UVA, UVB) and skin antioxidants. Free radical damage and its control, CA Rice-Evans, RH Burdon. Elsevier Science, Amsterdam 1994
  • Cole C. Sunscreen protection in the ultraviolet A region: How to measure effectiveness. Photodermatol Photoimmunol Photomed 2001; 17: 2–10
  • Autier P, Pedeux R, Doré JF. Sunscreen use and duration of sun exposure: A double-blind randomised trial. J Natl Cancer Inst 1999; 91: 1304–1309
  • Zastrow L, Ferrero L, Herrling T, Groth N. Integrated sun protection factor: A new sun protection factor based on free radicals generated by UV irradiation. Skin Pharmacol Physiol 2004; 17: 219–231
  • Haywood R, Wardman P, Sanders R, Linge C. Sunscreens inadequately protect against ultraviolet-A-induced free radicals in skin: Implications for skin ageing and melanoma?. J Invest Dermatol 2003; 121: 862–868
  • Lin J-Y, Selim MA, Shea CR, Grichnik JM, Omar MM, Monteiro-Riviere NA, Pinnel SR. UV photoprotection by combination topical antioxidants vitamin C and vitamin E. J Am Acad Dermatol 2003; 48: 866–874
  • Chiu A, Kimball AB. Topical vitamins, minerals and botanical ingredients as modulators of environmental and chronological skin damage. Br J Dermatol 2003; 149: 681–691
  • Elmets CA, Singh D, Tubesing K, Matsui M, Katiyar S, Mukhtar H. Cutaneous photoprotection from ultraviolet injury by green tea polyphenols. J Am Acad Dermatol 2001; 44: 425–432
  • Damiani E, Castagna R, Greci L. The effects of derivatives of the nitroxide TEMPOL on UVA-mediated in vitro lipid and protein oxidation. Free Radic Biol Med 2002; 33: 128–136
  • Damiani E, Greci L, Parsons R, Knowland J. Nitroxide radicals protect DNA from damage when illuminated in vitro in the presence of dibenzoylmethane and a common sunscreen ingredient. Free Radic Biol Med 1999; 26: 809–816
  • Damiani E, Carloni P, Biondi C, Greci L. Increased oxidative modification of albumin when illuminated in vitro in the presence of a common sunscreen ingredient: Protection by nitroxide radicals. Free Radic Biol Med 2000; 28: 193–201
  • Bernstein EF, Kong SK, Brown DB, Kwak BC, Takeuchi T, Gasparro FP, Uitto J. The nitroxide TEMPOL affords protection against ultraviolet radiation in a transgenic murine fibroblast culture model of cutaneous photoaging. Exp Dermatol 2001; 10: 55–61
  • Yan S, Hong X, Hu Y, Liao K. Tempol, one of nitroxides, is a novel ultraviolet-A1 radiation protector for human dermal fibroblasts. J Dermatol Sci 2005; 37: 137–143
  • Schwack W, Rudolph T. Photochemistry of dibenzoylmethane UVA filters. Part 1. J Photochem Photobiol B 1995; 28: 229–234
  • Roscher NM, Lindeman MKO, Kong SB, Cho CG, Jiang P. Photodecomposition of several compounds commonly used as sunscreen agents. J Photochem Photobiol A 1994; 80: 417–421
  • Dragutan I. Connecting hindered amines with aminoxyl radicals. I. One-step synthesis of spin-labelled esters. Free Radic Res Commun 1990; 9: 379–382
  • Danek S, Kelly DP, Serelis AK, Steel PJ. A stereospecific synthesis of azonitriles. J Org Chem 1987; 52: 2911–2919
  • Buege J, Aust SD. Microsomal lipid peroxidation. Meth Enzymol 1978; 52: 302–310
  • Seite S, Moyal D, Richard S, de Rigal J, Leveque J, Hoursequ C, Fourtanier A. Mexoryl SX: A broad absorption UVA filter protects human skin from the effects of repeated suberythemal doses of UVA. J Photochem Photobiol 1998; 44: 69–76
  • Maier H, Schauberger G, Brunnhofer K, Honigsmann H. Change of ultraviolet absorbance of sunscreens by exposure to solar-simulated radiation. J Invest Dermatol 2001; 117: 256–262
  • Damiani E, Rosati L, Castagna R, Carloni P, Greci L. Changes in ultraviolet absorbance and hence in protective efficacy against lipid peroxidation of organic sunscreens after UVA irradiation. J Photochem Photobiol B, 2006 Jan 24; [Epub ahead of print] PMID: 16442301
  • Serpone N, Salinaro A, Emeline AV, Horikoshi S, Hidaka H, Zhao J. An in vitro systematic spectroscopic examination of the photostabilities of a random set of commercial sunscreen lotions and their chemical UVB/UVA active agents. Photochem Photobiol Sci 2002; 1: 970–981
  • Tarras-Wahlberg N, Stenhagen G, Larko O, Rosén A, Wennberg A-M, Wennerstrom O. Changes in ultraviolet absorption of sunscreens after ultraviolet irradiation. J Invest Dermatol 1999; 113: 547–553
  • Broadbent JK, Martincigh BS, Raynor MW, Salter LF, Moulder R, Sjoberg P, Markides KE. Capillary supercritical fluid chromatography combined with atmospheric pressure chemical ionisation mass spectrometry for the investigation of photoproduct formation in the sunscreen absorber 2-ethylhexyl-p-methoxycinnamate. J Chromatogr 1996; 732: 101–110
  • Pattanaargson S, Limphong P. Stability of octyl methoxycinnamate and identification of its photo-degradation product. Int J Cosmet Sci 2001; 23: 153–160
  • Schrader A, Jakupovic J, Baltes W. Photochemical studies on trans-3-methyl-4-methoxycinnamate. J Soc Cosmet Chem 1994; 45: 43–52
  • Damiani E, Castagna R, Astolfi P, Greci L. Aromatic and aliphatic mono- and bis-nitroxides: A study on their radical scavenging abilities. Free Radic Res 2005; 39: 325–336
  • Chateauneuf J, Lusztyk J, Inglold KU. Absolute rate constants for the reactions of some carbon-centered radicals with 2,2,6,6-tetramethylpiperidine-N-oxyl. J Org Chem 1988; 53: 1629–1632
  • Morlière P, Moysan A, Santus R, Huppe G, Mazière J-C, Dubertret L. UVA-induced lipid peroxidation in cultured human fibroblasts. Biochim Biophys Acta 1991; 1084: 261–268
  • Morlière P, Moysan A, Tirache I. Action Spectrum for UV-induced lipid peroxidation in cultured human skin fibroblasts. Free Radic Biol Med 1995; 19: 365–371
  • Esterbauer H, Cheeseman KH. Determination of aldehydic lipid peroxidation products: Malodialdehyde and 4-hydroxynonenal. Meth Enzymol 1990; 186: 407–421
  • Vile GF, Tyrrell RM. UVA radiation-induced oxidative damage to lipids and proteins in vitro and in human skin fibroblasts is dependent on iron and singlet oxygen. Free Radic Biol Med 1995; 18: 721–730
  • Cantrell A, McGarvey DJ. Photochemical studies of 4-tert-butyl-4-methoxydibenzoylmethane (BM-DBM). J Photochem Photobiol B 2001; 64: 117–122
  • Andrae I, Bringhen A, Boehm F, Gonzenbach H, Hill T, Mulroy L, Truscott TG. A UVA filter (4-tert-butyl-4-methoxydibenzoylmethane): Photoprotection reflects photophysical properties. J Photochem Photobiol B 1997; 37: 147–150
  • Johncock W. Sunscreen interaction in formulations. Cosmet Toil 1999; 114: 75–80
  • Sayre RM, Dowdy JC, Gerwig AM, Shields WM, Lloyd RV. Unexpected photolysis of the sunscreen octinoxate in the presence of the sunscreen avobenzone. Photochem Photobiol 2005; 81: 452–456
  • Shindo Y, Hashimoto T. Time course of changes in antioxidant enzymes in human skin fibroblasts after UVA irradiation. J Dermatol Sci 1997; 14: 225–232
  • Shindo Y, Witt E, Han D, Epstein W, Packer L. Enzymic and non-enzymic antioxidants in epidermis and dermis of human skin. J Invest Dermatol 1994; 102: 122–124
  • Shindo Y, Witt E, Packer L. Dose-response effects of acute ultraviolet irradiation on antioxidants and molecular markers of oxidation in murine epidermis and dermis. J Invest Dermatol 1994; 102: 470–475
  • Sander CS, Chang H, Salzmann S, Muller CSL, Ekanayake-Mudiyanselage S, Elsner P, Thiele JJ. Photoaging is associated with protein oxidation in human skin in vivo. J Invest Dermatol 2002; 118: 618–625
  • Podda M, Traber MG, Weber C, Yan LJ, Packer L. UV-irradiation depletes antioxidants and causes oxidative damage in a model of human skin. Free Radic Biol Med 1998; 24: 55–65
  • Dunford R, Salinaro A, Cai L, Serpone N, Horikoshi S, Hidaka H, Knowland J. Chemical oxidation and DNA damage catalyzed by inorganic sunscreen ingredients. FEBS Lett 1997; 418: 87–90
  • Armeni T, Damiani E, Battino M, Greci L, Principato G. Lack of in vitro protection by a common sunscreen ingredient on UVA-induced cytotoxicity in keratinocytes. Toxicology 2004; 203: 165–178
  • Schallreuter KU, Wood JM, Farwell DW, Moore J, Edwards HGM. Oxybenzone oxidation following solar irradiation of skin: Photoprotection versus antioxidant inactivation. J Invest Dermatol 1996; 106: 583–586
  • Allen JM, Gossett CM, Allen SK. Photochemical formation of singlet molecular oxygen (1O2) in illuminated aqueous solutions of p-aminobenzoic acid (PABA). J Photochem Photobiol 1996; 32: 33–37
  • Inbaraj JJ, Bilski P, Chignell CF. Photophysical and photochemical studies of 2-phenylbenzimidazole and UVB sunscreen 2-phenylbenzimidazole-5-sulfonic acid. Photochem Photobiol 2002; 75: 107–116
  • Allen JM, Gossett CJ, Allen SK. Photochemical formation of singlet molecular oxygen in illuminated aqueous solutions of several commercially available sunscreen active agents. Chem Res Toxicol 1996; 9: 605–609
  • Mitchell JB, Krishna MC, Samuni A. Nitroxides as protectors against oxidative stress. Reactive oxygen species in biological systems, C Colton, D Gilbert. Plenum Press, New York 1997; 293–313
  • Samuni A, Krishna MC. Antioxidant properties of nitroxides and nitroxide SOD mimics. Handbook of synthetic antioxidants, L Packer, E Cadenas. Marcel Dekker Inc, New York 1997; 351–373
  • Nitroxide spin labels: Reactions in biology and chemistry, N Kocherginsky, HM Swartz. CRC Press, Boca Raton 1995
  • Fuchs J, Groth N, Herrling T. Cutaneous tolerance to nitroxide free radicals in human skin. Free Radic Biol Med 1998; 24: 643–648
  • Pospisil J. Mechansims of aromatic amine antidegradants. Polymer stabilization and degradation, PP Klemchuk. ACS Symposium series, Washington 1985; 157–172
  • Sedlar J. Hindered amines as photostabilizers. Oxidation inhibition in organic materials, PP Klemchuk. CRC Press, Boca Raton 1990; vol. II: 2–28
  • Bauer DR, Herlock JL, Miewlewski DF. Photostabilization and photodegradation in organic coatings containing hindered amine light stabilizers VII. HALS effectiveness in acrylic melamine coatings having different free radical formation rates. Polym Degrad Stab 1992; 36: 9–15
  • Beaton CR, Argyropoulos DS. Photostabilizing milled wood lignin with benzotriazoles and hindered nitroxides. Photochem Photobiol 2001; 73: 605–610

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