Synthesis and application of a novel sunscreen-antioxidant

Free Radical Research

Volumn 40, Issue 5, 2006, Pages 485-494

  Damiani, Elisabetta ^a   Astolfi, Paola ^a   Cionna, Laura ^a   Ippoliti, Francesca ^a   Greci, Lucedio ^a  

^a UNIVERSITÀ POLITECNICA DELLE MARCHE   (Italy)

Author keywords

2 ethylhexyl 4 methoxycinnamate; 4 tert butyl 4 methoxydibenzoylmethane; Antioxidant; Lipid peroxidation; Nitroxide; Sunscreen; UVA

Indexed keywords

2,2,6,6 TETRAMETHYLPIPERIDIN 4 YLMETHOXYCINNAMOYL 1 OXYL; 4 METHOXYCINNAMIC ACID 2 ETHYLHEXYL ESTER; ALPHA TOCOPHEROL; ANTIOXIDANT; BUTYLCRESOL; LIPOSOME; SUNSCREEN; TEMPOL; THIOBARBITURIC ACID REACTIVE SUBSTANCE; UNCLASSIFIED DRUG;

ANTIOXIDANT ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG EFFICACY; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTRON SPIN RESONANCE; LIPID PEROXIDATION; OXIDATIVE STRESS; SKIN DEFECT; SUNLIGHT; ULTRAVIOLET A RADIATION; ULTRAVIOLET B RADIATION;

ANTIOXIDANTS; CINNAMATES; CYCLIC N-OXIDES; ELECTRON SPIN RESONANCE SPECTROSCOPY; FREE RADICAL SCAVENGERS; LIPID PEROXIDATION; LIPOSOMES; OXIDATION-REDUCTION; SPIN LABELS; SUNSCREENING AGENTS; THIOBARBITURIC ACID REACTIVE SUBSTANCES; ULTRAVIOLET RAYS;

EID: 33645100967     PISSN: 10715762     EISSN: 10292470     Source Type: Journal    
DOI: 10.1080/10715760600590065     Document Type: Article

References (63)

1. Clydesdale, GJ and Dandie, GW and Muller, HK. (2001) Ultraviolet light induced injury: Immunological and inflammatory effects Immunol Cell Biol, 79, pp. 547-568.
2. Lucas, RM and Ponsonby, AL. (2002) Ultraviolet radiation and health: Friend and foe Med J Aust, 177, pp. 594-598.
3. Elwood, JM and Jopson, J. (1997) Melanoma and sun exposure: An overview of published studies Int J Cancer, 73, pp. 198-203.
4. Wikonai, NM and Brash, DE. (1999) Ultraviolet radiation induced signature mutations in photocarcinogenesis J Investig Dermatol Symp Proc, 4, pp. 6-10.
5. Sliney, DH. (1994) Epidemiological studies of sunlight and cataract: The critical factor of ultraviolet exposure geometry Opthalmic Epidemiol, 1, pp. 107-119.
6. Gruijl, FR. (2000) Photocarcinogensis: UVA vs UVB Meth Enzymol, 319, pp. 359-366.
7. Scharffetter-Kochanek, K and Wlaschek, M and Brenneisen, P and Schauen, M and Blaudschun, R and Wenk, J. (1997) UV-induced reactive oxygen species in photocarcinogenesis and photoageing Biol Chem, 378, pp. 1247-1257.
8. Phillipson, RP and Robi, SE and Morris, MA and McMillan, TJ. (2002) UV-A induces persistent genomic instability in human keratinocytes through an oxidative stress mechanism Free Radic Biol Med, 32, pp. 474-480.
9. Packer, L. (1994) Ultraviolet radiation (UVA, UVB) and skin antioxidants. In Free radical damage and its control. Amsterdam: Elsevier Science.
10. Cole, C. (2001) Sunscreen protection in the ultraviolet A region: How to measure effectiveness Photodermatol Photoimmunol Photomed, 17, pp. 2-10.
11. Autier, P and Pedeux, R and Doré, JF. (1999) Sunscreen use and duration of sun exposure: A double-blind randomised trial J Natl Cancer Inst, 91, pp. 1304-1309.
12. Zastrow, L and Ferrero, L and Herrling, T and Groth, N. (2004) Integrated sun protection factor: A new sun protection factor based on free radicals generated by UV irradiation Skin Pharmacol Physiol, 17, pp. 219-231.
13. Haywood, R and Wardman, P and Sanders, R and Linge, C. (2003) Sunscreens inadequately protect against ultraviolet-A-induced free radicals in skin: Implications for skin ageing and melanoma? J Invest Dermatol, 121, pp. 862-868.
14. Lin, J-Y and Selim, MA and Shea, CR and Grichnik, JM and Omar, MM and Monteiro-Riviere, NA and Pinnel, SR. (2003) UV photoprotection by combination topical antioxidants vitamin C and vitamin E J Am Acad Dermatol, 48, pp. 866-874.
15. Chiu, A and Kimball, AB. (2003) Topical vitamins, minerals and botanical ingredients as modulators of environmental and chronological skin damage Br J Dermatol, 149, pp. 681-691.
16. Elmets, CA and Singh, D and Tubesing, K and Matsui, M and Katiyar, S and Mukhtar, H. (2001) Cutaneous photoprotection from ultraviolet injury by green tea polyphenols J Am Acad Dermatol, 44, pp. 425-432.
17. Damiani, E and Castagna, R and Greci, L. (2002) The effects of derivatives of the nitroxide TEMPOL on UVA-mediated in vitro lipid and protein oxidation Free Radic Biol Med, 33, pp. 128-136.
18. Damiani, E and Greci, L and Parsons, R and Knowland, J. (1999) Nitroxide radicals protect DNA from damage when illuminated in vitro in the presence of dibenzoylmethane and a common sunscreen ingredient Free Radic Biol Med, 26, pp. 809-816.
19. Damiani, E and Carloni, P and Biondi, C and Greci, L. (2000) 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, 28, pp. 193-201.
20. Bernstein, EF and Kong, SK and Brown, DB and Kwak, BC and Takeuchi, T and Gasparro, FP and Uitto, J. (2001) The nitroxide TEMPOL affords protection against ultraviolet radiation in a transgenic murine fibroblast culture model of cutaneous photoaging Exp Dermatol, 10, pp. 55-61.
21. Yan, S and Hong, X and Hu, Y and Liao, K. (2005) Tempol, one of nitroxides, is a novel ultraviolet-A1 radiation protector for human dermal fibroblasts J Dermatol Sci, 37, pp. 137-143.
22. Schwack, W and Rudolph, T. (1995) Photochemistry of dibenzoylmethane UVA filters. Part 1 J Photochem Photobiol B, 28, pp. 229-234.
23. Roscher, NM and Lindeman, MKO and Kong, SB and Cho, CG and Jiang, P. (1994) Photodecomposition of several compounds commonly used as sunscreen agents J Photochem Photobiol A, 80, pp. 417-421.
24. Dragutan, I. (1990) Connecting hindered amines with aminoxyl radicals. I. One-step synthesis of spin-labelled esters Free Radic Res Commun, 9, pp. 379-382.
25. Danek, S and Kelly, DP and Serelis, AK and Steel, PJ. (1987) A stereospecific synthesis of azonitriles J Org Chem, 52, pp. 2911-2919.
26. Buege, J and Aust, SD. (1978) Microsomal lipid peroxidation Meth Enzymol, 52, pp. 302-310.
27. Seite, S and Moyal, D and Richard, S and de Rigal, J and Leveque, J and Hoursequ, C and Fourtanier, A. (1998) Mexoryl SX: A broad absorption UVA filter protects human skin from the effects of repeated suberythemal doses of UVA J Photochem Photobiol, 44, pp. 69-76.
28. Maier, H and Schauberger, G and Brunnhofer, K and Honigsmann, H. (2001) Change of ultraviolet absorbance of sunscreens by exposure to solar-simulated radiation J Invest Dermatol, 117, pp. 256-262.
29. Damiani, E and Rosati, L and Castagna, R and Carloni, P and 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
30. Serpone, N and Salinaro, A and Emeline, AV and Horikoshi, S and Hidaka, H and Zhao, J. (2002) 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, 1, pp. 970-981.
31. Tarras-Wahlberg, N and Stenhagen, G and Larko, O and Rosén, A and Wennberg, A-M and Wennerstrom, O. (1999) Changes in ultraviolet absorption of sunscreens after ultraviolet irradiation J Invest Dermatol, 113, pp. 547-553.
32. Broadbent, JK and Martincigh, BS and Raynor, MW and Salter, LF and Moulder, R and Sjoberg, P and Markides, KE. (1996) 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, 732, pp. 101-110.
33. Pattanaargson, S and Limphong, P. (2001) Stability of octyl methoxycinnamate and identification of its photo-degradation product Int J Cosmet Sci, 23, pp. 153-160.
34. Schrader, A and Jakupovic, J and Baltes, W. (1994) Photochemical studies on trans-3-methyl-4-methoxycinnamate J Soc Cosmet Chem, 45, pp. 43-52.
35. Damiani, E and Castagna, R and Astolfi, P and Greci, L. (2005) Aromatic and aliphatic mono- and bis-nitroxides: A study on their radical scavenging abilities Free Radic Res, 39, pp. 325-336.
36. Chateauneuf, J and Lusztyk, J and Inglold, KU. (1988) Absolute rate constants for the reactions of some carbon-centered radicals with 2,2,6,6-tetramethylpiperidine-N-oxyl J Org Chem, 53, pp. 1629-1632.
37. Morlière, P and Moysan, A and Santus, R and Huppe, G and Mazière, J-C and Dubertret, L. (1991) UVA-induced lipid peroxidation in cultured human fibroblasts Biochim Biophys Acta, 1084, pp. 261-268.
38. Morlière, P and Moysan, A and Tirache, I. (1995) Action Spectrum for UV-induced lipid peroxidation in cultured human skin fibroblasts Free Radic Biol Med, 19, pp. 365-371.
39. Esterbauer, H and Cheeseman, KH. (1990) Determination of aldehydic lipid peroxidation products: Malodialdehyde and 4-hydroxynonenal Meth Enzymol, 186, pp. 407-421.
40. Vile, GF and Tyrrell, RM. (1995) 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, 18, pp. 721-730.
41. Cantrell A and McGarvey, DJ. (2001) Photochemical studies of 4-tert-butyl-4-methoxydibenzoylmethane (BM-DBM) J Photochem Photobiol B, 64, pp. 117-122.
42. Andrae, I and Bringhen, A and Boehm, F and Gonzenbach, H and Hill, T and Mulroy, L and Truscott, TG. (1997) A UVA filter (4-tert-butyl-4-methoxydibenzoylmethane): Photoprotection reflects photophysical properties J Photochem Photobiol B, 37, pp. 147-150.
43. Johncock, W. (1999) Sunscreen interaction in formulations Cosmet Toil, 114, pp. 75-80.
44. Sayre, RM and Dowdy, JC and Gerwig, AM and Shields, WM and Lloyd, RV. (2005) Unexpected photolysis of the sunscreen octinoxate in the presence of the sunscreen avobenzone Photochem Photobiol, 81, pp. 452-456.
45. Shindo, Y and Hashimoto, T. (1997) Time course of changes in antioxidant enzymes in human skin fibroblasts after UVA irradiation J Dermatol Sci, 14, pp. 225-232.
46. Shindo, Y and Witt, E and Han, D and Epstein, W and Packer, L. (1994) Enzymic and non-enzymic antioxidants in epidermis and dermis of human skin J Invest Dermatol, 102, pp. 122-124.
47. Shindo, Y and Witt, E and Packer, L. (1994) Dose-response effects of acute ultraviolet irradiation on antioxidants and molecular markers of oxidation in murine epidermis and dermis J Invest Dermatol, 102, pp. 470-475.
48. Sander, CS and Chang, H and Salzmann, S and Muller, CSL and Ekanayake-Mudiyanselage, S and Elsner, P and Thiele, JJ. (2002) Photoaging is associated with protein oxidation in human skin in vivo J Invest Dermatol, 118, pp. 618-625.
49. Podda, M and Traber, MG and Weber, C and Yan, LJ and Packer, L. (1998) UV-irradiation depletes antioxidants and causes oxidative damage in a model of human skin Free Radic Biol Med, 24, pp. 55-65.
50. Dunford, R and Salinaro, A and Cai, L and Serpone, N and Horikoshi, S and Hidaka, H and Knowland, J. (1997) Chemical oxidation and DNA damage catalyzed by inorganic sunscreen ingredients FEBS Lett, 418, pp. 87-90.
51. Armeni, T and Damiani, E and Battino, M and Greci, L and Principato, G. (2004) Lack of in vitro protection by a common sunscreen ingredient on UVA-induced cytotoxicity in keratinocytes Toxicology, 203, pp. 165-178.
52. Schallreuter, KU and Wood, JM and Farwell, DW and Moore, J and Edwards, HGM. (1996) Oxybenzone oxidation following solar irradiation of skin: Photoprotection versus antioxidant inactivation J Invest Dermatol, 106, pp. 583-586.
53. 2) in illuminated aqueous solutions of p-aminobenzoic acid (PABA) J Photochem Photobiol, 32, pp. 33-37.
54. Inbaraj, JJ and Bilski, P and Chignell, CF. (2002) Photophysical and photochemical studies of 2-phenylbenzimidazole and UVB sunscreen 2-phenylbenzimidazole-5-sulfonic acid Photochem Photobiol, 75, pp. 107-116.
55. Allen, JM and Gossett, CJ and Allen, SK. (1996) Photochemical formation of singlet molecular oxygen in illuminated aqueous solutions of several commercially available sunscreen active agents Chem Res Toxicol, 9, pp. 605-609.
56. Mitchell, JB and Krishna, MC and Samuni, A.(1997) Nitroxides as protectors against oxidative stress. In Reactive oxygen species in biological systems. (pp.293- 313). New York: Plenum Press.
57. Samuni, A and Krishna, MC.(1997) Antioxidant properties of nitroxides and nitroxide SOD mimics. In Handbook of synthetic antioxidants. (pp.351-373). New York: Marcel Dekker Inc.
58. (1995) Nitroxide spin labels: Reactions in biology and chemistry. Boca Raton: CRC Press.
59. Fuchs, J and Groth, N and Herrling, T. (1998) Cutaneous tolerance to nitroxide free radicals in human skin Free Radic Biol Med, 24, pp. 643-648.
60. Pospisil, J.(1985) Mechansims of aromatic amine antidegradants. In Polymer stabilization and degradation. (pp. 157-172). Washington: ACS Symposium series.
61. Sedlar, J.(1990) Hindered amines as photostabilizers. In Oxidation inhibition in organic materials. (pp. 2 - 28). Boca Raton: CRC Press.
62. Bauer, DR and Herlock, JL and Miewlewski, DF. (1992) 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, 36, pp. 9-15.
63. Beaton, CR and Argyropoulos, DS. (2001) Photostabilizing milled wood lignin with benzotriazoles and hindered nitroxides Photochem Photobiol, 73, pp. 605-610.