Protective properties of novel S-Acyl-glutathione thioesters against ultraviolet-induced oxidative stress

Photochemistry and Photobiology

Volumn 89, Issue 2, 2013, Pages 442-452

  Wright, Daniel ^a   Zampagni, Mariagioia ^a   Evangelisti, Elisa ^a   Conti, Simona ^a   D'Adamio, Giampiero ^a   Goti, Andrea ^a   Becatti, Matteo ^a   Fiorillo, Claudia ^a   Taddei, Niccolò ^a   Cecchi, Cristina ^a   Liguri, Gianfranco ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIOXIDANT; CASPASE 3; DRUG DERIVATIVE; GLUTATHIONE; REACTIVE OXYGEN METABOLITE;

ARTICLE; CELL SURVIVAL; CYTOLOGY; DRUG ANTAGONISM; DRUG EFFECT; ENZYME ACTIVATION; ENZYMOLOGY; FIBROBLAST; HUMAN; LIPID PEROXIDATION; METABOLISM; OXIDATIVE STRESS; PRIMARY CELL CULTURE; RADIATION EXPOSURE; SKIN; SYNTHESIS; TUMOR CELL LINE; ULTRAVIOLET RADIATION;

ANTIOXIDANTS; CASPASE 3; CELL LINE, TUMOR; CELL SURVIVAL; ENZYME ACTIVATION; FIBROBLASTS; GLUTATHIONE; HUMANS; LIPID PEROXIDATION; OXIDATIVE STRESS; PRIMARY CELL CULTURE; REACTIVE OXYGEN SPECIES; SKIN; ULTRAVIOLET RAYS;

EID: 84874695889     PISSN: 00318655     EISSN: 17511097     Source Type: Journal    
DOI: 10.1111/j.1751-1097.2012.01231.x     Document Type: Article

References (57)

1. Taylor, C. R., and, A. J. Sober, (1996) Sun exposure and skin disease. Annu. Rev. Med. 147, 181-191.
2. Heinrich, U., K. Neukam, H. Tronnier, H. Sies, and, W. Stahl, (2006) Long-term ingestion of high flavanol cocoa provides photoprotection against UV-induced erythema and improves skin condition in women. J. Nutr. 136, 1565-1569.
3. Mittal, A., C. A. Elmets, and, S. K. Katiyar, (2003) CD11b+ cells are the major source of oxidative stress in UV radiation-irradiated skin: Possible role in photoaging and photocarcinogenesis. Photochem. Photobiol. 77, 259-264.
4. 2 or ultraviolet B light. Arch. Dermatol. Res. 290, 113-118.
5. Renzing, J., S. Hansen, and, D. P. Lane, (1996) Oxidative stress is involved in the UV activation of p53. J. Cell Sci. 109, 1105-1112.
6. Chan, W. H., and, J. S. Yu, (2000) Inhibition of UV irradiation-induced oxidative stress and apoptotic biochemical changes in human epidermal carcinoma A431 cells by genistein. J. Cell. Biochem. 78, 73-84.
7. Clydesdale, G. J., G. W. Dandie, and, H. K. Muller, (2001) Ultraviolet light induced injury: Immunological and inflammatory effects. Immunol. Cell Biol. 79, 547-568.
8. Bertling, C. J., F. Lin, and, A. W. Girotti, (1996) Role of hydrogen peroxide in the cytotoxic effects of UVA/B radiation on mammalian cells. Photochem. Photobiol. 64, 137-142.
9. 2 is an important mediator of UVB-induced EGF-receptor phosphorylation in cultured keratinocytes. J. Invest. Dermatol. 110, 966-971.
10. Katiyar, S. K., F. Afaq, K. Azizuddin, and, H. Mukhtar, (2001) Inhibition of UVB-induced oxidative stress-mediated phosphorylation of mitogen-activated protein kinase signaling pathways in cultured human epidermal keratinocytes by green tea polyphenol (2)-epigallocatechin-3-gallate. Toxicol. Appl. Pharmacol. 176, 110-117.
11. Katiyar, S. K., F. Afaq, A. Perez, and, H. Mukhtar, (2001) Green tea polyphenol (-)-epigallocatechin-3-gallate treatment of human skin inhibits ultraviolet radiation-induced oxidative stress. Carcinogenesis 22, 287-294.
12. Vayalil, P. K., C. A. Elmets, and, S. K. Katiyar, (2003) Treatment of green tea polyphenols in hydrophilic cream prevents UVB-induced oxidation of lipids and proteins, depletion of antioxidant enzymes and phosphorylation of MAPK proteins in SKH-1 hairless mouse skin. Carcinogenesis 24, 927-936.
13. Prasad, N. R., K. Jeyanthimala, and, S. Ramachandran, (2009) Caffeic acid modulates ultraviolet radiation-B induced oxidative damage in human blood lymphocytes. J. Photochem. Photobiol. 95, 196-203.
14. Katiyar, S. K., (2002) Treatment of silymarin, a plant flavonoid, prevents ultraviolet light-induced immune suppression and oxidative stress in mouse skin. Int. J. Oncol. 21, 1213-1222.
15. Afaq, F., V. M. Adhami, and, N. Ahmad, (2003) Prevention of short-term ultraviolet B radiation-mediated damages by resveratrol in SKH-1 hairless mice. Toxicol. Appl. Pharmacol. 186, 28-37.
16. Nichols, J. A., and, S. K. Katiyar, (2010) Skin photoprotection by natural polyphenols: Anti-inflammatory, anti-oxidant and DNA repair mechanisms. Arch. Dermatol. Res. 302, 71-83.
17. Afaq, F., (2011) Natural agents: Cellular and molecular mechanisms of photoprotection. Arch. Biochem. Biophys. 508, 144-151.
18. Pence, B. C., and, M. F. Naylor, (1990) Effects of single-dose ultraviolet radiation on skin superoxide dismutase, catalase, and xanthine oxidase in hairless mice. J. Invest. Dermatol. 95, 213-216.
19. Slyshenkov, V. S., K. Piwocka, E. Sikora, and, L. Wojtczak, (2001) Pantothenic acid protects jurkat cells against ultraviolet light-induced apoptosis. Free Radic. Biol. Med. 30, 1303-1310.
20. Hanada, K., D. Sawamura, K. Tamai, I. Hashimoto, and, S. Kobayashi, (1997) Photoprotective effect of esterified glutathione against ultraviolet B-induced sunburn cell formation in the hairless mice. J. Invest. Dermatol. 108, 727-730.
21. Hayes, J. D., and, L. I. McLellan, (1999) Glutathione and glutathione-dependent enzymes represent a co-ordinately regulated defence against oxidative stress. Free Radic. Res. 31, 273-300.
22. Connor, M. J., and, L. A. Wheeler, (1987) Depletion of cutaneous glutathione by ultraviolet radiation. Photochem. Photobiol. 46, 239-245.
23. Lu, S. C., (1999) Regulation of hepatic glutathione synthesis: Current concept and controversies. FASEB J. 13, 1169-1183.
24. Cacciatore, I., C. Cornacchia, F. Pinnen, A. Mollica, and, A. Di Stefano, (2010) Prodrug approach for increasing cellular glutathione levels. Molecules 15, 1242-1264.
25. James, S. J., W. Slikker, S. Melnyk, E. New, M. Pogribna, and, S. Jernigan, (2005) Thimerosal neurotoxicity is associated with glutathione depletion: Protection with glutathione precursors. Neurotoxicology 26, 1-8.
26. Ehrlich, K., S. Viirlaid, R. Mahlapuu, K. Saar, T. Kullisaar, M. Zilmer, U. Langel, and, U. Soomets, (2007) Design, synthesis and properties of novel powerful antioxidants, glutathione analogues. Free Radic. Res. 41, 779-787.
27. Wellner, V. P., M. E. Anderson, R. N. Puri, G. L. Jensen, and, A. Meister, (1984) Radioprotection by glutathione ester: Transport of glutathione ester into human lymphoid cells and fibroblasts. Proc. Natl. Acad. Sci. U.S.A. 81, 4732-4735.
28. Zampagni, M., D. Wright, R. Cascella, G. D'Adamio, F. Casamenti, E. Evangelisti, F. Cardona, A. Goti, B. Nacmias, S. Sorbi, G. Liguri, and, C. Cecchi, (2012) Novel S-acyl-glutathione derivatives prevent amyloid oxidative stress and cholinergic dysfunction in Alzheimer's disease models. Free Radic. Biol. Med. 15, 1362-1371.
29. Pensalfini, A., C. Cecchi, M. Zampagni, M. Becatti, F. Favilli, P. Paoli, S. Catarzi, S. Bagnoli, B. Nacmias, S. Sorbi, and, G. Liguri, (2008) Protective effect of new S-acylglutathione derivatives against amyloid-induced oxidative stress. Free Radic. Biol. Med. 44, 1624-1636.
30. Kamencic, H., A. Lyon, P. G. Paterson, and, B. H. Juurlink, (2000) Monochlorobimane fluorometric method to measure tissue glutathione. Anal. Biochem. 286, 35-37.
31. Becatti, M., N. Taddei, C. Cecchi, N. Nassi, P.A. Nassi, and, C. Fiorillo, (2012) SIRT1 modulates MAPK pathways in ischemic-reperfused cardiomyocytes. Cell. Mol. Life Sci. 69, 2245-2260.
32. Drummen, G. P. C., B. M. Gadella, J. A. Post, and, J. F. Brouwers, (2004) Mass spectrometric characterization of the oxidation of the fluorescent lipid peroxidation reporter molecule C11-BODIPY581/591. Free Radic. Biol. Med. 36, 1635-1644.
33. Becatti, M., F. Prignano, C. Fiorillo, L. Pescitelli, P. Nassi, T. Lotti, and, N. Taddei, (2010) The involvement of Smac/DIABLO, p53, NF-kB, and MAPK pathways in apoptosis of keratinocytes from perilesional vitiligo skin: Protective effects of curcumin and capsaicin. Antioxid. Redox Signal. 13, 1309-1321.
34. Thornberry, N. A., T. A. Ran, E. P. Peterson, D. M. Rasper, T. Timkey, M. Garcia-Calvo, V. M. Houtzager, P. A. Nordstrom, S. Roy, J. P. Vaillancourt, K. T. Chapman, and, D. W. Nicholson, (1997) A combinatorial approach defines specificities of members of the caspase family and granzyme B. Functional relationships established for key mediators of apoptosis. J. Biol. Chem. 272, 17907-17911.
35. Schulz, J. B., J. Lindenau, J. Seyfried, and, J. Dichgans, (2000) Glutathione, oxidative stress and neurodegeneration. Eur. J. Biochem. 267, 4904-4911.
36. Griffith, O. W., (1999) Biologic and pharmacologic regulation of mammalian glutathione synthesis. Free Radic. Biol. Med. 27, 922-935.
37. Schwarz, T., (1998) UV light affects cell membrane and cytoplasmic targets. J. Photochem. Photobiol. 44, 91-96.
38. Dunkern, T. R., G. Fritz, and, B. Kain, (2001) Ultraviolet light-induced DNA damage triggers apoptosis in nucleotide excision repair-deficient cells via Bcl-2 decline and caspase-3/-8 activation. Oncogene 20, 6026-6038.
39. Heck, D. E., A. M. Vetrano, T. M. Mariano, and, J. D. Laskin, (2003) UVB light stimulates production of reactive oxygen species. J. Biol. Chem. 278, 22432-22436.
40. Bossi, O., M. Gartsbein, M. Leitges, T. Kuroki, S. Grossman, and, T. Tennenbaum, (2008) UV irradiation increases ROS production via PKC delta signaling in primary murine fibroblasts. J. Cell. Biochem. 105, 194-207.
41. Trouba, K. J., H. K. Hamadeh, R. P. Amin, and, D. R. Germolec, (2002) Oxidative stress and its role in skin disease. Antioxid. Redox Signal. 4, 665-673.
42. He, Y. Y., J. L. Huang, M. L. Block, J. S. Hong, and, C. F. Chignell, (2005) Role of phagocyte oxidase in UVA-induced oxidative stress and apoptosis in keratinocytes. J. Invest. Dermatol. 125, 560-566.
43. Dissemond, J., L. A. Schneider, P. Brenneisen, K. Briviba, J. Wenk, M. Wlaschek, and, K. Scharffetter-Kochanek, (2003) Protective and determining factors for the overall lipid peroxidation in ultraviolet A1-irradiated fibroblasts: In vitro and in vivo investigations. Br. J. Dermatol. 149, 341-349.
44. Gentile, M., L. Latonen, and, M. Laiho, (2003) Cell cycle arrest and apoptosis provoked by UV radiation-induced DNA damage are transcriptionally highly divergent responses. Nucleic Acids Res. 31, 4779-4790.
45. Prasad, N. R., S. Ramachandran, K. V. Pugalendi, and, V. P. Menon, (2007) Ferulic acid inhibits UV-B-induced oxidative stress in human lymphocytes. Nutr. Res. 27, 559-564.
46. Marionnet, C., C. Pierrard, F. Lejeune, J. Sok, M. Thomas, and, F. Bernerd, (2010) Different oxidative stress response in keratinocytes and fibroblasts of reconstructed skin exposed to non extreme daily-ultraviolet radiation. PLoS ONE 5, e12059.
47. Brugè, F., L. Tiano, T. Cacciamani, F. Principi, and, G. P. Littarru, (2003) Effect of UV-C mediated oxidative stress in leukemia cell lines and its relation to ubiquinone content. BioFactors 18, 51-63.
48. Tülüce, Y., H. Özkol, and, I. Koyuncu, (2012) Photoprotective effect of flax seed oil (Linum usitatissimum L.) against ultraviolet C-induced apoptosis and oxidative stress in rats. Toxicol. Ind. Health 28, 99-107.
49. Hartley, D. P., K. L. Kalaja, J. Reichard, and, D. R. Petersen, (1999) 4-Hydroxynonenal and malondialdehyde hepatic protein adducts in rats treated with carbon tetrachloride: Immunochemical detection and lobular localization. Toxicol. Appl. Pharmacol. 161, 23-33.
50. Kanner, J., J. B. German, and, J. E. Kinsella, (1987) Initiation of lipid peroxidation in biological systems. Crit. Rev. Food Sci. Nutr. 25, 317-364.
51. Mantena, S. K., and, S. K. Katiyar, (2006) Grape seed proanthocyanidins inhibit UV-radiation-induced oxidative stress and activation of MAPK and NF-κB signaling in human epidermal keratinocytes. Free Radic. Biol. Med. 40, 1603-1614.
52. Goodson, A. G., M. A. Cotter, P. Cassidy, M. Wade, S. R. Florell, T. Liu, K. M. Boucher, and, D. Grossman, (2009) Use of oral N-acetylcysteine for protection of melanocytic nevi against UV-induced oxidative stress: Towards a novel paradigm for melanoma chemoprevention. Clin. Cancer Res. 15, 7434-7440.
53. Richard, D., K. Kefi, U. Barbe, P. Bausero, and, F. Visioli, (2008) Polyunsaturated fatty acids as antioxidants. Pharmacol. Res. 57, 451-455.
54. Gogus, U., and, C. Smith, (2010) n-3 Omega fatty acids: A review of current knowledge. Int. J. Food Sci. Tech. 45, 417-436.
55. McArdle, F., L. E. Rhodes, R. A. G. Parslew, G. L. Close, C. I. A. Jack, P. S. Friedmann, and, M. J. Jackson, (2004) Effects of oral vitamin E and β-carotene supplementation on ultraviolet radiation-induced oxidative stress in human skin. Am. J. Clin. Nutr. 80, 1270-1275.
56. Placzek, M., S. Gaube, U. Kerkmann, K. P. Gilbertz, T. Herzinger, E. Haen, and, B. Przybilla, (2005) Ultraviolet B-induced DNA damage in human epidermis is modified by the antioxidants ascorbic acid and d -α-tocopherol. J. Invest. Dermatol. 124, 304-307.
57. Zhu, M., and, G. T. Bowden, (2004) Molecular mechanism(s) for UV-B irradiation-induced glutathione depletion in cultured human keratinocytes. Photochem. Photobiol. 80, 191-196.