Photodecomposition of retinyl palmitate in ethanol by UVA light-formation of photodecomposition products, reactive oxygen species, and lipid peroxides

Chemical Research in Toxicology

Volumn 18, Issue 2, 2005, Pages 129-138

  Cherng, Shu Hui ^a,c   Xia, Qingsu ^a   Blankenship, Lonnie R ^a   Freeman, James P ^a   Wamer, Wayne G ^b   Howard, Paul C ^a   Fu, Peter P ^a  

^a NATIONAL CENTER FOR TOXICOLOGICAL RESEARCH   (United States)

^b CENTER FOR DRUG EVALUATION AND RESEARCH   (United States)

^c HUNGKUANG UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

11 ETHOXY 12 HYDROXYRETINYL PALMITATE; 13 ETHOXY 14 HYDROXYRETINYL PALMITATE; 2,2' AZOBIS(2,4 DIMETHYLVALERONITRILE); 4 KETORETINYL PALMITATE; 5,6 EPOXYRETINYL PALMITATE; ALCOHOL; DEUTERIUM OXIDE; DITHIOTHREITOL; FREE RADICAL; LIPID PEROXIDE; PALMITIC ACID; PALMITIC ACID ETHYL ESTER; REACTIVE OXYGEN METABOLITE; RETINOL; RETINOL PALMITATE; SODIUM AZIDE; SODIUM NITRATE; UNCLASSIFIED DRUG;

ARTICLE; GENOTOXICITY; LIPID PEROXIDATION; PHOTODEGRADATION; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SALMONELLA TYPHIMURIUM; SPECTROSCOPY; ULTRAVIOLET A RADIATION; ULTRAVIOLET IRRADIATION; ULTRAVIOLET RADIATION;

ETHANOL; LIPID PEROXIDES; MOLECULAR STRUCTURE; PHOTOCHEMISTRY; PHOTOLYSIS; REACTIVE OXYGEN SPECIES; ULTRAVIOLET RAYS; VITAMIN A;

EID: 13844289461     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx049807l     Document Type: Article

References (55)

1. Mukhtar, H., Ed. (1995) Skin Cancer: Mechanisms and Human Relevance, CRC Press, Boca Raton, FL.
2. Ahmad, H., and Mukhtar, H. (2004) Toxicology of the skin: new and emerging concepts. Toxicol. Appl. Pharm. 195, 265-266.
3. (IARC) International Agency for Research on Cancer. (1992) Solar and ultraviolet radiation, IARC Monographs on the Evaluation of Carcinogenic Risks to Humans, Vol 55, IARC, Geneva, Switzerland.
4. Forbes, P. D. (1981) Photocarcinogenesis: an overview. J. Invest. Dermatol. 77, 139-143.
5. Forbes, P. D., Davies, R. E., Sambuco, C. P., and Urbach, F. (1989) Inhibition of ultraviolet radiation-induced skin tumors in hairless mice by topical application of the sunscreen 2-ethyl hexyl-p-methoxycinnamate. J. Toxicol., Cutaneous Ocul. Toxicol. 8, 209-226.
6. Forbes, P. D. (1996) Carcinogenesis and photocarcinogenesis test methods, in Dermatotoxicology, 5th ed., (Marzulli, F. N. and Maibach, H. I., Eds.) pp 535-544, Taylor & Francis, New York.
7. Forbes, P. D., Sambuco, C. P., Dearlove, G. E., Parker, R. M., Kiorpes, A. L., and Wedig, J. H. (1998) Sample protocols for carcinogenesis and photocarcinogenesis, in Dermatotoxicology Methods (Marzulli, F. N., Maibach, H. I., Eds.) pp 281-302, Taylor & Francis, New York.
8. (IARC) International Agency for Research on Cancer. (1998) Handbooks of Cancer Prevention, Vitamin A, Vol. 3, French, Lyon.
9. Tee, E. S. (1992) Carotenoids and retinoids in human nutrition. Crit. Rev. Food Sci. Nutr. 31, 103-163.
10. Idson, B. (1990) Vitamins in cosmetics, an update I. Overview and Vitamin A. Drug Cosmet. Ind. 146, 26-91.
11. Data from the U. S. Food and Drug Administration's Voluntary Cosmetics Registration Program.
12. The Cosmetic, Toiletry and Fragrance Association. (1999) in International Cosmetic Ingredient Dictionary and Handbook, 8th ed. (Wenninger, J., Canterbery, R. C., McEwen, G. N., Jr., Eds.) p 1279, CTFA, Washington, DC.
13. Fu, P. P., Howard, P. C., Culp, S., Xia, Q., Webb, P. J., Blankenship, L., Wamer, W. G., and Bucher, J. R. (2002) Do topically applied skin creams containing retinyl palmitate affect the photocarcinogenicity of simulated solar light? J. Food Drug Anal. 10, 262-268.
14. Boehnlein, J., Sakr, A., Lichtin, J. L., and Bronaugh, R. L. (1994) Characterization of esterase and alcohol dehydrogenase activity in skin. Metabolism of retinyl palmitate to retinol (vitamin A) during percutaneous absorption. Pharm. Res. 11, 1155-1159.
15. Duell, E. A., Kang, S., and Voorhees, J. J. (1997) Unoccluded retinol penetrates human skin in vivo more effectively than unoccluded retinyl palmitate or retinoic acid. J. Invest. Dermatol. 109, 301-305.
16. Ihara, H., Hashizume, N., Hirase, N., and Suzue, R. (1999) Esterification makes retinol more labile to photolysis. J. Nutr. Sci. Vitaminol. 45, 353-358.
17. Derguini, F., Nakanishi, K., Buck, J., Hammerling, U., and Grun, F. (1994) Spectroscopic studies of anhydroretinol, as endogenous mammalian and insect retro-retinoid. Angew Chem, Int Ed Engl 33, 1837-1839.
18. Matsui, K., Kanwara, T., Hatanaka, A. W., D., and Schreier, P. (1994) 5,6-epoxidation of all-trans-retinoic acid with soybean lipoxygenase-2 and -3. Biosci., Biotechnol., Biochem. 58, 140-145.
19. 2-dependent cleavage of DNA by quinocarcin. J. Am. Chem. Soc. 114, 733-740.
20. Basu-Modak, S., and Tyrrell, R. M. (1993) Singlet oxygen: a primary effector in the ultraviolet A/near-visible light induction of the human heme oxygenase gene. Cancer Res. 53, 4505-4510.
21. Yamauchi, R., Miyake, N., Kato, K., and Ueno, Y. (1992) Peroxyl-radical reaction of retinyl acetate in solution. Biosci., Biotechnol., Biochem. 56, 1529-1532.
22. 2-deoxyguanosinyl DNA adducts upon nitroreduction of the environmental mutagen 1-nitropyrene. Chem. Res. Toxicol. 8, 269-277.
23. 32P-labeled 3′, 5′-bisphosphate nucleotides of polycyclic aromatic hydrocarbon anti-diol-epoxides and derivatives. J. Chromatogr. A. 710, 149-157.
24. 2-propanodeoxyguanosine DNA adduct in animal and human tissues. Chem. Res. Toxicol. 11, 1032-1041.
25. Maron, D. M., and Ames, B. N. (1983) Revised methods for the Salmonella mutagenicity test. Mutat. Res. 113, 173-215.
26. Wang, L., Yan, J., Fu, P. P., Parekh, K, A., and Yu, H. (2003) Photomutagenicity of cosmetic ingredient chemicals azulene and guaiazulene. Mutat. Res. 530, 19-26.
27. Utesch, D., and Splittgerber, J. (1996) Bacterial photomutagenicity testing: Distinction between direct, enzyme-mediated and light-induced events. Mutat. Res. 361, 41-48.
28. Chetalat, A. A., Albertini, S., Dresp, J. H., Strobel, R., and Gocke, E. (1993) Photomutagenesis test development: I. 8-methoxypsoralen, chlopromazine and sunscreen compounds during exposure to UV light. Mutat. Res. 292, 241-250.
29. Dean, S. W., Dunmore, R. H., Ruddock, S. P., Dean, J. C., Martin, C. N., and Kirkland, D. J. (1992) Development of assays for the detection of photomutagenicity of chemicals during exposure to UV light. II. Results of testing 3 sunscreen ingredients. Mutagenesis 7, 179-182.
30. Henderson, L., Fedyk, J., Bourner, C., Windebank, S., Fletcher, S., and Lovell, W. (1994) Photomutagenicity assays in bacteria: Factors affecting assay design and assessment of photomutagenic potential of para-aminobenzoic acid. Mutagenesis 9, 459-465.
31. Tokita, M., and Morita, M. (2000) Identification of new geometric isomers of methyl linoleate hydroperoxide and their chromatographic behavior. Biosci., Biotechnol., Biochem. 64, 1044-1056.
32. Reddy, A. M., and Rao, V. J. (1992) Ionic photodissociation of polyenes via a highly polarized singlet excited state. J. Org. Chem. 57, 6727-6731.
33. Ciulla, T. A., van Camp, J. R., Rosenfeld, E., and Kochevar, I. E. (1989) Photosensitization of single-strand breaks in pBR322 DNA by Rose Bengal. Photochem. Photobiol. 49, 293-298.
34. Sortino, S., Condorelli, G., de Guidi, G., and Giuffrida, S. (1998) Molecular mechanism of photosensitization XI. Membrane damage and DNA cleavage photoinduced by Enoxacin. Photochem. Photobiol. 68, 652-659.
35. g) in liquid water as determined by time-resolved infrared luminescence measurements. J. Am. Chem. Soc. 104, 5541-5543.
36. Blatz, P. E., and Pipper, D. L. (1968) The carbonium ion of all-trans-retinyl acetate. Spectroscopic detection and identification of absorbing species. Effect of environment on spectral properties. J. Am. Chem. Soc. 90, 1296-1300.
37. Buck, J., Derguini, F., Levi, E., Nakanishi, K., and Hammerling, U. (1991) Intracellular signaling by 14-hydroxy-4, 14-retro-retinol. Science 254, 1654-1656.
38. Lo, K. K., Land, E. J., and Truscott, T. G. (1982) Primary intermediates in the pulsed irradiation of retinoids. Photochem. Photobiol. 36, 139-145.
39. McBee, J. K., Kuksa, V., Alvarez, R., de Lera, A. R., Prezhdo, O., Haeseleer, F., Sokal, I., and alczewski, K. (2000) Isomerization of all-trans-retinol to cis-retinols in bovine retinal pigment epithelial cells: dependence on the specificity of retinoid-binding proteins. Biochemistry 39, 11370-11380.
40. Delmelle, M. (1997) Retinal damage by light: possible implication of singlet oxygen. Biophys. Struct. Mech. 3, 195-198.
41. Delmelle, M. (1979) Possible implication of photooxidation reactions in retinal photodamage. Photochem. Photobiol. 29, 713-716.
42. Tyrrell, R. M. (2000) Role for singlet oxygen in biological effects of ultraviolet A radiation. Methods Enzymol. 319, 290-296.
43. Stadtman, E. R., and Berlett, B. S. (1997) Reactive oxygen-mediated protein oxidation in aging and disease. Chem. Res. Toxicol. 10, 485-494.
44. Burkle, A. (2001) Mechansim of Aging. Eye June 15 (Part 3), 371-375.
45. Floyd, R. A., West, M., and Hensley, K. (2001) Oxidative biochemical markers: clues to understanding aging in long-lived species. Exp. Gerontol. 36, 619-640.
46. Loft, S., and Poulsen, H. E. (1996) Cancer risk and oxidative DNA damage in man, J. Mol. Med. 74 (6), 297-312.
47. 2-propanodeoxyguanosine adducts as common DNA lesions in rodents and humans. Proc Natl Acad Sci USA 91, 7491-7495.
48. 4-ethenodeoxycytidine by lipid peroxidation products and nucleic acid bases. Chem. Res. Toxicol. 8, 278-283.
49. Ni, Y.-C., Kadlubar, F. F., and Fu, P. P. (1995) Formation of malondialdehyde-modified 2′-deoxyguanosyl adduct from metabolism of chloral hydrate by mouse liver microsomes. Biochem. Biophys. Res. Commun. 216, 1110-1117.
50. Ni, Y.-C., Wong, T.-Y., Lloyd, R. V., Heinze, T. M., Shelton, S., Casciano, D., Kadlubar, F. F., and Fu, P. P. (1996) Mouse liver microsomal metabolism of chloral hydrate, trichloroacetic acid, and trichloroethanol leading to induction of lipid peroxidation via a free radical mechanism. Drug Metab. Dispos. 24, 81-90.
51. 32P-postlabeling and nucleotide chromatography. Carcinogenesis 12, 1483-1490.
52. Wang, M.-Y, and Liehr, J. G. (1995). Induction by estrogens of lipid peroxidation and lipid peroxide-derived malondialdehyde-DNA adducts in male Syrian hamsters: role of lipid peroxidation in estrogen-induced kidney carcinogenesis. Carcinogenesis 16, 1941-1945.
53. Humphries, K. A., and Curley, R. W., Jr. (1991) Triplet-sensitized photooxygenation of therapeutic retinoids. Pharm. Res. 8, 353-358.
54. Shealy, Y. F., Hill, D. L., Sani, B. P., Eto, I., Juliana, M. M., and Grubbs, C. J. (1998) Anhydroretinol, a retinoid active in preventing mammary cancer induced in rats by N-methyl-N-nitrosourea. Oncol. Rep. 5, 857-860.
55. Chen, Y., Buck, J., and Derguini, F. (1999) Anhydroretinol induces xidative stress and cell death. Cancer Res. 59, 3985-3990.