Bioavailability of selenium from the selenotrisulphide derivative of lipoic acid

Photodermatology Photoimmunology and Photomedicine

Volumn 22, Issue 6, 2006, Pages 315-323

  Alonis, Melenie ^a   Pinnell, Sheldon ^b   Self, William T ^a  

^a UNIVERSITY OF CENTRAL FLORIDA COLLEGE OF MEDICINE   (United States)

^b DUKE UNIVERSITY MEDICAL CENTER   (United States)

Author keywords

Antioxidant; Lipoic acid; Selenocysteine; Selenoproteins; Selenotrisulphide

Indexed keywords

SELENATE; SELENITE; SELENIUM 75; SELENIUM DERIVATIVE; SELENIUM TRISULFIDE DERIVATIVE; SELENOCYSTINE; SELENOMETHIONINE; SELENOPROTEIN; THIOCTIC ACID; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; ARTICLE; BIOAVAILABILITY; CELL LINE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG STRUCTURE; HUMAN; HUMAN CELL; KERATINOCYTE; MOLECULAR STABILITY; NONHUMAN; PRIORITY JOURNAL; PROTEIN SYNTHESIS; SKIN ABSORPTION; SKIN BIOPSY; SUPPLEMENTATION; SWINE;

ADMINISTRATION, CUTANEOUS; ANIMALS; ANTIOXIDANTS; BIOLOGICAL AVAILABILITY; HUMANS; KERATINOCYTES; MODELS, ANIMAL; RADIATION DOSAGE; SELENIUM COMPOUNDS; SELENIUM RADIOISOTOPES; SKIN; SULFIDES; SWINE; THIOCTIC ACID; ULTRAVIOLET RAYS;

EID: 33750840600     PISSN: 09054383     EISSN: 16000781     Source Type: Journal    
DOI: 10.1111/j.1600-0781.2006.00257.x     Document Type: Article

References (41)

1. Brigelius-Flohe R. Tissue-specific functions of individual glutathione peroxidases. Free Radic Biol Med 1999; 27: 951-965.
2. Stadtman TC. Selenium biochemistry. Mammalian selenoenzymes. Ann NY Acad Sci 2000; 899: 399-402.
3. Tamura T, Stadtman TC. Mammalian thioredoxin reductases. Methods Enzymol 2002; 347: 297-306.
4. Kryukov GV, Castellano S, Novoselov SV, et al. Characterization of mammalian selenoproteomes. Science 2003; 300: 1439-1443.
5. Whanger PD. Selenium and its relationship to cancer: An update dagger. Br J Nutr 2004; 91: 11-28.
6. Painter HE. The chemistry and toxicity of selenium compounds. Chem Rev 1941; 28: 179-213.
7. Ganther HE. Selenotrisulfides. Formation by the reaction of thiols with selenious acid. Biochemistry 1968; 7: 2898-2905.
8. Ganther HE. Reduction of the selenotrisulfide derivative of glutathione to a persulfide analog by glutathione reductase. Biochemistry 1971; 10: 4089-4098.
9. Lindemann T, Hintelmann H. Identification of selenium-containing glutathione S-conjugates in a yeast extract by two-dimensional liquid chromatography with inductively coupled plasma MS and nanoelectrospray MS/MS detection. Anal Chem 2002; 74: 4602-4610.
10. Nakagawa T, Aoyama E, Kobayashi N, et al. Thiol exchange reactions involving selenotrisulfides. Biochem Biophys Res Commun 1988; 150: 1149-1154.
11. Nakagawa T, Hasegawa Y, Yamaguchi Y, et al. Isolation, characterization and thiol exchange reaction of penicillamine selenotrisulfides. Biochem Biophys Res Commun 1986; 135: 183-188.
12. Self WT, Tsai L, Stadtman TC. Synthesis and characterization of selenotrisulfide-derivatives of lipoic acid and lipoamide. Proc Natl Acad Sci USA 2000; 97: 12481-12486.
13. Stadtman TC. Selenocysteine. Annu Rev Biochem 1996; 65: 83-100.
14. Burke KE, Clive J, Combs GF Jr., Nakamura RM. Effects of topical L-selenomethionine with topical and oral vitamin E on pigmentation and skin cancer induced by ultraviolet irradiation in Skh: 2 hairless mice. J Am Acad Dermatol 2003; 49: 458-472.
15. Duffield-Lillico AJ, Slate EH, Reid ME, et al. Selenium supplementation and secondary prevention of nonmelanoma skin cancer in a randomized trial. J Natl Cancer Inst 2003; 95: 1477-1481.
16. Lamberg L. Diet may affect skin cancer prevention. JAMA 1998; 279: 1427-1428.
17. McKenzie RC. Selenium, ultraviolet radiation and the skin. Clin Exp Dermatol 2000; 25: 631-636.
18. Rafferty TS, Walker C, Hunter JA, Beckett GJ, McKenzie RC. Inhibition of ultraviolet B radiation-induced interleukin 10 expression in murine keratinocytes by selenium compounds. Br J Dermatol 2002; 146: 485-489.
19. Rafferty TS, McKenzie RC, Hunter JA, et al. Differential expression of selenoproteins by human skin cells and protection by selenium from UVB-radiation-induced cell death. Biochem J 1998 ; 332 (Part 1): 231-236.
20. Rafferty TS, Green MH, Lowe JE, et al. Effects of selenium compounds on induction of DNA damage by broadband ultraviolet radiation in human keratinocytes. Br J Dermatol 2003; 148: 1001-1009.
21. Esaki N, Nakamura T, Tanaka H, Suzuki T, Morino Y, Soda K. Enzymatic synthesis of selenocysteine in rat liver. Biochemistry 1981; 20: 4492-4496.
22. Pinnell SR. Cutaneous photodamage, oxidative stress, and topical antioxidant protection. J Am Acad Dermatol 2003; 48: 1-19 ; quiz 20-12.
23. Packer L, Kraemer K, Rimbach G. Molecular aspects of lipoic acid in the prevention of diabetes complications. Nutrition 2001; 17: 888-895.
24. Gunsalus IC, Barton LS, Gruber W. Biosynthesis and structure of lipoic acid derivatives. J Am Chem Soc 1956; 78: 1763-1766.
25. Boukamp P, Petrussevska RT, Breitkreutz D, Hornung J, Markham A, Fusenig NE. Normal keratinization in a spontaneously immortalized aneuploid human keratinocyte cell line. J Cell Biol 1988; 106: 761-771.
26. Bradford MM. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 1976; 72: 248-254.
27. Burk RF, Hill KE. Selenoprotein P: An extracellular protein with unique physical characteristics and a role in selenium homeostasis. Annu Rev Nutr 2005; 25: 215-235.
28. Green LM, Reade JL, Ware CF. Rapid colorimetric assay for cell viability: Application to the quantitation of cytotoxic and growth inhibitory lymphokines. J Immunol Methods 1984; 70: 257-268.
29. Heider J, Bock A. Selenium metabolism in micro-organisms. Adv Microb Physiol 1993; 35: 71-109.
30. Thanbichler M, Bock A. Selenoprotein biosynthesis: Purification and assay of components involved in selenocysteine biosynthesis and insertion in Escherichia coli. Methods Enzymol 2002; 347: 3-16.
31. Berry MJ, Tujebajeva RM, Copeland PR, et al. Selenocysteine incorporation directed from the 3'UTR: Characterization of eukaryotic EFsec and mechanistic implications. Biofactors 2001; 14: 17-24.
32. Ogasawara Y, Lacourciere GM, Ishii K, Stadtman TC. Characterization of potential selenium-binding proteins in the selenophosphate synthetase system. Proc Natl Acad Sci USA 2005; 102: 1012-1016.
33. Lacourciere GM, Levine RL, Stadtman TC. Direct detection of potential selenium delivery proteins by using an Escherichia coli strain unable to incorporate selenium from selenite into proteins. Proc Natl Acad Sci USA 2002; 99: 9150-9153.
34. Lacourciere GM. Selenium is mobilized in vivo from free selenocysteine and is incorporated specifically into formate dehydrogenase H and tRNA nucleosides. J Bacteriol 2002; 184: 1940-1946.
35. Lacourciere GM, Stadtman TC. Utilization of selenocysteine as a source of selenium for selenophosphate biosynthesis. Biofactors 2001; 14: 69-74.
36. Kohrl J, Brigelius-Flohe R, Bock A, Gartner R, Meyer O, Flohe L. Selenium in biology: Facts and medical perspectives. Biol Chem 2000; 381: 849-864.
37. Stratton SP, Dorr RT, Alberts DS. The state-of-the-art in chemoprevention of skin cancer. Eur J Cancer 2000; 36: 1292-1297.
38. Ichihashi M, Ueda M, Budiyanto A, et al. UV-induced skin damage. Toxicology 2003; 189: 21-39.
39. Rafferty TS, Beckett GJ, Walker C, Bisset YC, McKenzie RC. Selenium protects primary human keratinocytes from apoptosis induced by exposure to ultraviolet radiation. Clin Exp Dermatol 2003; 28: 294-300.
40. Meuillet E, Stratton S, Prasad Cherukuri D, et al. Chemoprevention of prostate cancer with selenium: An update on current clinical trials and preclinical findings. J Cell Biochem 2004; 91: 443-458.
41. Stratton MS, Reid ME, Schwartzberg G, et al. Selenium and inhibition of disease progression in men diagnosed with prostate carcinoma: Study design and baseline characteristics of the 'Watchful Waiting'Study. Anticancer Drugs 2003; 14: 595-600.