Reduction of lipoic acid by lipoamide dehydrogenase

Biochemical Pharmacology

Volumn 51, Issue 3, 1996, Pages 233-238

  Biewenga, Gerreke Ph ^a   Dorstijn, Marco A ^a   Verhagen, Justus V ^a   Haenen, Guido R M M ^a   Bast, Aalt ^a  

^a VU UNIVERSITY AMSTERDAM   (Netherlands)

Author keywords

antioxidant; dihydrolipoic acid; enzymatic reduction; lipoamide dehydrogenase; lipoic acid; thioctic acid

Indexed keywords

BETA LIPOIC ACID; DIHYDROLIPOAMIDE DEHYDROGENASE; DINORTHIOCTIC ACID; DRUG METABOLITE; MITOCHONDRIAL ENZYME; TETRANORLIPOIC ACID; THIOCTIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DRUG MECHANISM; DRUG METABOLISM; ENANTIOMER; ENZYME KINETICS; ENZYME SUBSTRATE; HEART; MITOCHONDRION; NONHUMAN; PRIORITY JOURNAL; REDUCTION; STEREOSPECIFICITY; SWINE;

EID: 0030020503     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/0006-2952(95)02124-8     Document Type: Article

References (30)

1. Benen J, Studies on Dihydrolipoamide dehydrogenase. PhD thesis, Agricultural University, Wageningen, the Netherlands, 1992.
2. Bast A and Haenen GRMM, Interplay between lipoic acid and glutathione in the protection against microsomal lipid peroxidation. Biochim Biophys Acta 963: 558-561, 1988.
3. Haenen GRMM and Bast A, Scavenging of hypochlorous acid by lipoic acid. Biochem Pharmacol 42: 2244-2246, 1991.
4. Scott BC, Aruoma OI, Evans PJ, Oneill C, Van der Vliet A, Cross CE, Tritschler H and Halliwell B, Lipoic and dihydrolipoic acids as antioxidants - a critical evaluation. Free Radical Res 20: 119-133, 1994.
5. Kagan VE, Shvedova A, Serbinova E, Khan S, Swanson C, Powell R and Packer L, Dihydrolipoic acid - a universal antioxidant both in the membrane and in the aqueous phase. Biochem Pharmacol 44: 1637-1649, 1992.
6. Kaiser S, Di Mascio P and Sies H, Lipoat und Singlettsauerstoff. In: Thioctsäure: "Neue biochemische, pharmakologische und klinische Erkenntnisse zur Thioctsäure" (Eds. Borbe HO and Ulrich H), pp. 69-74. pmi Verlag, Frankfurt am Main, 1989.
7. Haenen GRMM and Bast A, Modulation of microsomal lipid peroxidation by dihydrolipoate in interplay with vitamin E, vitamin C and glutathione. In: Neue biochemische, pharmakologische und klinische Erkenntnisse zur Thioctsäure (Eds. Borbe HO and Ulrich H), pp. 137-151. pmi Verlag, Frankfurt am Main, 1989.
8. Krieglstein J, Peruche B, Prehn J, Nuglisch J and Karkoutly C, The neuroprotective effect of dihydrolipoic acid. In: The Role of the Redox System Alpha-lipoic acid/Dihydrolipoic acid in Organ-specific Models of Impaired Oxygen Supply (Eds. Schmidt K and Ulrich H), pp. 89-103. Universimed Verlag, Frankfurt am Main, 1992.
9. Cameron NE, Cotter MA and Maxfield EK, Anti-oxidant treatment prevents the development of peripheral nerve dysfunction in streptozotocin-diabetic rats. Diabetologia 36: 299-304, 1993.
10. Natraj CV, Gandhi VM and Menon KKG, Lipoic acid and diabetes: Effect of dihydrolipoic acid administration in diabetic rats and rabbits. J Biosci 6: 37-46, 1984.
11. Reed JK, Studies on the kinetic mechanism of lipoamide dehydrogenase from rat liver mitochondria. J Biol Chem 248: 4834-4839, 1973.
12. Massey V, Gibson QH and Veeger C, Intermediates in the catalytic action of lipoyl dehydrogenase (diaphorase). Biochem J 77: 341-351, 1960.
13. Bunik V and Follmann H, Thioredoxin reduction dependent on alpha-ketoacid oxidation by alpha-ketoacid dehydrogenase complexes. FEBS Lett 336: 197-200, 1993.
14. Böhm M, Ebeling M and Bisswanger H, Neuere erkentnisse über die funktionen von a-liponsäure in mitochondriale multienzym-Komplexen. In: Neue biochemische, pharmakologische und klinische Erkenntnisse zur Thiocsäure (Eds. Borbe HO and Ulrich H), pp. 44-56. pmi Verlag, Frankfurt am Main, 1989.
15. Armstrong M and Webb M, The reversal of phenylarsenoxide inhibition of keto acid oxidation in mitochondrial and bacterial suspensions by lipoic acid and other disulfides. Biochem J 103: 913-922, 1967.
16. Danson MJ, Dihydrolipoamide dehydrogenase: A 'new" function for an old enzyme? Biochem Soc Trans 16: 87-89, 1988.
17. Ellman GL, Tissue sulfhydryl groups. Arch Biochem Biophys 82: 70-77, 1959.
18. Furr HC, Chang H-H and McCormick DB, Lipoate metabolism in Pseudomonas putida LP: Thiolsulfinates of lipoate and bisnorlipoate. Arch Biochem Biophys 185: 576-583, 1978.
19. Spence JT and McCormick DB, Lipoic acid metabolism in the rat? Arch Biochem Biophys 174: 13-19, 1976.
20. Nakamura M and Yamazaki I, Salts-induced oxidase activity of lipoamide dehydrogenase from pig heart. Eur J Biochem 96: 417-422, 1979.
21. Massey V, The identity of diaphorase and lipoyl dehydrogenase. Biochim Biophys Acta 37: 314-322, 1960.
22. Schempp H, Ulrich H and Elstner EF, Stereospecific reduction of R(+)-thioctic acid by porcine heart lipoamide dehydrogenase/ diaphorase. Z Naturforsch C 49: 691-692, 1994.
23. Suzuki YJ and Packer L, Alpha-lipoic acid is a potent inhibitor of NF-kB activation in human T cells: Does the mechanism involve anti-oxidant activities? In: Biological Oxidants and Antioxidants (Eds. Packer L and Cadenas E), pp. 87-96. Hippokrates Verlag, Stuttgart, 1994.
24. Yang Y-S and Frey PA, 2-Ketoacid dehydrogenase complexes of Escherichia coli: Stereospecificities of the three components for R-lipoate. Arch Biochem Biophys 268: 465-474, 1989.
25. Arscott LD and Williams Jr CH, R-and S-Dihydrolipoic acid derivatives as substrates of lipoamide dehydrogenase. In: Flavins And Flavoproteins, Proceedings of the Eleventh International Symposium, Nagoya, Japan, 27-31 July 1993 (Ed. Yagi K), Walter de Gruyter & Co., Berlin, New York, 1994.
26. Handelman GJ, Han D, Tritschler H and Packer L, Lipoic acid reduction by mammalian cells to the dithiol form, and release into the culture medium. Biochem Pharmacol 47: 1725-1730, 1994.
27. Fuchs J and Milbradt R, Antioxidant inhibition of skin inflammation induced by reactive oxidants: Evaluation of the redox couple dihydrolipoate/lipoate. Skin Pharmacol 7: 278-284, 1994.
28. Pick U, Haramaki N, Constantinescu A, Handelman GJ, Tritschler HJ and Packer L, Glutathione reductase and lipoamide dehydrogenase have opposite stereospecificities for alpha-lipoic acid enantiomers. Biochem Biophys Res Commun 206: 724-730, 1995.
29. Suzuki YJ, Tsuchiya M and Packer L, Antioxidant activities of dihydrolipoic acid and its structural homologues. Free Rad Res Comms 18: 115-122, 1993.
30. Biewenga GP, de Jong J and Bast A, Lipoic acid favors thiolsulfinate formation after hypochlorous acid scavenging: A study with lipoic acid derivatives. Arch Biochem Biophys 312: 114-120, 1994.