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Chemical Compound Review

DHLA     6,8-bis-sulfanyloctanoic acid

Synonyms: dihydrolipoate, AG-F-59264, AG-K-85460, CHEBI:18047, T8260_FLUKA, ...
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Disease relevance of Dihydrothioctic acid


Psychiatry related information on Dihydrothioctic acid


High impact information on Dihydrothioctic acid


Biological context of Dihydrothioctic acid


Anatomical context of Dihydrothioctic acid


Associations of Dihydrothioctic acid with other chemical compounds


Gene context of Dihydrothioctic acid

  • Inhibition of gelatinase B (matrix metalloproteinase-9) by dihydrolipoic acid [23].
  • We conclude that both thioredoxin and dihydrolipoic acid may be involved in the regulation of cellular S-nitrosothiols [19].
  • When cells were preincubated with dihydrolipoic acid (0.2 mM) the expression of c-fos mRNA was suppressed at 30 min after stimulation of TPA (0.5 microM) whereas in the case of preincubation of alpha-lipoic acid (0.2 microM), the expression was enhanced at 30 min [24].
  • Here, we describe the effects of LA and its reduced form, dihydrolipoic acid (DHLA), in neuron cultures treated with amyloid beta-peptide (Abeta 25-35) and iron/hydrogen peroxide (Fe/H2O2) [25].
  • When plasma was incubated with 1 mM acrolein in the presence of 2.5 mM glutathione or dihydrolipoic acid, 100 and 57% of LCAT activity, respectively, remained after incubation [26].

Analytical, diagnostic and therapeutic context of Dihydrothioctic acid


  1. Thioredoxin and dihydrolipoic acid inhibit elastase activity in cystic fibrosis sputum. Lee, R.L., Rancourt, R.C., del Val, G., Pack, K., Pardee, C., Accurso, F.J., White, C.W. Am. J. Physiol. Lung Cell Mol. Physiol. (2005) [Pubmed]
  2. Dihydrolipoic acid prevents hypoxic/reoxygenation and peroxidative damage in rat heart mitochondria. Scheer, B., Zimmer, G. Arch. Biochem. Biophys. (1993) [Pubmed]
  3. Cardiac recovery during post-ischemic reperfusion is improved by combination of vitamin E with dihydrolipoic acid. Haramaki, N., Packer, L., Assadnazari, H., Zimmer, G. Biochem. Biophys. Res. Commun. (1993) [Pubmed]
  4. Effect of alpha-lipoic acid and dihydrolipoic acid on ischemia/reperfusion injury of the heart and heart mitochondria. Schönheit, K., Gille, L., Nohl, H. Biochim. Biophys. Acta (1995) [Pubmed]
  5. The effects of alpha-lipoic acid on nitric oxide synthetase dispersion in penile function in streptozotocin-induced diabetic rats. Hurdag, C., Ozkara, H., Citci, S., Uyaner, I., Demirci, C. International journal of tissue reactions. (2005) [Pubmed]
  6. A test for patency of the cystic duct in acute cholecystitis. Eikman, E.A., Cameron, J.L., Colman, M., Natarajan, T.K., Dugal, P., Wagner, H.N. Ann. Intern. Med. (1975) [Pubmed]
  7. Role of Reduced Lipoic Acid in the Redox Regulation of Mitochondrial Aldehyde Dehydrogenase (ALDH-2) Activity: IMPLICATIONS FOR MITOCHONDRIAL OXIDATIVE STRESS AND NITRATE TOLERANCE. Wenzel, P., Hink, U., Oelze, M., Schuppan, S., Schaeuble, K., Schildknecht, S., Ho, K.K., Weiner, H., Bachschmid, M., M??nzel, T., Daiber, A. J. Biol. Chem. (2007) [Pubmed]
  8. alpha-Lipoic acid inhibits inflammatory bone resorption by suppressing prostaglandin E2 synthesis. Ha, H., Lee, J.H., Kim, H.N., Kim, H.M., Kwak, H.B., Lee, S., Kim, H.H., Lee, Z.H. J. Immunol. (2006) [Pubmed]
  9. Sulfur-centered radical formation from the antioxidant dihydrolipoic acid. Mottley, C., Mason, R.P. J. Biol. Chem. (2001) [Pubmed]
  10. Dihydrolipoic acid inhibits 15-lipoxygenase-dependent lipid peroxidation. Lapenna, D., Ciofani, G., Pierdomenico, S.D., Giamberardino, M.A., Cuccurullo, F. Free Radic. Biol. Med. (2003) [Pubmed]
  11. Antioxidant inhibition of thymocyte apoptosis by dihydrolipoic acid. Bustamante, J., Slater, A.F., Orrenius, S. Free Radic. Biol. Med. (1995) [Pubmed]
  12. Reduction of phenoxyl radicals by thioredoxin results in selective oxidation of its SH-groups to disulfides. An antioxidant function of thioredoxin. Goldman, R., Stoyanovsky, D.A., Day, B.W., Kagan, V.E. Biochemistry (1995) [Pubmed]
  13. Alpha-lipoic acid and cardiovascular disease. Wollin, S.D., Jones, P.J. J. Nutr. (2003) [Pubmed]
  14. Dihydrolipoic acid maintains ubiquinone in the antioxidant active form by two-electron reduction of ubiquinone and one-electron reduction of ubisemiquinone. Kozlov, A.V., Gille, L., Staniek, K., Nohl, H. Arch. Biochem. Biophys. (1999) [Pubmed]
  15. Alpha lipoic acid inhibits human T-cell migration: implications for multiple sclerosis. Marracci, G.H., McKeon, G.P., Marquardt, W.E., Winter, R.W., Riscoe, M.K., Bourdette, D.N. J. Neurosci. Res. (2004) [Pubmed]
  16. In vitro effects of vitamin C, thioctic acid and dihydrolipoic acid on the cytotoxicity of post-ethanol serum. Wickramasinghe, S.N., Hasan, R. Biochem. Pharmacol. (1992) [Pubmed]
  17. Dihydrolipoic acid activates oligomycin-sensitive thiol groups and increases ATP synthesis in mitochondria. Zimmer, G., Mainka, L., Krüger, E. Arch. Biochem. Biophys. (1991) [Pubmed]
  18. Toxicity of chemically generated nitric oxide towards pancreatic islet cells can be prevented by nicotinamide. Kallmann, B., Burkart, V., Kröncke, K.D., Kolb-Bachofen, V., Kolb, H. Life Sci. (1992) [Pubmed]
  19. Thioredoxin and lipoic acid catalyze the denitrosation of low molecular weight and protein S-nitrosothiols. Stoyanovsky, D.A., Tyurina, Y.Y., Tyurin, V.A., Anand, D., Mandavia, D.N., Gius, D., Ivanova, J., Pitt, B., Billiar, T.R., Kagan, V.E. J. Am. Chem. Soc. (2005) [Pubmed]
  20. Luminescence and stability of aqueous thioalkyl acid capped CdSe/ZnS quantum dots correlated to ligand ionization. Algar, W.R., Krull, U.J. Chemphyschem : a European journal of chemical physics and physical chemistry (2007) [Pubmed]
  21. Synthesis and properties of 2-acetylthiamin pyrophosphate: an enzymatic reaction intermediate. Gruys, K.J., Halkides, C.J., Frey, P.A. Biochemistry (1987) [Pubmed]
  22. Arsenate reductase II. Purine nucleoside phosphorylase in the presence of dihydrolipoic acid is a route for reduction of arsenate to arsenite in mammalian systems. Radabaugh, T.R., Sampayo-Reyes, A., Zakharyan, R.A., Aposhian, H.V. Chem. Res. Toxicol. (2002) [Pubmed]
  23. Inhibition of gelatinase B (matrix metalloproteinase-9) by dihydrolipoic acid. Cantin, A.M., Martel, M., Drouin, G., Paquette, B. Can. J. Physiol. Pharmacol. (2005) [Pubmed]
  24. Effects of alpha-lipoic acid and dihydrolipoic acid on expression of proto-oncogene c-fos. Mizuno, M., Packer, L. Biochem. Biophys. Res. Commun. (1994) [Pubmed]
  25. Protection against amyloid beta peptide and iron/hydrogen peroxide toxicity by alpha lipoic acid. Lovell, M.A., Xie, C., Xiong, S., Markesbery, W.R. J. Alzheimers Dis. (2003) [Pubmed]
  26. Inhibition of lecithin: cholesterol acyltransferase activity in human blood plasma by cigarette smoke extract and reactive aldehydes. Chen, C., Loo, G. J. Biochem. Toxicol. (1995) [Pubmed]
  27. High-performance liquid chromatography methods for determination of lipoic and dihydrolipoic acid in human plasma. Teichert, J., Preiss, R. Meth. Enzymol. (1997) [Pubmed]
  28. Fluoroimmunoassays using antibody-conjugated quantum dots. Goldman, E.R., Mattoussi, H., Anderson, G.P., Medintz, I.L., Mauro, J.M. Methods Mol. Biol. (2005) [Pubmed]
  29. Bifunctional anti/prooxidant potential of metallothionenin: redox signaling of copper binding and release. Fabisiak, J.P., Pearce, L.L., Borisenko, G.G., Tyhurina, Y.Y., Tyurin, V.A., Razzack, J., Lazo, J.S., Pitt, B.R., Kagan, V.E. Antioxid. Redox Signal. (1999) [Pubmed]
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