Quantum-chemical investigation of the structure and the antioxidant properties of α-lipoic acid and its metabolites

Journal of Molecular Modeling

Volumn 18, Issue 7, 2012, Pages 2907-2916

  Szela̧g, Małgorzata ^a   Mikulski, Damian ^a   Molski, Marcin ^a  

^a ADAM MICKIEWICZ UNIVERSITY   (Poland)

Author keywords

lipoic acid; Antioxidant; C PCM model; DFT method; Metabolites; MP2 method

Indexed keywords

ACETYLCYSTEINE; ALPHA TOCOPHEROL; ANTIOXIDANT; ASCORBIC ACID; CARBOXYLIC ACID DERIVATIVE; CYSTEINE; DIHYDROLIPOATE; DINORTHIOCTIC ACID; FREE RADICAL; GLUTATHIONE; HYDROGEN; HYDROXYL RADICAL; HYPOCHLOROUS ACID; PEROXYNITRITE; PROTON; REACTIVE OXYGEN METABOLITE; RESVERATROL; SATURATED FATTY ACID; SINGLET OXYGEN; SUPEROXIDE; TETRANORLIPOIC ACID; THIOCTIC ACID; THIOREDOXIN; UNCLASSIFIED DRUG; WATER;

ADIABATIC IONIZATION POTENTIAL; ARTICLE; BOND DISSOCIATION ENTHALPY; CHEMICAL PARAMETERS; CHEMICAL STRUCTURE; DISULFIDE BOND; ELECTRON TRANSPORT; ENANTIOMER; ENZYME SYNTHESIS; HYDROGEN BOND; MOLECULAR ORBITAL ENERGY; OXIDATION; PRIORITY JOURNAL; QUANTUM CHEMISTRY; SIGNAL TRANSDUCTION; SPIN DENSITY; STATIC ELECTRICITY; STEREOISOMERISM;

ANTIOXIDANTS; COMPUTER SIMULATION; MODELS, CHEMICAL; QUANTUM THEORY; THIOCTIC ACID;

EID: 84864688209     PISSN: 16102940     EISSN: 09485023     Source Type: Journal    
DOI: 10.1007/s00894-011-1306-y     Document Type: Article

References (62)

1. Carreau JP (1979) Biosynthesis of lipoic acid via unsaturated fatty acids. Methods Enzymol 62:152-158
2. Reed LJ (2001) A trail of research from lipoic acid to alpha-keto acid dehydrogenase complexes. J Biol Chem 276:38329-38336
3. Biewenga GP, Haenen GR, Bast A (1997) The pharmacology of the antioxidant lipoic acid. Gen Pharmacol 29:315-331
4. Lodge JK, Youn HD, Handelman GJ, Konishi T, Matsugo S, Mathur VV, Packer L (1997) Natural sources of lipoic acid: determination of lipoyllysine released from protease-digested tissues by high performance liquid chromatography incorporating electrochemical detection. J Appl Nutr 49:3-11
5. Reed LJ, DeBusk BG, Gunsalus IC, Hornberger CS (1951) Crystalline á-lipoic acid: a catalytic agent associated with pyruvate dehydrogenase. Science 114:93-94
6. 2. Acta Crystallogr B 28:304-307
7. Shay KP, Moreau RF, Smith EJ, Smith AR, Hagen TM (2009) Alpha-lipoic acid as a dietary supplement: molecular mechanisms and therapeutic potential. Biochim Biophys Acta 1790:1149-1160
8. Aruoma OI, Halliwell B, Hoey BM, Butler J (1989) The antioxidant action of N-acetylcysteine: its reaction with hydrogen peroxide, hydroxyl radical, superoxide, and hypochlorous acid. Free Rad Biol Med 6:593-597
9. Agnihotri N, Mishra PC (2009) Mechanism of scavenging action of N-acetylcysteine for the OH radical: a quantum computational study. J Phys Chem B 113:12096-12104
10. Suzuki YJ, Tsuchiya M, Packer L (1991) Thioctic acid and dihydrolipoic acid are novel antioxidants which interact with reactive oxygen species. Free Radic Res Commun 15:255-263
11. Devasagayam TP, Di Mascio P, Kaiser S, Sies H (1991) Singlet oxygen induced singlestrand breaks in plasmid pBR322 DNA: the enhancing effect of thiols. Biochim Biophys Acta 1088:409-412
12. Haenen GR, Bast A (1991) Scavenging of hypochlorous acid by lipoic acid. Biochem Pharmacol 42:2244-2246
13. Xu DP, Wells WW (1996) alpha-Lipoic acid dependent regeneration of ascorbic acid from dehydroascorbic acid in rat liver mitochondria. J Bioenerg Biomembranes 28:77-85
14. Lykkesfeldt J, Hagen TM, Vinarsky V, Ames BN (1998) Age-associated decline in ascorbic acid concentration, recycling, and biosynthesis in rat hepatocytes-eversal with (R)-alpha-lipoic acid supplementation. FASEB J 12:1183-1189
15. Suh JH, Shigeno ET, Morrow JD, Cox B, Rocha AE, Frei B, Hagen TM (2001) Oxidative stress in the aging rat heart is reversed by dietary supplementation with (R) - (alpha)-lipoic acid. FASEB J 15:700-706
16. Michels AJ, Joisher N, Hagen TM (2003) Age-related decline of sodium-dependent ascorbic acid transport in isolated rat hepatocytes. Arch Biochem Biophys 410:112-120
17. Han D, Handelman G, Marcocci L, Sen CK, Roy S, Kobuchi H, Tritschler HJ, Flohe L, Packer L (1997) Lipoic acid increases de novo synthesis of cellular glutathione by improving cystine utilization. Biofactors 6:321-338
18. Ou P, Tritschler HJ, Wolff SP (1995) Thioctic (lipoic) acid: a therapeutic metal chelating antioxidant? Biochem Pharmacol 50:123-126
19. Suh JH, Moreau R, Heath SH, Hagen TM (2005) Dietary supplementation with (R)-alpha-lipoic acid reverses the agerelated accumulation of iron and depletion of antioxidants in the rat cerebral cortex. Redox Rep 10:52-60
20. Lodge JK, Traber MG, Packer L (1998) Thiol chelation of Cu2+ by dihydrolipoic acid prevents human low density lipoprotein peroxidation. Free Radic Biol Med 25:287-297
21. Bush AI (2002) Metal complexing agents as therapies for Alzheimer's disease. Neurobiol Aging 23:1031-1038
22. Goralska M, Dackor R, Holley B, McGahan MC (2003) Alphalipoic acid changes iron uptake and storage in lens epithelial cells. Exp Eye Res 76:241-248
23. Patel MS, Packer L (2008) Lipoic acid: energy production, antioxidant activity and health effects (oxidative stress and disease). Taylor & Francis, Boca Raton
24. Vasdev S, Ford CA, Parai S, Longerich L, Gadag V (2000) Dietary lipoic acid supplementation prevents fructose-induced hypertension in rats. Nutr Metab Cardiovasc Dis 10:339-346
25. Vasdev S, Ford CA, Parai S, Longerich L, Gadag V (2000) Dietary alpha-lipoic acid supplementation lowers blood pressure in spontaneously hypertensive rats. J Hypertens 18:567-573
26. Vasdev S, Gill V, Longerich L, Parai S, Gadag V (2003) Saltinduced hypertension in WKY rats: prevention by alpha-lipoic acid supplementation. Mol Cell Biochem 254:319-326
27. Vasdev S, Gill V, Parai S, Gadag V (2005) Dietary lipoic acid supplementation attenuates hypertension in Dahl salt sensitive rats. Mol Cell Biochem 275:135-141
28. Louhelainen M, Merasto S, Finckenberg P, Lapatto R, Cheng ZJ, Mervaala EM (2006) Lipoic acid supplementation prevents cyclosporine-induced hypertension and nephrotoxicity in spontaneously hypertensive rats. J Hypertens 24:947-956
29. Takaoka M, Kobayashi Y, Yuba M, Ohkita M, Matsumura Y (2001) Effects of alpha-lipoic acid on deoxycorticosterone acetatesaltinduced hypertension in rats. Eur J Pharmacol 424:121-129
30. Midaoui AE, de Champlain J (2002) Prevention of hypertension, insulin resistance, and oxidative stress by alpha-lipoic acid. Hypertension 39:303-307
31. Midaoui AE, Elimadi A, Wu L, Haddad PS, de Champlain J (2003) Lipoic acid prevents hypertension, hyperglycemia, and the increase in heart mitochondrial superoxide production. Am J Hypertens 16:173-179
32. Kramer K, Packer L (2001) R-alpha-lipoic acid. In: Kramer K, Hoppe P, Packer L (eds) Nutraceuticals in health and disease prevention. Marcel Dekker, New York, pp 129-164
33. Marracci GH, Jones RE, McKeon GP, Bourdette DN (2002) Alpha-lipoic acid inhibits T cell migration into the spinal cord and suppresses and treats experimental autoimmune encephalomyelitis. J Neuroimmunol 131:104-114
34. Morini M, Roccatagliata L, Dell'Eva R, Pedemonte E, Furlan R, Minghelli S, Giunti D, Pfeffer U, Marchese M, Noonan D, Mancardi G, Albini A, Ucelli A (2004) Alpha-lipoic acid is effective in prevention and treatment of experimental autoimmune encephalomyelitis. J Neuroimmunol 148:146-153
35. Yadav V, Marracci G, Lovera J, Woodward W, Bogardus K, Marquardt W, Shinto L, Morris C, Bourdette D (2005) Lipoic acid in multiple sclerosis: a pilot study. Mult Scler 11:159-165
36. Yadav V, Marracci GH, Munar MY, Cherala G, Stuber LE, Alvarez L, Shinto L, Koop DR, Bourdette DN (2010) Pharmacokinetic study of lipoic acid in multiple sclerosis: comparing mice and human pharmacokinetic parameters. Mult Scler 16:387-397
37. Schupke H, Hempel R, Peter G, Hermann R, Wessel K, Engel J, Kronbach T (2001) New metabolic pathways of alpha-lipoic acid. Drug Metab Dispos 29:855-862
38. Harrison EE, McCormick DB (1974) Themetabolizm of dl-(1, 6-14C) lipoic acid in the rat. Arch Biochem Biophys 160:514-522
39. Shang YJ, Qian YP, Liu XD, Dai F, Shang XL, Jia WQ, Liu Q, Fang JG, Zhou B (2009) Radical-scavenging activity and mechanism of resveratrol-oriented analogues: influence of the solvent, radical, and substitution. J Org Chem 74:5025-5031
40. Klein E, Rimarčík J, Lukeš V (2009) DFT/B3LYP study of the O. H bond dissociation enthalpies and proton affinities of para-and meta-substituted phenols in water and benzene. Acta Chim Slovaca 2:37-51
41. Mikulski D, Gorniak R, Molski M (2010) A theoretical study of the structure-radical scavenging activity of trans-resveratrol analogues and cis-resveratrol in gas phase and water environment. Eur J Med Chem 45:1015-1027
42. Wright JS, Johnson ER, DiLabio GA (2001) Predicting the activity of phenolic antioxidants: theoretical method, analysis of substituent effects, and application to major families of antioxidants. J Am Chem Soc 123:1173-1183
43. Leopoldini M, Marino T, Russo N, Toscano M (2004) Antioxidant properties of phenolic compounds: H-atom versus electron transfer mechanism. J Phys Chem A 108:4916-4922
44. Cao H, Pan XL, Li C, Zhou C, Deng FY, Li TH (2003) Density functional theory calculations for resveratrol. Bioorg Med Chem Lett 13:1869-1871
45. 2. Gaussian Inc., Wallingford
46. Hohenberg K, Kohn W (1964) Inhomogeneous electron gas. Phys Rev 136:B864-B871
47. Kohn W, Sham LJ (1965) Self-consistent equations including exchange and correlation effects. Phys Rev A 140:1133-1138
48. Lee C, Yang W, Parr RG (1988) Development of the Cole. Salvetti correlation energy formula into a functional of the electron density. Phys Rev B 37:785-789
49. Moller C, Plesset MP (1934) Note on an approximation treatment for many-electron systems. Phys Rev 46:618-622
50. Leopoldini M, Russo N, Toscano M (2011) The molecular basis of working mechanism of natural polyphenolic antioxidants. Food Chem 125:288-306
51. Foti MC, Daquino C, Geraci C (2004) Electron-transfer reaction of cinnamic acids and their methyl esters with the DPPH'E radical in alcoholic solutions. J Org Chem 69:2309-2314
52. Litwinienko G, Ingold KU (2004) Abnormal solvent effects on hydrogen atom abstraction. 2. Resolution of the curcumin antioxidant controversy. The role of sequential proton loss electron transfer. J Org Chem 69:5888-5896
53. Musialik M, Litwinienko G (2005) Scavenging of dpph'E radicals by vitamin E is accelerated by its partial ionization: the role of sequential proton loss electron transfer. Org Lett 7:4951-4954
54. Nakanishi I, Kawashima T, Ohkubo K, Kanazawa H, Inami K, Mochizuki M, Fukuhara K, Okuda H, Ozawa T, Itoh S, Fukuzumi S, Ikota N (2005) Electron-transfer mechanism in radicalscavenging reactions by a vitamin E model in a protic medium. Org Biomol Chem 3:626-629
55. Litwinienko G, Ingold KU (2007) Solvent effects on the rates and mechanisms of reaction of phenols with free radicals. Acc Chem Res 40:222-230
56. +/H) couple. J Am Chem Soc 114:7458-7462
57. Bizarro MM, Cabral BJC, dos Santos RMB, Simoes JAM (1999) Substituent effects on the O. H bond dissociation enthalpies in phenolic compounds: agreements and controversies. Pure Appl Chem 71:1249-1256
58. Atkins PW (1998) Physical chemistry, 6th edn. Oxford University Press, Oxford
59. Cossi M, Rega N, Scalmani G, Barone V (2003) Energies, structures, and electronic properties of molecules in solution with the C-PCM solvation model. J Comput Chem 24:669-681
60. 2+ complexes with resveratrol. J Mol Struct THEOCHEM 956:66-76
61. Mikulski D, Szela̧g M, Molski M, Gorniak R (2010) Quantumchemical study on the antioxidation mechanisms of trans-resveratrol reactions with free radicals. In the gas phase, water and ethanol environment. J Mol Struct THEOCHEM 951:37-48
62. Mikulski D, Szela̧g M, Molski M (2011) Quantum-chemical study of interactions of trans-resveratrol with guanine-thymine dinucleotide and DNA-nucleobases. J Mol Model. doi:10-1007/s00894-011-0999-2