Different behaviors of glutathione in aqueous and DMSO solutions: Molecular dynamics simulation and NMR experimental study

Journal of Solution Chemistry

Volumn 40, Issue 10, 2011, Pages 1784-1795

  Zhang, Rong ^a   Wu, Wenjuan ^a   Luo, Sanlai ^a  

^a GUANGDONG PHARMACEUTICAL UNIVERSITY   (China)

Author keywords

All atom simulation; Aqueous solutions; DMSO; GSH; NMR

Indexed keywords

EID: 84862957322     PISSN: 00959782     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10953-011-9752-9     Document Type: Article

References (45)

1. Kibria, F.M., Lees, W.J.: Balancing conformational and oxidative kinetic traps during the folding of bovine pancreatic trypsin inhibitor (BPTI) with glutathione and glutathione disulfide. J. Am. Chem. Soc. 130, 796-797 (2008)
2. Ralat, L.A., Manevich, Y., Fisher, A.B., Colman, R.F.: Direct evidence for the formation of a complex between 1-cysteine peroxiredoxin and glutathione S-transferase π with activity changes in both enzymes. Biochem. 45, 360-372 (2006) (Pubitemid 43100403)
3. Berg, P.A.W., Hoek, A., Visser, A.J.W.G.: Evidence for a novel mechanism of time-resolved flavin fluorescence depolarization in glutathione reductase. Biophys. J. 87, 2577-2586 (2004)
4. More, S.S., Vince, R.: Design, synthesis and biological evaluation of glutathione peptidomimetics as components of anti-Parkinson prodrugs. J. Med. Chem. 51, 4581-4588 (2008)
5. Visioli, F., Wolfram, R., Richard, D., Abdullah, M.I.C., Crea, R.: Olive phenolics increase glutathione levels in healthy volunteers. J. Agric. Food Chem. 57, 1793-1796 (2009)
6. Louzada, P.R., Sebollela, A., Scaramello, M.E., Ferreira, S.T.: Predissociated dimers and molten globule monomers in the equilibrium unfolding of yeast glutathione reductase. Biophys. J. 85, 3255-3261 (2003) (Pubitemid 37345812)
7. Zhang, X., Xu, H., Dong, Z., Wang, Y., Liu, J., Shen, J.: Highly efficient dendrimer-based mimic of glutathione peroxidase. J. Am. Chem. Soc. 126, 10556-10557 (2004) (Pubitemid 39129153)
8. Odriozola, I., Loinaz, I., Pomposo, J.A., Grande, H.J.: Gold-glutathione supramolecular hydrogels. J. Mater. Chem. 17, 4843-4846 (2007)
9. Anderson, M.F., Nilsson, M., Sims, N.R.: Glutathione monoethylester prevents mitochondrial glutathione depletion during focal cerebral ischemia. Neurochem. Int. 44, 153-159 (2004) (Pubitemid 37249433)
10. Maher, P.: The effects of stress and aging on glutathione metabolism. Ageing Res. Rev. 4, 288-314 (2005) (Pubitemid 41114862)
11. Cunha, I., García, L.M., Guilhermino, L.: Sea-urchin (Paracentrotus lividus) glutathione S-transferases and cholinesterase activities as biomarkers of environmental contamination. J. Environ. Monit. 4, 288-294 (2005) (Pubitemid 40547155)
12. Shinichi, E., Hoffmann, M.R., Colussi, A.J.: Ozone oxidizes glutathione to a sulfonic acid. Chem. Res. Toxicol. 22, 35-40 (2009)
13. Petzold, H., Sadler, P.J.: Oxidation induced by the antioxidantglutathione (GSH). Chem. Commun. 37, 4413-4415 (2008)
14. Balogh, L.M., Trong, I.L., Kripps, K.A., Shireman, L.M., Stenkamp, R.E., Zhang, W., Mannervik, B., Atkins, W.M.: Substrate specificity combined with stereopromiscuity in glutathione transferase A4-4- dependent metabolism of 4-hydroxynonenal. Biochemistry 49, 1541-1548 (2010)
15. Mahajan, S.S., Paranji, R., Mehta, R., Lyon, R.P., Atkins, W.M.: A glutathione-based hydrogel and its site-selective interactions with water. Bioconjug. Chem. 16, 1019-1026 (2005) (Pubitemid 41026188)
16. Usta, M., Wortelboer, H.M., Vervoort, J., Boersma, M.G., Rietjens, I.M.C.M., Bladeren, P.J., Cnubben, N.H.P.: Human glutathione s-transferase-mediated glutathione conjugation of curcumin and efflux of these conjugates in caco-2 cells. Chem. Res. Toxicol. 20, 1895-1902 (2007)
17. Raghunathan, S., Chandross, J., Kretsinger, R.H., Alliston, T.J., Penington, C.J., Rule, G.S.: Crystal structure of human class mu glutathione transferase GSTM2-2. Effects of lattice packing on conformational heterogeneity. J. Mol. Biol. 238, 815-832 (1994)
18. Bieri, M., Bürgi, T.: Adsorption kinetics of L-glutathione on gold and structural changes during selfassembly: an in situ ATR-IR and QCM study. Phys. Chem. Chem. Phys. 8, 513-520 (2006)
19. Meredith, J.J., Dufour, A., Bruch, M.D.: Comparison of the structure and dynamics of the antibiotic peptide polymyxin B and the inactive nonapeptide in aqueous trifluoroethanol by NMR spectroscopy. J. Phys. Chem. B 113, 544-551 (2009)
20. Walderhaug, H., Johannessen, E.: Partition equilibria for alcohols in reverse micellar AOT-oil-water systems studied by PGSE-FT NMR. A comparison between AOT-containing and the corresponding AOTfree systems. J. Solution Chem. 35, 979-989 (2006) (Pubitemid 44172733)
21. Rauk, A., Armstrong, D.A., Berges, J.: Glutathione radical: intramolecular H abstraction by the thiyl radical. Can. J. Chem. 79, 405-417 (2001) (Pubitemid 32744996)
22. Guttmann, D., Poage, G., Johnston, T., Zhitkovich, A.: Reduction with glutathione is a weakly mutagenic pathway in chromium(VI) metabolism. Chem. Res. Toxicol. 21, 2188-2194 (2008)
23. Basu, S., Panigrahi, S., Praharaj, S., Ghosh, S.K., Pande, S., Jana, S., Pal, T.: Dipole-dipole plasmon interactions in self-assembly of gold organosol induced by glutathione. New J. Chem. 30, 1333-1339 (2006) (Pubitemid 44315880)
24. Prabhakar, R., Vreven, T., Morokuma, K., Musaev, D.G.: Elucidation of the mechanism of selenoprotein glutathione peroxidase (GPx)-catalyzed hydrogen peroxide reduction by two glutathione molecules: a density functional study. Biochem. 44, 11864-11871 (2005) (Pubitemid 41262721)
25. Mahajan, S.S., Paranji, R., Mehta, R., Lyon, R.P., Atkins, W.M.: A glutathione-based hydrogel and its site-selective interactions with water. Bioconjug. Chem. 16, 1019-1026 (2005) (Pubitemid 41026188)
26. Lampela, O., Juffer, A.H., Rauk, A.: Conformational analysis of glutathione in aqueous solution with molecular dynamics. J. Phys. Chem. A 107, 9208-9220 (2003)
27. Rignanese, G., Angelis, F.D., Melchionna, S., Vita, A.D.: Glutathione transferase: a first-principles study of the active site. J. Am. Chem. Soc. 122, 11963-11970 (2000)
28. Ridder, L., Rietjens, I.M.C.M., Vervoort, J., Mulholland, A.J.: Quantum mechanical/molecular mechanical free energy simulations of the glutathione s-transferase (M1-1) reaction with phenanthrene 9,10- oxide. J. Am. Chem. Soc. 124, 9926-9936 (2002)
29. Morin, C., Besset, T., Moutet, J., Fayolle, M., Brückner, M., Limosin, D., Becker, K., Davioud- Charvet, E.: The aza-analogues of 1,4-naphthoquinones are potent substrates and inhibitors of plasmodial thioredoxin and glutathione reductases and of human erythrocyte glutathione reductase. Org. Biomol. Chem. 15, 2731-2742 (2008) (Pubitemid 352027703)
30. Ralat, L.A., Manevich, Y., Fisher, A.B., Colman, R.F.: direct evidence for the formation of a complex between 1-cysteine peroxiredoxin and glutathione S-transferase π with activity changes in both enzymes. Biochem. 45, 360-372 (2006) (Pubitemid 43100403)
31. Lei, Y., Li, H., Han, S.: An all-atom simulation study on intermolecular interaction of DMSO-water system. Chem. Phys. Lett. 380, 542-548 (2003)
32. Vaismant, I.I., Berkowitz, M.L.: Local structural order and molecular associations in water-DMSO mixtures. Molecular dynamics study. J. Am. Chem. Soc. 114, 7889-7896 (1992)
33. Berweger, C.D., Gunsteren, W.F., Müller-Plathe, F.: Force field parametrization by weak coupling reengineering SPC water. Chem. Phys. Lett. 232, 429-436 (1995)
34. Mark, P., Nilsson, L.: Structure and dynamics of the TIP3P, SPC, and SPC/E water models at 298 K. J. Phys. Chem. A 105, 9954-9960 (2001) (Pubitemid 35378507)
35. Jorgensen, W.L., Maxwell, D.S., Tirado-Rives, J.: Development and testing of the OPLS all-atom force field on conformational energetics and properties of organic liquids. J. Am. Chem. Soc. 118, 11225-11236 (1996) (Pubitemid 26399746)
36. Jorgensen, W.L., Swenson, C.J.: Optimized intermolecular potential functions for amides and peptides. Structure and properties of liquid amides. J. Am. Chem. Soc. 107, 569-578 (1985)
37. Dudek, M.J., Ramnarayan, K., Ponder, J.W.: Protein structure prediction using a combination of sequence homology and global energy minimization: II. Energy functions. J. Comput. Chem. 19, 548-573 (1998). Available from http://dasher.wustl.edu/tinker (Pubitemid 128562875)
38. Lei, Y., Li, H., Zhang, R., Han, S.: Molecular dynamics simulations of biotin in aqueous solution. J. Phys. Chem. B 108, 10131-10137 (2004)
39. The PDB website is http://www.rcsb.org/pdb/
40. Connolly, M.L.: Analytical molecular surface calculation. J. Appl. Crystallogr. 16, 548-558 (1983)
41. Jiang, T., Cui, Q., Shi, G., Ma, S.: Protein folding simulations of the hydrophobic-hydrophilic model by combining tabu search with genetic algorithms. J. Chem. Phys. 119, 4592-4596 (2003)
42. Bastolla, U., Porto, M., Ortíz, A.R.: Local interactions in protein folding determined through an inverse folding model. Proteins 71, 278-299 (2008) (Pubitemid 351358610)
43. Zhang, R., Li, H., Lei, Y., Han, S.: Different weak C- H···O contacts in N-Methylacetamide-water system: molecular dynamics simulations and NMR experimental study. J. Phys. Chem. B 108, 12596-12601 (2004)
44. Zhang, R., Li, H., Lei, Y., Han, S.: All-atom molecular dynamic simulations and relative NMR spectra study of weak C-H···O contacts in amide-water system. J. Phys. Chem. B 109, 7482-7487 (2005) (Pubitemid 40609883)
45. Viswanathan, R., Asensio, A., Dannenberg, J.J.: Cooperative hydrogen-bonding in models of antiparallel β-sheets. J. Phys. Chem. A 108, 9205-9212 (2004)