Antioxidant enzyme mimics with synergism

Mini-Reviews in Medicinal Chemistry

Volumn 10, Issue 4, 2010, Pages 342-356

  Yan, Fei ^a   Mu, Ying ^a,b   Yan, Ganglin ^a   Liu, Junqiu ^a   Shen, Jiacong ^a   Luo, Guimin ^a  

^a JILIN UNIVERSITY   (China)

^b STATE KEY LABORATORY OF INDUSTRIAL CONTROL TECHNOLOGY   (China)

Author keywords

Antioxidant enzymes; Catalase (CAT); Enzyme mimics; Glutathione peroxidase (GPx); Glutathione s transferases (GST); Reactive oxygen species (ROS); Superoxide dismutase (SOD); Synergism

Indexed keywords

ANTIOXIDANT; BETA CYCLODEXTRIN; CATALASE; CYCLODEXTRIN; GLUTAREDOXIN; GLUTATHIONE DISULFIDE; GLUTATHIONE PEROXIDASE; GLUTATHIONE TRANSFERASE; HYBRID PROTEIN; NITRIC OXIDE SYNTHASE; REACTIVE OXYGEN METABOLITE; SUPEROXIDE DISMUTASE; THIOBARBITURIC ACID REACTIVE SUBSTANCE; BIOMIMETIC MATERIAL; ENZYME; PROTEIN;

ANTIOXIDANT ACTIVITY; BIOCATALYST; CROSS LINKING; DRUG POTENTIATION; ESCHERICHIA COLI; HUMAN; NONHUMAN; OXIDATIVE STRESS; REVIEW; SCHISTOSOMA JAPONICUM; ANIMAL; CHEMISTRY; GENETICS; METABOLISM; MOLECULAR WEIGHT; SYNTHESIS;

ANIMALS; ANTIOXIDANTS; BIOMIMETIC MATERIALS; DRUG SYNERGISM; ENZYMES; HUMANS; MOLECULAR WEIGHT; PROTEINS;

EID: 77956621157     PISSN: 13895575     EISSN: 18755607     Source Type: Journal    
DOI: 10.2174/138955710791330972     Document Type: Review

References (57)

1. Marnett, L.J. Oxyradicals and DNA damage. Carcinogenesis, 2000, 21, 361-70.
2. Stadtman, E.R.; Levine, R.L. Protein Oxidation. Ann. N. Y. Acad. Sci., 2000, 899, 191-208.
3. Day, B.J. Catalytic antioxidants: a radical approach to new therapeutics. Drug Discov. Today, 2004, 9, 557-66.
4. McCord, J.M.; Fridovich, I. Superoxide dismutase. An enzymic function for erythrocuprein (hemocuprein). J. Biol. Chem., 1969, 244, 6049-55.
5. Masaki, H; Okano, Y.; Sakurai, H. Differential role of catalase and glutathione peroxidase in cultured human fibroblasts under exposure of H2O2 or ultraviolet B light. Arch. Dermatol. Res., 1998, 290, 113-8.
6. Wendel, A. Glutathione peroxidase. Methods Enzymol., 1981, 77, 325-33.
7. Armstrong, R.N. Structure, catalytic mechanism, and evolution of the glutathione transferases. Chem. Res. Toxicol., 1997, 10, 2-18.
8. Zhang, W.; Jacobsen, E.N. Asymmetric olefin epoxidation with sodium hypochlorite catalyzed by easily prepared chiral manganese(III) salen complexes. J. Org. Chem., 1991, 56, 2296-98.
9. Zhang, W.; Loebach, J.L.; Wilson, S.R.; Jacobsen, E.N. Enantioselective epoxidation of unfunctionalized olefins catalyzed by salen manganese complexes. J. Am. Chem. Soc., 1990, 112, 2801-3.
10. Baudry, M.; Etienne, S.; Bruce, A.; Palucki, M.; Jacobsen, E.; Malfroy, B. Salen-manganese complexes are superoxide dismutasemimics. Biophys. Res. Commun., 1993, 192, 964-8.
11. Gonzalez, P.K.; Zhuang, J.; Doctrow, S.R.; Malfroy, B.; Benson, P.F.; Menconi, M.J.; Fink, M.P. J. EUK-8, a synthetic superoxide dismutase and catalase mimetic, ameliorates acute lung injury in endotoxemic swine. Pharmacol. Exp. Ther., 1995, 275, 798-806.
12. Stallings, W.C.; Pattridge, K.A.; Strong, R.K.; Ludwing, M.L. The structure of manganese superoxide dismutase from Thermus thermophilus HB8 at 2.4-A resolution. J. Biol. Chem., 1985, 260, 16424-32.
13. Osman, R.; Basch, H. On the mechanism of action of superoxide dismutase: a theoretical study. J. Am. Chem. Soc., 1984, 106, 5710-4.
14. Doctrow, S.R., Huffman, K.; Marcus, C.B.; Tocco, G.; Malfroy, E.; Adinolfi, C.A.; Kruk, H.; Baker, K.; Lazarowvch, N.; Mascarenhas, J.; Malfrov, B. Salen-manganese complexes as catalytic scavengers of hydrogen peroxide and cytoprotective agents: structure-activity relationship studies. J. Med. Chem., 2002, 45, 4549-58.
15. Sharpe, M.A.; Ollosson, R.; Stewart, V.C.; Clark, J.B. Oxidation of nitric oxide by oxomanganese-salen complexes: a new mechanism for cellular protection by superoxide dismutase/catalase mimetics. Biochem. J., 2002, 366, 97-107.
16. Novotny, M.J.; Laughlin, M.H.; Adams, H.R. Evidence for lack of importance of oxygen free radicals in Escherichia coli endotoxemia in dogs. Am. J. Physiol., 1988, 254, 954-62.
17. Bruce, A.J.; Malfroy, B.; Baudry, M. Beta-Amyloid toxicity in organotypic hippocampal cultures: protection by EUK-8, a synthetic catalytic free radical scavenger. Proc. Natl. Acad. Sci. USA., 1996, 93, 2312-6.
18. Tanguy, S.; Boucher, F.R.; Malfroy, B.; de Leiris, J.G. Free radicals in reperfusion-induced arrhythmias: study with EUK 8, a novel nonprotein catalytic antioxidant. Free. Radic. Biol. Med., 1996, 21, 945-54.
19. van Empel, V.P.; Bertrand, A.T.; van Oort, R.J.; van der Nagel, R.; Engelen, M., van Rijen, H.V.; Doevendans, P.A.; Crijns, H.J.; Ackerman, S.L.; Sluiter, W.; De Windt, L.J. EUK-8, a superoxide dismutase and catalase mimetic, reduces cardiac oxidative stress and ameliorates pressure overload-induced heart failure in the harlequin mouse mutant. http://www.journals.elsevierhealth.com/periodicals/jac/article/PIIS0735109706013398/abstract-articlefootnote-1#article-footnote-1 J. Am. Coll. Cardiol., 2006, 48, 824-32.
20. Baker, K.; Marcus, C.B.; Huffman, K.; Kruk, H.; Malfroy, B.; Doctrow, S.R. Synthetic combined superoxide dismutase/catalase mimetics are protective as a delayed treatment in a rat stroke model: a key role for reactive oxygen species in ischemic brain injury. J. Pharmacol. Exp. Ther., 1998, 284, 215-221.
21. Rong, Y.; Doctrow, S.R.; Tocco, G.; Baudry, M. EUK-134, a synthetic superoxide dismutase and catalase mimetic, prevents oxidative stress and attenuates kainateinduced neuropathology. Proc. Natl. Acad. Sci. USA., 1999, 96, 9897-902.
22. Pong, K.; Doctrow, S.R.; Baudry, M. Prevention of 1-methyl-4-phenylpyridinium-and 6-hydroxydopamine-induced nitration of tyrosine hydroxylase and neurotoxicity by EUK-134, a superoxide dismutase and catalase mimetic, in cultured dopaminergic neurons. Brain Res., 2000, 881, 182-9.
23. Chen, S.Y.; Dehart, D.B.; Sulik, K.K. Protection from ethanolinduced limb malformations by the superoxide dismutase/catalase mimetic, EUK-134. FASEB J., 2004, 18, 1234-6.
24. Melov, S.; Ravenscroft, J.; Malik, S.; Gill, M.S.; Walker, D.W.; Clayton, P.E.; Wallace, D.C.; Malfroy, B.; Doctrow, S.R.; Lithgow, G.J. Extension of life-span with superoxide dismutase/catalase mimetics. Science, 2000, 289, 1567-9.
25. Jung, C.; Rong, Y.; Doctrow, S.; Baudry, M.; Malfroy, B.; Xu, Z. Synthetic superoxide dismutase/catalase mimetics reduce oxidative stress and prolong survival in a mouse amyotrophic lateral sclerosis model. Neurosci. Lett., 2001, 304, 157-60.
26. Melov S.; Doctrow, S.R.; Schneider, J.A.; Haberson, J., Patel, M., Coskun, P.E.; Huffman, K.; Wallace, D.C.; Malfroy, B. Lifespan extension and rescue of spongiform encephalopathy in superoxide dismutase 2 nullizygous mice treated with superoxide dismutase- catalase mimetics. J. Neurosci., 2001, 21, 8348-53.
27. Liu, R.; Liu, I.Y.; Bi, X.; Thompson, R.F.; Doctrow, S.R.; Malfroy, B.; Baudry, M. Reversal of age-related learning deficits and brain oxidative stress in mice with superoxide dismutase/catalase mimetics. Proc. Natl. Acad. Sci. USA, 2003, 100, 8526-31.
28. Xu, Y.; Liu, B.; Zweier, J.L.; He, G. Formation of hydrogen peroxide and reduction of peroxynitrite via dismutation of superoxide at reperfusion enhances myocardial blood flow and oxygen consumption in postischemic mouse heart. J. Pharmacol. Exp. Ther., 2008, 327, 402-10.
29. Asayama, S.; Mori, T.; Nagaoka, S.; Kawakami, H. Chemical modification of manganese porphyrins with biomolecules for new functional antioxidants. J. Biomater. Sci. Polym. Edn., 2003, 14, 1169-79.
30. Park, W.; Lim, D. Effect of the oligo(ethylene glycol) group on the antioxidant activity of manganese salen complexes. Bioorg. Med. Chem. Lett., 2009, 19, 614-7.
31. Dong, Z.Y.; Huang, X.; Mao, S.Z.; Liu, J.Q.; Luo, G.M.; Shen, J.C. A synthetic bifunctional enzyme model with superoxide dismutase and glutathione peroxidase activities. Chem. Lett., 2005, 34, 820-1.
32. Li, H.M.; Gao, N.; Shen, S.L.; Luo, G.M. A novel trifunctional salicylaldehyde Schiff derivative with GPx, SOD and CAT activities. Chem. J. Chin. Univ., 2009, 30, 1353-6.
33. Szejtli, Introduction and general overview of cyclodextrin chemistry. J. Chem. Rev., 1998, 98, 1743-54.
34. Liu, Y.; Li, B.; Li, L.; Zhang, H.Y. Synthesis of organoseleniummodified-β-cyclodextrins possessing a 1,2-benzisoselenazol-3(2H)-one moiety and their enzyme-mimic study. Helv. Chim. Acta, 2002, 85, 9-18.
35. Villalonga, R.; Cao, R.; Fragoso, A.; Damiao, A.E.; Ortiz, P.D.; Caballero, J. Supramolecular assembly of β-cyclodextrin-modified gold nanoparticles and Cu, Zn-superoxide dismutase on catalase. J. Mol. Catal. B-Enzyme, 2005, 35, 79-85.
36. Valdivia, A.; Pérez, Y.; Cao, R.; Baños, M.; García, A.; Villalonga, R. Bienzymatic supramolecular complex of catalase modified with cyclodextrin-branched carboxymethylcellulose and superoxide dismutase: stability and anti-inflammatory properties. Macromol. Biosci., 2007, 7, 70-5.
37. Puglisi, A.; Tabbì, G.; Vecchio, G. Bioconjugates of cyclodextrins of manganese salen-type ligand with superoxide dismutase activity. J. Inorg. Biochem., 2004, 98, 969-76.
38. Lanza, V.; Vecchio, G. New conjugates of superoxide dismutase/catalase mimetics with cyclodestrins. J. Inorg. Biochem., 2009, 103, 381-8.
39. Hirayama, F.; Uekama, K. Cyclodextrin-based controlled drug release system. Adv. Drug. Deliv. Rev., 1999, 36, 125-41.
40. Parks, D.A. Oxygen radicals: mediators of gastrointestinal pathophysiology. Gut, 1989, 30, 293-8.
41. Mao, G.D.; Thomas, P.D.; Lopaschuk, G.D.; Poznansky, M.J. Superoxide dismutase (SOD)-catalase conjugates. Role of hydrogen peroxide and the Fenton reaction in SOD toxicity. J. Biol. Chem., 1993, 268, 416-20.
42. Luo, G.M.; Liu, W.H.; Sun, Q.A.; Ding, L.; Zhu, Z.Q.; Yan, G.L.; Yang, T.S. Preparation of bifunctional enzyme with both superoxide dismutase and glutathione peroxidase activities by using chemical mutation. Ann. N.Y. Acad. Sci., 1996, 799, 50-5.
43. Wu, Z.P. and Hilvert, D. Selenosubtilisin as a glutathione peroxidase mimic. J. Am. Chem. Soc., 1990, 112, 5647-8.
44. Habig, W.H.; Pabst, M.J.; Jakoby, W.B. Glutathione S-transferases. The first enzymatic step in mercapturic acid formation. J. Biol. Chem., 1974, 249, 7130-9.
45. Yu, H.J.; Liu, J.Q.; Böck, A.; Li, J.; Luo, G.M.; Shen, J.C. Engineering glutathione transferase to a novel glutathione peroxidase mimic with high catalytic efficiency. J. Biol. Chem., 2005, 280, 11930-5.
46. Yu, H.J.; Liu, J.Q.; Li, J.; Zang, T.Z.; Luo, G.M.; Shen, J.C. Protection of mitochondrial integrity from oxidative stress by selenium-containing glutathione transferase. Appl. Biochem. Biotechnol., 2005, 127, 133-42.
47. Zheng, K.Y.; Board, P.G.; Fei, X.F.; Sun, Y.; Lv, S.W.; Yan, G.L.; Liu, J.Q.; Shen, J.C.; Luo, G.M. A novel selenium-containing glutathione transferase zeta1-1, the activity of which surpasses the level of some native glutathione peroxidases. Int. Biochem. Cell. Biol., 2008, 40, 2090-7.
48. Board, P.G.; Baker, R.T.; Chelvanayagam, G.; Jermiin, L.S. Zeta, a novel class of glutathione transferases in a range of species from plants to humans. Biochem. J., 1997, 328, 929-35.
49. Wilce, M.C.J.; Board, P.G.; Feil, S.C.; Parker, M.W. Crystal structure of a theta-class glutathione transferase. EMBO J., 1995, 14, 2133-43.
50. Martin, J. L. Thioredoxin-a fold for all reasons. Structure, 1995, 3, 245-50.
51. Zhang, K.; Zang, T.Z.; Yang, W.; Sun, Y.; Mu, Y.; Liu, J.Q.; Shen, J.C.; Luo, G.M. Single chain antibody displays glutathione stransferase activity. J. Biol. Chem., 2006, 281, 12516-20.
52. Casi, G.; Roelfes, G.; Hilvert, D. Selenoglutaredoxin as a glutathione peroxidase mimic. ChemBioChem., 2008, 9, 1623-31.
53. Ge, Y.; Qi, Z.H.; Wang, Y.; Liu, X.M.; Li, J.; Xu, J.Y.; Liu, J.Q.; Shen, J.C. Engineered selenium-containing glutaredoxin displays strong glutathione peroxidase activity rivaling natural enzyme. Int. J. Biochem. Cell. Biol., 2009, 41, 900-6.
54. Holmgren, A. Thioredoxin and glutaredoxin systems. J. Biol. Chem., 1989, 264, 13963-6.
55. Yu, H.J.; Ge, Y.; Wang, Y.; Lin, C.T.; Li, J; Liu, X.; Zang, T.Z.; Xu, J.Q.; Liu, J.Q.; Luo, G.M.; Shen, J.C. A fused seleniumcontaining protein with both GPx and SOD activities. Biochem. Biophys. Res. Commun., 2007, 358, 873-8.
56. Yan, F.; Yang, W.K.; Li, X.Y.; Lin, T.T.; Lun, Y.N.; Lin, F.; Lv, S.W.; Yan, G.L.; Liu, J.Q.; Shen, J.C.; Mu, Y; Luo, G.M. A trifunctional enzyme with glutathione S-transferase, glutathione peroxidase and superoxide dismutase activity. BBA-Gen. Subjects, 2008, 1780, 869-72.
57. Zou, X.F.; Ji, Y.T.; Gao, G.; Zhu, X.J.; Lv, S.W.; Yan, F.; Han, S.P.; Chen, X.; Gao, C.C.; Liu, J.Q.; Luo, G.M. A novel seleniumand copper-containing peptide with both superoxide dismutase and glutathione peroxidase activities. J. Microbiol. Biotechnol., 2010, 20, 88-93.