Functional mimicry of the active site of glutathione peroxidase by glutathione imprinted selenium-containing protein

Biomacromolecules

Volumn 9, Issue 1, 2008, Pages 363-368

  Liu, Lei ^a,b   Mao, Shi Zhong ^a,b   Liu, Xiao Man ^a   Huang, Xin ^a   Xu, Jia Yun ^a   Liu, Jun Qiu ^a   Luo, Gui Min ^b   Shen, Jia Cong ^a  

^a Jilin University   (China)

^b JILIN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BIOIMPRINTING; FUNCTIONAL MIMICRY; GLUTATHIONE PEROXIDASE; SELENOSUBTILISIN;

CATALYSIS; ENZYMES; PEROXIDES; PROTEINS; SELENIUM;

PEPTIDES;

ANTIOXIDANT; EBSELEN; GLUTATHIONE PEROXIDASE; HYDROGEN PEROXIDE; SELENIUM; SELENIUM DERIVATIVE; SELENOSUBTILISIN; THIOL GROUP; UNCLASSIFIED DRUG;

ARTICLE; BINDING SITE; CATALYSIS; COMPLEX FORMATION; CONTROLLED STUDY; COVALENT BOND; ENZYME ACTIVE SITE; ENZYME ACTIVITY; ENZYME KINETICS; ENZYME SUBSTRATE; MOLECULAR IMPRINTING; MOLECULAR MIMICRY; MOLECULAR RECOGNITION; PRIORITY JOURNAL; PROTEIN BINDING; PROTEIN CONFORMATION; STEADY STATE;

BINDING SITES; CATALYSIS; ELECTROPHORESIS, POLYACRYLAMIDE GEL; GLUTATHIONE PEROXIDASE; MOLECULAR MIMICRY; SELENIUM; SUBSTRATE SPECIFICITY;

EID: 38849152163     PISSN: 15257797     EISSN: None     Source Type: Journal    
DOI: 10.1021/bm7008312     Document Type: Article

References (41)

1. Sies, H. Oxidative Stress: Introductory Remarks. In Oxidative Stress; Sies, H., Ed.; Academic Press: London, 1985, p 1.
2. Sies, H. Biochemistry of oxidative stress. Angew. Chem., Int. Ed. Engl. 1986, 25, 1058-1071.
3. Aust, S. D.; Svingen, B. A. In Free Radicals in Biology; Pryor, W. A., Ed.; Academic Press: New York, 1982; Vol. 5, p 1.
4. Diplock, A. T. Antioxidants and Free Radical Scavengers. In Free Radical Damage and Its Control; Rice-Evans, C. A., Burdon, R. H., Eds.; Elsevier: Amsterdam, 1994; p 113.
5. McCord, J. M.; Fridovich, I. Superoxide dismutase:an enzymic function for erythrocuprein (hemocuprein). J Biol. Chem. 1969, 244, 6049-6055.
6. Mills, G. C. Hemoglobin catabolism.I. Glutathione peroxidase, an erythrocyte efizyme witch protects hemoglobin from peroxidase breakdown. J. Biol. Chem. 1957, 229, 189-197.
7. Boschi-Muller, S.; Muller, S.; Dorsselaer, A. V.; Böck, A.; Branlant, G. Substituting selenocysteine for active site cysteine 149 of phosphorylating glyceraldehyde 3-phosphate dehydrogenase reveals a peroxidase activity. FEBS Lett. 1998, 439 (3), 241-245.
8. Müller, A.; Cadenas, E.; Graf, P.; Sies, H. A novel biologically active organic selenium compound. 1:Glutathione peroxidase-like activity in vitro and antioxidant capacity of PZ51 (ebselen). Biochem. Pharmacol. 1984, 33 (20), 3235-3239.
9. Cotgreave, I. A.; Moldeus, P.; Brattsand, R.; Hallberg, A.; Andersson, C. M.; Engman, L. α-(phenylselenenyl) acetophenone derivatives with glutathione peroxidase-like activity: a comparison with ebselen. Biochem. Pharmacol. 1992, 43 (4), 793-802.
10. 1H NMR method. J. Am. Chem. Soc. 1992, 114 (25), 9737-9743.
11. Engman, L.; Stern, D.; Pelcman, M.; Andersson, C. M. Thiol peroxidase activity of diorganyl tellurides. J. Org. Chem. 1994, 59 (8), 1973-1979.
12. Reich, H. J.; Jasperse, C. P. Organoselenium chemistry. Redox chemistry of selenocysteine model systems. J. Am. Chem. Soc. 1987, 109 (18), 5549-5551.
13. Back, T. G.; Dyck, B. P. A novel camphor-derived selenamide that acts as a glutathione peroxidase mimetic. J. Am. Chem. Soc. 1997, 119 (9), 2079-2083.
14. Wilson, S. R.; Zucker, P. A.; Huang, R. R. C.; Spector, A. Development of synthetic compounds with glutathione peroxidase activity. J Am. Chem. Soc. 1989, 111 (15), 5936-5939.
15. Mugesh, G.; Singh, H. B. Synthetic organoselenium compounds as antioxidants: glutathione peroxidase activity. Chem. Soc. Rev. 2000, 29, 347-357.
16. Nogueira, C. W.; Zeni, G.; Rocha, J. B. T. Organoselenium and organotellurium compounds: toxicology and pharmacology. Chem. Rev. 2004, 104 (12), 6255-6286.
17. Iwaoka, M.; Tomoda, S. A Model Study on the Effect of an Amino Group on the antioxidant activity of glutathione peroxidase. J. Am. Chem. Soc. 1994, 116 (6), 2557-2561.
18. Liu, J. Q.; Jiang, M. S.; Luo, G. M.; Yan, G. L.; Shen, J. C. Conversion of trypsin into a selenium-containing enzyme by using chemical mutation. Biotechnol. Lett. 1998, 20, 693-696.
19. Ren, X.; Jemth, P.; Board, P. G.; Luo, G.; Mannervik, B.; Liu, J.; Zhang, K.; Shen, J. An semisynthetic glutathione peroxidase with high catalytic efficiency: selenoglutathione transferase. Chem. Biol. 2002, 9, 789-794.
20. Liu, J. Q.; Luo, G. M.; Ren, X. J.; Mu, Y.; Bai, Y.; Shen, J. C. A bis-cyclodextrin diselenide with glutathione peroxidase-like activity. Biochim. Biophys. Acta 2000, 1481, 222-228.
21. Liu, J. Q.; Gao, S. J.; Luo, G. M.; Yan, G. L.; Shen, J. C. Artificial imitation of glutathione peroxidase with 6-selenium-bridged β-cyclodextrin. Biochem. Biophys. Res. Commun. 1998, 247, 397-400.
22. Ren, X. J.; Yang, L. Q.; Liu, J. Q.; Su, D.; You, D. L.; Liu, C. P.; Luo, G. M.; Zhang, K.; Mu, Y.; Yan, G. L.; Shen, J. C. A novel glutathione peroxidase mimic with antioxidant activity. Arch. Biochem. Biophys. 2001, 387 (2), 250-256.
23. Luo, G. M.; Zhu, Z. Q.; Ding, L.; Gao, G.; Sun, Q. A.; Liu, Z.; Yang, T. S.; Shen, J. C. Generation of selenium-containing abzyme by using chemical mutation. Biochem. Biophys. Res. Commun. 1994, 198, 1240-1247.
24. Ding, L.; Liu, Z.; Zhu, Z.; Luo, G.; Zhao, D.; Ni, J. Biochemical characterization of selenium-containing catalytic antibody as a cytosolic glutathione peroxidase mimic. Biochem. J. 1998, 332, 251-255.
25. Liu, J. Q.; Shi, C. B.; Luo, G. M.; Liu, Z.; Zhang, G. L.; Ma, W.; Shen, J. C. An Fv catalytic antibody with high glutathione peroxidase activity. Mater. Sci. Eng. 1999, 10, 131-134.
26. Liu, J. Q.; Luo, G. M.; Gao, S.; Zhang, K.; Chen, X.; Shen, J. C. Generation of glutathione peroxidase-like mimic by using bioimprinting and chemical mutation. Chem. Commun. 1999, (2), 199-200.
27. Liu, J. Q.; Wulff, G. Functional mimicry of the active site of carboxypeptidase A by a molecular imprinting strategy: cooperativity of an amidinium and a copper ion in a transition-state imprinted cavity giving rise to high catalytic activity. J. Am. Chem. Soc. 2004, 126 (24), 7452-7453.
28. Liu, J. Q.; Wulff, G. Molecularly imprinted polymers with strong carboxypeptidase A-Like activity: combination of an amidinium function with a zinc-ion binding site in transition-state imprinted cavities. Angew. Chem., Int. Ed. 2004, 43, 1287-1290.
29. Turner, N. W.; Jeans, C. W.; Brain, K. R.; Allender, C. J.; Hlady, V.; Britt, D. W. From 3D to 2D: A review of the molecular imprinting of proteins. Biotechnol. Prog. 2006, 22, 1474-1489.
30. Dickert, F. L.; Hayden, O. Bioimprinting of polymers and sol-gel phases. Selective detection of yeasts with imprinted polymers. Anal. Chem. 2002, 74, 1302-1306.
31. Özcan, A. A.; Say, R.; Denizli, A.; ErsÖz; A. L-Histidine imprinted synthetic receptor for biochromatography applications. Anal. Chem. 2006, 78, 7253-7258.
32. Wulff, G. Enzyme-like catalysis by molecularly imprinted polymers. Chem. Rev. 2002, 102, 1-28.
33. Murakami, Y.; Kikuchi, J.-I.; Hisaeda, Y.; Hayashida, O. Artificial Enzymes. Chem. Rev. 1996, 96, 721-758.
34. Wu, Z. P.; Hilvert, D. Selenosubtilisin as a Glutathione peroxidase mimic. J. Am. Chem. Soc. 1990, 112 (14), 5647-5648.
35. Daniel, L. K.; Klayman, D. L.; Griffin, T. S. Reaction of selenium with sodium borohydride in protic solvents. A facile method for the introduction of selenium into organic molecules. J. Am. Chem. Soc. 1973, 95 (1), 197-199.
36. Bell, I. M.; Fisher, M. L.; Wu, Z.-P.; Hilvert, D. Kinetic studies on the peroxidase activity of selenosubtilisin. Biochemistry. 1993, 32 (14), 3754-3762.
37. Cavallini, D.; Graziani, M. T.; Duprë, S. Determination of disulphide groups in proteins. Nature. 1966, 212, 294-295.
38. Wilson, S. R.; Zucker, P. A.; Huang, R. R. C.; Spector, A. Development of synthetic compounds with glutathione peroxidase activity. J. Am. Chem. Soc. 1989, 111 (15), 5936-5939.
39. Mao, S. Z.; Dong, Z. Y.; Liu, J. Q.; Li, X. M.; Liu, X. M.; Luo, G. M.; Yang, T. S.; Shen, J. C. Semisynthetic tellurosubtilisin with glutathione peroxidase activity. J. Am. Chem. Soc. 2005, 127 (33), 11588-11589.
40. Luo, G. M.; Zhu, Z. Q.; Ding, L.; Gao, G.; Sun, Q. A.; Liu, Z.; Shen, J. C. Generation of selenium-containing abzyme by using chemical mutation. Biochem, Biophys. Res. Commun. 1994, 198 (3), 1240-1247.
41. Epp, O.; Ladenstein, R.; Wendel, A. The refined structure of the selenoenzyme glutathione peroxidase at 0.2-nm resolution. Eur. J. Biochem. 1983, 133, 51-69.