Horseradish peroxidase inactivation: Heme destruction and influence of polyethylene glycol

Scientific Reports

Volumn 3, Issue , 2013, Pages

  Mao, Liang ^a   Luo, Siqiang ^a   Huang, Qingguo ^b   Lu, Junhe ^c  

^a NANJING UNIVERSITY   (China)

^b UNIVERSITY OF GEORGIA   (United States)

^c NANJING AGRICULTURAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

HEME; HORSERADISH PEROXIDASE; HYDROGEN PEROXIDE; IRON; MACROGOL DERIVATIVE; PHENOL;

ANTAGONISTS AND INHIBITORS; CHEMISTRY; ENZYME ACTIVATION; METABOLISM;

ENZYME ACTIVATION; HEME; HORSERADISH PEROXIDASE; HYDROGEN PEROXIDE; IRON; PHENOL; POLYETHYLENE GLYCOLS;

EID: 84889683703     PISSN: None     EISSN: 20452322     Source Type: Journal    
DOI: 10.1038/srep03126     Document Type: Article

References (42)

1. Chance, B. The properties of the enzyme-substrate compounds of HRP and peroxides. Arch. Biochem. Biophys. 22, 224-252 (1949).
2. George, P. The chemical nature of the 2nd-hydrogen peroxide compound formed by cytochrome C-peroxidase and horseradish peroxidase. Formation and decomposition. Biochem. J. 54, 220-230 (1953).
3. George, P. The chemical nature of the 2nd-hydrogen peroxide compound formed by cytochrome C-peroxidase and horseradish peroxidase. Titration with reducing agents. Biochem. J. 54, 267-276 (1953).
4. Yu, J., Taylor, K. E., Zou, H., Biswas, N. & Bewtra, J. K. Phenol conversion and dimeric intermediates in horseradish peroxidase-catalyzed phenol removal from water. Environ. Sci. Technol. 28, 2154-2160 (1994).
5. Junker, K., Zandomeneghi, G., Guo, Z., Kissner, R., Ishikawa, T., Kohlbrechere, T. & Walde, P. Mechanistic aspects of the horseradish peroxidase-catalysed polymerisation of aniline in the presence of AOT vesicles as templates. RSC Adv. 2, 6478-6495 (2012).
6. Auriol, M., Filali-Meknassi, Y., Tyagi, R. D. & Adams, C. D. Oxidation of natural and synthetic hormones by the horseradish peroxidase enzyme in wastewater. Chemosphere 68, 1830-1837 (2007). (Pubitemid 46908929)
7. Klibanov, A. M., Tu, T. & Scott, K. P. Peroxidase-catalyzed removal of phenols from coal-conversion waste waters. Science 221, 259-261 (1983). (Pubitemid 13062616)
8. Weber, W. J. Jr. & Huang, Q. Inclusion of persistent organic pollutants in humification processes: Direct chemical incorporation of phenanthrene via oxidative coupling. Environ. Sci. Technol. 37, 4221-4227 (2003). (Pubitemid 37108309)
9. Bollag, J. M. Decontaminating soil with enzymes. Environ. Sci. Technol. 26, 1876-1881 (1992).
10. Dec, J. & Bollag, J. M. Phenoloxidase-mediated interactions of phenols and anilines with humic materials. J. Environ. Qual. 29, 665-676 (2000). (Pubitemid 30329201)
11. Huang, Q. & Weber, W. J. Jr. Peroxidase-catalyzed coupling of phenol in the presence of model inorganic and Organic Solid Phases. Environ. Sci. Technol. 38, 5238-5245 (2004). (Pubitemid 39332059)
12. Bhandari, A. & Xu, F. Impact of peroxidase addition on the sorption-desorption behavior of phenolic contaminants in surfaces soils. Environ. Sci. Technol. 35, 3163-3168 (2001). (Pubitemid 32881749)
13. Nakajima, R. & Yamazaki, I. The mechanism of oxyperoxidase formation from freely peroxidase and hydrogen-peroxide. J. Biol. Chem. 262, 2576-2581 (1987).
14. Arnao, M. B., Acosta, M., Del Rio, J. A., Varon, R. & Garcia-Canovas, F. A kinetic study on the suicide inactivation of peroxidase by hydrogen peroxide. Biochim. Biophys. Acta. 1041, 43-47 (1990). (Pubitemid 20335916)
15. Nakamoto, S. & Machida, N. Phenol removal from aqueous-solutions by peroxidase-catalyzed reaction using additives. Water Res. 26, 49-54 (1992).
16. Ator, M. A. & Ortiz de Montellano, P. R. Protein control of prosthetic heme reactivity: reaction of substrates with the heme edge of horseradish peroxidase. J. Biol. Chem. 262, 1542-1551 (1987).
17. Ator, M. A., David, S. K. & Ortiz de Montellano, P. R. Structure and catalytic mechanism of horseradish peroxidase: region specific meso alkylation of the prosthetic heme group by alkylhydrazines. J. Biol. Chem. 262, 14954-14960 (1987).
18. Arnao, M. B., Acosta, M., Del Rio, J. A. & Garcia-Canovas, F. Inactivation of peroxidase by hydrogen peroxide and its protection by a reductant agent. Biochim. Biophys. Acta. 1038, 85-89 (1990). (Pubitemid 20086749)
19. Choi, Y. J., Chae, H. J. & Kim, E. Y. J. Steady-state oxidation model by horseradish peroxidase for the estimation of the noninactivation zone in the enzymatic removal of pentacholorophenol. Biosci. Bioengin. 88, 368-373 (1999). (Pubitemid 29535636)
20. Huang, Q. et al. Inactivation of horseradish peroxidase by phenoxyl radical attack. J. Am. Chem. Soc. 127, 1431-1437 (2005). (Pubitemid 40204518)
21. Buchanan, I. D. & Nicell, J. A. Kinetics of peroxidase interactions in the presence of a protective additive. J. Chem. Technol. Biotechnol. 72, 23-32 (1998). (Pubitemid 28221329)
22. Caza, N., Bewtra, J. K., Biswas, N.& Taylor, K. E. Removal of phenolic compounds from synthetic wastewater using soybean peroxidase. Water Res. 33, 3012-3018 (1999). (Pubitemid 29417887)
23. Wu, Y., Taylor, K. E., Biswas, N. & Bewtra, J. K. Comparison of additives in the removal of phenolic compounds by peroxidase catalyzed polymerization. Water Res. 31, 2699-2704 (1997). (Pubitemid 27487562)
24. Nicell, J. A. Kinetics of horseradish peroxidase-catalyzed polymerization and precipitation of aqueous 4-cholorophenol. J. Chem. Technol. Biotechnol. 60, 203-215 (1994). (Pubitemid 24191217)
25. Colosi, L. M., Huang, Q. & Weber, W. J. Jr. Quantitative structure activity relationship based quantification of the impacts of enzyme-substrate binding on rates of peroxidase-mediated reactions of estrogenic phenolic chemicals. J. Am. Chem. Soc. 128, 4041-4047 (2006).
26. Poulos, T. L. & Kraut, J. The stereochemistry of peroxidase catalysis. J. Biol. Chem. 255, 8199-8205 (1980).
27. Rodŕguez-López, J. N. et al. Mechanism of reaction of hydrogen peroxide with horseradish peroxidase: Identification of intermediates in the catalytic cycle. J. Am. Chem. Soc. 123, 11838-11847 (2001).
28. Dawson, J. H. Probing structure-function relations in heme containing oxygenases and peroxidases. Science 240, 433-439 (1988).
29. Huang, L., Colas, C. & Ortiz de Montellano, P. R. Oxidation of carboxylic acids by horseradish peroxidase results in prosthetic heme modification and inactivation. J. Am. Chem. Soc. 126, 12865-12873 (2004). (Pubitemid 39372316)
30. Pipirou, Z. et al. The reactivity of heme in biological systems: Autocatalytic formation of both tyrosine-heme and tryptophan-heme covalent links in a single protein architecture. Biochemistry 46, 13269-13278 (2007). (Pubitemid 350136368)
31. Huang, L., Wojciechowski, G. & Ortiz de Montellano, P. R. Prosthetic heme modification during halide ion oxidation.Demonstration of chloride oxidation by horseradish peroxidase. J. Am. Chem. Soc. 127, 5345-5353 (2005). (Pubitemid 40569846)
32. Wojciechowski, G., Huang, L. & Ortiz de Montellano, P. R. Autocatalytic modification of the prosthetic heme of horseradish but not lactoperoxidase by thiocyanate oxidation products. A role for heme-protein covalent cross-linking. J. Am. Chem. Soc. 127, 15871-15879 (2005). (Pubitemid 41644007)
33. Lad, L. et al. Crystal structure of human heme oxygenase-1 in a complex with biliverdin. Biochemistry 43, 3793-3801 (2004). (Pubitemid 38437046)
34. Ortiz de Montellano, P. R. Control of the catalytic activity of prosthetic heme by the structure of hemoprotein. Acc. Chem. Res. 20, 289-294 (1987).
35. Wojciechowski, G. & Ortiz de Montellano, P. R. Radical energies and the regiochemistry of addition to heme groups. Methylperoxy and nitrite radical additions to the heme of horseradish peroxidase. J. Am. Chem. Soc. 129, 1663-1672 (2007).
36. Denisov, E. & Denisova, T. Dissociation energies of O-H bonds of phenols and hydroperoxides. In Application of thermodynamics to biological and materials science (ed Mizutani, T.). ISBN: 978-953-307-980-6, In Tech, p406-440 (2011). (Available from: Http://cdn.intechopen.com/pdfs/13122/InTech- Dissociation-energies-of-o-h-bonds-of-phenols-and-hydroperoxides.pdf. Date of access, August 24 2013).
37. Colosi, L. M., Huang, Q. & Weber, W. J. Jr. Validation of a two-parameter quantitative structure activity relationship as a legitimate tool for rational redesign of horseradish peroxidase. Biotechnol. Bioeng. 98, 295-299 (2007). (Pubitemid 47325846)
38. Strutt, J., Wilson, S., Shorney-Darby, H., Shaw, A. & Byers, A. Assessing the carbon footprint of water production. J. Am. Water Works Assoc. 100, 80-91 (2008).
39. Lu, J., Huang, Q. & Mao, L. Removal of acetaminophen using enzyme-mediated oxidative coupling processes: Reaction rates and pathways. Environ. Sci. Technol. 43, 7062-7067 (2009).
40. Mao, L. et al. Ligninase-mediated removal of natural and synthetic estrogens from water: II. Reactions of 17b-estradiol. Environ. Sci. Technol. 44, 2599-2604 (2010).
41. Davies, E. M. Protein assays: A review of common techniques. Amer. Biotech. Lab. July, 28-37 (1988).
42. Putter, J. & Becker, R. Peroxidases. In Methods of Enzymatic Analysis (ed Bergmeyer,H. U., Bergmeyer, J. & Grassl, M.) 286-293 (Verlag Chemie, Deerfield Beach, 1983).