Orthogonal, spectroscopic high throughput screening of laccase-catalyzed p-cresol oxidation

Combinatorial Chemistry and High Throughput Screening

Volumn 12, Issue 7, 2009, Pages 678-689

  Achyuthan, Komandoor E ^a,b   McClain, Jaime L ^a   Raj, Dominic ^c  

^a SANDIA NATIONAL LABORATORIES   (United States)

^b JOINT BIOENERGY INSTITUTE   (United States)

^c UNIVERSITY OF NEW MEXICO   (United States)

Author keywords

Absorption; Fluorescence; High throughput screening; Laccase; p cresol; Spectroscopy

Indexed keywords

HALIDE; LACCASE; PARA CRESOL; SODIUM CHLORIDE; SODIUM HYDROXIDE;

ABSORPTION; ABSORPTION SPECTROSCOPY; ACIDITY; ALKALINITY; ARTICLE; BLEACHING; CATALYSIS; ENZYME ACTIVITY; ENZYME KINETICS; ENZYME METABOLISM; FLUORESCENCE; FLUORESCENCE SPECTROSCOPY; HIGH THROUGHPUT SCREENING; IC 50; MOLECULAR STABILITY; PH; PHOTODEGRADATION; PRIORITY JOURNAL; REACTION OPTIMIZATION;

CRESOLS; DOSE-RESPONSE RELATIONSHIP, DRUG; KINETICS; LACCASE; OXIDATION-REDUCTION; SPECTROMETRY, FLUORESCENCE; SUBSTRATE SPECIFICITY;

EID: 68549127178     PISSN: 13862073     EISSN: None     Source Type: Journal    
DOI: 10.2174/138620709788923773     Document Type: Article

References (43)

1. Veeresh, G.S.; Kumar, P.; Mehrotra, I. Treatment of phenol and cresols in upflow anaerobic sludge blanket (UASB) process: a review. Water Res., 2005, 39(1), 154-170 (Pubitemid 40017765)
2. Peters, F.; Heintz, D.; Johannes, J.; van Dorsselaer, A.; Boll, M. Genes, enzymes, and regulation of para-cresol metabolism in Geobacter metallireducens. J. Bacteriol., 2007, 189(13), 4729-4738
3. Han, K.H.; Ko, J.H.; Yang, S.H. Optimizing lignocellulosic feedstock for improved biofuel productivity and processing. Biofuels, Bioprod. Bioref., 2007, 1, 135-146
4. Vanholder, R.; De Smet, R.; Lesaffer, G. p-cresol: a toxin revealing many neglected but relevant aspects of uraemic toxicity. Nephrol. Dial. Transplant., 1999, 14(12), 2813-2815
5. Johannes, T.W.; Woodyer, R.D.; Zhao, H. In Enzyme Assays: High Throughput Screening, Genetic Selection and Fingerprinting; Raymond, J-L. Ed.; Wiley-VCH, Verlag GmbH & Co.: Weinheim, 2006, pp. 77-93.
6. Baldrian, P. Fungal laccases - occurrence and properties. FEMS Microbiol. Rev., 2006, 30(2), 215-242
7. Kunamneni, A.; Ballesteros, A.; Plou, F.J.; Alcalde, M. In Communicating Current Research and Educational Topics and Trends in Applied Microbiology; Mendez-Vilas, A. Ed.; Formatex, Badajoz: Spain, 2007, Vol.1, pp. 233-245
8. Hewson, W.D.; Dunford, H.B. Stoichiometry of the reaction between horseradish peroxidase and p-cresol. J. Biol. Chem., 1976, 251(19), 6043-6052
9. Raven, E.L.; Celik, A.; Cullis, P.M.; Sangar, R.; Sutcliffe, M.J. Engineering the active site of ascorbate peroxidase. Biochem. Soc. Trans., 2001, 29(2), 105-111.
10. Kobayashi, S.; Higashimura, H. Oxidative polymerization of phenols revisited. Prog. Polym. Sci., 2003, 28(6), 1015-1048
11. Liu, Z.; Cai, R.; Mao, L.; Huang, H.; Ma, W. Highly sensitive spectrofluorimetric determination of hydrogen peroxide with β- cyclodextrin-hemin as catalyst. Analyst, 1999, 124(2), 173-176 (Pubitemid 29092398)
12. Celik, A.; Cullis, P.M.; Lloyd, E.R. Catalytic oxidation of p-cresol by ascorbate peroxidase. Arch. Biochem. Biophys., 2000, 373(1), 175-181
13. McIlvaine, T.C. A buffer solution for colorimetric comparison. J. Biol. Chem., 1921, 49(1), 183-186
14. Achyuthan, K.E.; Whitten, D.G. Design considerations for high throughput screening and in vitro diagnostic assays. Comb. Chem. High Throughput Screen., 2007, 10(6), 399-412.
15. Achyuthan, K.E. Thiols enhance the sensitivity of luminescent assays for non-crosslinked and covalently cross-linked aminophthalhydrazides. Luminescence, 2001, 16(4), 257-262
16. Simon, L.T.; Bishop, D.S.; Hooper, G.R. Ultrastructure and cytochemical localization of laccase in two strains of Leptosphaerulina briosiana (Pollaci) Graham and Luttrell. J. Bacteriol., 1979, 137(1), 537-544
17. Bao, W.; O'Malley, D.M.; Whetten, R.; Sederoff, R.R. A laccase associated with lignification in Loblolly pine xylem. Science, 1993, 260(5108), 672-674 (Pubitemid 23167589)
18. Garzillo, A.M.; Colao, M.C.; Caruso, C.; Caporale, C.; Celletti, D.; Buonocore, V. Laccase from the white-rot fungus Trametes trogii. Appl. Microbiol. Biotechnol., 1998, 49(5), 545-551
19. Haghighi, B.; Gorton, L.; Ruzgas, T.; Jonsson, L.J. Characterization of graphite electrodes modified with laccase from Trametes versicolor and their use for bioelectrochemical monitoring of phenolic compounds in flow injection analysis. Anal. Chim. Acta, 2003, 487, 3-14.
20. Bollag, J-M.; Shuttleworth, K.L.; Anderson, D.H. Laccase-mediated detoxification of phenolic compounds. Appl. Environ. Microbiol., 1988, 54(12), 3086-3091
21. Junghanns, C.; Moeder, M.; Krauss, G.; Martin, C.; Schlosser, D. Degradation of the xenoestrogen nonylphenol by aquatic fungi and their laccases. Microbiology, 2005, 151(1), 45-57. (Pubitemid 40207668)
22. Corvini, P.F.; Schaffer, A.; Schlosser, D. Microbial degradation of nonylphenol and other alkylphenols - our evolving view. Appl. Microbiol. Biotechnol., 2006, 72(2), 223-243
23. Sahay, R.; Yadav, R.S.S.; Yadav, K.D.S. Purification and characterization of laccase secreted by L. lividus. Appl. Biochem. Biotechnol., 2009, 157(2), 311-320
24. Xu, F. Effects of redox potential and hydroxide inhibition on the pH activity profile of fungal laccases. J. Biol. Chem., 1997, 272(2), 924-928
25. Shuttleworth, K.L.; Bollag, J-M. Soluble and immobilized laccase as catalysts for the transformation of substituted phenols. Enzyme Microbiol. Technol., 1986, 8(3), 171-177
26. Tsuruta, Y.; Kitai, S.; Watanabe, S.; Inoue, H. 2-Methoxy-4-(2- phthalimidinyl)phenylsulfonyl chloride as a fluorescent labeling reagent for determination of phenols in high-performance liquid chromatography and application for determination of urinary phenol and p-cresol. Anal. Biochem., 2000, 280(1), 36-41.
27. Gomes, S.A.S.S.; Rebelo, M.J.F. A new laccase biosensor for polyphenols determination. Sensors, 2003, 3(6), 166-175
28. Orenes-Pinero, E.; Garcia-Carmona, F.; Sanchez-Ferrer, A. A kinetic study of p-cresol oxidation by quince fruit polyphenol oxidase. J. Agric. Food Chem., 2005, 53(4), 1196-1200
29. Murao, S.; Arai, M.; Tanaka, H.; Ishikawa, K.; Matsumoto, K.; Watanabe, S. A method for assaying α-glucosidase and α-amylase using laccase. Agric. Biol. Chem., 1985, 49(4), 981-985
30. Akbar, U.; Aschenbrenner, C.D.; Harper, M.R.; Johnson, H.R.; Dordick, J.S.; Clark, D.S. Direct solubilization of enzyme aggregates with enhanced activity in nonaqueous media. Biotechnol. Bioeng., 2007, 96(6), 1030-1039
31. Kai, M.; Noguchi, S.; Baba, H.; Ohkura, Y. Sensitive fluorimetric assay for human thyroid peroxidase using p-cresol as a substrate. Chem. Pharm. Bull.(Tokyo), 1984, 32(10), 4017-4022
32. Tchaikovskaya, O.; Sokolova, I.; Svetlichnyi, V.; Karetnikova, E.; Federova, E.; Kudryasheva, N. Fluorescence and bioluminescence analysis of sequential UV-biological degradation of p-cresol in water. Luminescence, 2007, 22(1), 29-34.
33. Zaitsu, K.; Ohkura, Y. New fluorogenic substrates for horseradish peroxidase: rapid and sensitive assays for hydrogen peroxide and the peroxidase. Anal. Biochem., 1980, 109(1), 109-113
34. Westerfield, W. W.; Lowe, C. The oxidation of p-cresol by peroxidase. J. Biol. Chem., 1942, 145(2), 463-470
35. Piontek, K; Antorini, M.; Choinowski, T. Crystal structure of a laccase from the fungus Trametes versicolor at 1.90-A° resolution containing a full complement of coppers. J. Biol. Chem., 2002, 277(40), 37663-37669
36. Bohlin, C.; Jonsson, L.J.; Roth, R.; van Zyl, W.H. Heterologous expression of Trametes versicolor laccase in Pichia pastoris and Aspergillus niger. Appl. Biochem. Biotechnol., 2006, 129-132, 195-214.
37. Setti, L.; Giuliani, S.; Spinozzi, G.; Pifferi, P.G. Laccase catalyzed-oxidative coupling of 3-methyl 2-benzothiazolinone hydrazone and methoxyphenols. Enzyme Microbiol. Technol., 1999, 25(3-5), 285-289
38. Yoshikawa, M.; Taguchi, Y.; Arashidani, K. Determination of cresols in urine by high-performance liquid chromatography. J. Chromatogr., 1986, 362(3), 425-429 (Pubitemid 16048750)
39. Rogers, K.R.; Becker, J.Y.; Wang, J.; Lu, F. Determination of phenols in environmentally relevant matrices using a liquid chromatographic system with an enzyme based biosensor. Field Anal. Chem. Technol., 1999, 3(1), 161-169
40. Solna, R.; Sapelnikova, S.; Skladal, P.; Winther-Nielsen, M.; Carlsson, C.; Emneus, J.; Ruzgas, T. Multienzyme electrochemical array sensor for determination of phenols and pesticides. Talanta, 2005, 65(2), 349-357
41. Niwa, T. Phenol and p-cresol accumulated in uremic serum measured by HPLC with fluorescence detection. Clin. Chem., 1993, 39(1), 108-111
42. Smet, R.D.; David, F.; Sandra, P.; Kaer, J.V.; Lesaffer, G.; Dhondt, A.; Lameire, N.; Vanholder, R. A sensitive HPLC method for the quantification of free and total p-cresol in patients with chronic renal failure. Clin. Chim. Acta., 1998, 278(1), 1-21.
43. Martinez, A.W.; Recht, N.S.; Hostetter, T.H.; Meyer, T.W. Removal of P-cresol sulfate by hemodialysis. J. Am. Soc. Nephrol., 2005, 16(11), 3430-3436