Biodegradation of bisphenols with immobilized laccase or tyrosinase on polyacrylonitrile beads

Biodegradation

Volumn 22, Issue 3, 2011, Pages 673-683

  Nicolucci, Carla ^a,b   Rossi, Sergio ^a   Menale, Ciro ^b,c   Godjevargova, Tzonka ^d   Ivanov, Yavor ^d   Bianco, Mariangela ^b,c   Mita, Luigi ^b,c   Bencivenga, Umberto ^a   Mita, Damiano G ^a,b,c   Diano, Nadia ^a,b,c  

^a INSTITUTE OF GENETICS AND BIOPHYSICS ADRIANO BUZZATI TRAVERSO   (Italy)

^b NATIONAL INSTITUTE OF BIOSTRUCTURES AND BIOSYSTEMS   (Italy)

^c SECOND UNIVERSITY OF NAPLES   (Italy)

^d ASSEN ZLATAROV UNIVERSITY   (Bulgaria)

Author keywords

Biodegradation; Bisphenols; Laccase; PAN beads; Tyrosinase

Indexed keywords

BIOCHEMICAL PARAMETERS; BISPHENOL A; BISPHENOL F; BISPHENOLS; CATALYTIC POWER; CATALYTIC SYSTEM; DEGRADATION RATE CONSTANTS; ENDOCRINE ACTIVITY; ENZYME TREATMENT; FLUIDIZED BED BIOREACTORS; FLUIDIZED BED REACTORS; FREE ENZYME; IMMOBILIZATION PROCESS; INITIAL ACTIVITY; LACCASE; LACCASES; OPERATIONAL STABILITY; PAN BEADS; REMOVAL EFFICIENCIES; SUBSTRATE CONCENTRATIONS; TETRACHLOROBISPHENOL-A; TYROSINASE;

CHEMICAL REACTORS; DEGRADATION; ENZYME IMMOBILIZATION; ENZYMES; FLUID CATALYTIC CRACKING; FLUIDIZATION; FLUIDIZED BEDS; MICROBIOLOGY; PHENOLS; RATE CONSTANTS; REMOVAL;

BIODEGRADATION;

4,4' ISOPROPYLIDENEDIPHENOL; ACRYLIC ACID RESIN; BISPHENOL B; FUNGAL PROTEIN; IMMOBILIZED ENZYME; LACCASE; MONOPHENOL MONOOXYGENASE; PHENOL DERIVATIVE; POLYACRYLONITRILE;

BIOCHEMICAL COMPOSITION; BIODEGRADATION; BIOREACTOR; ENZYME ACTIVITY; PH; PHENOL; SUBSTRATE; TEMPERATURE EFFECT;

AGARICALES; ARTICLE; BIOREMEDIATION; CHEMISTRY; ENZYMOLOGY; KINETICS; TRAMETES;

ACRYLIC RESINS; AGARICALES; BIODEGRADATION, ENVIRONMENTAL; ENZYMES, IMMOBILIZED; FUNGAL PROTEINS; KINETICS; LACCASE; MONOPHENOL MONOOXYGENASE; PHENOLS; TRAMETES;

EID: 79955693581     PISSN: 09239820     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10532-010-9440-2     Document Type: Article

References (53)

1. Ashby J, Tinwell H (1998) Uterotrophic activity of bisphenol A in the immature rat. Environ Health Persp 106: 716-720.
2. Ashby J, Odum J, Paton D, Lefevre PA, Beresford N, Sumpter JP (2000) Re-evaluation of the first synthetic estrogen, 1-keto-1, 2, 3, 4-tetrahydrophenanthrene, and bisphenol A, using both the ovariectomised rat model used in 1933 and additional assays. Toxicol Lett 115: 231-238.
3. Attanasio A, Diano N, Grano V, Sicuranza S, Rossi S, Bencivenga U, Fraconte L, Di Martino S, Canciglia P, Mita DG (2005) Nonisothermal bioreactors in the treatment of vegetation waters from olive oil: laccase versus syringic acid as bioremediation model. Biotechnol Progr 21: 806-815.
4. Bollag JM (1992) Decontaminating soil with enzymes. Environ Sci Technol 26: 1876-1881.
5. Buchanan ID, Nicell JA (1997) Model development for horseradish peroxidase catalyzed removal of aqueous phenol. Biotechnol Bioeng 54: 251-261.
6. Cabana H, Jiwan JLH, Rozenberg R, Elisashvili V, Penninckx M, Agathos SN, Jones JP (2007) Elimination of endocrine disrupting chemicals nonylphenol and bisphenol A and personal care product ingredient triclosan using enzyme preparation from the white rot fungus Coriolopsis polyzona. Chemosphere 67: 770-778.
7. Cabana H, Jones JP, Agathos SN (2009) Utilization of cross-linked laccase aggregates in a perfusion basket reactor for the continuous elimination of endocrine-disrupting chemicals. Biotechnol Bioeng 102: 1582-1592.
8. D'Annibale A, Rita Stazi S, Vinciguerra V, Di Mattia E, Giovannozzi Sermanni G (1999) Characterization of immobilized laccase from Lentinula edodes and its use in olive-mill wastewater treatment. Process Biochem 34: 697-706.
9. Dec J, Bollag JM (1994) Dehalogenation of chlorinated phenols during oxidative coupling. Environ Sci Technol 28: 484-490.
10. Dec J, Bollag JM (2000) Phenoloxidase-mediated interactions of phenols and anilines with humic materials. J Environ Qual 29: 665-667.
11. Diano N, Grano V, Fraconte L, Caputo P, Ricupito A, Attanasio A, Bianco M, Bencivenga U, Rossi S, Manco I, Mita L, Del Pozzo G, Mita DG (2007) Nonisothermal bioreactors in enzymatic remediation of waters polluted by endocrine disruptors: the BPA as model of pollutant. Appl Catal B Environ 69: 252-261.
12. Dodor D, Hwang H, Sin E (2004) Oxidation of anthracene and benzo[a]pyrene by immobilized laccase from Trametes versicolor. Enzyme Microb Technol 35: 210-217.
13. Durante D, Casadio R, Martelli L, Tasco G, Portaccio M, De Luca P, Bencivenga U, Rossi S, Di Martino S, Grano V, Diano N, Mita DG (2004) Isothermal and non-isothermal bioreactors in the detoxification of waste waters polluted by aromatic compounds by means of immobilised laccase from Rhus veinicifera. J Mol Catal B Enzym 27: 191-206.
14. Elsby R, Maggs JL, Ashby J, Park BK (2001) Comparison of the modulatory effects of human and rat liver microsomal metabolism on the estrogenicity of bisphenol A: implications for extrapolation to humans. J Pharmacol Exp Ther 297: 103-113.
15. Filazzola M, Sannino F, Rao M, Gianfreda L (1999) Effect of various pollutants and soil-like constituents on laccase from Cerrena unicolor. J Environ Qual 28: 1929-1938.
16. Fukazawa H, Hoshino K, Shiozawa T, Matsushita H, Terao Y (2001) Identification and quantification of chlorinated bisphenol A in wastewater from wastepaper recycling plants. Chemosphere 44: 973-979.
17. Fukazawa H, Watanabw M, Shiraishi F, Shiraishi H, Shiozawa T, Matsushita H, Terao Y (2002) Formation of chlorinated derivatives of bisphenol A in waste paper recycling plants and their estrogenic activities. J Health Sci 48: 242-249.
18. Fukuda T, Uchida H, Takashima Y, Uwajima T, Kawabata T, Suzuki M (2001) Degradation of bisphenol A by purified laccase from Trametes villosa. Biochem Biophys Res Commun 284: 704-706.
19. Gaido KW, Leonard LS, Lovell S, Gould JC, Babai D, Portier CJ, McDonnell DP (1997) Evaluation of chemicals with endocrine modulating activity in a yeast-based steroid hormone receptor gene transcription assay. Toxicol Appl Pharm 143: 205-212.
20. Galliker P, Hommes G, Schlosser D, Corvini PFX, Shahgaldian P (2010) Laccase-modified silica nanoparticles efficiently catalyze the transformation of phenolic compounds. J Colloid Int Sci 349: 98-105.
21. Georgieva S, Godjevargova T, Portaccio M, Lepore M, Mita DG (2008) Advantages in using non-isotermal bioreactors in bioremediation of water polluted by phenol by means of immobilized laccase from Rhus vernicifera. J Molecular Catal B Enzym 55: 177-184.
22. Helleday T, Tuominen KL, Bergman A, Jenssen D (1999) Brominated flame retardants induce intragenic recombination in mammalian cells. Mutat Res 439: 137-147.
23. Ikehata K, Nicell JA (2000) Characterization of tyrosinase for the treatment of aqueous phenols. Biores Technol 74: 191-199.
24. Ispas CR, Ravalli MT, Steere A, Andreescu S (2010) Multifunctional biomagnetic capsules for easy removal of phenol and bisphenol A. Water Res 44: 1961-1969.
25. Kim YJ, Nicell JA (2006a) Laccase-catalyzed oxidation of bisphenol A with the aid of additives. Process Biochem 41: 1029-1037.
26. Kim YJ, Nicell JA (2006b) Impact of reaction conditions on the laccase-catalyzed conversion of bisphenol A. Biores Technol 97: 1431-1442.
27. Kim HS, Han SY, Yoo SD, Lee BM, Park KL (2001) Potential estrogenic effects of bisphenol-A estimated by in vitro and in vivo combination assays. J Toxicol Sci 26: 111-118.
28. Kitamura S, Ohmegi M, Sanoh S, Sugihara K, Yoshihara S, Fujimoto N, Ohta S (2003) Estrogenic activity of styrene oligomers after metabolic activation by rat liver microsomes. Environ Health Persp 111: 329-334.
29. Kitamura S, Suzuki T, Sanoh S, Kohta R, Jinno N, Sugihara K, Yoshihara S, Fujimoto N, Watanabe H, Ohta S (2005) Comparative study of the endocrine-disrupting activity of bisphenol A and 19 related compounds. Toxicol Sci 84: 249-259.
30. Krishnan AV, Stathis P, Permuth SF, Tokes L, Feldman D (1993) Bisphenol-A: an estrogenic substance is released from polycarbonate flasks during autoclaving. Endocrinology 132: 2279-2286.
31. Kuruto-Niwa R, Terao Y, Nozawa R (2002) Identification of estrogenic activity of chlorinated bisphenol A using a GFP expression system. Environ Toxicol Pharm 12: 27-35.
32. Lante A, Crapisi A, Krastanov A, Spettoli P (2000) Biodegradation of phenols by laccase immobilised in a membrane reactor. Process Biochem 36: 51-58.
33. Lowry OH, Rosebrough NJ, Farr AL, Randall RJ (1951) Protein measurement with the Folin phenol reagent. J Biol Chem 193: 265-275.
34. Marin-Zamora ME, Rojas-Melgarejo F, Garcia-Canovas F, Garcia-Ruiz PA (2007) Effects of the immobilization supports on the catalytic properties of immobilized mushroom tyrosinase: a comparative study using several substrates. J Biotechnology 131: 388-396.
35. Matthews JB, Twomey K, Zacharewski TR (2001) In vitro and in vivo interactions of bisphenol A and its metabolite, bisphenol A glucuronide, with estrogen receptors alpha and beta. Chem Res Toxicol 14: 149-157.
36. Mita L, Sica V, Guida M, Nicolucci T, Grrimaldi T, Caputo L, Bianco M, Rossi S, Bencivenga U, Mohy Eldin MS, Tufano MA, Mita DG, Diano N (2010) Employment of immobilised lipase from Candida rugosa for the bioremediation of waters polluted by dimethylphthalate, as a model of endocrine disruptors. J Mol Catal B Enzym 62: 133-141.
37. Moeder M, Martin C, Koeller G (2004) Degradation of hydroxylated compounds using laccase and horseradish peroxidase immobilized on microporous polypropylene hollow fiber membranes. J Membrane Sci 245: 183-190.
38. Nakagawa Y, Suzuki T (2001) Metabolism of bisphenol A in isolated rat hepatocytes and oestrogenic activity of a hydroxylated metabolite in MCF-7 human breast cancer cells. Xenobiotica 31: 113-123.
39. Olsen CM, Meussen-Elholm ET, Samuelsen M, Holme JA, Hongslo JK (2003) Effects of the environmental oestrogens bisphenol A, tetrachlorobisphenol A, tetrabromobisphenol A, 4-hydroxybiphenyl and 4, 4'-dihydroxybiphenyl on oestrogen receptor binding, cell proliferation and regulation of oestrogen sensitive proteins in the human breast cancer cell line MCF-7. Pharmacol Toxicol 92: 180-188.
40. Pottenger LH, Domoradzki JY, Markham DA, Hansen SC, Cagen SZ, Waechter JM Jr (2000) The relative bioavailability and metabolism of bisphenol A in rats is dependent upon the route of administration. Toxicol Sci 54: 3-18.
41. Qiu L, Huang Z (2010) The treatment of chlorophenols with laccase immobilized on sol-gel-derived silica. World J Microbiol Biotechnol 26: 775-781.
42. Rasera K, Ferla J, Dillon AJP, Riveiros R, Zeni M (2009) Immobilization of laccase from Pleurotus sajor-caju in polyamide membranes. Desalination 245: 657-661.
43. Saito T, Kato K, Yokogawa Y, Nishida M, Yamashita N (2004) Detoxification of bisphenol A and nonylphenol by purified extracellular laccase from a fungus isolated from soil. J Biosci Bioeng 98: 64-66.
44. Sjodin A, Carlsson H, Thuresson K, Sjolin S, Bergman A, Ostman C (2001) Flame retardants in indoor air at an electronics recycling plant and at other work environments. Environ Sci Technol 35: 448-454.
45. Snyder RW, Maness SC, Gaido KW, Welsch F, Sumner SC, Fennell TR (2000) Metabolism and disposition of bisphenol A in female rats. Toxicol Appl Pharmacol 168: 225-234.
46. Sun H, Shen OX, Wang XR, Zhou L, Zhen SQ, Chen XD (2009) Anti-thyroid hormone activity of bisphenol A, tetrabromobisphenol A and tetrachlorobisphenol A in an improved reporter gene assay. Toxicol In Vitro 23(5): 950-954.
47. Synder SA, Westerhoff P, Yoon Y, Sedlak DL (2003) Metabolism and disposition of bisphenol A in female rats. Toxicol Appl Pharmacol 168: 225-234.
48. Tamura A, Satoh E, Kashiwada A, Matsuda K, Yamada K (2010) Removal of alkylphenols by the combined use of tyrosinase immobilized on ion-exchange resins and chitosan beads. J Appl Polym Sci 115(1): 137-145.
49. Thomsen C, Janak K, Lundanes E, Becher G (2001) Determination of phenolic flame-retardants in human plasma using solid-phase extraction and gas chromatography-electron-capture mass spectrometry. J Chromatogr B Biomed Sci Appl 750: 1-11.
50. Tinwell H, Joiner R, Pate I, Soames A, Foster J, Ashby J (2000) Uterotrophic activity of bisphenol A in the immature mouse. Regul Toxicol Pharmacol 32: 118-126.
51. Tsutsumi Y, Haneda T, Nishida T (2001) Removal of estrogenic activities of bisphenol A and nonylphenol by oxidative enzymes from lignin-degrading basidiomycetes. Chemosphere 42: 271-276.
52. Uchida H, Fukuda T, Miyamoto H, Kawabata T, Suzuki M, Uwajima T (2001) Polymerization of bisphenol A by purified laccase from Trametes villosa. Biochem Biophys Res Commun 287: 355-358.
53. Zhang J, Liu X, Xu Z, Chen H, Yang Y (2008) Degradation of chlorophenols catalyzed by laccase. Int Biodeter Biodegr 61: 351-356.