Ahmed MM, Barbati S, Doumenq P, Chiron S (2012) Sulfate radical anion oxidation of diclofenac and sulfamethoxazole for water decontamination. Chem Eng J 197:440–447
Article
Google Scholar
Ammann EM, Gasser CA, Hommes G, Corvini PF (2014) Immobilization of defined laccase combinations for enhanced oxidation of phenolic contaminants. Appl Microbiol Biotechnol 98(3):1397–1406. https://doi.org/10.1007/s00253-013-5055-y
Article
CAS
PubMed
Google Scholar
Arca-Ramos A, Eibes G, Feijoo G, Lema JM, Moreira MT (2015) Potentiality of a ceramic membrane reactor for the laccase-catalyzed removal of bisphenol A from secondary effluents. Appl Microbiol Biotechnol 99:9299–9308. https://doi.org/10.1007/s00253-015-6826-4
Article
CAS
PubMed
Google Scholar
Asif MB, Hai FI, Hou J, Price WE, Nghiem LD (2017a) Impact of wastewater derived dissolved interfering compounds on growth, enzymatic activity and trace organic contaminant removal of white rot fungi—a critical review. J Environ Manag 201:89–109
Article
CAS
Google Scholar
Asif MB, Hai FI, Kang J, van de Merwe JP, Leusch FDL, Yamamoto K, Price WE, Nghiem LD (2017b) Degradation of trace organic contaminants by a membrane distillation—enzymatic bioreactor 7(879):1–15. https://doi.org/10.3390/app7090879
Google Scholar
Auriol M, Filali-Meknassi Y, Adams CD, Tyagi RD, Noguerol TN, Pina B (2008) Removal of estrogenic activity of natural and synthetic hormones from a municipal wastewater: efficiency of horseradish peroxidase and laccase from Trametes versicolor. Chemosphere 70(3):445–452. https://doi.org/10.1016/j.chemosphere.2007.06.064
Article
CAS
PubMed
Google Scholar
Baiocco P, Barreca AM, Fabbrini M, Galli C, Gentili P (2003) Promoting laccase activity towards non-phenolic substrates: a mechanistic investigation with some laccase-mediator systems. Org Biomol Chem 1(1):191–197. https://doi.org/10.1039/B208951c
Article
CAS
PubMed
Google Scholar
Barnabe S, Brar SK, Tyagi RD, Beauchesne I, Surampalli RY (2009) Pre-treatment and bioconversion of wastewater sludge to value-added products-fate of endocrine disrupting compounds. Sci Total Environ 407:1471–1488. https://doi.org/10.1016/j.scitotenv.2008.11.015
Article
CAS
PubMed
Google Scholar
Bhandari RK, Deem SL, Holliday DK, Jandegian CM, Kassotis CD, Nagel SC, Tillitt DE, Vom Saal FS, Rosenfeld CS (2015) Effects of the environmental estrogenic contaminants bisphenol A and 17α-ethinyl estradiol on sexual development and adult behaviors in aquatic wildlife species. Gen Comp Endocrinol 214:195–219. https://doi.org/10.1016/j.ygcen.2014.09.014
Article
CAS
PubMed
Google Scholar
Bollag JM, Shuttleworth KL, Anderson DH (1988) Laccase-mediated detoxification of phenolic compounds. Appl Environ Microbiol 54(12):3086–3091
CAS
PubMed
PubMed Central
Google Scholar
Bourbonnais R, Paice MG (1990) Oxidation of non-phenolic substrates: an expanded role for laccase in lignin biodegradation. FEBS Lett 267(1):99–102. https://doi.org/10.1016/0014-5793(90)80298-W
Article
CAS
PubMed
Google Scholar
Carmona E, Andreu V, Picó Y (2014) Occurrence of acidic pharmaceuticals and personal care products in Turia River Basin: from waste to drinking water. Sci Total Environ 484:53–63
Article
CAS
PubMed
Google Scholar
Catapane M, Nicolucci C, Menale C, Mita L, Rossi S, Mita DG, Diano N (2013) Enzymatic removal of estrogenic activity of nonylphenol and octylphenol aqueous solutions by immobilized laccase from Trametes versicolor. J Hazard Mater 248:337–346. https://doi.org/10.1016/j.jhazmat.2013.01.031
Article
PubMed
Google Scholar
Chairin T, Nitheranont T, Watanabe A, Asada Y, Khanongnuch C, Lumyong S (2013) Biodegradation of bisphenol A and decolorization of synthetic dyes by laccase from white-rot fungus, Trametes polyzona. Appl Biochem Biotechnol 169:539–545. https://doi.org/10.1007/s12010-012-9990-3
Article
CAS
PubMed
Google Scholar
Commission 24 August 2013. Directive 2013/39/EU of the European Parliament and of the Council of 12 August 2013 amending Directives 2000/60/EC and 2008/105/EC as regards priority substances in the field of water policy. Luxembourg: Off J Eur Union 226:1–17
Commission 24 March 2015. Commission implementing decision (EU) 2015/495 of 20 March 2015 establishing a watch list of substances for Union-wide monitoring in the field of water policy pursuant to Directive 2008/105/EC of the European Parliament and of the Council. Luxembourg: Off J Eur Union 78:40–42
Davies NM, Anderson KE (1997) Clinical pharmacokinetics of diclofenac. Therapeutic insights and pitfalls. Clin Pharmacokinet 33(3):184–213
Article
CAS
PubMed
Google Scholar
Deblonde T, Cossu-Leguille C, Hartemann P (2011) Emerging pollutants in wastewater: a review of the literature. Int J Hyg Environ Health 214(6):442–448. https://doi.org/10.1016/j.ijheh.2011.08.002
Article
CAS
PubMed
Google Scholar
Dorado P, Berecz R, Cáceres MC, LLerena A (2003) Analysis of diclofenac and its metabolites by high-performance liquid chromatography: relevance of CYP2C9 genotypes in diclofenac urinary metabolic ratios. J Chromatogr B 789:437–442
Article
CAS
Google Scholar
Faber H, Melles D, Brauckmann C, Wehe CA, Wentker K, Karst U (2012) Simulation of the oxidative metabolism of diclofenac by electrochemistry/(liquid chromatography/) mass spectrometry. Anal Bioanal Chem 403(2):345–354. https://doi.org/10.1007/s00216-011-5665-0
Article
CAS
PubMed
Google Scholar
Frasconi M, Favero G, Boer H, Koivula A, Mazzei F (2010) Kinetic and biochemical properties of high and low redox potential laccases from fungal and plant origin. Biochim Biophys Acta 1804:899–908
Article
CAS
PubMed
Google Scholar
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(3):704–706. https://doi.org/10.1006/bbrc.2001.5021
Article
CAS
PubMed
Google Scholar
Fukuda T, Uchida H, Suzuki M, Miyamoto H, Morinaga H, Nawata H, Uwajima T (2004) Transformation products of bisphenol A by a recombinant Trametes villosa laccase and their estrogenic activity. J Chem Technol Biot 79:1212–1218
Article
CAS
Google Scholar
Galli C, Gentili P, Jolivalt C, Madzak C, Vadalà R (2011) How is the reactivity of laccase affected by single-point mutations? Engineering laccase for improved activity towards sterically demanding substrates. Appl Microbiol Biotechnol 91:123–131. https://doi.org/10.1007/s00253-011-3240-4
Article
CAS
PubMed
Google Scholar
Gracia-Lor E, Sancho JV, Serrano R, Hernández F (2012) Occurrence and removal of pharmaceuticals in wastewater treatment plants at the Spanish Mediterranean area of Valencia. Chemosphere 87:453–462
Article
CAS
PubMed
Google Scholar
Hahn V, Mikolasch A, Wende K, Bartrow H, Lindequist U, Schauer F (2009) Synthesis of model morpholine derivatives with biological activities by laccase-catalysed reactions. Biotechnol Appl Biochem 54:187–195. https://doi.org/10.1042/Ba20090219
Article
CAS
PubMed
Google Scholar
Hahn V, Mikolasch A, Schauer F (2014) Cleavage and synthesis function of high and low redox potential laccases towards 4-morpholinoaniline and aminated as well as chlorinated phenols. Appl Microbiol Biotechnol 98(4):1609–1620. https://doi.org/10.1007/s00253-013-4984-9
Article
CAS
PubMed
Google Scholar
Heberer T (2002a) Occurrence, fate, and removal of pharmaceutical residues in the aquatic environment: a review of recent research data. Toxicol Lett 131(1–2):5–17
Article
CAS
PubMed
Google Scholar
Heberer T (2002b) Tracking persistent pharmaceutical residues from municipal sewage to drinking water. J Hydrol 266(3–4):175–189
Article
CAS
Google Scholar
Heberer T, Feldmann D (2005) Contribution of effluents from hospitals and private households to the total loads of diclofenac and carbamazepine in municipal sewage effluents-modeling versus measurements. J Hazard Mater 122(3):211–218. https://doi.org/10.1016/j.jhazmat.2005.03.007
Article
CAS
PubMed
Google Scholar
Iimura Y, Hartikainen P, Tatsumi K (1996) Dechlorination of tetrachloroguaiacol by laccase of white-rot basidiomycete Coriolus versicolor. Appl Microbiol Biotechnol 45:434–439
Article
CAS
Google Scholar
Jonas U, Hammer E, Schauer F, Bollag JM (1997) Transformation of 2-hydroxydibenzofuran by laccases of the white rot fungi Trametes versicolor and Pycnoporus cinnabarinus and characterization of oligomerization products. Biodegradation 8(5):321–328. https://doi.org/10.1023/a:1008220120431
Article
CAS
PubMed
Google Scholar
Keilin D, Mann T (1939) Laccase, a blue copper-protein oxidase from the latex Rhus succedanea. Nature 143:23–24
Article
CAS
Google Scholar
Kim Y-J, Nicell JA (2006) Impact of reaction conditions on the laccase-catalyzed conversion of bisphenol A. Bioresour Technol 97:1431–1442. https://doi.org/10.1016/j.biortech.2005.06.017
Article
CAS
PubMed
Google Scholar
Kordon K, Mikolasch A, Schauer F (2010) Oxidative dehalogenation of chlorinated hydroxybiphenyls by laccases of white-rot fungi. Int Biodeterior Biodegrad 64(3):203–209. https://doi.org/10.1016/j.ibiod.2009.10.010
Article
CAS
Google Scholar
Kunamneni A, Camarero S, Garcia-Burgos C, Plou FJ, Ballesteros A, Alcalde M (2008) Engineering and applications of fungal laccases for organic synthesis. Microb Cell Fact 7:1–17
Article
Google Scholar
Levy G, Lutz I, Krüger A, Kloas W (2004) Bisphenol A induces feminization in Xenopus laevis tadpoles. Environ Res 94(1):102–111. https://doi.org/10.1016/S0013-9351(03)00086-0
Article
CAS
PubMed
Google Scholar
Li KC, Xu F, Eriksson KEL (1999) Comparison of fungal laccases and redox mediators in oxidation of a nonphenolic lignin model compound. Appl Environ Microbiol 65:2654–2660
CAS
PubMed
PubMed Central
Google Scholar
Lloret L, Eibes G, Lú-Chau TA, Moreira MT, Feijoo G, Lema JM (2010) Laccase-catalyzed degradation of anti-inflammatories and estrogens. Biochem Eng J 51:124–131
Article
CAS
Google Scholar
Loos R, Gawlik BM, Locoro G, Rimaviciute E, Contini S, Bidoglio G (2009) EU-wide survey of polar organic persistent pollutants in European river waters. Environ Pollut 157(2):561–568. https://doi.org/10.1016/j.envpol.2008.09.020
Article
CAS
PubMed
Google Scholar
Loos R, Locoro G, Comero S, Contini S, Schwesig D, Werres F, Balsaa P, Gans O, Weiss S, Blaha L, Bolchi M, Gawlik BM (2010) Pan-European survey on the occurrence of selected polar organic persistent pollutants in ground water. Water Res 44(14):4115–4126. https://doi.org/10.1016/j.watres.2010.05.032
Article
CAS
PubMed
Google Scholar
Mai C, Schormann W, Hüttermann A (2001) Chemo-enzymatically induced copolymerization of phenolics with acrylate compounds. Appl Microbiol Biotechnol 55:177–186
Article
CAS
PubMed
Google Scholar
Manda K, Gordes D, Mikolasch A, Hammer E, Schmidt E, Thurow K, Schauer F (2007) Carbon-oxygen bond formation by fungal laccases: cross-coupling of 2,5-dihydroxy-N-(2-hydroxyethyl)-benzamide with the solvents water, methanol, and other alcohols. Appl Microbiol Biotechnol 76(2):407–416. https://doi.org/10.1007/s00253-007-1024-7
Article
CAS
PubMed
Google Scholar
Marco-Urrea E, Perez-Trujillo M, Cruz-Morato C, Caminal G, Vicent T (2010) Degradation of the drug sodium diclofenac by Trametes versicolor pellets and identification of some intermediates by NMR. J Hazard Mater 176(1–3):836–842. https://doi.org/10.1016/j.jhazmat.2009.11.112
Article
CAS
PubMed
Google Scholar
Margot J, Maillard J, Rossi L, Barry DA, Holliger C (2013) Influence of treatment conditions on the oxidation of micropollutants by Trametes versicolor laccase. N Biotechnol 30(6):803–813. https://doi.org/10.1016/j.nbt.2013.06.004
Article
CAS
PubMed
Google Scholar
Mehinto AC, Hill EM, Tyler CR (2010) Uptake and biological effects of environmentally relevant concentrations of the nonsteroidal anti-inflammatory pharmaceutical diclofenac in rainbow trout (Oncorhynchus mykiss). Environ Sci Technol 44(6):2176–2182. https://doi.org/10.1021/es903702m
Article
CAS
PubMed
Google Scholar
Mikolasch A, Schauer F (2009) Fungal laccases as tools for the synthesis of new hybrid molecules and biomaterials. Appl Microbiol Biotechnol 82(4):605–624. https://doi.org/10.1007/s00253-009-1869-z
Article
CAS
PubMed
Google Scholar
Minard RD, Liu SY, Bollag JM (1981) Oligomers and quinones from 2,4-dichlorophenol. J Agr Food Chem 29(2):250–253
Article
CAS
Google Scholar
Mogharabi M, Faramarzi MA (2014) Laccase and laccase-mediated systems in the synthesis of organic compounds. Adv Synth Catal 356:897–927. https://doi.org/10.1002/adsc.201300960
Article
CAS
Google Scholar
Munk L, Andersen ML, Meyer AS (2017) Direct rate assessment of laccase catalysed radical formation in lignin by electron paramagnetic resonance spectroscopy. Enzyme Microb Technol 106:88–96
Article
CAS
PubMed
Google Scholar
Nadanaciva S, Aleo MD, Strock CJ, Stedman DB, Wang H, Will Y (2013) Toxicity assessments of nonsteroidal anti-inflammatory drugs in isolated mitochondria, rat hepatocytes, and zebrafish show good concordance across chemical classes. Toxicol Appl Pharmacol 272(2):272–280. https://doi.org/10.1016/j.taap.2013.06.019
Article
CAS
PubMed
Google Scholar
Nagai M, Sato T, Watanabe H, Saito K, Kawata M, Enei H (2002) Purification and characterization of an extracellular laccase from the edible mushroom Lentinula edodes, and decolorization of chemically different dyes. Appl Microbiol Biotechnol 60(3):327–335. https://doi.org/10.1007/s00253-002-1109-2
Article
CAS
PubMed
Google Scholar
Nair RR, Demarche P, Agathos SN (2013) Formulation and characterization of an immobilized laccase biocatalyst and its application to eliminate organic micropollutants in wastewater. N Biotechnol 30(6):814–823. https://doi.org/10.1016/j.nbt.2012.12.004
Article
CAS
PubMed
Google Scholar
Nakamura T (1960) On the process of enzymatic oxidation of hydroquinone. Biochem Biophys Res Commun 2:111–113
Article
CAS
Google Scholar
Nguyen LN, Hai FI, Price WE, Leusch FDL, Roddick F, McAdam EJ, Magram SF, Nghiem LD (2014) Continuous biotransformation of bisphenol A and diclofenac by laccase in an enzymatic membrane reactor. Int Biodeterior Biodegrad 95:25–32
Article
CAS
Google Scholar
Quednow K, Püttmann W (2008) Endocrine disruptors in freshwater streams of Hesse, Germany: changes in concentration levels in the time span from 2003 to 2005. Environ Pollut 152:476–483
Article
CAS
PubMed
Google Scholar
Ramírez-Cavazos LI, Junghanns C, Ornelas-Soto N, Cárdenas-Chávez DL, Hernández-Luna C, Demarche P, Enaud E, García-Morales R, Agathos SN, Parra R (2014) Purification and characterization of two thermostable laccases from Pycnoporus sanguineus and potential role in degradation of endocrine disrupting chemicals. J Mol Catal B Enzym 108:32–42
Article
Google Scholar
Reinhammar BRM (1972) Oxidation-reduction potentials of the electron acceptors in laccases and stellacyanin. Biochim Biophys Acta 275:242–245
Article
Google Scholar
Samaras VG, Stasinakis AS, Mamais D, Thomaidis NS, Lekkas TD (2013) Fate of selected pharmaceuticals and synthetic endocrine disrupting compounds during wastewater treatment and sludge anaerobic digestion. J Hazard Mater 244–245:259–267
Article
PubMed
Google Scholar
Shen S, Marchick MR, Davis MR, Doss GA, Pohl LR (1999) Metabolic activation of diclofenac by human cytochrome P450 3A4: role of 5-hydroxydiclofenac. Chem Res Toxicol 12(2):214–222
Article
CAS
PubMed
Google Scholar
Solomon EI, Chen P, Metz M, Lee SK, Palmer AE (2001) Oxygen binding, activation, and reduction to water by copper proteins. Angew Chem Int Ed 40(24):4570–4590
Article
CAS
Google Scholar
Solomon EI, Augustine AJ, Yoon J (2008) O2 reduction to H2O by the multicopper oxidases. Dalton Trans 30:3921–3932. https://doi.org/10.1039/b800799c
Article
Google Scholar
Tadesse MA, D’Annibale A, Galli C, Gentili P, Sergi F (2008) An assessment of the relative contributions of redox and steric issues to laccase specificity towards putative substrates. Org Biomol Chem 6(5):868–878. https://doi.org/10.1039/b716002j
Article
CAS
PubMed
Google Scholar
Ternes TA (1998) Occurence of drugs in German sewage treatment plants and rivers. Water Res 32(11):3245–3260
Article
CAS
Google Scholar
Thurston CF (1994) The structure and function of fungal laccases. Microbiology 140:19–26
Article
CAS
Google Scholar
Tran NH, Urase T, Kusakabe O (2010) Biodegradation characteristics of pharmaceutical substances by whole fungal culture Trametes versicolor and its laccase. J Water Environ Technol 8(2):125–140
Article
Google Scholar
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(2):355–358. https://doi.org/10.1006/bbrc.2001.5593
Article
CAS
PubMed
Google Scholar
Webster R, Pacey M, Winchester T, Johnson P, Jezequel S (1998) Microbial oxidative metabolism of diclofenac: production of 4′-hydroxydiclofenac using Epiccocum nigrum IMI354292. Appl Microbiol Biotechnol 49(4):371–376
Article
CAS
PubMed
Google Scholar
Wesenberg D, Kyriakides I, Agathos SN (2003) White-rot fungi and their enzymes for the treatment of industrial dye effluents. Biotechnol Adv 22(1–2):161–187
Article
CAS
PubMed
Google Scholar
Xu F (1996) Oxidation of phenols, anilines, and benzenethiols by fungal laccases: correlation between activity and redox potentials as well as halide inhibition. Biochemistry 35(23):7608–7614. https://doi.org/10.1021/bi952971a
Article
CAS
PubMed
Google Scholar
Xu F, Berka RM, Wahleithner JA, Nelson BA, Shuster JR, Brown SH, Palmer AE, Solomon EI (1998) Site-directed mutations in fungal laccase: effect on redox potential, activity and pH profile. Biochem J 334:63–70
Article
CAS
PubMed
PubMed Central
Google Scholar
Xu F, Kulys JJ, Duke K, Li KC, Krikstopaitis K, Deussen HJW, Abbate E, Galinyte V, Schneider P (2000) Redox chemistry in laccase-catalyzed oxidation of N-hydroxy compounds. Appl Environ Microbiol 66:2052–2056
Article
CAS
PubMed
PubMed Central
Google Scholar
Zwiener C, Glauner T, Frimmel FH (2000) Biodegradation of pharmaceutical residues investigated by SPE-GC/ITD-MS and on-line derivatization. J High Resolut Chrom 23(7/8):474–478
Article
CAS
Google Scholar