Quantitative structure-activity relationship (QSAR) models for fungal laccase-catalyzed degradation of different hydroxylated polychlorinated biphenyls (OH-PCBs) were developed using some fundamental quantum chemical descriptors. The cross-validated Q 2 cum values for the two optimal QSAR models are as high as 0.958 and 0.961 for laccases from Trametes versicolor and Pleurotus ostreatus, respectively, indicating good predictive abilities for laccase-catalyzed degradation of OH-PCBs. Results from this study show that increasing heat of formation (ΔH f) and frontier molecular orbital energy (i.e. E LUMO + E HOMO) values or decreasing frontier molecular orbital energy (i.e. E HOMO−1) and core-core repulsion energy (CCR) values leads to the increase of OH-PCB degradation rates by laccases.
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Bollag JM, Chu H-L, Rao MA, Gianfreda L (2003) Enzymatic oxidative transformation of chlorophenol mixtures. J Environ Qual 32:63–69
Bollag JM, Shuttleworth KL, Anderson DH (1988) Laccase-mediated detoxification of phenolic compounds. Appl Environ Microbiol 54:3086–3091
Cassidy D, Hampton D, Kohler S (2002) Combined chemical (ozone) and biological treatment of polychlorinated biphenyls (PCBs) adsorbed to sediments. J Chem Technol Biotechnol 77:663–670
Chen JW, Peijnenburg WJGM, Quan X, Yang FL (2000) Quantitative structure-property relationships for direct photolysis quantum yields of selected polycyclic aromatic hydrocarbons. Sci Total Environ 246:11–20
Dodor DE, Hwang HM, Ekunwe SIN (2004) Oxidation of anthracene and benzo[a]pyrene by immobilized laccase from Trametes versicolor. Enzyme Microbiol Technol 35:210–217
Durán N, Rosa MA, D’Annibale A, Gianfreda L (2002) Applications of laccases and tyrosinases (phenoloxidases) immobilized on different supports: a review. Enzyme Microbiol Technol 31:907–931
Faucon JC, Bureau R, Faisant J, Briens F, Rault S (1999) Predicting of the fish acute toxicity from heterogeneous data coming from notification files. Chemosphere 38:3261–3276
Hovander L, Linderholm L, Athanasiadou M, Athanassiadis I, Bignert A, Fängström B, Kocan A, Petrik J, Trnovec T, Bergman Å (2006) Levels of PCBs and their metabolites in the serum of residents of a highly contaminated area in eastern slovakia. Environ Sci Technol 40:3696–3703
Keum YS, Li QX (2004) Fungal laccase-catalyzed degradation of hydroxyl polychlorinated biphenyls. Chemosphere 56:23–30
Kimura-Kuroda J, Nagata I, Kuroda Y (2007) Disrupting effects of hydroxy-polychlorinated biphenyl (PCB) congeners on neuronal development of cerebellar Purkinje cells: a possible causal factor for developmental brain disorders? Chemosphere 67:S412–S420
Kitamura S, Jinno N, Suzuki T, Sugihara K, Ohta S, Kuroki H, Fujimoto N (2005) Thyroid hormone-like and estrogenic activity of hydroxylated PCBs in cell culture. Toxicology 208:377–387
Niu JF, Long XX, Shi SQ (2007) Quantitative structure-activity relationships for prediction of the toxicity of hydroxylated and quinoid PCB metabolites. J Mol Model 13:163–169
Niu JF, Shen ZY, Yang ZF, Long XX, Yu G (2006) Quantitative structure-property relationships on photodegradation of polybrominated diphenyl ethers. Chemosphere 64:658–665
Pearson PG (1986) Absolute electronegativity and hardness correlated with molecular orbital theory. Proc Natl Acad Sci 83:8440–8441
Pedroza AM, Mosqueda R, Alonso-Vante N, Rodriguez-Vazquez R (2007) Sequential treatment via Trametes versicolor and UV/TiO2/RuxSey to reduce contaminants in waste water resulting from the bleaching process during paper production. Chemosphere 67:793–801
Pozdnyakova NN, Rodakiewicz-Nowak J, Turkovskaya OV, Haber J (2006) Oxidative degradation of polyaromatic hydrocarbons catalyzed by blue laccase from Pleurotus ostreatus D1 in the presence of synthetic mediators. Enzyme Microbiol Technol 39:1242–1249
Schultz A, Jonas U, Hammer E, Schauer F (2001) Dehalogenation of chlorinated hydroxybiphenyls by fungal laccase. Appl Environ Microbiol 67:4377–4381
Shumakovich GP, Shleev SV, Morozova OV, Khohlov PS, Gazaryan IG, Yaropolov AI (2006) Electrochemistry and kinetics of fungal laccase mediators. Bioelectrochemistry 69:16–24
Soffers AEMF, Boersma MG, Vaes WHJ, Vervoort J, Tyrakowska B, Hermens JLM, Rietjens IMCM (2001) Computer-modeling-based QSARs for analyzing experimental data on biotransformation and toxicity. Toxicol Vitro 15:539–551
Veith GD, Mekenyan OG, Ankley GT, Call DJ (1995) A QSAR analysis of substitutent effects on the photoinduced acute toxicity of PAHs. Chemosphere 30:2129–2142
Wold S, Sjöström M, Eriksson L (2001) PLS-regression: a basic tool of chemometrics. Chemomet Intell Lab Syst 58:109–130
Zille A, Munteanu FD, Gubitz G.M, Artur CP (2005) Laccase kinetics of degradation and coupling reactions. J Mol Catal B: Enzym 33:23–28
The research was supported by the National High Technology Research and Development Program of China (863 Project, 2006AA06Z323).
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Jiang, G.X., Niu, J.F., Zhang, S.P. et al. Prediction of Biodegradation Rate Constants of Hydroxylated Polychlorinated Biphenyls by Fungal Laccases from Trametes versicolor and Pleurotus ostreatus . Bull Environ Contam Toxicol 81, 1–6 (2008). https://doi.org/10.1007/s00128-008-9433-6
- Hydroxylated PCBs