QSAR modelling of water quality indices of alkylphenol pollutants

The aim of this study was to determine the degradability of 26 Alkylphenols (APs) by Chemical Oxygen Demand (COD) and/or 5-day Biochemical Oxygen Demand (BOD5), and to describe these data from Quantitative Structure-activity Relationships (QSARs). Statistical analysis techniques, such as Multiple Linear Regression (MLR), Principal Component Regression (PCR), Partial Least-Squares (PLS) Regression and Neural Network (NN) were carried out to calibrate and validate four-descriptor QSAR models using two different types of descriptor sets. Stable MLR-QSAR models using Leave-One-Out (LOO) were obtained with high predictability performance: r 2 = 0.924,  = 0.854 for log (1/BOD) model on 24 APs and r 2 = 0.888,  = 0.818 for log (1/COD) on all the studied APs. The MLR models, built with four Dragon descriptors selected by Genetic Algorithm (GA), presented the following performances on 24 APs: r 2 = 0.889,  = 0.848 for log (1/BOD5) and r 2 = 0.885,  = 0.834 for log (1/COD) on 26 compounds. From these results, it is expected that the QSAR models generated could be successfully expanded to predict the biological and chemical activities of structurally diverse AP compounds.

[1]  Franklin W. Schwartz,et al.  Kinetics and Mechanisms for TCE Oxidation by Permanganate , 2000 .

[2]  S. Eykyn.  Microbiology , 1950, The Lancet.

[3]  Gerrit Schüürmann,et al.  Quantitative structure-activity relationships in environmental sciences, VII , 1997 .

[4]  Michael C. Hutter,et al.  Prediction of blood–brain barrier permeation using quantum chemically derived information , 2003, J. Comput. Aided Mol. Des..

[5]  Anita C Jones,et al.  The nature of conformational preference in a number of p-alkyl phenols and p-alkyl benzenes , 2002 .

[6]  H. Destaillats,et al.  Degradation of Alkylphenol Ethoxylate Surfactants in Water with Ultrasonic Irradiation , 2000 .

[7]  W. Giger,et al.  Aqueous solubility of alkylphenols and alkylphenol polyethoxylates , 1993 .

[8]  W. E. Gledhill,et al.  Ultimate biodegradation of alkylphenol ethoxylate surfactants and their biodegradation intermediates , 2001, Environmental toxicology and chemistry.

[9]  Dragan Gamberger,et al.  Evaluation of artificial intelligence based models for chemical biodegradability prediction. , 2004, Molecules.

[10]  Awwa,et al.  Standard Methods for the examination of water and wastewater , 1999 .

[11]  T. Dutta.  Origin, occurrence, and biodegradation of long-side-chain alkyl compounds in the environment: a review , 2005, Environmental geochemistry and health.

[12]  Stephen R. Johnson,et al.  Molecular properties that influence the oral bioavailability of drug candidates. , 2002, Journal of medicinal chemistry.

[13]  N. Sinha,et al.  Differences in electrostatic properties at antibody-antigen binding sites: implications for specificity and cross-reactivity. , 2002, Biophysical journal.

[14]  Gerald J. Niemi,et al.  Structural features associated with degradable and persistent chemicals , 1987 .

[15]  M. Reinhard,et al.  Occurrence and Behavior of Alkylphenol Polyethoxylates in the Environment , 2003 .

[16]  Remo Guidieri.  Res , 1995, RES: Anthropology and Aesthetics.

[17]  Chao Wang,et al.  Quantitative structure‐biodegradation relationship study for biodegradation rates of substituted benzenes by river bacteria , 2003, Environmental toxicology and chemistry.

[18]  David J. Hopper,et al.  Alkylphenol Biotransformations Catalyzed by 4-Ethylphenol Methylenehydroxylase , 2003, Applied and Environmental Microbiology.

[19]  Andrew G. Glen,et al.  APPL , 2001 .

[20]  Jiří Damborský,et al.  A Mechanistic Approach to Deriving Quantitative Structure Biodegradablity Relationships , 1996 .

[21]  G. Mortensen,et al.  Degradation and mobility of linear alkylbenzene sulfonate and nonylphenol in sludge-amended soil. , 2004, Journal of environmental quality.

[22]  B. Mattiasson,et al.  Aerobic biodegradation of nonylphenol by cold-adapted bacteria , 2003, Biotechnology Letters.

[23]  Robert S Boethling,et al.  Recent developments in broadly applicable structure‐biodegradability relationships , 2003, Environmental toxicology and chemistry.

[24]  Paul G Tratnyek,et al.  Kinetics of contaminant degradation by permanganate. , 2006, Environmental science & technology.

[25]  Bindu Ajithkumar,et al.  Degradation of 4-amylphenol and 4-hexylphenol by a new activated sludge isolate of Pseudomonas veronii and proposal for a new subspecies status. , 2003, Research in microbiology.

[26]  D. Schlosser,et al.  Microbial degradation of nonylphenol and other alkylphenols—our evolving view , 2006, Applied Microbiology and Biotechnology.

[27]  M. Reinhard,et al.  Occurrence and fate of pharmaceuticals and alkylphenol ethoxylate metabolites in an effluent‐dominated river and wetland , 2004, Environmental toxicology and chemistry.

[28]  D. Schlosser,et al.  Degradation of the xenoestrogen nonylphenol by aquatic fungi and their laccases. , 2005, Microbiology.

[29]  Gilles Klopman,et al.  Structure–biodegradability study and computer‐automated prediction of aerobic biodegradation of chemicals , 1997 .

[30]  W. Giger,et al.  Photochemical degradation of nonylphenol and nonylphenol polyethoxylates in natural waters , 1994 .

[31]  G. G. Stokes.  "J." , 1890, The New Yale Book of Quotations.

[32]  Paola Gramatica,et al.  The Importance of Being Earnest: Validation is the Absolute Essential for Successful Application and Interpretation of QSPR Models , 2003 .

[33]  Anniek G. van Haelst,et al.  Priority setting for existing chemicals: Automated data selection routine , 2000 .

[34]  Y. H. Zhao,et al.  Quantitative Structure–Biodegradability Relationships of Substituted Benzenes and Their Biodegradability in River Water , 2002, Bulletin of environmental contamination and toxicology.

[35]  L. Kier.  Shape Indexes of Orders One and Three from Molecular Graphs , 1986 .

[36]  James R. Mihelcic,et al.  Relationship between chemical and theoretical oxygen demand for specific classes of organic chemicals , 1999 .

[37]  Riccardo Leardi,et al.  Nature-Inspired Methods in Chemometrics: Genetic Algorithms and Artificial Neural Networks , 2005 .

[38]  G. Pojana,et al.  Aerobic biodegradation of monobranched aliphatic alcohol polyethoxylates , 2000 .

[39]  T. N. Rogers,et al.  A review of structure-based biodegradation estimation methods. , 2001, Journal of hazardous materials.

[40]  Paul G Tratnyek,et al.  Quantitative structure‐activity relationships for oxidation reactions of organic chemicals in water , 2003, Environmental toxicology and chemistry.

[41]  T W Schultz,et al.  Comparison of the QSAR models for toxicity and biodegradability of anilines and phenols. , 1997, Chemosphere.

[42]  E. Topp,et al.  Rapid mineralization of the endocrine‐disrupting chemical 4‐nonylphenol in soil , 2000 .

[43]  J. Williams,et al.  Measuring the biodegradability of nonylphenol ether carboxylates, octylphenol ether carboxylates, and nonylphenol. , 1999, Chemosphere.

[44]  Ingyu Hwang,et al.  3- and 4-alkylphenol degradation pathway in Pseudomonas sp. strain KL28: genetic organization of the lap gene cluster and substrate specificities of phenol hydroxylase and catechol 2,3-dioxygenase. , 2003, Microbiology.

[45]  Rafael Najmanovich,et al.  Side‐chain flexibility in proteins upon ligand binding , 2000, Proteins.

[46]  M. Agnolucci,et al.  Biodegradation of 4-(1-nonyl)phenol by axenic cultures of the yeast Candida aquaetextoris: identification of microbial breakdown products and proposal of a possible metabolic pathway , 2001 .

[47]  S Vajda,et al.  Empirical potentials and functions for protein folding and binding. , 1997, Current opinion in structural biology.

[48]  Robert Boethling,et al.  Estimating biodegradation half-lives for use in chemical screening. , 2006, Chemosphere.

[49]  Roberto Todeschini,et al.  Handbook of Molecular Descriptors , 2002 .

[50]  K. Houk,et al.  Mechanism of Permanganate Oxidation of Alkanes: Hydrogen Abstraction and Oxygen “Rebound” , 2000 .

[51]  C. Staples,et al.  Biodegradation of [14C] Ring-Labeled Nonylphenol Ethoxylate , 2006, Archives of environmental contamination and toxicology.

[52]  Robert M. Nicholson,et al.  The prediction of biodegradability by the use of quantitative structure–activity relationships: Correlation of biological oxygen demand with atomic charge difference† , 1986 .

[53]  D. Vaishnav,et al.  Comparison of occurrence and rates of chemical biodegradation in natural waters , 1987, Bulletin of environmental contamination and toxicology.

[54]  A. E. Greenberg,et al.  Standard methods for the examination of water and wastewater : supplement to the sixteenth edition , 1988 .