An improved QSPR study of the toxicity of aliphatic carboxylic acids using genetic algorithm

Medicinal Chemistry Research

Volumn 18, Issue 2, 2009, Pages 143-157

  Kompany Zareh, M ^a,b,c  

^a INSTITUTE FOR ADVANCED STUDIES IN BASIC SCIENCES IASBS   (Iran)

^b SHIRAZ UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^c UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

Aliphatic carboxylic acids; Genetic algorithm; QSTR; Toxicity

Indexed keywords

ALIPHATIC CARBOXYLIC ACID;

ARTICLE; DISSOCIATION CONSTANT; GENETIC ALGORITHM; LIPOPHILICITY; MOLECULAR MODEL; NONHUMAN; PARTIAL LEAST SQUARES REGRESSION; QUANTITATIVE STRUCTURE ACTIVITY RELATION; QUANTITATIVE STRUCTURE PROPERTY RELATION; RELIABILITY; STATISTICAL MODEL; SURFACE TENSION; TETRAHYMENA; TOXICITY TESTING;

EID: 58849088896     PISSN: 10542523     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00044-008-9114-3     Document Type: Article

References (28)

1. ACD/ILAB software http://www.acdIlabs.com, Advanced Chemistry Development, 2001
2. S Agatanovic-Kustrin IG Tucker M Zecevic LJ Zivanovic 2000 Prediction of drug transfer into human milk from theoretically derived descriptors Anal Chim Acta 418 181 195 10.1016/S0003-2670(00)00963-6
3. RF Cookson 1974 Determination of acidity constants Chem Rev 74 5 28 10.1021/cr60287a002
4. Devillers J, Balaban AT (1999) Topological indices and related descriptors in QSAR and QSPR. Gordon and Breach Science, The Netherlands
5. E-Cal Version 1.1- Sci Vision and Lowell H. Hall. Sci Vision, Inc., Burlington, MA, 1999
6. AK Ghose GM Crippen 1987 Atomic physicochemical parameters for three-dimensional-structure-directed quantitative structure-activity relationships. 2. Modeling dispersive and hydrophobic interactions J Chem Inf Comput Sci 27 21 35 10.1021/ci00053a005
7. AK Ghose P Pritchett G Crippen 1988 Atomic physicochemical parameters for three-dimensional structure-directed quantitative structure-activity relationships J Comput Chem 9 80 90 10.1002/jcc.540090111
8. Hall LH, Kier LB (1991) The molecular connectivity chi indexes and kappa shape indexes in structure-property modeling. In: Lipkowitz KB, Boyd DB (eds) Rev in Comp Chem, vol 2. VCH, New York, pp 367-422
9. Hansch C, Leo A (1995) Exploring QSAR. Fundamentals and applications in chemistry and biology. ACS Professional Reference Book, American Chemical Society, Washington DC
10. T Hou X Xu 2001 Three-dimensional quantitative structure-activity relationship analyses of a series of cinnamamides Chemom Intell Lab Syst 56 123 132 10.1016/S0169-7439(01)00116-2
11. M Karelson VS Lobanov AR Katritzky 1996 Quantum-chemical descriptors in QSAR/QSPR studies Chem Rev 96 1027 1043 10.1021/cr950202r
12. Kier LB, Hall LH (1999) Molecular structure description. The Electrotopological State, Academic, San Diego, CA
13. H Könemann A Musch 1981 Quantitative structure-activity relationships in fish toxicity studies. Part 2: the influence of pH on the QSAR of chlorophenols Toxicology 19 223 228 10.1016/0300-483X(81)90131-1
14. R Leardi R Boggia M Terrile 1992 Genetic algorithms as a strategy for feature selection J Chemometr 6 267 281 10.1002/cem.1180060506
15. R Leardi 1994 Application of a genetic algorithm to feature selection under full validation conditions and to outlier detection J Chemometr 8 65 79 10.1002/cem.1180080107
16. R Leardi MB Seasholtz RJ Pell 2002 Variable selection for multivariate calibration using a genetic algorithm: prediction of additive concentrations in polymer films from Fourier transform-infrared spectral data Anal Chim Acta 461 189 200 10.1016/S0003-2670(02)00272-6
17. Maguna FP Núňez MB, Okulik NB, Castro EA (2000) http://www.preprint.chemweb.com/physchem/0205006
18. March J (1992) Advanced organic chemistry-reactions, mechanisms and structure. 4th edn. Wiley-Interscience, New York, Chapter 8
19. Massart DL, Vandeginste BGM, Buydens LMC, De Jong S, Lewi PJ, Smeyers-Verbeke J (1997) Handbook of chemometrics and qualimetrics: Part A, Elsevier, Amsterdam, p 280. MATLAB version 6.5, The Math Works, Natick, MA, 2002
20. KJ Miller 1990 Additivity methods in molecular polarizability J Am Chem Soc 112 8533 8542 10.1021/ja00179a044
21. Randic M, Basak SC (2000) Variable molecular descriptors. In: Sinha DK, Basak SC, Mohany RK, Busa Mallic JN (eds) Some aspects of mathematical chemistry. Visva-Bharati University Press, Santiniketan, India, p 24
22. D Roger AJ Hopfinger 1994 Application of genetic function approximation to quantitative structure-activity relationships and quantitative structure-property relationships J Chem Inf Comput Sci 34 854 866 10.1021/ci00020a020
23. Russom CL, Bradbury SP, Broderius SJ (1997) Predicting modes of toxic action from chemical structure: acute toxicity in the fathead minnow (Pimephales promelas). Environ Toxicol Chem 16:948-967. doi:10.1897/1551-5028(1997) 016<0948:PMOTAF>2.3.CO;2
24. TW Schultz 1997 TETRATOX: Tetrahymena pyriformis population growth impairment endpoint-A surrogate for fish lethality Toxicol Method 7 289 309 10.1080/105172397243079
25. JR Seward TW Schultz 1999 QSAR analyses of the toxicity of aliphatic carboxylic acids and salts to Tetrahymena pyriformis SAR QSAR Environ Res 10 557 567 10.1080/10629369908033224
26. BM Smith PJ Gemperline 2000 Wavelength selection and optimization of pattern recognition methods using the genetic algorithm Anal Chim Acta 423 167 177 10.1016/S0003-2670(00)01114-4
27. VN Visvanadhan AK Ghose G Revankar RK Robins 1989 Atomic physicochemical parameters for three dimensional structure directed quantitative structure-activity relationships. 4. Additional parameters for hydrophobic and dispersive interactions and their application for an automated superposition of certain naturally occurring nucleoside antibiotics J Chem Inf Comput Sci 29 163 172 10.1021/ci00063a006
28. Wise BM, Gallagher NB (1995) PLS-Toolbox, ver. 2.0, Eigenvector Research, Inc., Natick, MA