Quantitative structure-activity relationship (QSAR). V. Analysis of the toxicity of aliphatic esters by means of molecular compressibility descriptors

Farmacia

Volumn 57, Issue 5, 2009, Pages 549-561

  Vlaia, Vicenţiu ^a   Olariu, Tudor ^a   Vlaia, Lavinia ^a   Butur, Marius ^a   Ciubotariu, Ciprian ^b   Medeleanu, Mihai ^b   Ciubotariu, Dan ^a  

^a University of Medicine and Pharmacy Victor Babe   (France)

^b POLITEHNICA UNIVERSITY OF TIMISOARA   (Romania)

Author keywords

Aliphatic esters; Compressibility molecular descriptors (C iD); Cross validation (CV); QSAR; Tetrahymena pyriformis; Toxicity

Indexed keywords

2 ETHYLBUTYL ACETATE; ALIPHATIC COMPOUND; ALIPHATIC ESTER; AMYL PROPIONATE; BUTYL PROPANOATE; BUTYRIC ACID BUTYL ESTER; BUTYRIC ACID ETHYL ESTER; BUTYRIC ACID PROPYL ESTER; DECANOIC ACID METHYL ESTER; DECYL ACETATE; ESTER; ETHYL VALERATE; HEPTANOIC ACID ALLYL ESTER; HEXANOIC ACID ALLYL ESTER; HEXANOIC ACID ETHYL ESTER; HEXYL ACETATE; ISOPROPENYL ACETATE; METHYL HEPTANOATE; METHYL HEXANOATE; METHYL UNDECANOATE; N HEXYL FORMATE; NONANOIC ACID METHYL ESTER; OCTANOIC ACID METHYL ESTER; OCTYL ACETATE; PENTYL ACETATE; PROPYL VALERATE; TERT BUTYL PROPIONATE; UNCLASSIFIED DRUG; UNINDEXED DRUG; VINYL 2 ETHYLHEXANOATE; VINYL BUTYRATE;

ARTICLE; BOOTSTRAPPING; CHEMICAL STRUCTURE; EXTERNAL VALIDITY; IC 50; NONHUMAN; PARTITION COEFFICIENT; PREDICTION; QUANTITATIVE STRUCTURE ACTIVITY RELATION; STATISTICAL ANALYSIS; TETRAHYMENA PYRIFORMIS; TOXICITY TESTING;

EID: 73349134633     PISSN: 00148237     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (26)

1. Toropov A. A., Rasulev B. F. and Leszczynski J, QSAR modeling of acute toxicity by balance of correlations, Bioorg. Med. Chem. 2008, 16, 5999-6008.
2. Schultz T. W., Cronin M. T. D., Netzeva T. I. and Aptula, A. O., Structure - Toxicity Relationships for Aliphatic Chemicals Evaluated with Tetrahymena pyriformis. Chem. Res. Toxicol. 2002, 15, 1602-1609.
3. Schultz T. W., Cronin M. T. D., Walker J. D., and Aptula A. O., Quantitative structure - activity relationships (QSARs) in toxicology: a historical perspective. J. Mol. Struct. (THEOCHEM) 2003, 622, 1-22.
4. Crisan O., Oprean Luminita, Marchand J., Influence de l'isomerie sur les effets toxiques, Farmacia 2007, LV, 2, 144-156.
5. Cronin M. T. D., Schultz T. W., Pitfalls in QSAR, J. Mol. Struct. (THEOCHEM) 2003, 622, 39-51.
6. Schultz T. W., Cronin M. T. D., Netzeva T. I., The present status of QSAR in toxicology. J. Mol. Struct. (THEOCHEM) 2003, 622, 23-38.
7. f in QSAR: Toxicity of Aliphatic Ethers, J. Chem. Inf. Comput. Sci. 2001, 41, 614-618.
8. Hawkins D. M., Basak S. C., Kraker J., Geiss K. T. and Witzmann F. A., Combining Chemodescriptors and Biodescriptors in Quantitative Structure - Activity Relationship Modeling, J. Chem Inf. Model,. 2006, 46, 9-16.
9. Vlaia V., Olariu T., Ciubotariu C., Medeleanu M., Dragos D., Ursica L., Ciubotariu C., Quantitative Structure-Activity Relationship (QSAR). III. Generalized Topological Descriptors Based on Reciprocal Distance Matrix for development of toxicological QSARs, Farmacia, 2007, LV, 3, 284-296.
10. Toropov A. A. and Schultz T. W., Prediction of Aquatic Toxicity: Use of Optimization of Correlation Weights of Local Graph Invariant. J. Chem. Inf. Comput. Sci., 2003, 43, 560-567.
11. Ciubotariu D., Gogonea V., Medeleanu M., Van der Waals Molecular Descriptors. Minimal Steric Difference, in QSPR/QSAR Studies by Molecular Descriptors, M. V. Diudea (Ed.), Nova Science Publishers, Inc., Huntington, New York, 2001, 281-361.
12. Ciubotariu D., Medeleanu M., Vlaia V., Olariu T., Ciubotariu C., Dragos D. and Seiman C., Molecular van der Waals Space and Topological Indices from The Distance Matrix, Molecules, 2004, 9, 1053-1078.
13. Medeleanu M., Dragos D., Olariu T., Vlaia V., Ciubotariu C., Seiman C., and Ciubotariu D., Molecular Descriptors in QSPR/QSAR Studies. I. Molecular van der Waals Space, Chem. Bull. "Politehnica" Univ. Timisoara, 2004, 49, 8-13.
14. Chiriac A., Ciubotariu D., Timofei-Funar S., Kurunczi L., Mracec M., Szabadai Z., Seclaman E., Simon Z., QSAR and 3D-QSAR in Timisoara. 1972-2005, Rev. Roum. Chim., 2006, 51, 79-99.
15. th International Workshop on Quantitative Structure-Activity Relationships in Environmental Toxicology, 8-12 May 2006, Lyon, France, 90.
16. Ciubotariu D., Structure - Reactivity Relationships in the Series of Carbonic Acid Derivatives, PhD Thesis (in Romanian language), Polytechnic Institute of Bucharest, 1987.
17. Niculescu-Duvaz I., Ciubotariu D., Simon Z. and Voiculetz N., Quantitative Approach to Carcinogenesis Inhibition: a QSAR Analysis, in Modeling of Cancer Genesis and Prevention, N. Voiculetz, A. T. Balaban, I. Niculescu-Duvaz and Z. Simon (Eds.), CRC Press, Boca Raton, 1991, 157-214.
18. http://www.vet.utk.edu/TETRaTOX/
19. Schultz T. W., TETRATOX: The Tetrahymena pyriformis population growth impairment endpoint. A surrogate for fish lethality. Toxicol. Methods, 1997, 7, 289-309.
20. Larsen J., Schultz T. W., Rasmussen L., Hoofman R., Pauli W., Progress in an ecotoxicological standard protocol with protozoa: Results from a pilot ring test with Tetrahymena pyriformis, Chemosphere, 1997, 35, 1023-1041.
21. Ciubotariu C., Medeleanu M., Ciubotariu D., IRS - a Computer Program Package for QSAR and QSPR Studies, Chem. Bull. "Politehnica" Univ. Timisoara, 2006, 51, 13-16.
22. MobyDigs software package
23. Konovalov D. A., Llewellyn L. E., Heyden Y. V. and Coomans D., Robust Cross-Validation of Linear Regression QSAR Models. J. Chem. Inf. Model. 2008, 48, 2081-2094.
24. Tropsha A, Gramatica P., Gombar V. K., The importance of Being Earnest: Validation is the Absolute Essential for Successful Application and Interpretation of QSPR Models, QSAR Comb. Sci. 2003, 22, 69-77.
25. Ciubotariu D., Deretey E., Oprea T. J., Sulea T., Simon Z., Kurunczi L., Chiriac A., Multiconformational Minimal Steric Difference. Structure - Acetylcholinesterase Hydrolysis Rates Relations for Acetic Acid Esters. Quant. Struct.-Act. Relat., 1993, 12, 367-372.
26. Gedeck P., Rohde B., Bartels C. QSAR - How Good Is It in Practice? Comparison of Descriptor Sets on an Unbiased Cross Section of Corporate Data Sets. J. Chem. Inf. Model., 2006, 46, 1924-1936.