Quantitative Structure–Toxicity Relationships Using Tops-Mode. 1. Nitrobenzene Toxicity to Tetrahymena Pyriformis

References

• Lewis , D. F. V. 1992 . “ Computer-assisted methods in the evaluation of chemical toxicity. ” . In Reviews in Computational Chemistry Vol. III. , Edited by: Lipkowitz , K. B. and Boyd , D. B. 173 – 222 . New York : VCH Publishers, Inc. .
   Google Scholar
• Cronin , M. T. D. and Dearden , J. C. 1995 . QSAR in toxicology. 1. Prediction of aquatic toxicity . Quant. Struct.-Act. Relat. , 14 : 1 – 7 .
   Web of Science ®Google Scholar
• Cronin , M. T. D. and Dearden , J. C. 1995 . QSAR in toxicology. 2. Prediction of acute mammalian toxicity and interspecies correlations . Quant. Struct.-Act. Relat. , 14 : 117 – 120 .
   Google Scholar
• Cronin , M. T. D. and Dearden , J. C. 1995 . QSAR in toxicology. 3. Prediction of chronic toxicities . Quant. Struct.-Act. Relat. , 14 : 329 – 334 .
   Google Scholar
• Cronin , M. T. D. and Dearden , J. C. 1995 . QSAR in toxicology. 4. Prediction of nonlethal mammalian toxicological endpoints, and expert systems for toxicity prediction . Quant. Struct.-Act. Relat. , 14 : 518 – 523 .
   Google Scholar
• Dearden , J. C. , Cronin , M. T. D. and Dobbs , A. J. 1995 . Quantitative structure-activity relationships as a tool to assess the comparative toxicity of organic chemicals . Chemosphere , 31 : 2521 – 2528 .
   PubMed Web of Science ®Google Scholar
• Cronin , M. T. D. 1998 . Computer-aided prediction of drug toxicity in high throughput screening . Pharm. Pharmacol. Commun. , 4 : 157 – 163 .
   Google Scholar
• 2000 . The method was originally introduced with the name TOSS-MODE that is now changed to TOPS-MODE: Estrada, E. On the topological sub-structural molecular design (TOSS-MODE) in QSPR/QSAR and drug design research . SAR QSAR Environ. Res. , 11 : 55 – 73 .
   PubMed Web of Science ®Google Scholar
• Estrada , E. 1996 . Spectral moments of the edge adjacency matrix in molecular graphs. 1. Definition and applications to the prediction of physical properties of alkanes . J. Chem. Inf. Comput. Sci. , 36 : 844 – 849 .
   Google Scholar
• Estrada , E. 1997 . Spectral moments of the edge adjacency matrix in molecular graphs. 2. Molecules containing heteroatoms and QSAR applications . J. Chem. Inf. Comput. Sci. , 37 : 320 – 328 .
   Google Scholar
• Estrada , E. 1998 . Spectral moments of the edge adjacency matrix in molecular graphs. 3. Molecules containing cycles . J. Chem. Inf. Comput. Sci. , 38 : 23 – 27 .
   Google Scholar
• Estrada , E. 1998 . Modelling the diamagnetic susceptibilities of organic compounds by a substructural graph theoretical approach . J. Chem. Soc. Faraday Trans. , 94 : 1407 – 1411 .
   Google Scholar
• Estrada , E. and Gutierrez , Y. 1999 . Modeling chromatographic parameters by a novel graph theoretical sub-structural approach . J. Chromatogr. A , 858 : 187 – 199 .
   PubMed Web of Science ®Google Scholar
• Estrada , E. , Peña , A. and García-Domenech , R. 1998 . Designing sedative/hypnotic compounds from a novel substructural graph-theoretical approach . J. Comput.-Aided Mol. Des. , 12 : 583 – 595 .
   PubMed Web of Science ®Google Scholar
• Estrada , E. , Gutiérrez , Y. and González , H. 2000 . Modeling diamagnetic and maenetooptic properties of organic compounds with the TOPS-MODE approach . J. Chem. Inf. Comput. Sci. , 40 : 1386 – 1399 .
   PubMedGoogle Scholar
• Estrada , E. , Uriarte , E. , Montero , A. , Teijeira , M. , Santana , L. and De Clercq , E. 2000 . A novel approach to the rational selection and design of anticancer compounds . J. Med. Chem. , 43 : 1975 – 1985 .
   PubMed Web of Science ®Google Scholar
• Estrada , E. and Peña , A. 2000 . In Silico studies for the rational discovery of anticonvulsant compounds . Bioorg. Med. Chem. , 8 : 2755 – 2770 .
   PubMed Web of Science ®Google Scholar
• Estrada , E. 2000 . Characterization of 3D molecular structure . Chem. Phys. Lett. , 319 : 713 – 718 .
   Web of Science ®Google Scholar
• Estrada , E. 1999 . Generalized spectral moments of the iterated line graphs. A novel approach to QSPR studies . J. Chem. Inf. Comput. Sci. , 39 : 90 – 95 .
   Google Scholar
• Estrada , E. 2000 . A computer-based approach to describe the 13C NMR chemical shifts of alkanes by the generalized spectral moments of iterated line graphs . Com. Chem. , 24 : 193 – 201 .
   Google Scholar
• Estrada , E. 1999 . “ Novel strategies in the search of topological indices. ” . In Topological Indices and Related Descriptors , Edited by: Devillers , dJ. and Balaban , A. T. 403 – 453 . The Netherlands : Gordon and Breach Sci. Pub. .
   Google Scholar
• Roberts , D. W. 1987 . “ An analysis of published data on fish toxicity of nitrobenzenes and aniline derivatives. ” . In QSAR in Environmental Toxicology-II , Edited by: Kaiser , K. L. E. 295 – 308 . Dordrecht, , The Netherlands : D. Reidel .
   Google Scholar
• Dearden , J. C. , Cronin , M. T. D. , Schultz , T. W. and Lin , D. T. 1995 . QSAR study of the toxicity of nitrobenzenes to . Tetrahymena pyriformis. Quant.-Struct.-Act. Relat. , 14 : 427 – 432 .
   Web of Science ®Google Scholar
• Debnath , A. K. , de Compadre , R. L. L. , Debnath , G. , Shusterman , A. J. and Hansch , C. 1991 . Structure-activity relationship of mutagenic aromatic and heteroaromatic nitro compounds. Correlation with molecular orbital energies and hydrophobicity . J. Med. Chem. , 34 : 786 – 797 .
   PubMed Web of Science ®Google Scholar
• Roberts , D. W. 1995 . Linear free energy relationships for reactions of electrophilic halo- and pseudohalobenzenes, and their application in prediction of skin sensitization potential for SNAr electrophiles . Chem. Res. Toxicol. , 8 : 545 – 551 .
   PubMed Web of Science ®Google Scholar
• Mekenyan , O. , Roberts , D. W. and Karcher , W. 1997 . Molecular orbital parameters as predictors of skin sensitization potential of halo- and pseudohalobenzenes acting as SNAr electrophiles . Chem. Res. Toxicol. , 10 : 994 – 1000 .
   PubMed Web of Science ®Google Scholar
• Devillers , J. 2000 . New trends in (Q)SAR modeling with topological indices . Curr. Op. Drug. Discovery Dev. , 3 : 275 – 279 .
   PubMedGoogle Scholar
• Cronin , M. T. D. , Gregory , B. W. and Schultz , T. W. 1998 . Quantitative structure-activity analyses of nitrobenzene toxicity to . Tetrahymena pyriformis. Chem. Res. Toxicol. , 11 : 902 – 908 .
   PubMed Web of Science ®Google Scholar
• Ivanciuc , O. , Ivanciuc , T. and Balaban , A. T. “ Vertex- and edge-weighted molecular graphs and derived structural descriptors. ” . In Topological Indices and Related Descriptors , Edited by: Devillers , J. and Balaban , A. T. 169 – 220 . The Netherlands : Gordon and Breach Sci. Pub. .
   Google Scholar
• Hall , L. H. , Kier , L. B. and Phipps , G. 1984 . Structure-activity relationship studies on the toxicities of benzene derivatives: I. An additive model . Environ. Toxicol. Chem. , 3 : 355 – 365 .
   Google Scholar
• Hall , L. H. , Kier , L. B. and Phipps , G. 1984 . Structure-activity relationship studies on the toxicities of benzene derivatives: II. An analysis of benzene substituent effects on toxicity . Environ. Toxicol. Chem. , 5 : 333 – 337 .
   Google Scholar
• Hall , L. H. , Maynard , E. L. and Kier , L. B. 1989 . Structure-activity relationship studies on the toxicities of benzene derivatives: III. Predictions and extension to new substituents . Environ. Toxicol. Chem. , 8 : 431 – 436 .
   Web of Science ®Google Scholar
• Yang , G. , Lien , E. J. and Guo , Z. 1986 . Physical factors contributing to hydrophobic constant . Quant. Struct.-Act. Relat. , 5 : 12 – 18 .
   Google Scholar
• Gutierrez , Y. and Estrada , E. 1997 . “ TOPS-MODE (Topological sub-structural molecular design) for Windows version 4.0. ” . Spain. : Universidad de Santiago de Compostela .
   Google Scholar
• Mannhold , R. and Rekker , R. F. 2000 . The hydrophobic fragmental constant approach for calculating log P in octanol/water and aliphatic hydrocarbon water systems . Persp. Drug Discov. Des. , 18 : 1 – 18 .
   Web of Science ®Google Scholar
• Hansch , C. 1969 . A quantitative approach to biochemical structure-activity relationships . Acc. Chem. Res. , 2 : 232 – 239 .
   Web of Science ®Google Scholar
• Craig , P. N. 1990 . “ Comprehensive Medicinal Chemistry. The Rational Design, Mechanistic Study and Therapeutic Application of Chemical Compounds. Quantitative Drug Design ” . In Substructural analysis and compound selection. , Edited by: Hansch , C. , Sammes , P. G. and Taylor , J. B. Vol. 4 , 645 – 666 . Oxford : Pergamon Press .
   Google Scholar