183
Views
44
CrossRef citations to date
0
Altmetric
Original Articles

Predicting Acute Toxicity (LC50) of Benzene Derivatives Using Theoretical Molecular Descriptors: A Hierarchical QSAR Approach

&
Pages 117-131 | Received 03 Mar 1997, Accepted 10 Jun 1997, Published online: 05 Oct 2006

References

  • 1997 . Personal communication with W. Fisanick . : 20
  • Menzel , D. B. 1995 . Extrapolating the future; research trends in modeling. Toxicol. Lett. , 79 : 299 – 303g .
  • Hansch , C. and Leo , A. 1995 . Exploring QSAR; Fundamental and Applications in Chemistry and Biology. , 557 Washington, D.C. : American Chemical Society .
  • Dearden , J. C. 1990 . “ Practical Applications of Quantitative Structure-Activity Relationships (QSAR) in Environmental Chemistry and Toxicology ” . In Physico-chemical descriptors. , Edited by: Karcher , W. and Devillers , J. 25 – 59 . Dordrecht : Kluwer Academic Publishers .
  • Lipnick , R. L. 1990 . “ Practical Applications of Quantitative Structure-Activity Relationships (QSAR) in Environmental Chemistry and Toxicology ” . In Narcosis: Fundamental and baseline toxicity mechanism for nonelectrolyte organic chemicals. , Edited by: Karcher , W. and Devillers , J. 281 – 293 . Dordrecht : Kluwer Academic Publishers .
  • Van de Waterbeemd , H. 1995 . “ Discriminant analysis for activity prediction. ” . In Chemometric Methods in Molecular Design , Edited by: Van de Waterbeemd , H. 283 – 294 . New York : VCH Publishers, Inc. .
  • Kamlet , M. J. , Abboud , J.-L. M. and Taft , R. W. 1977 . Solvatochromic comparison method 6. π∗ scale of solvent polarities. . J. Am. Chem. Soc. , 99 : 6027 – 6038 .
  • Kamlet , M. J. , Abboud , J.-L. M. , Abraham , M. H. and Taft , R. W. 1983 . Linear solvation energy relationships. 23. A comprehensive collection of the solvatochromic parameters, π∗ α, and β, and some methods for simplifying the generalized solvatochromic equation. . J. Org. Chem. , 48 : 2877 – 2887 .
  • Hansch , C. 1976 . On the structure of medicinal chemistry. . J. Med. Chem. , 19 : 1 – 6 .
  • Randic , M. 1980 . A graph theoretical approach to structure-property and structureactivity correlations. . Theoret. Chim. Acta (Berl.) , 58 : 45 – 68 .
  • Randic , M. 1984 . Nonempirical approach to structure-activity studies. . Int. J. Quant. Chem. , 11 : 137 – 153 .
  • Randic , M. 1995 . Molecular topographic indices. . J. Chem. Inf. Comput. Sci. , 35 : 140 – 147 .
  • Sabljic , A. and Trinajstic , N. 1981 . Quantitative structure-activity relationships: the role of topological indices. . Acta Pharm. Jugosl. , 31 : 189 – 214 .
  • Basak , S. C. 1987 . Use of molecular complexity indices in predictive pharmacology and toxicology: a QSAR approach. . Med. Sci. Res. , 15 : 605 – 609 .
  • Balaban , A. T. , Bertelsen , S. and Basak , S. C. 1994 . New centric topological indexes for acyclic molecules (trees) and substituents (rooted trees), and coding of rooted trees. . MATCH , 30 : 55 – 72 .
  • Basak , S. C. and Grunwald , G. D. 1995 . Estimation of lipophilicity from molecular structural similarity. . New J. Chem. , 19 : 231 – 237 .
  • Diudea , M. V. , Horvath , D. and Graovac , A. 1995 . Molecular topology. 15. 3D distance matrices and related topological indices. . J. Chem. Inf. Comput. Sci. , 35 : 129 – 135 .
  • Estrada , E. 1995 . Three-dimensional molecular descriptors based on electron charge density; weighted graphs. . J. Chem. Inf. Comput. Sci. , 35 : 708 – 713 .
  • Voelkel , A. 1994 . Structural descriptors in organic chemistry – new topological parameter based on electrotopological state of graph vertices. . Computers Chem. , 18 : 1 – 4 .
  • Basak , S. C. , Gute , B. D. and Grunwald , G. D. 1996 . Estimation of normal boiling points of haloalkanes using molecular similarity. . Croat. Chem. Acta , 69 : 1159 – 1173 .
  • Basak , S. C. , Gute , B. D. and Drewes , L. R. 1996 . Predicting blood-brain transport of drugs: a computational approach. . Pharm. Res. , 13 : 775 – 778 .
  • Basak , S. C. , Gute , B. D. and Grunwald , G. D. 1997 . Development and application of molecular similarity methods: using nonempirical parameters. . Mathl. Model. And Sci. Comput. , in press.
  • Basak , S. C. and Gute , B. D. 1997 . Use of graph-theoretic parameters in predicting inhibition of microsomal p-hydroxylation of aniline by alcohols: a molecular similarity approach. Proceedings of the 2nd international Congress on Hazardous Waste: Impact on Human and Ecological Health . 1997 . Edited by: Johnson , B. L. , Xintaras , C. and Andrews , J. S. Jr. pp. 492 – 504 . New Jersey : Princeton Scientific Publishing Co., Inc. .
  • Basak , S. C. , Gute , B. D. and Ghatak , S. 1997 . Prediction of complement-inhibitory activity of benzamidines using topological and geometric parameters. . J. Chem. Inf. Comput. Sci. , submitted.
  • Famini , G. R. , Penski , C. A. and Wilson , L. Y. 1992 . Using theoretical descriptors in quantitative structure activity relationships: some physicochemical properties. . J. Phys. Org. Chem. , 5 : 395 – 408 .
  • Cramer , C. J. , Famini , G. R. and Lowrey , A. H. 1993 . Use of calculated quantum chemical properties as surrogates for solvatochromic parameters in structure-activity relationships. . Acc. Chem. Res. , 26 : 599 – 605 .
  • Famini , G. R. , Wilson , L. Y. and DeVito , S. C. 1994 . “ Modeling cytochrome P-450 mediated acute nitrile toxicity using theoretical linear solvation energy relationships. ” . In Biomarkers of Human Exposures to Pesticides , Edited by: Saleh , M. A. , Blancato , J. N. and Nauman , C. H. 22 – 36 . American Chemical Society .
  • Basak , S. C. , Gute , B. D. and Grunwald , G. D. 1996 . A comparative study of topological and geometrical parameters in estimating normal boiling point and octanol/water partition coefficient. . J. Chem. Inf. Comput. Sci. , 36 : 1054 – 1060 .
  • Basak , S. C. , Gute , B. D. and Grunwald , G. D. 1997 . Use of topostructural, topochemical, and geometric parameters in the prediction of vapor pressure: a hierarchical QSAR approach. . J. Chem. Inf. Comput. Sci. , 37 : 651 – 655 .
  • Basak , S. C. , Gute , B. D. and Grunwald , G. D. 1997 . “ The relative effectiveness of topological, geometrical, and quantum chemical parameters in estimating mutagenicity of chemicals. ” . In Quantitative Structure-Activity Relationships in Environmental Sciences , Edited by: Chen , F. and Schüürman , G. SETAC Press . in press
  • Basak , S. C. , Gute , B. D. and Grunwald , G. D. 1997 . Development of a quantitative structure-activity relationship (QSAR) for estimating bioconcentration factor . Pimephales promelas: , a hierarchical approach. In progress
  • Hall , L. H. , Kier , L. B. and Phipps , G. 1984 . Structure-activity relationship studies on the toxicities of benzene derivatives: I. An additivity model. . Environ. Toxicol. Chem. , 3 : 355 – 365 .
  • Basak , S. C. , Harriss , D. K. and Magnuson , V. R. 1988 . POLLY 2.3: Copyright of the University of Minnesota. .
  • Wiener , H. 1947 . Structural determination of paraffin boiling points. . J. Am. Chem. Soc. , 69 : 17 – 20 .
  • Randic , M. 1975 . On characterization of molecular branching. . J. Am. Chem. Soc. , 97 : 6609 – 6615 .
  • Kier , L. B. and Hall , L. H. 1986 . Molecular Connectivity in Structure-Activity Analysis. , Letchworth, Hertfordshire, , UK : Research Studies Press .
  • Basak , S. C. and Magnuson , V. R. 1988 . Determining structural similarity of chemicals using graph-theoretic indices. . Discrete Appl. Math. , 19 : 17 – 44 .
  • Raychaudhury , C. , Ray , S. K. , Ghosh , J. J. , Roy , A. B. and Basak , S. C. 1984 . Discrimination of isomeric structures using information theoretic topological indices. . J. Comput. Chem. , 5 : 581 – 588 .
  • Bonchev , D. and Trinajstic , N. 1977 . Information theory, distance matrix and molecular branching. . J. Chem. Phys. , 67 : 4517 – 4533 .
  • Basak , S. C. , Roy , A. B. and Ghosh , J. J. 1980 . Study of the structure-function relationship of pharmacological and toxicological agents using information theory. Proceedings of the Second International Conference on Mathematical Modelling . 1980 . Edited by: Avula , X. J. R. , Bellman , R. , Luke , Y. L. and Rigler , A. K. pp. 851 – 856 . Rolla : University of Missouri .
  • Roy , A. B. , Basak , S. C. , Harriss , D. K. and Magnuson , V. R. 1984 . “ Neighborhood complexities and symmetry of chemical graphs and their biological applications. ” . In Mathematical Modelling in Science and Technology , Edited by: Avula , X. J. R. , Kalman , R. E. , Lapis , A. I. and Rodin , E. Y. 745 – 750 . New York : Pergamon Press .
  • Balaban , A. T. 1982 . Highly discriminating distance-based topological index. . Chem. Phys. Lett. , 89 : 399 – 404 .
  • Balaban , A. T. 1983 . Topological indices based on topological distances in molecular graphs. . Pure and Appl. Chem. , 55 : 199 – 206 .
  • Balaban , A. T. 1986 . Chemical graphs. Part 48. Topological index J for heteroatom-containing molecules taking into accout periodicities of element properties. . Math. Chem. (MATCH) , 21 : 115 – 122 .
  • Bondi , A. 1964 . Van der Waals volumes and radii. . J. Phys. Chem. , 68 : 441 – 451 .
  • Moriguchi , I. and Kanada , Y. 1977 . Use of van der Waals volume in structure-activity studies. . Chem. Pharm. Bull. , 25 : 926 – 935 .
  • Moriguchi , I. , Kanada , Y. and Komatsu , K. 1976 . Van der Waals volume and the related parameters for hydrophobicity in structure-activity studies. . Chem. Pharm. Bull. , 24 : 1799 – 1806 .
  • 1994 . St. Louis, MO : Tripos Associates, Inc . SYBYL Version 6.1.
  • Mekenyan , O. , Peitchev , D. , Bonchev , D. , Trinajstic , N. and Bangov , I. 1986 . Modelling the interaction of small organic molecules with biomacromolecules. I. Interaction of substituted pyridines with anti-3-azopyridine antibody. . Arzneim.-Forsch./Drug Research , 36 : 176 – 183 .
  • 1993 . St. Louis, MO : Tripos Associates, Inc. . CONCORD Version 3.0.1.
  • Stewart , J. J. P. 1990 . MOPAC Version 6.00. QCPE # 455. Frank J Seiler Research Laboratory: US Air Force Academy, CO. .
  • 1998 . Cary, NC : SAS Institute Inc., SAS/STAT User's Guide, Release 6.03 Edition, SAS Institute Inc. .
  • Topliss , J. G. and Edwards , R. P. 1979 . Chance factors in studies of quantitative structure-activity relationships. . J. Med. Chem. , 22 : 1238 – 1244 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.