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Original Articles

Prediction of tissue-air partition coefficients: A comparison of structure-based and property-based methods

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Pages 649-665 | Published online: 29 Oct 2010

References

  • Gargas , M.L. , Burgess , R.J. , Voisard , D.E. , Cason , G.H. and Andersen , M.E. 1989 . “Partition coefficients of low molecular weight volatile chemicals in various tissues and liquids” . Toxicol. Appl. Pharmacol. , 98 : 87 – 99 .
  • USEPA . 2002 . “ What is the TSCA Chemical Substance Inventory? ” . http://www.epa.gov/opptintr/newchems/invntory.htm
  • USEPA . 2002 . “ ChemRTK HPV Challenge Program Chemical List ” . http://www.epa.gov/opptintr/chemrtk/hpvchmlt.htm
  • ATSDR . 2002 . “ 2001 CERCLA Priority List of Hazardous Substances ” . http://www.atsdr.cdc.gov/clist.html
  • Basak , S.C. , Hawkins , D.M. and Mills , D. 2002 . “Predicting blood:air partition coefficient of structurally diverse chemicals using theoretical molecular descriptors” . In Advances in Molecular Similarity , Edited by: Girones , X. , Carbo-Dorca , R. and Mezey , P.G. Dordrecht : Kluwer Academic Publishers . (in press)
  • Basak , S.C. , Harriss , D.K. and Magnuson , V.R. 1984 . “Comparative study of lipophilicity versus topological molecular descriptors in biological correlations” . J. Pharm. Sci. , 73 : 429 – 437 .
  • Basak , S.C. and Grunwald , G.D. 1995 . “Estimation of lipophilicity from molecular structural similarity” . N. J. Chem. , 19 : 231 – 237 .
  • Basak , S.C. , Monsrud , L.J. , Rosen , M.E. , Frane , C.M. and Magnuson , V.R. 1986 . “A comparative study of lipophilicity and topological indices in biological correlation” . Acta Pharm. Yugosl. , 36 : 81 – 95 .
  • Niemi , G.J. , Basak , S.C. , Veith , G.D. and Grunwald , G. 1992 . “Prediction of octanol-water partition coefficient (K ow) using algorithmically-derived variables” . Environ. Toxicol. Chem. , 11 : 891 – 898 .
  • 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 approach” . J. Chem. Inf. Comput. Sci. , 37 : 651 – 655 .
  • Basak , S.C. and Mills , D. 2001 . “Quantitative structure-property relationships (QSPRs) for the estimation of vapor pressure: a hierarchical approach using mathematical structural descriptors” . J. Chem. Inf. Comput. Sci. , 41 : 692 – 701 .
  • 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. and Mills , D. 2001 . “Use of mathematical structural invariants in the development of QSPR models” . MATCH (Commun. Math. Comput. Chem.) , 44 : 15 – 30 .
  • Basak , S.C. , Gute , B.D. and Grunwald , G.D. 1999 . “Assessment of the mutagenicity of aromatic amines from theoretical structural parameters: a hierarchical approach” . SAR QSAR Environ. Res. , 10 : 117 – 129 .
  • Basak , S.C. , Mills , D.R. , Balaban , A.T. and Gute , B.D. 2001 . “Prediction of mutagenicity of aromatic and heteroaromatic amines from structure: a hierarchical QSAR approach” . J. Chem. Inf. Comput. Sci. , 41 : 671 – 678 .
  • Basak , S.C. and Mills , D. 2001 . “Prediction of mutagenicity utilizing a hierarchical QSAR approach” . SAR QSAR Environ. Res. , 12 : 481 – 496 .
  • Basak , S.C. , Mills , D. , Gute , B.D. and Hawkins , D.M. 2002 . “Predicting mutagenicity of congeneric and diverse sets of chemicals using computed molecular descriptors: a hierarchical approach” . In Quantitative Structure-Activity Relationship (QSAR) Models of Mutagens and Carcinogens , Edited by: Benigni , R. Boca Raton , FL : CRC Press . (in press)
  • Basak , S.C. , Grunwald , G.D. , Host , G.E. , Niemi , G.J. and Bradbury , S.P. 1998 . “A comparative study of molecular similarity, statistical, and neural network methods for predicting toxic modes of action of chemicals” . Environ. Toxicol. Chem. , 17 : 1056 – 1064 .
  • Sato , A. and Nakajima , T. 1979 . “Partition coefficients of some aromatic hydrocarbons and ketones in water, blood and oil” . Br. J. Ind. Med. , 36 : 231 – 234 .
  • Fiserova-Bergerova , V. , Tichy , M. and DiCarlo , F.J. 1984 . “Effects of biosolubility on pulmonary uptake and disposition of gases and vapors for lipophilic chemicals” . Drug Metab. Rev. , 15 : 1033 – 1070 .
  • Basak , S.C. , Harriss , D.K. and Magnuson , V.R. 1988 . POLLY, Version 2.3 , University of Minnesota . Copyright of the
  • Filip , P.A. , Balaban , T.S. and Balaban , A.T. 1987 . “A new approach for devising local graph invariants: derived topological indices with low degeneracy and good correlational ability” . J. Math. Chem. , 1 : 61 – 83 .
  • Basak , S.C. , Balaban , A.T. , Grunwald , G.D. and Gute , B.D. 2000 . “Topological indices: their nature and mutual relatedness” . J. Chem. Inf. Comput. Sci. , 40 : 891 – 898 .
  • 2000 . Hall Associates Consulting, Molconn-Z Version 3.50 Quincy , MA
  • Kier , L.B. and Hall , L.H. 1986 . Molecular Connectivity in Structure-Activity Analysis , Letchworth, Hertfordshire , , UK : Research Studies Press .
  • Kier , L.B. , Murray , W.J. , Randic , M. and Hall , L.H. 1976 . “Molecular connectivity. V. Connectivity series concept applied to diversity” . J. Pharm. Sci. , 65 : 1226 – 1230 .
  • Randic , M. 1975 . “On characterization of molecular branching” . J. Am. Chem. Soc. , 97 : 6609 – 6615 .
  • Basak , S.C. , Magnuson , V.R. , Niemi , G.J. and Regal , R.R. 1988 . “Determining structural similarity of chemicals using graph-theoretic indices” . Discrete Appl. Math. , 19 : 17 – 44 .
  • Balaban , A.T. 1982 . “Highly discriminating distance-based topological indices” . Chem. Phys. Lett. , 89 : 399 – 404 .
  • Balaban , A.T. 1983 . “Topological indices based on topological distances in molecular graphs” . Pure Appl. Chem. , 55 : 199 – 206 .
  • Balaban , A.T. 1985 . “Chemical graphs. Part 48. Topological index J for heteroatom-containing molecules taking into account periodicities of element properties” . Math. Chem. (MATCH) , 21 : 115 – 122 .
  • 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 .
  • Basak , S.C. 1999 . “Information theoretic indices of neighborhood complexity and their applications” . In Topological Indices and Related Descriptors in QSAR and QSPR , Edited by: Devillers , J. and Balaban , A.T. 563 – 593 . The Netherlands : Gordon and Breach Science Publishers .
  • Kier , L.B. and Hall , L.H. 1999 . Molecular Structure Description: The Electrotopological State , San Diego , CA : Academic Press .
  • Hall , L.H. , Mohney , B. and Kier , L.B. 1991 . “The electrotopological state: structure information at the atomic level for molecular graphs” . J. Chem. Inf. Comput. Sci. , 31 : 76 – 82 .
  • Basak , S.C. 1988 . H-Bond , University of Minnesota . Copyright of the
  • Parham, M., Hall, L.H. and Kier, L.B. (2000) Log P www.logP.com (www.logP.com)
  • SAS Institute, Inc. 1988 . SAS/STAT User Guide, Release , 6.03 Edition Cary , NC
  • Hoerl , A.E. and Kennard , R.W. 1970 . “Ridge regression: biased estimation for non-orthogonal problems” . Technometrics , 8 : 27 – 51 .
  • Massy , W.F. 1965 . “Principal components regression in exploratory statistical research” . J. Am. Stat. Assoc. , 60 : 234 – 246 .
  • Hoskuldsson , A. 1988 . “PLS regression methods” . J. Chemometrics , 2 : 211 – 228 .
  • Hoskuldsson , A. 1995 . “A combined theory for PCA and PLS” . J. Chemometrics , 9 : 91 – 123 .
  • Wold , H. 1975 . “Soft modeling by latent variables: the non-linear iterative partial least squares approach” . In Perspectives in Probability and Statistics , Edited by: Gani , J. London : Academic Press . Papers in Honor of M.S. Bartlett
  • Miller , A.J. 1990 . Subset Selection in Regression , New York : Chapman and Hall .
  • Rencher , A.C. and Pun , F.C. 1980 . “Inflation of R2 in best subset regression” . Technometrics , 22 : 49 – 53 .
  • Hawkins , D. , Basak , S. and Shi , X. 2001 . “QSAR with few compounds and many features” . J. Chem. Inf. Comput. Sci. , 41 : 663 – 670 .
  • Basak , S.C. , El-Masri , H. , Hawkins , D.M. and Mills , D. 2001 . “Exposure assessment of volatile organic chemicals (VOCs): predicting blood:air partition coefficients of diverse chemicals using theoretical descriptors” . J. Chem. Inf. Comput. Sci. , Submitted for Publication
  • Basak , S. , Mills , D. , Hawkins , D.M. and El-Masri , H. 2002 . “Prediction of human blood:air partition coefficient: a comparison of structure-based and property-based methods” . Risk Analysis , Submitted for Publication
  • 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 solvatochromatic parameters, π*, α and β, and some methods for simplifying the general solvatochromatic equation” . J. Org. Chem. , 48 : 2877 – 2887 .
  • Basak , S.C. , Niemi , G.J. and Veith , G.D. 1990 . “Optimal characterization of structure for prediction of properties” . J. Math. Chem. , 4 : 185 – 205 .
  • Basak , S.C. , Niemi , G.J. and Veith , G.D. 1990 . “Recent developments in the characterization of chemical structure using graph-theoretic indices” . In Computational Chemical Graph Theory Edited by: Rouvray , D.H. 235 – 277 .

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