Use of quantitative shape-activity relationships to model the photoinduced toxicity of polycyclic aromatic hydrocarbons: Electron density shape features accurately predict toxicity

Environmental Toxicology and Chemistry

Volumn 17, Issue 7, 1998, Pages 1207-1215

  Mezey, Paul G ^a   Zimpel, Zbigniew ^a   Warburton, Peter ^a   Walker, P Duane ^a   Irvine, Donald G ^a   Huang, Xiag Dong ^b   Dixon, D George ^b   Greenberg, Bruce M ^b  

^a UNIVERSITY OF SASKATCHEWAN   (Canada)

^b UNIVERSITY OF WATERLOO   (Canada)

Author keywords

Electron density; Molecular topology; Polycyclic aromatic hydrocarbons; Quantitative shape activity relationships; Toxicity

Indexed keywords

PHOTOINDUCED TOXICITY; POLYCYCLIC AROMATIC HYDROCARBONS; QUANTITATIVE SHAPE ACTIVITY RELATIONSHIP METHODS;

AROMATIC HYDROCARBONS; CARRIER CONCENTRATION; DATABASE SYSTEMS; MATHEMATICAL MODELS; MOLECULAR STRUCTURE; PHOTOCHEMICAL REACTIONS; THREE DIMENSIONAL;

TOXICITY;

POLYCYCLIC AROMATIC HYDROCARBON;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; ELECTRON; INTOXICATION; PRIORITY JOURNAL; STRUCTURE ANALYSIS;

LEMNA GIBBA;

EID: 0032125161     PISSN: 07307268     EISSN: None     Source Type: Journal    
DOI: 10.1897/1551-5028(1998)017<1207:UOQSAR>2.3.CO;2     Document Type: Article

References (25)

1. Huang X-D, Dixon DG, Greenberg BM. 1993. Impacts of UV radiation and photomodification on the toxicity of PAHs to the higher plant Lemna gibba (duckweed). Environ Toxicol Chem 12:1067-1077.
2. Ren L, Zeiler LF, Dixon DG, Greenberg BM. 1996. Photoinduced effects of polycyclic aromatic hydrocarbons on Brassica napus (Canola) during germination and early seedling development. Ecotoxicol Environ Saf 33:73-80.
3. Ren L, Huang X-D, McConkey BJ, Dixon DG, Greenberg BM. 1994. Photoinduced toxicity of polycyclic aromatic hydrocarbons III. Ecotoxicol Environ Saf 28:160-170.
4. Huang X-D, Dixon DG, Greenberg BM. 1995. Toxicity of polycyclic aromatic hydrocarbons to the duckweed Lemna gibba L. G-3 in natural sunlight. Ecotoxicol Environ Saf 34:194-200.
5. Krylov SN, Huang X-D, Zeiler LF, Dixon DG, Greenberg BM. 1996. Mechanistic QSAR model for the photoinduced toxicity of polycyclic aromatic hydrocarbons I: Physical model based on chemical kinetics in a two-compartment system. Environ Toxicol Chem 16:2283-2295.
6. Huang X-D, Krylov SN, Ren L, McConkey BJ, Dixon DG, Greenberg BM. 1996. Mechanistic QSAR model for the photoinduced toxicity of polycyclic aromatic hydrocarbons II: An empirical model for the toxicity of 16 PAHs to the duckweed Lemna gibba L. G-3. Environ Toxicol Chem 16:2296-2314.
7. Mezey PG, Zimpel Z, Warburton P, Walker PD, Irvine DG, Dixon DG, Greenberg BM. 1996. A high-resolution shape-fragment MEDLA database for toxicological shape analysis of PAHs. J Chem Inf Comput Sci 36:602-611.
8. Mezey PG. 1998. Molecular structure-reactivity-toxicity relationships. In Huang PM, ed, Soil Chemistry and Ecosystem Health. Soil Science Society of America Publishers, Pittsburgh, PA, USA (in press).
9. Mezey PG. 1986. Group theory of electrostatic potentials: A tool for quantum chemical drug design. Int J Quantum Chem Quantum Biol Symp 12:113-122.
10. Mezey PG. 1987. The shape of molecular charge distributions: Group theory without symmetry. J Comput Chem 8:462-469.
11. Mezey PG. 1987. Group theory of shapes of asymmetric biomolecules. Int J Quantum Chem Quantum Biol Symp 14:127- 132.
12. Mezey PG. 1988. Shape group studies of molecular similarity: Shape groups and shape graphs of molecular contour surfaces. J Math Chem 2:299-323.
13. Mezey PG. 1993. Shape in Chemistry: Introduction to Molecular Shape and Topology. VCH, New York, NY, USA.
14. Walker PD, Arteca GA, Mezey PG. 1990. Program GSHAPE 90 Database. University of Saskatchewan, Saskatoon, SK, Canada.
15. Frisch MJ, et al. 1990. Program GAUSSIAN 90 Database. Carnegie-Mellon Quantum Chemistry Publishing Unit, Pittsburgh, PA, USA.
16. Mezey PG. 1995. Methods of molecular shape-similarity analysis and topological shape design. In Dean PM, ed, Molecular Similarity in Drug Design. Chapman and Hall, Glasgow, UK, pp 241-268.
17. Mezey PG. 1995. Density domain bonding topology and molecular similarity measures. In Sen K, ed, Topics in Current Chemistry, Vol 173-Molecular Similarity. Springer-Verlag, Heidelberg, Germany, pp 63-83.
18. Mezey PG. 1995. Shape analysis of macromolecular electron densities. Struct Chem 6:261-270.
19. Mezey PG. 1996. Local shape analysis of macromolecular electron densities. In Leszczynski J, ed, Computational Chemistry: Reviews and Current Trends. World Scientific Publishers, Singapore, pp 109-137.
20. Walker PD, Mezey PG. 1993. Molecular electron density Lego approach to molecule building. J Am Chem Soc 115:12423-12430.
21. Walker PD, Mezey PG. 1994. Ab initio quality electron densities for proteins: A MEDLA approach, J Am Chem Soc 116:12022- 12032.
22. Walker PD, Mezey PG. 1994. Realistic, detailed images of proteins and tertiary structure elements: Ab initio quality electron density calculations for bovine insulin. Can J Chem 72:2531- 2536.
23. Walker PD, Mezey PG. 1995. A new computational microscope for molecules: High resolution MEDLA images of taxol and HIV- 1 protease, using additive electron density fragmentation principles and fuzzy set methods. J Math Chem 17:203-234.
24. Walker PD, Mezey PG. 1995. Towards similarity measures for macromolecular bodies: MEDLA test calculations for substituted benzene systems. J Comput Chem 16:1238-1249.
25. Walker PD, Mezey PG. 1993. Program MEDLA 93. Database. University of Saskatchewan, Saskatoon, SK, Canada.