Structure-activity relationships for the toxicity of substituted poly-hydroxylated benzenes to Tetrahymena pyriformis: Influence of free radical formation

QSAR and Combinatorial Science

Volumn 22, Issue 6, 2003, Pages 575-582

  Netzevaa, Tatiana I ^a,c   Aptula, Aynur O ^b   Chaudary, Shaqil H ^a   Duffy, Judith C ^a   Schultz, T Wayne ^d   Schüürmann, Gerrit ^b   Cronin, Mark T D ^a  

^a LIVERPOOL JOHN MOORES UNIVERSITY   (United Kingdom)

^b HELMHOLTZ CENTRE FOR ENVIRONMENTAL RESEARCH UFZ   (Germany)

^c MEDICAL UNIVERSITY OF SOFIA   (Bulgaria)

^d UNIVERSITY OF TENNESSEE   (United States)

Author keywords

Absolute hardness; Bond dissociation energy; Distribution coefficient; Free radicals; Hydroquinones

Indexed keywords

BENZENE; CHEMICAL BONDS; COMPUTATIONAL CHEMISTRY; DISSOCIATION; ELECTRONEGATIVITY; EQUILIBRIUM CONSTANTS; HARDNESS; HYDROPHOBICITY; MOLECULAR ORBITALS; TOXICITY;

ABSOLUTE HARDNESS; BOND DISSOCIATION ENERGIES; DISTRIBUTION COEFFICIENT; HYDROQUINONE; PHYSICO-CHEMICAL DESCRIPTORS; QUANTITATIVE STRUCTURE ACTIVITY RELATIONSHIP; RADICAL FORMATION; STRUCTURE-ACTIVITY RELATIONSHIPS; SUBSTITUTED POLIES; TETRAHYMENA PYRIFORMIS;

FREE RADICALS;

BENZENE DERIVATIVE; FREE RADICAL; HYDROXYL GROUP;

ARTICLE; CALCULATION; COMPUTER PROGRAM; DISSOCIATION; ECOTOXICITY; ELECTRON; ENERGY; EQUILIBRIUM CONSTANT; HARDNESS; HYDROPHOBICITY; NONHUMAN; OXIDATION; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; TETRAHYMENA PYRIFORMIS;

TETRAHYMENA; TETRAHYMENA PYRIFORMIS;

EID: 0041968542     PISSN: 1611020X     EISSN: None     Source Type: Journal    
DOI: 10.1002/qsar.200330816     Document Type: Article

References (31)

1. M. Gillner, G. A. Moore, H. Cederberg, Hydroquinone, WHO Publications: The WHO Environmental Series, 1994, 157, 1-178.
2. T. W. Schultz, G. D. Sinks, M. T. D. Cronin, Identification of mechanisms of toxic action of phenols to Tetrahymena pyriformis from molecular descriptors, in: F. Chen, G. Schüürmann, (Eds.), Quantitative Structure-Activity Relationships in Environmental Sciences - VII, SETAC Press, Pensacola 1997, pp. 329-342.
3. C. Hansch, H. Gao, Comparative QSAR: radical reactions of benzene derivatives in chemistry and biology, Chem. Rev., 1997, 97, 2995-3059.
4. C. F. Chignell, Structure-activity relationships in the free-radical metabolism of xenobiotics, Environ. Health Perspect., 1985, 61, 133-137.
5. L. A. Oglesby, M. T. Ebron-McCoy, T. R. Logsdon, F. Copeland, P. E. Beyer, R. J. Kavlock, In vitro embryotoxicity of a series of para-substituted phenols: structure, activity, and correlation with in vivo data, Teratology, 1992, 45, 11-34.
6. H. L. Fisher, M. R. Sumler, S. P. Shrivastava, B. Edwards, L. A. Oglesby, M. T. Ebron-McCoy, F. Copeland, R. J. Kavlock, L. L. Hall, Pharmacokinetics and structure-activity relationships of 9 para-substituted phenols in rat embryos in vitro, Teratology, 1993, 48, 285-297.
7. S. Peelen, M. C. M. Rietjens, M. G. Boersma, J. and Vervoort, Conversion of phenol derivatives to hydroxylated products by phenol hydroxylase from Trichosporon cutaneum. A comparison of regioselectivity and rate of conversion with calculated molecular orbital substrate characteristics, Eur. J. Biochem., 1995, 227, 284-291 (1995).
8. K. Nakao, R. Shimizu, H. Kubota, M. Yasuhara, Y. Hashimura, T. Suzuki, T. Fujita, H. Ohmizu, Quantitative structure-activity analyses of novel hydroxyphenyl urea derivatives as antioxidants, Bioorg. Med. Chem., 1998, 6, 849-867.
9. H. Schmitt, R. Altenburger, B. Jastorff, G. Schüürmann, Quantitative structure-activity analysis of the algae toxicity of nitroaromatic compounds, Chem. Res. Toxicol., 2000, 13, 441-450.
10. R. Garg, S. Kurup, C. Hansch, Radical toxicity of phenols: a reference point for obtaining perspective in the formulation of QSAR, Med. Res. Rev., 2000, 21, 73-82.
11. R. Garg, A. Kapur, C. Hansch, Comparative QSAR: on the toxicology of the phenolic OH moiety, Crit. Rev. Toxicol., 2001, 31, 223-245.
12. C. D. Selassie, A. J. Shustermann, S. Kapur, R. P. Verma, L. Zhang, C. Hansch, On the toxicity of phenols to fast growing cells. A QSAR model for a radical based toxicity, J. Chem. Soc., Perkin Trans 2, 1999, 12, 2729-2733.
13. T. W. Schultz, G. D. Sinks, M. T. D. Cronin, Quinone induced toxicity to Tetrahymena: structure-activity relationships, Aquat. Toxicol., 1997, 39, 267-278.
14. T. W. Schultz, TETRATOX: Tetrahymena population growth impairment endpoint - a surrogate for fish lethality, Toxicol. Meth., 1997, 7, 289-309.
15. M. Dewar, E. Zoebisch, E. Healy, J. Stewart, AM1: A new general purpose quantum mechanical molecular model, J. Am. Chem. Soc., 1985, 107, 3902-3909.
16. Y. M. Sun, X. L. Wang, H. Y. Zhang, D. Z. Chen, Theoretical elucidation of structure-antioxidant activity relationships for thiasolidine derivatives, Quant. Struct.-Act. Relat., 2001, 20, 139-142.
17. G. Schüürmann, Ecotoxic modes of action of chemical substances, in: G. Schüürmann, B. Markert, B. (Eds.), Ecotoxicology, John Wiley and Spektrum Akademischer Verlag, New York 1998, pp. 665-749.
18. R. G. Parr, R. G. Pearson, Absolute hardness: companion parameter to absolute electronegativity, J. Am. Chem. Soc., 1983, 105, 7512-7516.
19. V. I. Minkin, Glossary of terms used in theoretical organic chemistry, Pure Appl. Chem., 1999, 71, 1919-1981.
20. M. T. D. Cronin, A. O. Aptula, J. C. Duffy, T. I. Netzeva, P. H. Rowe, I. V. Valkova, T. W. Schultz, Comparative assessment of methods to develop QSARs for the prediction of the toxicity of phenols to Tetrahymena pyriformis, Chemosphere, 2002, 49, 1201-1221.
21. A. O. Aptula, T. I. Netzeva, I. V. Valkova, M. T. D. Cronin, T. W. Schultz, R. Kühne, G. Schüürmann, Multivariate discrimination between modes of toxic action of phenols, Quant. Struct.-Act. Relat., 2002, 21, 12-22.
22. J. W. McFarland, On the parabolic relationship between drug potency and hydrophobicity, J. Med. Chem., 1970, 13, 1092-1196.
23. R. D. Kaufman, Biophysical mechanisms of anesthetic action: historical perspectives and review of current theories, Anesthesiology, 1977, 46, 49-62.
24. M. T. D. Cronin, T. T. Tran, The use of QSAR for the prediction of free radical toxicity, in: C. J. Rhodes (Ed.), Toxicology of Human the Environment: the Critical Role of Free Radicals, Taylor & Francis Inc., New York 2000, pp. 453-472.
25. C. D. Selassie, T. V. De Soyza, M. Rosario, H. Gao, C. Hansch, Phenol toxicity in cells: a radical process?, Chemico-Biol. Interact., 1998, 113, 175-190.
26. T. J. Monks, R. P. Hanzlik, G. M. Cohen, D. Ross, D. G. Graham, Quinone chemistry and toxicity, Toxicol. Appl. Pharmacol., 1992, 112, 2-16.
27. P. J. O'Brien, Molecular mechanisms of quinone toxicity, Chemico-Biol. Interact., 1991, 80, 1-41.
28. H. Y. Zhang, Y. M. Sun, D. Z. Chen, OH Bond dissociation energies of phenolic compounds are determined by field/inductive effect or resonance effect? A DFT study and its application, Quant. Struct.-Act. Relat., 2001, 20, 148-152.
29. E. M. Arnett, R. T. Ludwig, On the relevance of the Parr-Pearson principle of absolute hardness to organic chemistry, J. Am. Chem. Soc., 1995, 117, 6627-6628.
30. F. Guillén, M. J. Martínez, C. Muñoz, A. T. Martínez, Quinone redox cycling in the ligninolytic fungus Pleurotus eryngii leading to extracellular production of superoxide anion radical, Arch. Biochem. Biophys., 1997, 339, 190-199.
31. B. Goodel, J. Jellison, J. Liu, G. Daniel, A. Paszczynski, F. Fekete, S. Krishnamurthy, L. Jun, G. Xu, Low molecular weight chelators and phenolic compounds isolated from wood decay fungi and their role in the fungal biodegradation of wood, J. Biotechnol., 1997, 53, 133-162.