Mechanism-based quantitative structure-phytotoxicity relationships comparative inhibition of substituted phenols on root elongation of Cucumis sativus

被引：11

作者：

Wang X. ^{[1
]}

Wang Y. ^{[1
]}

Chunsheng Y. ^{[1
]}

Wang L. ^{[1
]}

Han S. ^{[1
]}

机构：

[1] State Key Laboratory of Pollution Control and Resources Reuse, School of Environment, Nanjing University

来源：

Archives of Environmental Contamination and Toxicology | 2002年 / 42卷 / 1期

关键词：

Phenol; Root Elongation; Logarithmic Form; Toxic Response; Cucumis Sativus;

D O I：

10.1007/s002440010288

中图分类号：

学科分类号：

摘要：

Phytotoxicity of selected substituted phenols to Cucumis sativus (log1/RC50, root elongation half inhibition concentration [mol/L] in logarithmic form) was determined by using a root elongation inhibition method and quantitative structure-activity relationships (QSARs) were developed. Hydrophobicity, described by 1-octanol/water partition coefficient in logarithmic form (log Kow) and electronic effect (characterized by the energy of the lowest unoccupied orbital, Elumo) proved to contribute mainly to the phytotoxicity of phenols in this study. Log Kow was used as a probe to classify the tested chemicals into subsets according to the modes of toxic action. The result indicated that the substituted phenols fell into two classes in general: narcotic phenols and bioreactive phenols. Most phenols elicited their toxic response via a polar narcosis mechanism and an excellent log Kow-dependent QSAR was developed (log1/RC50 = 0.94 log Kow + 2.04, n = 22, r2adj = 0.89). Selected phenols with bioreactive substructures exhibited elevated bioreactive toxicity and a strong Elumo-dependent correlation was achieved (log1/RC50 = -0.91 Elumo + 2.73, n = 6, r2adj = 0.81). This implied that their reactive toxicity involved mainly their in vivo electrophilic reactions. In an effort to model all chemicals without regard to their mechanisms, a highly predictive response-surface was developed with the phytotoxicity, hydrophobicity, and electrophilic reactivity (log1/RC50 = 0.66 log Kow - 0.57 Elumo + 2.31, n = 28, r2adj = 0.88).

引用

页码：29 / 35

页数：6

共 41 条

[1]

Bearden A.P., Schultz T.W., Structure-activity relationships for Pimephales and Tetrahymena: A mechanism of action approach, Environ Toxicol Chem, 16, pp. 1311-1317, (1997)

[2]

Blum D.J.W., Speece R.E., Quantitative structure-activity relationships for chemical toxicity to environmental bacteria, Ecotoxicol Environ Safe, 22, pp. 198-224, (1991)

[3]

Bradbury S.P., Predicting modes of toxic action from chemical structure: An overview, SAR QSAR Environ Res, 2, pp. 89-104, (1994)

[4]

Brunmark A., Cadenas E., Redox and addition chemistry of quinoid compounds and its biological implications, Free Radical Biol Med, 7, pp. 435-477, (1978)

[5]

Cronin M.T.D., Schultz T.W., Structure-toxicity relationships for phenols to Tetrahymena pyriformis, Chemosphere, 32, pp. 1453-1468, (1996)

[6]

Cronin M.T.D., Gregory B.W., Schultz T.W., Quantitative structure-activity analyses of nitrobenzene toxicity to Tetrahymena pyriformis, Chem Res Toxicol, 11, pp. 902-908, (1998)

[7]

Dean J.A., Lange's handbook of chemistry, 13th ed., (1985)

[8]

Dupuis G., Benezra C., Allergic contact dermatitis to simple chemicals, a molecular approach, (1982)

[9]

Franks H.B., Lien W.R., Mechanisms of general anesthesia, Environ Health Prospect, 87, pp. 199-205, (1990)

[10]

Freemark K., MacQuarrie P., Swanson S., Peterson H., ASTM STP 1091, pp. 14-29, (1990)

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