Structure-activity relationships for chloro- and nitrophenol toxicity in the pollen tube growth test
- UFZ Centre for Environmental Research, Leipzig (Germany). Dept. of Chemical Ecotoxicology
- Bangalore Univ. (India). Dept. of Botany
- Univ. Hamburg (Germany). Inst. fuer Allgemeine Botanik
Acute toxicity of 10 chlorophenols and 10 nitrophenols with identical substitution patterns is analyzed with the pollen tube growth (PTG) test. Concentration values of 50% growth inhibition (IC50) between 0.1 and 300 mg/L indicate that the absolute sensitivity of this alternative biotest is comparable to conventional aquatic test systems. Analysis of quantitative structure-activity relationships using lipophilicity (log K{sub ow}), acidity (pK{sub a}), and quantum chemical parameters to model intrinsic acidity, solvation interactions, and nucleophilicity reveals substantial differences between the intraseries trends of log IC50. With chlorophenols, a narcotic-type relationship is derived, which, however, shows marked differences in slope and intercept when compared to reference regression equations for polar narcosis. Regression analysis of nitrophenol toxicity suggests interpretation in terms of two modes of action: oxidative uncoupling activity is associated with a pK{sub a} window from 3.8 to 8.5, and more acidic congeners with diortho-substitution show a transition from uncoupling to a narcotic mode of action with decreasing pK{sub a} and log K{sub ow}. Model calculations for phenol nucleophilicity suggest that differences in the phenol readiness for glucuronic acid conjugation as a major phase-II detoxication pathway have no direct influence on acute PTG toxicity of the compounds.
- Sponsoring Organization:
- USDOE
- OSTI ID:
- 474291
- Journal Information:
- Environmental Toxicology and Chemistry, Journal Name: Environmental Toxicology and Chemistry Journal Issue: 10 Vol. 15; ISSN ETOCDK; ISSN 0730-7268
- Country of Publication:
- United States
- Language:
- English
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