QSAR for methyl- and/or chloro-substituted anilines and the polar narcosis mechanism of toxicity

L. Michelle Arnold; David T. Lin; T. Wayne Schultz

doi:10.1016/0045-6535(90)90390-F

QSAR for methyl- and/or chloro-substituted anilines and the polar narcosis mechanism of toxicity

L. Michelle Arnold
, David T. Lin
, T. Wayne Schultz

Veterinary Science

Research output: Contribution to journal › Article › peer-review

24 Scopus citations

Abstract

The relative toxicity of 32 methyl- and/or chloro-substituted anilines was assessed in the 48-h sublethal, static Tetrahymena pyriformis population growth assay. Quantitative structure-activity relationships (QSARs) were examined. Regression analysis of toxicity (log IGC₅₀^-1) versus the 1-octanol/water partition coefficient (log K_OW) showed excellent correlation as revealed by the equation log IGC₅₀^-1 = 0.698 (log K_OW) -1.190; n = 23, r-square = 0.931, s = 0.136, f = 282.47, Pr > f = 0.0001. This equation is considered to represent the polar narcosis mode of action. Nine derivatives were not included in the model. The parent compound aniline and the 4-chloro derivative were observed to be more toxic than predicted. The seven di- and trimethyl derivatives were observed to be less toxic than predicted. The latter seven derivatives could be included in the model with the addition of the summation of the Hammett sigma constants (∑σ) as a second descriptor, log IGC₅₀^-1 = 0.428 (log K_OW) + 0.733 (∑σ) -0.828; n = 30, r-square = 0.919, s = 0.169, f = 153.60, Pr > f = 0.0001. Abiotic loss was not considered to be a factor in the observed toxicities.

Original language	English
Pages (from-to)	183-191
Number of pages	9
Journal	Chemosphere
Volume	21
Issue number	1-2
DOIs	https://doi.org/10.1016/0045-6535(90)90390-F
State	Published - 1990

Funding

This study was supported in part by the U.S. Environmental Protection Agency (EPA) under Research Agreement R-815979. The analyses and conclusions herein are those of the authors and do not necessarily reflect views of EPA, and hence, no EPA endorsement should be inferred. David Lin was supported by the The University of Tennessee's Center of Excellence in Livestock Diseases and Human Health.

Funders	Funder number
University of Tennessee's Center of Excellence in Livestock Diseases and Human Health
U.S. Environmental Protection Agency	R-815979

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 3 Good Health and Well-being

ASJC Scopus subject areas

Environmental Engineering
General Chemistry
Environmental Chemistry
Pollution
Public Health, Environmental and Occupational Health
Health, Toxicology and Mutagenesis

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10.1016/0045-6535(90)90390-F

Cite this

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title = "QSAR for methyl- and/or chloro-substituted anilines and the polar narcosis mechanism of toxicity",

abstract = "The relative toxicity of 32 methyl- and/or chloro-substituted anilines was assessed in the 48-h sublethal, static Tetrahymena pyriformis population growth assay. Quantitative structure-activity relationships (QSARs) were examined. Regression analysis of toxicity (log IGC50-1) versus the 1-octanol/water partition coefficient (log KOW) showed excellent correlation as revealed by the equation log IGC50-1 = 0.698 (log KOW) -1.190; n = 23, r-square = 0.931, s = 0.136, f = 282.47, Pr > f = 0.0001. This equation is considered to represent the polar narcosis mode of action. Nine derivatives were not included in the model. The parent compound aniline and the 4-chloro derivative were observed to be more toxic than predicted. The seven di- and trimethyl derivatives were observed to be less toxic than predicted. The latter seven derivatives could be included in the model with the addition of the summation of the Hammett sigma constants (∑σ) as a second descriptor, log IGC50-1 = 0.428 (log KOW) + 0.733 (∑σ) -0.828; n = 30, r-square = 0.919, s = 0.169, f = 153.60, Pr > f = 0.0001. Abiotic loss was not considered to be a factor in the observed toxicities.",

author = "Arnold, \{L. Michelle\} and Lin, \{David T.\} and Schultz, \{T. Wayne\}",

year = "1990",

doi = "10.1016/0045-6535(90)90390-F",

language = "English",

volume = "21",

pages = "183--191",

number = "1-2",

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TY - JOUR

T1 - QSAR for methyl- and/or chloro-substituted anilines and the polar narcosis mechanism of toxicity

AU - Arnold, L. Michelle

AU - Lin, David T.

AU - Schultz, T. Wayne

PY - 1990

Y1 - 1990

N2 - The relative toxicity of 32 methyl- and/or chloro-substituted anilines was assessed in the 48-h sublethal, static Tetrahymena pyriformis population growth assay. Quantitative structure-activity relationships (QSARs) were examined. Regression analysis of toxicity (log IGC50-1) versus the 1-octanol/water partition coefficient (log KOW) showed excellent correlation as revealed by the equation log IGC50-1 = 0.698 (log KOW) -1.190; n = 23, r-square = 0.931, s = 0.136, f = 282.47, Pr > f = 0.0001. This equation is considered to represent the polar narcosis mode of action. Nine derivatives were not included in the model. The parent compound aniline and the 4-chloro derivative were observed to be more toxic than predicted. The seven di- and trimethyl derivatives were observed to be less toxic than predicted. The latter seven derivatives could be included in the model with the addition of the summation of the Hammett sigma constants (∑σ) as a second descriptor, log IGC50-1 = 0.428 (log KOW) + 0.733 (∑σ) -0.828; n = 30, r-square = 0.919, s = 0.169, f = 153.60, Pr > f = 0.0001. Abiotic loss was not considered to be a factor in the observed toxicities.

AB - The relative toxicity of 32 methyl- and/or chloro-substituted anilines was assessed in the 48-h sublethal, static Tetrahymena pyriformis population growth assay. Quantitative structure-activity relationships (QSARs) were examined. Regression analysis of toxicity (log IGC50-1) versus the 1-octanol/water partition coefficient (log KOW) showed excellent correlation as revealed by the equation log IGC50-1 = 0.698 (log KOW) -1.190; n = 23, r-square = 0.931, s = 0.136, f = 282.47, Pr > f = 0.0001. This equation is considered to represent the polar narcosis mode of action. Nine derivatives were not included in the model. The parent compound aniline and the 4-chloro derivative were observed to be more toxic than predicted. The seven di- and trimethyl derivatives were observed to be less toxic than predicted. The latter seven derivatives could be included in the model with the addition of the summation of the Hammett sigma constants (∑σ) as a second descriptor, log IGC50-1 = 0.428 (log KOW) + 0.733 (∑σ) -0.828; n = 30, r-square = 0.919, s = 0.169, f = 153.60, Pr > f = 0.0001. Abiotic loss was not considered to be a factor in the observed toxicities.

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ER -

QSAR for methyl- and/or chloro-substituted anilines and the polar narcosis mechanism of toxicity

Abstract

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UN SDGs

ASJC Scopus subject areas

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