Quantitative structure-toxicity relationships for halobenzenes in two species of bioluminescent bacteria, Pseudomonas fluorescens and Vibrio fischeri, using an atom-centered semi-empirical molecular-orbital based model

M A Warne, E M Boyd, A A Meharg, D Osborn, K Killham, J C Lindon, J K Nicholson

Research output: Contribution to journalArticle

Abstract

Literature data on the toxicity of substituted benzenes for two bioluminescent bacteria, Pseudomonas fluorescens and Vibrio fischeri have been compared and analysed in relation to a set of computed molecular physico-chemical properties using a quantitative structure-activity approach. The quantitative structure-toxicity relationships of the compounds in each species showed marked differences when based upon semi-empirical molecular-orbital whole molecule and atom based properties.

Multiple linear regression analysis of P. fluorescens data showed a good correlation with HOMO (highest occupied molecular orbital) atom based terms. In contrast, the V. fischeri toxicity data for halobenzenes showed superior correlations with LUMO (lowest unoccupied molecular orbital) atom based terms. These differences indicate that the toxicology of halobenzenes in the two species may have different molecular mechanisms, thus suggesting cautious interpretations of such in vitro toxicology data for other chemical classes.

Original languageEnglish
Pages (from-to)17-38
Number of pages22
JournalSAR and QSAR in Environmental Research
Volume10
Publication statusPublished - 1999

Keywords

  • bioluminescent bacteria
  • toxicity
  • halobenzenes
  • semi-empirical calculations
  • atom based properties
  • molecular properties
  • PHOTOBACTERIUM-PHOSPHOREUM
  • LUMINESCENT BACTERIA
  • CHEMICALS

Cite this

Quantitative structure-toxicity relationships for halobenzenes in two species of bioluminescent bacteria, Pseudomonas fluorescens and Vibrio fischeri, using an atom-centered semi-empirical molecular-orbital based model. / Warne, M A ; Boyd, E M ; Meharg, A A ; Osborn, D ; Killham, K ; Lindon, J C ; Nicholson, J K .

In: SAR and QSAR in Environmental Research, Vol. 10, 1999, p. 17-38.

Research output: Contribution to journalArticle

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abstract = "Literature data on the toxicity of substituted benzenes for two bioluminescent bacteria, Pseudomonas fluorescens and Vibrio fischeri have been compared and analysed in relation to a set of computed molecular physico-chemical properties using a quantitative structure-activity approach. The quantitative structure-toxicity relationships of the compounds in each species showed marked differences when based upon semi-empirical molecular-orbital whole molecule and atom based properties.Multiple linear regression analysis of P. fluorescens data showed a good correlation with HOMO (highest occupied molecular orbital) atom based terms. In contrast, the V. fischeri toxicity data for halobenzenes showed superior correlations with LUMO (lowest unoccupied molecular orbital) atom based terms. These differences indicate that the toxicology of halobenzenes in the two species may have different molecular mechanisms, thus suggesting cautious interpretations of such in vitro toxicology data for other chemical classes.",
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T1 - Quantitative structure-toxicity relationships for halobenzenes in two species of bioluminescent bacteria, Pseudomonas fluorescens and Vibrio fischeri, using an atom-centered semi-empirical molecular-orbital based model

AU - Warne, M A

AU - Boyd, E M

AU - Meharg, A A

AU - Osborn, D

AU - Killham, K

AU - Lindon, J C

AU - Nicholson, J K

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N2 - Literature data on the toxicity of substituted benzenes for two bioluminescent bacteria, Pseudomonas fluorescens and Vibrio fischeri have been compared and analysed in relation to a set of computed molecular physico-chemical properties using a quantitative structure-activity approach. The quantitative structure-toxicity relationships of the compounds in each species showed marked differences when based upon semi-empirical molecular-orbital whole molecule and atom based properties.Multiple linear regression analysis of P. fluorescens data showed a good correlation with HOMO (highest occupied molecular orbital) atom based terms. In contrast, the V. fischeri toxicity data for halobenzenes showed superior correlations with LUMO (lowest unoccupied molecular orbital) atom based terms. These differences indicate that the toxicology of halobenzenes in the two species may have different molecular mechanisms, thus suggesting cautious interpretations of such in vitro toxicology data for other chemical classes.

AB - Literature data on the toxicity of substituted benzenes for two bioluminescent bacteria, Pseudomonas fluorescens and Vibrio fischeri have been compared and analysed in relation to a set of computed molecular physico-chemical properties using a quantitative structure-activity approach. The quantitative structure-toxicity relationships of the compounds in each species showed marked differences when based upon semi-empirical molecular-orbital whole molecule and atom based properties.Multiple linear regression analysis of P. fluorescens data showed a good correlation with HOMO (highest occupied molecular orbital) atom based terms. In contrast, the V. fischeri toxicity data for halobenzenes showed superior correlations with LUMO (lowest unoccupied molecular orbital) atom based terms. These differences indicate that the toxicology of halobenzenes in the two species may have different molecular mechanisms, thus suggesting cautious interpretations of such in vitro toxicology data for other chemical classes.

KW - bioluminescent bacteria

KW - toxicity

KW - halobenzenes

KW - semi-empirical calculations

KW - atom based properties

KW - molecular properties

KW - PHOTOBACTERIUM-PHOSPHOREUM

KW - LUMINESCENT BACTERIA

KW - CHEMICALS

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EP - 38

JO - SAR and QSAR in Environmental Research

JF - SAR and QSAR in Environmental Research

SN - 1062-936X

ER -