Quantitative structure-toxicity relationships for chlorophenols to bioluminescent lux-marked bacteria using atom-based semi-empirical molecular-orbital descriptors

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

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Abstract

Literature data on the toxicity of chlorophenols for three luminescent bacteria (Vibrio fischeri, and the lux-marked Pseudomonas fluorescens 10586s pUCD607 and Burkholderia spp. RASC c2 (Tn4431)) have been analysed in relation to a set of computed molecular physico-chemical properties.

The quantitative structure-toxicity relationships of the compounds in each species showed marked differences when based upon semi-empirical molecular-orbital molecular and atom based properties. For mono-, di- and tri-chlorophenols multiple linear regression analysis of V. fischeri toxicity showed a good correlation with the solvent accessible surface area and the charge on the oxygen atom. This correlation successfully predicted the toxicity of the heavily chlorinated phenols, suggesting in V. fischeri only one overall mechanism is present for all chlorophenols. Good correlations were also found for RASC c2 with molecular properties, such as the surface area and the nucleophilic superdelocalisability of the oxygen. In contrast the best QSTR for P. fluorescens contained the 2nd order connectivity index and ELUMO suggesting a different, more reactive mechanism.

Cross-species correlations were examined, and between V. fischeri and RASC c2 the inclusion of the minimum value of the nucleophilic susceptibility on the ring carbons produced good results. Poorer correlations were found with P, fluorescens highlighting the relative similarity of V, fischeri and RASC c2, in contrast to that of P. fluorescens.

Original languageEnglish
Pages (from-to)473-495
Number of pages23
JournalSAR and QSAR in Environmental Research
Volume10
Publication statusPublished - 1999

Keywords

  • chlorophenols
  • lux-marked bacteria
  • semi-empirical calculations
  • atom based properties
  • molecular properties
  • LUMINESCENT BACTERIA
  • VIBRIO-FISHERI

Cite this

Quantitative structure-toxicity relationships for chlorophenols to bioluminescent lux-marked bacteria using atom-based semi-empirical molecular-orbital descriptors. / 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. 473-495.

Research output: Contribution to journalArticle

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T1 - Quantitative structure-toxicity relationships for chlorophenols to bioluminescent lux-marked bacteria using atom-based semi-empirical molecular-orbital descriptors

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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AB - Literature data on the toxicity of chlorophenols for three luminescent bacteria (Vibrio fischeri, and the lux-marked Pseudomonas fluorescens 10586s pUCD607 and Burkholderia spp. RASC c2 (Tn4431)) have been analysed in relation to a set of computed molecular physico-chemical properties.The quantitative structure-toxicity relationships of the compounds in each species showed marked differences when based upon semi-empirical molecular-orbital molecular and atom based properties. For mono-, di- and tri-chlorophenols multiple linear regression analysis of V. fischeri toxicity showed a good correlation with the solvent accessible surface area and the charge on the oxygen atom. This correlation successfully predicted the toxicity of the heavily chlorinated phenols, suggesting in V. fischeri only one overall mechanism is present for all chlorophenols. Good correlations were also found for RASC c2 with molecular properties, such as the surface area and the nucleophilic superdelocalisability of the oxygen. In contrast the best QSTR for P. fluorescens contained the 2nd order connectivity index and ELUMO suggesting a different, more reactive mechanism.Cross-species correlations were examined, and between V. fischeri and RASC c2 the inclusion of the minimum value of the nucleophilic susceptibility on the ring carbons produced good results. Poorer correlations were found with P, fluorescens highlighting the relative similarity of V, fischeri and RASC c2, in contrast to that of P. fluorescens.

KW - chlorophenols

KW - lux-marked bacteria

KW - semi-empirical calculations

KW - atom based properties

KW - molecular properties

KW - LUMINESCENT BACTERIA

KW - VIBRIO-FISHERI

M3 - Article

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JO - SAR and QSAR in Environmental Research

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