Development of QSARs to investigate the bacterial toxicity and biotransformation potential of aromatic heterocyclic compounds

J. G. Bundy, A. Morriss, D. G. Durham, D. G. Campbell, Graeme Iain Paton

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Abstract

A series of aromatic heterocyclic and hydrocarbon compounds were tested for toxicity and biotransformation potential against two contrasting lux-marked whole-cell microbial biosensors. Toxicity was determined by inhibition of light output of a Pseudomonas fluorescens construct that expresses lux constitutively. Biotransformation was tested by increase in light output of P. flourescens HK44 (pUTK21), which expresses lux when in the presence of a metabolic intermediate (salicylate). The data were then modelled against physical/chemical properties of the compounds tested to see if quantitative structure-activity relationships (QSARs) could be derived. Toxicity was found to be accurately predicted by log K-ow (R-2 = 0.95, Q(2) = 0.88), with the basic (pyridine-ring containing) heterocycles modelled separately. The biotransformation data were best modelled using lowest unoccupied molecular orbital (LUMO) energies (R-2 = 0.90, Q(2) = 0.87). (C) 2001 Elsevier Science Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)885-892
Number of pages7
JournalChemosphere
Volume42
DOIs
Publication statusPublished - 2001

Keywords

  • structure-activity relationship
  • NAH plasmid
  • biosensor
  • Lux fusion
  • PSEUDOMONAS-FLUORESCENS
  • BIODEGRADATION
  • NAPHTHALENE
  • PHENANTHRENE
  • ECOTOXICITY
  • DEGRADATION
  • CATABOLISM
  • TOXICOLOGY
  • ANTHRACENE
  • NARCOSIS

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