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Development of QSARs to investigate the bacterial toxicity and biotransformation potential of aromatic heterocylic compounds |
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| Authors: | Bundy J G Morriss A W Durham D G Campbell C D Paton G I |
| Institution: | a Department of Plant and Soil Science, University of Aberdeen, Aberdeen AB24 3UU, UK b Soil Science Group, Macaulay Land Use Research Institute, Craigiebuckler, Aberdeen AB15 8QH, UK c School of Pharmacy, Robert Gordon University, Schoolhill, Aberdeen AB10 1FE, UK |
| 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. fluorescens 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 Kow (R2=0.95, Q2=0.88), with the basic (pyridine-ring containing) heterocycles modelled separately. The biotransformation data were best modelled using lowest unoccupied molecular orbital (LUMO) energies (R2=0.90, Q2=0.87). |
| Keywords: | Structure–activity relationship NAH plasmid Biosensor Lux fusion |
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