QSAR studies of surfactant toxicity to Daphnia magna
The inherent nature of surfactants to aggregate at surfaces makes measurement of log P (octanoll water partition coefficient) for these substances extremely difficult. It is possible, however, to calculate a log P descriptor based on the method described by Hansch and Leo (1979). Work presented in this thesis describes the study of the acute toxicity of sulphonated esters (FAES) of general formula R-CH(S03"Na +)-C02-R' to Daphnia magna. Due to structural similarities of this class of anionic surfactant to linear alkylbenzene sulphonate (LAS), it was considered that the log P based QSAR originally developed to describe the toxicity of LAS to D. magna (Roberts, 1989) also would be a good predictor of the acute toxicity for FAES substances. Results of the toxicity studies showed that FAES substances were less toxic than predicted. However, when plotted against log P' Calculated using the conventional fragment approach of Hansch and Leo with the addition of a position dependent branching factor (PDBF) to account for water sharing between hydrocarbon chains, the regression slope was para"el to but distinct from that of LAS. This indicated that either FAES substances were not acting as by the same mode of action as LAS or that modification of the log P calculation was required. Further studies of the toxicity of binary mixtures of FAES with known polar and non-polar narcotics, established that FAES exhibited concentration addition with LAS and phenol. This indicated that they behaved with a similar mode of action and it would be expected that LAS and FAES would share the same QSAR. The difference of the regression slopes of FAES and LAS observed? earlier, therefore, suggested the requirement of a modification to the original log P calculation. The modified proximity factor developed in this thesis considers the effects of relative size of proximal polar fragments on log P.? Spherical hydration sheaths surrounding each fragment were assumed and 'overlapping volumes calculated for fragments at different carbon separation. When incorporated into the log P calculation, the new log P values now allow toxicity values for LAS and F AES substances to be incorporated into the same QSAR.