Multiple Computer-Automated Structure Evaluation Study of Aquatic Toxicity. Iii. Vibrio Fischeri

Klopman, Gilles; Stuart, Scott E.

doi:10.1897/1551-5028(2003)022<0466:mcases>2.0.co;2

Cited by 3 publications

(3 citation statements)

References 21 publications

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“…fischeri to grow. Both are inherently linked, since around 10% of the metabolic energy is converted into luminescence light production and in this way is related to cellular respiration. A series of validation experiments with SMX and SFA, as representatives for ionized and neutral compounds, showed that the growth medium does not interfere with the test results.…”

Section: Resultsmentioning

confidence: 99%

Antibacterial Activity of Sulfamethoxazole Transformation Products (TPs): General Relevance for Sulfonamide TPs Modified at the para Position

Majewsky

Wagner

Delay

et al. 2014

Chem. Res. Toxicol.

154

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Sulfonamide antibiotics undergo transformation in the aquatic environment through biodegradation, photolysis, or hydrolysis. In this study, the residual antibacterial activity of 11 transformation products (TPs) of sulfamethoxazole (SMX) was investigated with regard to their in vitro growth and luminescence inhibition on Vibrio fischeri (30 min and 24 h exposure). Two transformation products, 4-hydroxy-SMX and N(4)-hydroxy-acetyl-SMX, were synthesized in-house and confirmed by nuclear magnetic resonance and high-resolution mass spectrometry. Results of individual compound experiments showed that TPs modified at the para amino group still exhibit clear antibacterial effects, whereas TPs resulting from breakdown of the SMX structure lost this mechanism of action. 4-NO2- and 4-OH-SMX were found to inhibit growth to a clearly greater extent than the parent compound, SMX. In contrast, the N(4)-acetyl- and N(4)-hydroxy-acetyl-derivatives retain less than 10 and 5% of the effect of SMX on growth and luminescence inhibition, respectively. The effect of a mixture of para-modified TPs was observed to be additive. Considering the homologous series of sulfa drugs widely prescribed and their common mechanism of action, the potential environmental impact must consider the total amount of sulfonamide antibiotics and their derivative TPs, which might end up in a water body. Extrapolating the results obtained here for the para TPs of SMX to other sulfa drugs and determining the persistence and occurrence of these compounds in the aquatic environment is required for improved risk assessment.

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Section: Resultsmentioning

confidence: 99%

Antibacterial Activity of Sulfamethoxazole Transformation Products (TPs): General Relevance for Sulfonamide TPs Modified at the para Position

Majewsky

Wagner

Delay

et al. 2014

Chem. Res. Toxicol.

154

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“…These parameters are important in determining the mobility and bioavailability of organic chemicals (Tehrany et al 2004;Gramatica and Papa 2005). In particular, the log octanol-water partition coefficient (logK ow ) is a molecular property that has been used extensively to correlate and predict physico-chemical properties and biological activity based on hydrophobicity, which enable us to model the concentrations of certain pollutants in different compartments of the environment (Valsaraj et al 1999;Allen et al 2000;Klopman and Stuart 2003;Chen et al 2007). Quantitative knowledge of these properties enables us to model the concentrations of a certain pollutant in different compartments of the environment (Fenner et al 2005).…”

Section: Introductionmentioning

confidence: 99%

Determination and estimation of partitioning properties for substituted phosphates and thiophosphates

Dong

Ding

Cao

et al. 2008

Environ Monit Assess

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Substituted phenylglyoxylonitrile oximino phosphates and thiophosphates invested as a synergist of molluscicide killing snail eggs have been exposed to the environment with very little attention. The partitioning properties, aqueous solubility (S(w)), n-octanol-water partition coefficient (K(ow)) and soil organic carbon sorption coefficients (K(oc)) of 16 O, O'-dialkyl, O''-(substituted phenylglyoxylonitrile oximino) phosphates and thiophosphates, were determined by the traditional shaking flask method. The parameters of molecular fragment connectivity indices (MFCIs) and linear solvation energy relationships (LSERs) were used as molecular descriptors to establish a series of correlation equations successfully. The obtained correlation equations provided a quantitative method to predict the three partitioning properties for new exploited substituted phosphates and thiophosphates. More valuable, the successful application of MFCIs provides us with a good example and a good idea to improve traditional molecular connectivity indices (MCIs).

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“…Optimization of correlation weights of local graph invariants was used by Toropov et al [16] for the prediction of aquatic toxicity. Klopman et al [17] have reported modeling of acute toxicity data against Vibrio fischeri using Multiple Computer-Assisted Structure Evaluation (M-CASE) program. QSARs were developed for 43 aromatic compounds to Photobacterium phosphoreum and Daphnia magna using partition coefficient, linear solvation energy relationship, molecular connectivity index and group contributions [18].…”

Section: Introductionmentioning

confidence: 99%

QSTR with Extended Topochemical Atom Indices. 3. Toxicity of Nitrobenzenes to Tetrahymena pyriformis

Roy

Ghosh

2004

QSAR Comb. Sci.

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The experimental determination of toxicological properties of commercial chemicals being costly and time consuming process, there is a need to develop mathematical predictive tool to theoretically quantify such properties. In this background, we have modeled toxicity of nitrobenzene derivatives to Tetrahymena pyriformis using extended topochemical atom (ETA) indices recently introduced by us (Roy and Ghosh, 2003). We have also modeled the toxicity data using other topological descriptors (Balaban J, kappa shape indices, connectivity indices, Wiener index) and two physicochemical variables (AlogP98, MolRef) and compared the ETA models with non-ETA ones. Principal component factor analysis was used as the data-preprocessing step to reduce the dimensionality of the data matrix and identify the important variables that are devoid of collinearities. Multiple linear regression analyses show that the best non-ETA model involves (size), halogen and additional nitro substitutions in the nitrobenzene ring and negative contributions of the substituents like methyl and hydroxymethyl groups to the toxicity. An attempt to use non-ETA descriptors along with the ETA ones slightly improves the quality in comparison to the best ETA model. Interestingly, the ETA model developed by us for the nitrobenzene toxicity is comparable to the previously reported models on the same data set (Estrada et al., 2001;Cronin et al., 1998). Thus, it appears that the ETA descriptors have significant potential in QSAR/QSPR/ QSTR studies, which warrants extensive evaluation.

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Multiple Computer-Automated Structure Evaluation Study of Aquatic Toxicity. Iii. Vibrio Fischeri

Cited by 3 publications

References 21 publications

Antibacterial Activity of Sulfamethoxazole Transformation Products (TPs): General Relevance for Sulfonamide TPs Modified at the para Position

Antibacterial Activity of Sulfamethoxazole Transformation Products (TPs): General Relevance for Sulfonamide TPs Modified at the para Position

Determination and estimation of partitioning properties for substituted phosphates and thiophosphates

QSTR with Extended Topochemical Atom Indices. 3. Toxicity of Nitrobenzenes to Tetrahymena pyriformis

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