Acute toxicity of alkyl (1-phenylsulfonyl)cycloalsane-carboxylates to Daphnia magna and quantitative structure—Activity relationships

He, Yan; Wang, Liansheng; Liu, Zhengtao; Zheng, Z. P.

doi:10.1016/0045-6535(95)00129-v

Cited by 10 publications

(6 citation statements)

References 8 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The negative logarithm of acute toxicity of the compounds in unit of mol/L, medium effective immobilization concentration (EC 50 ) and median lethal concentration (LC 50 ) after 48 hours exposure are reproduced in Table 2. Those daphnia magna straus that were unable to swim but their hearts were still beating under microscope at the end of 48 hours were considered as immobilization, whilst those unable to swim and with hearts stopped beating under microscope at the end of 48 hours, were considered as mortality [14]. The variability in toxicity measurements of the present work was about 2 -3%.…”

Section: Methodsmentioning

confidence: 98%

“…However, there has been only limited investigation on their QSARs. Recently in our laboratory, twenty-eight alkyl (1-phenylsulfonyl) cycloalkane-carboxylates were synthesized, and their acute toxicity to daphnia magna straus was reported [14]. In addition, we once reported the QSAR of alkyl (1-phenylsulfonyl) cycloalkane-carboxylates using CoMFA, CoMSIA and semiempirical molecular orbital methods [15 -18].…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Quantitative Structure-activity Relationship of Toxicity of Alkyl(1-phenylsulfonyl) Cycloalkane-carboxylates Using MLSER Model and Ab initio

2005

Self Cite

View full text Add to dashboard Cite

Based on MLSER model and quantum chemical descriptors computed at HF/STO-3G, HF/ LANL2DZ, B3LYP/LANL2D and B3LYP/6-31G* levels, different quantitative structureactivity relationships (QSARs) to the toxicity -logEC 50 and -logLC 50 of 28 alkyl(1-phenylsulfonyl) cycloalkane-carboxylates were obtained. It is suggested that the eight models developed in the present study all have good correlation and relatively small error, in which the two models with three variables, polarizability, E HOMO and limit charge density from B3LYP/6-31G* level, exhibited the best optimal correlation (r 2 ¼ 0.9455, 0.9411; and q 2 ¼ 0.9289, 0.9162, respectively) and smallest error, and thus are advantageous to other models. It was also found that polarizability is the most significant factor influencing toxicity. The toxicity increased with increasing polarizability, while decreased with increasing dipole moment and decreasing of E HOMO .

show abstract

Section: Methodsmentioning

confidence: 98%

Section: Introductionmentioning

confidence: 99%

Quantitative Structure-activity Relationship of Toxicity of Alkyl(1-phenylsulfonyl) Cycloalkane-carboxylates Using MLSER Model and Ab initio

2005

Self Cite

View full text Add to dashboard Cite

show abstract

“…Note. All ID numbers starting with "1" are taken from Dai and Wang (2000), "2" from Liu et al (2003), "3" from Kamaya et al (2005), "4" from Jin et al (1998), "5" from He et al (1995) and "6" from Papa et al (2005). a General QSAR model of Table 6.…”

Section: Molecular Modelingmentioning

confidence: 99%

“…In addition to the EC 50 values, the LC 50 values were also extracted for 28 compounds from (He et al, 1995). A relationship with their corresponding EC 50 values was then searched.…”

Section: Data Setmentioning

confidence: 99%

“…The experimental data for a series of 130 diverse compounds (Table 2) was collected from Dai and Wang (2000), He et al (1995), Jin et al (1998, Kamaya et al (2005), Liu et al (2003), and Papa et al (2005). Benzoic acids, benzaldehydes, phenylsulfonyl acetates, cycloalkane-carboxylates, benzanilides, and other esters were combined together according to our recommended procedure (Katritzky et al, 2007) to form a data set, further separated into three different training and test subsets treated independently.…”

Section: Data Setmentioning

confidence: 99%

See 1 more Smart Citation

Quantitative Structure–Activity Relationship (QSAR) Modeling of EC₅₀of Aquatic Toxicities forDaphnia magna

Katritzky

Slavov

Stoyanova-Slavova

et al. 2009

Journal of Toxicology and Environmental Health, Part A

View full text Add to dashboard Cite

The experimental EC(50) toxicities toward Daphnia magna for a series of 130 benzoic acids, benzaldehydes, phenylsulfonyl acetates, cycloalkane-carboxylates, benzanilides, and other esters were studied using the Best multilinear regression algorithm (BMLR) implemented in CODESSA. A modified quantitative structure-activity relationships (QSAR) procedure was applied guaranteeing the stability and reproducibility of the results. Separating the initial data set into training and test subsets generated three independent models with an average R(2) of .735. A five-descriptor general model including all 130 compounds, constructed using the descriptors found effective for the independent subsets, was characterized by the following statistical parameters: R(2) = .712; R(2)(cv) = .676; F = 61.331; s(2) = 0.6. The removal of two extreme outliers improved significantly the statistical parameters: R(2) = .759; R(2)(cv) = .728; F = 77.032; s(2) = 0.499. The sensitivity of the general model to chance correlations was estimated by applying a scrambling procedure involving 20 randomizations of the original property values. The resulting R(2) = .192 demonstrated the high robustness of the model proposed. The descriptors appearing in the obtained models are related to the biochemical nature of the adverse effects. An additional study of the EC(50)/LC(50) relationship for a series of 28 compounds (part of our general data set) revealed that these endpoints correlated with R(2) = .98.

show abstract

Partial least square and k‐nearest neighbor algorithms for improved 3D quantitative spectral data–activity relationship consensus modeling of acute toxicity

Stoyanova-Slavova

Slavov

Pearce

et al. 2014

Enviro Toxic and Chemistry

View full text Add to dashboard Cite

A diverse set of 154 chemicals that included US Food and Drug Administration-regulated compounds tested for their aquatic toxicity in Daphnia magna were modeled by a 3-dimensional quantitative spectral data-activity relationship (3D-QSDAR). Two distinct algorithms, partial least squares (PLS) and Tanimoto similarity-based k-nearest neighbors (KNN), were used to process bin occupancy descriptor matrices obtained after tessellation of the 3D-QSDAR space into regularly sized bins. The performance of models utilizing bins ranging in size from 2 ppm × 2 ppm × 0.5 Å to 20 ppm × 20 ppm × 2.5 Å was explored. Rigorous quality-control criteria were imposed: 1) 100 randomized 20% hold-out test sets were generated and the average R(2) test of the respective models was used as a measure of their performance, and 2) a Y-scrambling procedure was used to identify chance correlations. A consensus between the best-performing composite PLS model using 0.5 Å × 14 ppm × 14 ppm bins and 10 latent variables (average R(2) test = 0.770) and the best composite KNN model using 0.5 Å × 8 ppm × 8 ppm and 2 neighbors (average R(2) test = 0.801) offered an improvement of about 7.5% (R(2) test consensus = 0.845). Projection of the most frequently occurring bins on the standard coordinate space indicated that the presence of a primary or secondary amino group-substituted aromatic systems-would result in an increased toxic effect in Daphnia. The presence of a second aromatic ring with highly electronegative substituents 5 Å to 7 Å apart from the first ring would lead to a further increase in toxicity.

show abstract

Acute toxicity of alkyl (1-phenylsulfonyl)cycloalsane-carboxylates to Daphnia magna and quantitative structure—Activity relationships

Cited by 10 publications

References 8 publications

Quantitative Structure-activity Relationship of Toxicity of Alkyl(1-phenylsulfonyl) Cycloalkane-carboxylates Using MLSER Model and Ab initio

Quantitative Structure-activity Relationship of Toxicity of Alkyl(1-phenylsulfonyl) Cycloalkane-carboxylates Using MLSER Model and Ab initio

Quantitative Structure–Activity Relationship (QSAR) Modeling of EC₅₀of Aquatic Toxicities forDaphnia magna

Partial least square and k‐nearest neighbor algorithms for improved 3D quantitative spectral data–activity relationship consensus modeling of acute toxicity

Contact Info

Product

Resources

About

Acute toxicity of alkyl (1-phenylsulfonyl)cycloalsane-carboxylates to Daphnia magna and quantitative structure—Activity relationships

Cited by 10 publications

References 8 publications

Quantitative Structure-activity Relationship of Toxicity of Alkyl(1-phenylsulfonyl) Cycloalkane-carboxylates Using MLSER Model and Ab initio

Quantitative Structure-activity Relationship of Toxicity of Alkyl(1-phenylsulfonyl) Cycloalkane-carboxylates Using MLSER Model and Ab initio

Quantitative Structure–Activity Relationship (QSAR) Modeling of EC50of Aquatic Toxicities forDaphnia magna

Partial least square and k‐nearest neighbor algorithms for improved 3D quantitative spectral data–activity relationship consensus modeling of acute toxicity

Contact Info

Product

Resources

About

Quantitative Structure–Activity Relationship (QSAR) Modeling of EC₅₀of Aquatic Toxicities forDaphnia magna