The assessment of the environmental fate and (eco)toxicological effects of pesticide compounds is of crucial importance. The present review is focused on Quantitative Structure-Property Relationships ...(QSPR) applications on three environmentally relevant physicochemical properties of pesticides, which can be used for assessing their environmental partition and transport, as well as exposure potential namely water solubility, octanol-water partition coefficient and vapour pressure. This article revises various interesting QSPR applications with special emphasis on studies developed during the 2009-2019 period.
The fumigant and topical activities exhibited by 27 plant-derived essentials oils (EOs) on adult M. domestica housefly are predicted through the Quantitative Structure-Activity Relationship (QSAR) ...theory. These molecular structure based calculations are performed on 253 structurally diverse compounds from the EOs, where the number of constituents in each essential oil mixture varies between 2 to 24. A large number of 86,048 non-conformational mixture descriptors are derived as linear combinations of the molecular descriptors of the EO components. Two strategies are compared for the mixture descriptor formulation, which consider or avoid the use of the chemical composition. The multivariable linear regression QSAR models of the present work are useful for fumigant and topical applications, describing predictive parallelisms for the insecticidal activity of the analysed complex mixtures.
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•The solvatochromism of trimethoprim (TMP) was studied by UV–Vis spectroscopy.•Absorption spectra of TMP were recorded in 13 solvents and 3 binary aqueous mixtures.•The solvent ...effects in pure and binary systems were interpreted by Kamlet–Taft LSER.•Specific solute–solvent interactions were considered in TD-DFT calculations.•Preferential solvation of organic solvent is observed in all analyzed binary mixtures.
The solvatochromic behavior of trimethoprim (TMP) was analyzed using UV–Vis spectroscopy and DFT methods in neat and binary aqueous solvent mixtures. The effects of solvent dipolarity/polarizability and solvent–solute hydrogen bonding interactions on the absorption maxima were evaluated by means of the linear solvation energy relationship concept of Kamlet and Taft. This analysis indicated that both interactions play an important role in the position of the absorption maxima in neat solvents. The simulated absorption spectra of TMP and TMP:(solvent)n complexes in ACN and H2O using TD-DFT methods were in agreement with the experimental ones. Binary aqueous mixtures containing as co-solvents DMSO, ACN and EtOH were studied. Preferential solvation was detected as a nonideal behavior of the wavenumber curve respective to the analytical mole fraction of co-solvent in all binary systems. TMP molecules were preferentially solvated by the organic solvent over the whole composition range. Index of preferential solvation, as well as the influence of solvent parameters were calculated as a function of solvent composition.
This article reviews multi-criteria QSAR applications on Acetylcholinesterase inhibitors as palliative drugs for Alzheimer's Disease, published in the period 2001-2011. It includes QSAR models for ...different series of compounds, comparative studies, and advances in methodologies. This period is marked by a shift in focus from palliative treatment to pathogenesis. However, we believe that research into palliative treatment should continue. More comparative studies are desirable. In order to facilitate comparative and general studies on Acetylcholinesterase inhibitors, a standard experimental protocol for measuring an inhibitor's potency is needed. Finally, we recommend chemists to work closely with system and molecular biologists.
A predictive Quantitative Structure-Property Relationship (QSPR) for the refractive indices of 370 solvents commonly used in the processing and analysis of polymers is presented, using as chemical ...information descriptors the simplified molecular input line entry system (SMILES). The model employs a flexible molecular descriptor and a conformation-independent approach. Various well-known techniques, such as the use of an external test set of compounds, the cross-validation method, and Y-randomization were used to test and validate the established equations. The predicted values were finally compared with published results from the literature. The simple model proposed correlates the refractive index values with good accuracy, and it is not dependent on 3D-molecular geometries.
We establish useful models that relate experimentally measured biological activities of compounds to their molecular structure. The
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Spodoptera litura species exhibited by ...aurones, chromones, 3-coumarones and flavones is analyzed in this work through the hypothesis encompassed in the Quantitative Structure–Activity Relationships (QSAR) Theory. This constitutes a first necessary computationally based step during the design of more bio-friendly repellents that could lead to insights for improving the insecticidal activities of the investigated compounds.
After optimizing the molecular structure of each furane and pyrane benzoderivative with the semiempirical molecular orbitals method PM3, more than a thousand of constitutional, topological, geometrical and electronic descriptors are calculated and multiparametric linear regression models are established on the antifeedant potencies. The feature selection method employed in this study is the Replacement Method, which has proven to be successful in previous analyzes. We establish the QSAR both for the complete molecular set of compounds and also for each chemical class, so that acceptably describing the variation of the inhibitory activities from the knowledge of their structure and thus achieving useful predictive results.
The main interest of developing trustful QSAR models is that these enable the prediction of compounds having no experimentally measured activities for any reason. Therefore, the structure–activity relationships are further employed for investigating the antifeedant activity on previously synthesized 2-,7-substituted benzopyranes, which do not pose any measured values on the biological expression. One of them, 2-(α-naphtyl)-4H-1-benzopyran-4-one, results in a promising structure to be experimentally analyzed as it has predicted
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► Aminograms account for fingerprints of free amino acids and ammonia in wines. ► Linear QSPR models for predicting aminograms in Merlot and Torrontés wines. ► Molecular structure represented through ...Dragon molecular descriptors. ► Validation of the QSPR models with an external test set and Cross-Validation. ► These are among the first QSPR for predicting aminograms of wines.
Quantitative structure–property relationships (QSPRs) were applied to the aminograms obtained by HPLC in our laboratories for Torrontés and Merlot wines. Dragon theoretical descriptors were derived for a set of optimized amino acid structures with the purpose of establishing QSPR models. The statistical Replacement Method was used for designing the best multi-parametric linear regression models, which included structural features selected from a pool containing 1497 constitutional, topological, geometrical or electronic molecular descriptors. Predicted QSPR results were in good agreement with experimental amino acid profiles. The developed QSPR approach showed to be of practical value for distinguishing each wine varietal, and for calculating experimentally non-available amino acid concentrations of Torrontés and Merlot wines. It was also useful for assessing wine authenticity; the models were especially suitable for Merlot and Torrontés wines.
The ANTARES dataset is a large collection of known and verified experimental bioconcentration factor data, involving 851 highly heterogeneous compounds from which 159 are pesticides. The BCF ANTARES ...data were used to derive a conformation-independent QSPR model. A large set of 27,017 molecular descriptors was explored, with the main intention of capturing the most relevant structural characteristics affecting the studied property. The structural descriptors were derived with different freeware tools, such as PaDEL, Epi Suite, CORAL, Mold
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, RECON, and QuBiLs-MAS, and so it was interesting to find out the way that the different descriptor tools complemented each other in order to improve the statistical quality of the established QSPR. The best multivariable linear regression models were found with the Replacement Method variable sub-set selection technique. The proposed QSPR model improves previous reported models of the bioconcentration factor in the present dataset.
We test a new algorithm for the search of an optimal subset of molecular descriptors from a large set of them. As a practical realistic application we predict the normal boiling points of 200 organic ...molecules by means of molecular descriptors selected from a set of more than thousand of rigid molecular descriptors produced by the DRAGON 5 evaluation software, plus two flexible descriptors. We thus improve previous results derived from the application of Correlation Weighting of Atomic Orbitals with Extended Connectivity of Zero- and First-Order Graphs of Atomic Orbitals.
In a continuing effort of our research group to identify new active compounds against
Mycobacterium tuberculosis, we resort to the quantitative structure–activity relationships (QSARs) theory. For ...this purpose, we employ certain parameters of potency, cytotoxicity and selectivity as given by the Tuberculosis Antimicrobial Acquisition & Coordinating Facility (TAACF) program. The molecular structure of 43 quinoxaline-2-carboxylate 1,4-di-
N-oxide derivatives is appropriately represented by 1497 DRAGON type of theoretical descriptors, and the best linear regression models established in this work are demonstrated to result predictive. The application of the QSAR equations developed now serves as a rational guide for the proposal of new candidate structures that still do not have experimentally assigned biological data.
