Phenolic Acid-ß-Cyclodextrin Complexation Study to Mask Bitterness in Wheat Bran: A Machine Learning-Based QSAR Study.

The need to solvate and encapsulate hydro-sensitive molecules drives noticeable trends in the applications of cyclodextrins in the pharmaceutical industry, in foods, polymers, materials, and in agricultural science. Among them, ß-cyclodextrin is one of the most used for the entrapment of phenolic acid compounds to mask the bitterness of wheat bran. In this regard, there is still a need for good data and especially for a robust predictive model that assesses the bitterness masking capabilities of ß-cyclodextrin for various phenolic compounds. This study uses a dataset of 20 phenolic acids docked into the ß-cyclodextrin cavity to generate three different binding constants. The data from the docking study were combined with topological, topographical, and quantum-chemical features from the ligands in a machine learning-based structure-activity relationship study. Three different models for each binding constant were computed using a combination of the genetic algorithm (GA) and multiple linear regression (MLR) approaches. The developed ML/QSAR models showed a very good performance, with high predictive ability and correlation coefficients of 0.969 and 0.984 for the training and test sets, respectively. The models revealed several factors responsible for binding with cyclodextrin, showing positive contributions toward the binding affinity values, including such features as the presence of six-membered rings in the molecule, branching, electronegativity values, and polar surface area.

Multi-Endpoint Acute Toxicity Assessment of Organic Compounds Using Large-Scale Machine Learning Modeling.

In recent years, alternative animal testing methods such as computational and machine learning approaches have become increasingly crucial for toxicity testing. However, the complexity and scarcity of available biomedical data challenge the development of predictive models. Combining nonlinear machine learning together with multicondition descriptors offers a solution for using data from various assays to create a robust model. This work applies multicondition descriptors (MCDs) to develop a QSTR (Quantitative Structure-Toxicity Relationship) model based on a large toxicity data set comprising more than 80,000 compounds and 59 different end points (122,572 data points). The prediction capabilities of developed single-task multi-end point machine learning models as well as a novel data analysis approach with the use of Convolutional Neural Networks (CNN) are discussed. The results show that using MCDs significantly improves the model and using them with CNN-1D yields the best result (R2train = 0.93, R2ext = 0.70). Several structural features showed a high level of contribution to the toxicity, including van der Waals surface area (VSA), number of nitrogen-containing fragments (nN+), presence of S-P fragments, ionization potential, and presence of C-N fragments. The developed models can be very useful tools to predict the toxicity of various compounds under different conditions, enabling quick toxicity assessment of new compounds.

A Novel Machine-Learning Framework Based on a Hierarchy of Dispute Models for the Identification of Fish Species Using Multi-Mode Spectroscopy.

Seafood mislabeling rates of approximately 20% have been reported globally. Traditional methods for fish species identification, such as DNA analysis and polymerase chain reaction (PCR), are expensive and time-consuming, and require skilled technicians and specialized equipment. The combination of spectroscopy and machine learning presents a promising approach to overcome these challenges. In our study, we took a comprehensive approach by considering a total of 43 different fish species and employing three modes of spectroscopy: fluorescence (Fluor), and reflectance in the visible near-infrared (VNIR) and short-wave near-infrared (SWIR). To achieve higher accuracies, we developed a novel machine-learning framework, where groups of similar fish types were identified and specialized classifiers were trained for each group. The incorporation of global (single artificial intelligence for all species) and dispute classification models created a hierarchical decision process, yielding higher performances. For Fluor, VNIR, and SWIR, accuracies increased from 80%, 75%, and 49% to 83%, 81%, and 58%, respectively. Furthermore, certain species witnessed remarkable performance enhancements of up to 40% in single-mode identification. The fusion of all three spectroscopic modes further boosted the performance of the best single mode, averaged over all species, by 9%. Fish species mislabeling not only poses health-related risks due to contaminants, toxins, and allergens that could be life-threatening, but also gives rise to economic and environmental hazards and loss of nutritional benefits. Our proposed method can detect fish fraud as a real-time alternative to DNA barcoding and other standard methods. The hierarchical system of dispute models proposed in this work is a novel machine-learning tool not limited to this application, and can improve accuracy in any classification problem which contains a large number of classes.

In Silico Prediction of the Toxicity of Nitroaromatic Compounds: Application of Ensemble Learning QSAR Approach.

In this work, a dataset of more than 200 nitroaromatic compounds is used to develop Quantitative Structure-Activity Relationship (QSAR) models for the estimation of in vivo toxicity based on 50% lethal dose to rats (LD50). An initial set of 4885 molecular descriptors was generated and applied to build Support Vector Regression (SVR) models. The best two SVR models, SVR_A and SVR_B, were selected to build an Ensemble Model by means of Multiple Linear Regression (MLR). The obtained Ensemble Model showed improved performance over the base SVR models in the training set (R2 = 0.88), validation set (R2 = 0.95), and true external test set (R2 = 0.92). The models were also internally validated by 5-fold cross-validation and Y-scrambling experiments, showing that the models have high levels of goodness-of-fit, robustness and predictivity. The contribution of descriptors to the toxicity in the models was assessed using the Accumulated Local Effect (ALE) technique. The proposed approach provides an important tool to assess toxicity of nitroaromatic compounds, based on the ensemble QSAR model and the structural relationship to toxicity by analyzed contribution of the involved descriptors.