Chromatographic descriptors in QSAR study of barbiturates

Apostolov, Suzana; Vastag, Gyöngyi; Mrdjan, Gorana; Nakomčić, Jelena; Stojiljković, Ivana

doi:10.1080/10826076.2019.1590207

Cited by 7 publications

(7 citation statements)

References 33 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Chromatographic techniques offer the possibility of taking the interactions of the molecules with different columns in several conditions (pH, solvent) into account, and then better characterizing the molecular interactions with the biological system. That is the reason why chromatographic descriptors were combined with molecular ones in the QSAR models [ 26 , 27 , 28 , 29 , 30 , 40 , 41 , 42 ]. The most commonly used chromatographic descriptors are the retention factors that can be determined on several orthogonal stationary phases with different pH and solvents [ 26 , 28 , 30 ].…”

Section: Discussionmentioning

confidence: 99%

“…It is, therefore, anticipated that the placental transfer efficiency of these structurally related BPs will be hardly predicted by descriptors based on molecular structure alone. In many cases, experimental descriptors such as chromatographic retention have been added to molecular ones to improve the QSAR models [ 26 , 27 ]. Indeed, the chromatographic retention depends on the interaction of the compound of interest, i.e., its structure, with the stationary phase and the mobile phase.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Contribution of Reliable Chromatographic Data in QSAR for Modelling Bisphenol Transport across the Human Placenta Barrier

et al. 2023

View full text Add to dashboard Cite

Regulatory measures and public concerns regarding bisphenol A (BPA) have led to its replacement by structural analogues, such as BPAF, BPAP, BPB, BPF, BPP, BPS, and BPZ. However, these alternatives are under surveillance for potential endocrine disruption, particularly during the critical period of fetal development. Despite their structural analogies, these BPs differ greatly in their placental transport efficiency. For predicting the fetal exposure of this important class of emerging contaminants, quantitative structure-activity relationship (QSAR) studies were developed to model and predict the placental clearance indices (CI). The most usual input parameters were molecular descriptors obtained by modelling, but for bisphenols (BPs) with structural similarities or heteroatoms such as sulfur, these descriptors do not contrast greatly. This study evaluated and compared the capacity of QSAR models based either on molecular or chromatographic descriptors or a combination of both to predict the placental passage of BPs. These chromatographic descriptors include both the retention mechanism and the peak shape on columns that reflect specific molecular interactions between solute and stationary and mobile phases and are characteristic of the molecular structure of BPs. The chromatographic peak shape such as the asymmetry and tailing factors had more influence on predicting the placental passage than the usual retention parameters. Furthermore, the QSAR model, having the best prediction capacity, was obtained with the chromatographic descriptors alone and met the criteria of internal and cross validation. These QSAR models are crucial for predicting the fetal exposure of this important class of emerging contaminants.

show abstract

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Contribution of Reliable Chromatographic Data in QSAR for Modelling Bisphenol Transport across the Human Placenta Barrier

et al. 2023

View full text Add to dashboard Cite

show abstract

“…Selected barbituric acid derivatives (Table 1) were subjected to RPTLC C18/UV 254s in different systems of water -organic modifier, during which the values of the chromatographic parameters R M 0 and m were determined [17,18].…”

Section: Methodsmentioning

confidence: 99%

“…In order to make the results easier to understand, Table 4 and Table 5 list the chromatographic parameters of the studied barbituric acid derivatives, previously determined in mixtures of water and various organic modifiers [17,18]. Application possibility of parameters R M 0 and m as QSRR descriptors in the assessment of pharmacokinetic and toxic properties of barbituric acid derivatives was examined by their correlation with software obtained ADMET predictors using the linear regression method.…”

Section: Quantitative Relationship Of Chromatographic Parameters and ...mentioning

confidence: 99%

QSRR Descriptors as a Tool in the Study of the Barbituric Acid Derivatives’ Biological Profile

Apostolov

Stojiljković

Vaštag

2022

View full text Add to dashboard Cite

Thanks to the in silico approach in drug design, the identification of new molecules is enabled and facilitated, as well as the optimization of the pharmacokinetics and toxicity of compounds obtained from different sources. Chromatographic methods, on the other hand, provide accurate and reliable information on the influence of the nature of substituents and applied organic modifiers on the pharmacological behavior of compounds, relying on the existence of similarities between intermolecular interactions that determine compound behavior in biological and chromatographic media. Barbituric acid derivatives were subjected to QSRR analysis and the parameters obtained by reversed phase thin layer chromatography (RP TLC18 F254s) were correlated with selected software-derived predictors of permeability, pharmacokinetics and toxicity using the method of linear regression. Тhus satisfactory mathematical models were obtained.

show abstract

“…Barbiturates: 2016 Rotaxanes comprising a macrocylic Hamilton receptor obtained using active template synthesis; synthesis, spectroscopic and structural characterization of barbiturate anions using Raman spectral analysis [ 884 ]; FT-IR, multinuclear NMR (1H, 13C) and MS characterization of Barbiturate bearing aroylhydrazine derivatives [ 885 ]; 2017 LC-MS/MS method developed for the simultaneous determination of four barbiturates (phenobarbital, pentobarbital, amobarbital and secobarbital) in raw milk [ 886 ]; synthesis and characterization by H-1 and C-13 NMR spectroscopy [ 887 ]; 2018 GC-MS/MS method for quantification of phenobarbital [ 888 ]; 2019 evaluation of chromatographic and computational lipophilicity of barbiturate derivatives [ 889 ]; quantitative determination of the barbiturate [ 890 ]; synthesis of spirodihydrofuryl barbiturates and spirocyclopropyl barbiturates [ 891 ].…”

Section: Routine and Improved Analyses Of Abused Substancesmentioning

confidence: 99%