Investigation of lipophilicity and pharmacokinetic properties of 2-(methoxy)phenylpiperazine dopamine D2 ligands

Šegan, Sandra; Penjišević, Jelena Z.; Šukalović, Vladimir; Andrić, Deana; Milojković‐Opsenica, Dušanka; Kostić-Rajačić, Slađana

doi:10.1016/j.jchromb.2019.06.006

Cited by 9 publications

(8 citation statements)

References 23 publications

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“…According to this rule, the lipophilicity (logP), molecular weight (MW), number of acceptors (HA), and donors (HD) of hydrogen bond should be a multiple of five [ 54 ]. In an attempt to improve the prediction of bioavailability, the rules were expanded by Veber to the number of rotatable bonds (RB) and topological polar surface area (TPSA) are also determined [ 55 , 56 ]. The molecular descriptors for tested hybrids 1 – 16 are presented in Table 5 .…”

Section: Resultsmentioning

confidence: 99%

Lipophilicity, Pharmacokinetic Properties, and Molecular Docking Study on SARS-CoV-2 Target for Betulin Triazole Derivatives with Attached 1,4-Quinone

et al. 2021

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A key parameter in the design of new active compounds is lipophilicity, which influences the solubility and permeability through membranes. Lipophilicity affects the pharmacodynamic and toxicological profiles of compounds. These parameters can be determined experimentally or by using different calculation methods. The aim of the research was to determine the lipophilicity of betulin triazole derivatives with attached 1,4-quinone using thin layer chromatography in a reverse phase system and a computer program to calculate its theoretical model. The physiochemical and pharmacokinetic properties were also determined by computer programs. For all obtained parameters, the similarity analysis and multilinear regression were determined. The analyses showed that there is a relationship between structure and properties under study. The molecular docking study showed that betulin triazole derivatives with attached 1,4-quinone could inhibit selected SARS-CoV-2 proteins. The MLR regression showed that there is a correlation between affinity scoring values (ΔG) and the physicochemical properties of the tested compounds.

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Section: Resultsmentioning

confidence: 99%

Lipophilicity, Pharmacokinetic Properties, and Molecular Docking Study on SARS-CoV-2 Target for Betulin Triazole Derivatives with Attached 1,4-Quinone

et al. 2021

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“…The highest correlation with the calculated log P values could be observed for parameters log D 11exp and C 0 in both chromatographic systems. Parameter C 0 , which comprises both chromatographically measured lipophilicity indexes ( R M 0 and b ), was also established as the most relevant in the previously studied series of arylpiperazines (Šegan et al, 2019). C 0 (Ac) and C 0 (THF) exhibited the highest correlation with mi log P ( r = 0.95 and 0.88, respectively).…”

Section: Resultsmentioning

confidence: 99%

“…RP‐TLC involves extrapolation of retention parameter R M to pure water with at least five isocratic mobile phase ratios to estimate the retention value of pure water, R M 0 (Apostolov et al, 2023). The reason for the use of pure water extrapolation is that a pure water mobile phase has very low elution strength (Ogden & Dorsey, 2019; Šegan et al, 2019). Another possibility is the use of an interpolation method with the calibration set of compounds with known log P and a single TLC run.…”

Section: Introductionmentioning

confidence: 99%

Evaluation of lipophilicity and drug‐likeness of donepezil‐like compounds using reversed‐phase thin‐layer chromatography

Šegan,

Krunić,

Andrić

et al. 2024

Biomedical Chromatography

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Fourteen donepezil‐like acetylcholinesterase (AChE) inhibitors from our library were analyzed using reversed‐phase thin‐layer chromatography to assess their lipophilicity and blood–brain barrier permeability. Compounds possessed N‐benzylpiperidine and N,N‐diarylpiperazine moieties connected via a short carboxamide or amine linker. Retention parameters RM0, b, and C0 were considered as the measures of lipophilicity. Besides, logD of the investigated compounds was determined chromatographically using standard compounds with known logPow and logD values at pH 11. Experimentally obtained lipophilicity parameters correlated well with in silico generated results, and the effect of the nature of the linker between two pharmacophores and substituents on the arylpiperazine part of the molecule was observed. As a result of drug‐likeness analysis, both Lipinski's rule of five and Veber's rule parameters were determined, suggesting that examined compounds could be potential candidates for further drug development. Principal component analysis was performed to obtain an insight into a grouping of compounds based on calculated structural descriptors, experimentally obtained values of lipophilicity, and AChE inhibitory activity.

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“…Several reports indicated that RP-TLC can be considered as an efficient tool for prediction of lipophilicity [11,12,13,14,15]. For this reason, two main RP-TLC stationary phases, C 8 and C 18 -bonded silica gels were investigated during this study.…”

Section: Resultsmentioning

confidence: 99%

Lipophilicity Determination of Quaternary (Fluoro)Quinolones by Chromatographic and Theoretical Approaches

Ciura

Fedorowicz

Andrić

et al. 2019

IJMS

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Lipophilicity is a vital physicochemical parameter of a molecule, which affects several biological processes such as absorption, tissue distribution, and pharmacokinetic properties. In this study, evaluation of lipophilicities of a series of novel fluoroquinolone-Safirinium dye hybrids using chromatographic and computational methods is presented. Fluoroquinolone-Safirinium dye hybrids have been synthesized as new dual-acting hydrophilic antibacterial agents. Reversed phase thin-layer chromatography and micellar electrokinetic chromatography experiments were carried out. Furthermore, logP values of the target structures were predicted by means of different software platforms and algorithms. In order to assess similarities and dissimilarities of the obtained lipophilicity indexes, cluster analysis and sum of ranking differences were performed. The significant differences of calculated logP values (α = 0.05, p < 0.001) indicated that an experimental approach is necessary for lipophilicity prediction of this class of antibiotics. Chromatographic data indicated that the newly synthesized hybrid (fluoro)quinolone-based quaternary ammonium derivatives show less lipophilic character than the parent (fluoro)quinolones. Additionally, the chromatographically obtained lipophilicity indexes were evaluated for possible application in quantitative retention–activity relationships. The established lipophilicity models have the potential to predict antimicrobial activities of a series of quaternary (fluoro)quinolones against Bacillus subtilis, Escherichia coli, and Proteus vulgaris.

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Investigation of lipophilicity and pharmacokinetic properties of 2-(methoxy)phenylpiperazine dopamine D2 ligands

Cited by 9 publications

References 23 publications

Lipophilicity, Pharmacokinetic Properties, and Molecular Docking Study on SARS-CoV-2 Target for Betulin Triazole Derivatives with Attached 1,4-Quinone

Lipophilicity, Pharmacokinetic Properties, and Molecular Docking Study on SARS-CoV-2 Target for Betulin Triazole Derivatives with Attached 1,4-Quinone

Evaluation of lipophilicity and drug‐likeness of donepezil‐like compounds using reversed‐phase thin‐layer chromatography

Lipophilicity Determination of Quaternary (Fluoro)Quinolones by Chromatographic and Theoretical Approaches

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