Lipophilicity study of fifteen fluoroquinolones by reversed-phase thin-layer chromatography

Hubicka, Urszula; Żuromska-Witek, Barbara; Komsta, Łukasz; Krzek, Jan

doi:10.1039/c4ay02203c

Cited by 18 publications

(10 citation statements)

References 26 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The main reason for this fact can be, for example, the different adsorbing properties of applied stationary phases or eluents such as their elution strength or surface tension, which show an influence on the results of the R M parameter. As was confirmed in previous studies, the pH value of distilled water used as a mobile phase component also has a large impact on the value of both the chromatographic lipophilicity parameters and the experimental partition coefficients [8,11,18,31].…”

Section: Resultssupporting

confidence: 55%

See 1 more Smart Citation

Comparison of the Utility of RP-TLC Technique and Different Computational Methods to Assess the Lipophilicity of Selected Antiparasitic, Antihypertensive, and Anti-inflammatory Drugs

2019

View full text Add to dashboard Cite

The aim of this study was to assess the lipophilicity of selected antiparasitic, antihypertensive and non-steroidal anti-inflammatory drugs (NSAIDs) by means of reversed phase–thin layer chromatography (RP-TLC) as well by using Soczewiński–Wachtmeister’s and J. Ościk’s equations. The lipophilicity parameters of all examined compounds obtained under various chromatographic systems (i.e., methanol-water and acetone-water, respectively) and those determined on the basis of Soczewiński-Wachtmeister’s and Ościk’s equations (i.e., RMWS and RMWO) were compared with the theoretical ones (e.g., AlogPs, AClogP, milogP, AlogP, MlogP, XlogP2, XlogP3) and the experimental value of the partition coefficient (logPexp). It was found that the RMWS parameter may be a good alternative tool in describing the lipophilic nature of biologically active compounds with a high and low lipophilicity (i.e., antihypertensive and antiparasitic drugs). Meanwhile, the RMWO was more suitable for compounds with a medium lipophilicity (i.e., non-steroidal anti-inflammatory drugs). The chromatographic parameter 0(a) can be helpful for the prediction of partition coefficients, i.e., AClogP, XlogP3, as well as logPexp of examined compounds.

show abstract

Section: Resultssupporting

confidence: 55%

“…Many various lipophilicity descriptors and methods have been well described and proposed for the evaluation of the lipophilic properties of different compounds in review articles from recent years [7,8,9]. Currently, the chromatographic approach is used the most [10,11,12,13,14,15,16,17,18].…”

Section: Introductionmentioning

confidence: 99%

Comparison of the Utility of RP-TLC Technique and Different Computational Methods to Assess the Lipophilicity of Selected Antiparasitic, Antihypertensive, and Anti-inflammatory Drugs

2019

View full text Add to dashboard Cite

show abstract

“…showed very weak changes of retention compared to unbuffered systems. Similar results have been reported by Hubicka and co-workers for non-buffered TLC lipophilicity determination of FQs [16]. As proposed by Komsta, who examined the impact of several organic modifiers of mobile phase in terms of log P predictions [17], methanol was chosen as mobile phase organic component.…”

Section: Resultssupporting

confidence: 61%

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

Ciura

Fedorowicz

Andrić

et al. 2019

IJMS

View full text Add to dashboard Cite

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.

show abstract

“…In this way, the intercept R M 0 is practically the R M value of the compound that corresponds to the extrapolated zero organic phase concentration in the eluent. In the same manner, the slope b is the change in the lipophilicity caused by a unit concentration change in the organic phase [ 28 , 29 ].…”

Section: Resultsmentioning

confidence: 99%

Biological Evaluation and Structural Analysis of Some Aminodiphenylamine Derivatives

et al. 2023

View full text Add to dashboard Cite

4-Aminodiphenylamino derivatives were investigated for their antioxidant and hydrophobicity character, together with other biological measurements, such as antimicrobial and antibiofilm activity. Among these nine compounds used, we obtained novel derivatives via reaction of the starting material with NBD-chloride. Therefore, we performed a full structural analysis for these compounds, i.e., elemental analysis, IR, UV-Vis, 1H- and 13C-NMR, ESI-MS, X-ray diffraction on single crystal, etc. The hydrophobicity of all the compounds was measured either experimentally using the RP-TLC technique, or via calculation using the fragments method. The other structural characteristics were analyzed, and a correlation between the experimental and computed properties was found. Moreover, the results of the biological evaluation showed that some of the synthesized compounds have antimicrobial and antibiofilm activity.

show abstract

Lipophilicity study of fifteen fluoroquinolones by reversed-phase thin-layer chromatography

Abstract: The lipophilicity of fifteen fluoroquinolones has been investigated.

Cited by 18 publications

References 26 publications

Comparison of the Utility of RP-TLC Technique and Different Computational Methods to Assess the Lipophilicity of Selected Antiparasitic, Antihypertensive, and Anti-inflammatory Drugs

Comparison of the Utility of RP-TLC Technique and Different Computational Methods to Assess the Lipophilicity of Selected Antiparasitic, Antihypertensive, and Anti-inflammatory Drugs

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

Biological Evaluation and Structural Analysis of Some Aminodiphenylamine Derivatives

Contact Info

Product

Resources

About