A comparative study of chromatographic behavior and lipophilicity of selected natural styryl lactones, their derivatives and analogues

Karadžić, Milica; Lončar, Davor M.; Benedeković, Goran; Kovačević, Ivana; Popsavin, Velimir; Kоvаčеvić, Strаhinjа; Jevrić, Lidija R.; Podunavac‐Kuzmanović, Sanja O.

doi:10.1016/j.ejps.2017.05.006

Cited by 11 publications

(5 citation statements)

References 35 publications

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“…Hierarchical Cluster Analysis (HCA) has become widely used clustering method in chemometrics. 25,26 It is well-known that HCA is based on the division of the analysed objects (samples, molecules, models) in that way, so the most similar objects (considering the space of the analysed variables) are placed in the same cluster. 27 A graphical representation known as a dendrogram is shaped like a tree where the peripheral branches represent objects.…”

Section: Chemometric Analysismentioning

confidence: 99%

New protic ionic liquids for fungi and bacteria removal from paper heritage artefacts

et al. 2019

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Section: Chemometric Analysismentioning

confidence: 99%

New protic ionic liquids for fungi and bacteria removal from paper heritage artefacts

et al. 2019

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“…Among other separation techniques, micellar liquid chromatography (MLC) or micellar electrokinetic chromatography (MEEKC), respectively, in which the mobile phase comprises surfactants that allow better mapping of penetration of molecules through biomembranes can be also be used for lipophilicity determination [ 7 ]. The literature review shows that numerous publications have dealt with the subject of determining the lipophilicity of various bioactive compounds using chromatographic methods [ 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 ].…”

Section: Introductionmentioning

confidence: 99%

Assessment of Lipophilicity Parameters of Antimicrobial and Immunosuppressive Compounds

2023

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Lipophilicity in addition to the solubility, acid-base character and stability is one of the most important physicochemical parameters of a compound required to assess the ADMET properties (absorption, distribution, metabolism, excretion and toxicity) of a bioactive molecule. Therefore, the subject of this work was to determine the lipophilicity parameters of selected antimicrobial and immunosuppressive compounds such as delafloxacin, linezolid, sutezolid, ceftazidime, everolimus and zotarolimus using thin-layer chromatography in reversed phase system (RP-TLC). The chromatographic parameters of lipophilicity (RMW) for tested compounds were determined on different stationary phases: RP18F254, RP18WF254 and RP2F254 using ethanol, acetonitrile, and propan-2-ol as organic modifiers of mobile phases used. Chromatographically established RMW values were compared with partition coefficients obtained by different computational methods (AlogPs, AClogP, AlogP, MlogP, XlogP2, XlogP3, logPKOWWIN, ACD/logP, milogP). Both cluster and principal component analysis (CA and PCA) of the received results allowed us to compare the lipophilic nature of the studied compounds. The sum of ranking differences analysis (SRD) of all lipophilicity parameters was helpful to select the most effective method of determining the lipophilicity of the investigated compounds. The presented results demonstrate that RP-TLC method may be a good tool in determining the lipophilic properties of studied substances. Obtained lipophilic parameters of the compounds can be valuable in the design of their new derivatives as efficient antimicrobial and immunosuppressive agents.

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“…Another parameter, C 0 , expresses the concentration of an organic change in the mobile phase for which the distribution of the solute between the two phases is equal. One of the essential elements of the chromatographic system, the mobile phase, has a significant role in chromatographic behavior of different solvents [2,19,20].…”

Section: Introductionmentioning

confidence: 99%

Lipophilicity as a Central Component of Drug-Like Properties of Chalchones and Flavonoid Derivatives

2019

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Lipophilcity is an important physico-chemical parameter that influences membrane transport and binding ability to action. Migration distance following complete elution of compounds was used to calculate different lipophilicity-related parameters. The aim of this study is to show that lipophilicity is a central component of thiazole chalcones and flavonoid derivatives regarding their drug-like properties. Experimental and computational methods were used. This study considers 44 previously synthesized compounds (thiazole chalcones, flavanones, flavones, 3-hydroxyflavones, and their acetylated derivatives). The concerned compounds have shown antitumoral hallmarks and antibacterial activity in vitro. The experimental method used to determine compounds’ lipophilicity was the reverse-phase thin layer chromatography (RP-TLC). Lipophilicity related parameters—isocratic retention factor (RM), relative lipophily (RM0), slope (b), chromatographic hydrophobic index (φ0), scores of principal components (PC1/RM)—were determined based on reverse-phase chromatography results.

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A comparative study of chromatographic behavior and lipophilicity of selected natural styryl lactones, their derivatives and analogues

Cited by 11 publications

References 35 publications

New protic ionic liquids for fungi and bacteria removal from paper heritage artefacts

New protic ionic liquids for fungi and bacteria removal from paper heritage artefacts

Assessment of Lipophilicity Parameters of Antimicrobial and Immunosuppressive Compounds

Lipophilicity as a Central Component of Drug-Like Properties of Chalchones and Flavonoid Derivatives

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