Rapid experimental and computational determination of phenethylamine drug analogue lipophilicity

McBride, Ethan M.; Kretsch, Amanda; Garibay, Luis K.; Brigance, Katie; Frey, B. Y.; Buss, Brandon; Verbeck, Guido F.

doi:10.1016/j.forc.2016.07.004

Cited by 6 publications

(4 citation statements)

References 24 publications

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“…The mixed system with two phases eventually achieved equilibrium by shaking for 24 h at preset temperature. The quantity of the drug was determined by HPLC, K O/W , and logP were calculated according to the literature (26)(27)(28).…”

Section: Measurements Of Physicochemical Parameters For Shmentioning

confidence: 99%

Characterization and In Vitro Permeation Study of Cubic Liquid Crystal Containing Sinomenine Hydrochloride

Chu

Gui

et al. 2018

AAPS PharmSciTech

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This study developed a new transdermal delivery system for the improved delivery of sinomenine hydrochloride (SH). The delivery system utilized the advantages of lyotropic liquid crystals (LLC) creating an adaptable system that offers a variety of options for the field of transdermal delivery. The formulation was prepared, characterized, and evaluated for its skin penetration in vitro. In the study, the appearance of samples was characterized by visual observation, and these LLC gels were colorless and transparent. Polarizing light microscopy (PLM) and small-angle X-ray diffraction (SAXS) were used to analyze the internal structures of gels, and the gels displayed a cubic double-diamond (P3) internal structure with a dark field of vision. The Franze diffusion cell was used to evaluate its skin penetration. There were several factors which might influence the skin penetration of drugs, such as drug loading, water content, and the layer spacing of the LLC. In our case, drug concentration gradient played a more powerful role. The result of in vitro permeation studies demonstrated that the drug concentration was higher; the cumulative osmotic quantity of SH (Q) was greater. Therefore, the system was a promising formulation for successful percutaneous delivery of SH through the skin.

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Section: Measurements Of Physicochemical Parameters For Shmentioning

confidence: 99%

Characterization and In Vitro Permeation Study of Cubic Liquid Crystal Containing Sinomenine Hydrochloride

Chu

Gui

et al. 2018

AAPS PharmSciTech

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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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“…There are many computational variants for predicting this property, using simple methods based on a small number of descriptors up to sophisticated neural network algorithms and involving thousands of correction factors. These methods can be greatly improved by local corrections; it is essential to compare the results with those provided by experimental methods [17,18].…”

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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Rapid experimental and computational determination of phenethylamine drug analogue lipophilicity

Cited by 6 publications

References 24 publications

Characterization and In Vitro Permeation Study of Cubic Liquid Crystal Containing Sinomenine Hydrochloride

Characterization and In Vitro Permeation Study of Cubic Liquid Crystal Containing Sinomenine Hydrochloride

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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