Molecular mechanism of retention in reversed-phase high-performance liquid chromatography and classification of modern stationary phases by using quantitative structure–retention relationships

Kaliszan, Roman; Straten, Marion A. van; Markuszewski, Michał J.; Cramers, C.A.M.G.; Claessens, H.A.

doi:10.1016/s0021-9673(99)00742-6

Cited by 197 publications

(91 citation statements)

References 36 publications

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“…from log k w )ϩ0. 27 One can see from Eq. 8a that V w and b are the two main structural properties that govern the partitioning mechanism in 1-octanol/water, whereas p* is of lesser significance and a is devoid of any significance.…”

Section: ϭ097)mentioning

confidence: 98%

“…Good relationship between log k w and log P oct was established for the compounds examined. Linear solvation free-energy relationships (LSERs) based on the solvatochromic parameters [25][26][27][28][29] was used to unravel the retention mechanism of the solutes on this novel stationary phase and to compare the mechanism with the partitioning mechanism in 1-octanol/water. In addition, the log k w /log P oct relationship was validated using a test set of 13 neutral, acidic and basic drugs.…”

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confidence: 99%

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Lipophilicity Measurement of Drugs by Reversed Phase HPLC over Wide pH Range Using an Alkaline-Resistant Silica-Based Stationary Phase, XBridgeTM Shield RP18

et al. 2008

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The lipophilicity of solutes, conventionally expressed by their partition coefficient in the 1-octanol/water system (log P oct ), is of high significance from both physicochemical and pharmacological viewpoints.1,2) A number of intermolecular forces between a solute and its environment (i.e., solvents) determine the partitioning process and its equilibration. In pharmacology, the forces are particularly important because they control the migration of solutes (drugs) to biomembranes. Not a few studies have been reported on the relationship between log P oct and adsorption/permeation of drugs in cell cultures and/or tissue preparations. 3-7)The reference procedure to measure log P oct is shake-flask method. The method is, however, time-consuming and narrow in applicable range (ca. Ϫ3Ͻlog PϽ4). The reversedphase HPLC (RP-HPLC) came to be a promising alternative to the shake-flask method, because it has advantages such as high throughput rate (which is of key importance to pharmaceutical industry with a vast number of potential drug candidates), insensitivity to impurities and/or degradation products, broad applicable range, low sample consumption, good accuracy and automation possibilities. In RP-HPLC, lipophilicity indices are derived from the capacity factor log k, which is calculated from Eq. 1,where t r and t 0 are the retention times of the solute and of an unretained compound, respectively. Some workers have used isocratic log k values, measured in an appropriate mobile phase, as a lipophilicity parameter. 8-10) However, the majority of investigators use the capacity factors extrapolated to the 100% water (log k w ) condition in order to eliminate the effects of organic solvent.11-15) Indeed, the log k W has been proved to be useful for the investigation of a series of solutes covering broad lipophilicity range. Generally, the extrapolation is based on a quadratic relationship between the isocratic capacity factor log k and the volume fraction of organic solvent in the mobile phase, j.16) When methanol is used as an organic modifier, a linear relationship (Eq. 2) is often obtained for neutral solutes, 17,18) log kϭϪSjϩlog k wwhere S and log k w are the slope and the intercept of the regression curve, respectively. Until recently, most lipophilicity studies based on RP-HPLC had employed octadecyl silica (ODS) stationary phases 19,20) and silanol deactivated stationary phases. 15,21,22) As for ODS stationary phases, the correlations between log P oct and log k w (or log k) are generally good for structurally related solutes. 19,20) The decrease in correlation between them with increasing structural diversity of solutes is attributed to the specific interactions between the compounds and the residual silanol groups in such stationary phases. 23)Some studies have been done on silanol deactivated stationary phases, Supelcosil LC-ABZ and Discovery RP Amide C18, where their alkyl chains contain amide groups that electrostatically shield silanols from highly polar analytes. High correlations were found between log P ...

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Section: ϭ097)mentioning

confidence: 98%

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confidence: 99%

Lipophilicity Measurement of Drugs by Reversed Phase HPLC over Wide pH Range Using an Alkaline-Resistant Silica-Based Stationary Phase, XBridgeTM Shield RP18

et al. 2008

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“…The SiAlC18 phase had a lower chemical modification of the support surface with C18 groups compared to those C18 silica bonded phases (~3 μmol m -2 ), 33 only 6.1 carbon percent or 0.96 μmol m -2 . Although the aluminized silica surface had a lower chemical modification, the SiAlC18 phase separated completely the mixture of amines, and the solute elution order followed their reversed-phase characteristics (Fig.…”

Section: C18 Bonded Aluminized Silica Phasementioning

confidence: 89%

New Support for High-Performance Liquid Chromatography Based on Silica Coated with Alumina Particles

2014

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A new material based on silica coated with alumina nanoparticles was proposed for use as a chromatographic support for reversed-phase high-performance liquid chromatography. Alumina nanoparticles were synthesized by a sol-gel process in reversed micelles composed of sodium bis(2-ethylhexyl)sulfosuccinate, and the support material was formed by the self-assembly of alumina layers on silica spheres. Spectroscopic and 29 Si nuclear magnetic resonance results showed evidence of chemical bonds between the alumina nanoparticles and the silica spheres, while morphological characterizations showed that the aluminized silica maintained the morphological properties of silica desired for chromatographic purposes after alumina incorporation. Stability studies indicated that bare silica showed high dissolution (~83%), while the aluminized silica remained practically unchanged (99%) after passing one liter of the alkaline mobile phase, indicating high stability under alkaline conditions. The C18 bonded aluminized silica phase showed great potential for use in high-performance liquid chromatography to separate basic molecules in the reversed-phase mode.

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“…7,8 In chromatographic processes, strict control of experimental conditions can be obtained and that qualifies reversed-phase thin-layer chromatography as suitable technique for estimating physicochemical parameters and biological activity of molecules. [9][10][11][12] For understanding the chromatographic processes, it is very convenient to establish mathematical models. Quantitative structure-retention relationship (QSRR) is a useful technique for determining relationships between chromatographic properties of investigated molecules and molecular descriptors.…”

Section: Introductionmentioning

confidence: 99%

QSRR Analysis in Characterization of Some Benzimidazole Derivatives

Karadžić

Podunavac‐Kuzmanović

Jevrić

et al. 2015

ACSi

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In this paper, quantitative structure-retention relationship study has been applied in order to correlate obtained retention parameter R M 0 and two groups of molecular descriptors, for eleven investigated benzimidazole derivatives. Principal component analysis (PCA), followed by hierarchical cluster analysis (HCA), linear regression (LR) and multiple linear regression (MLR), was applied in order to identify the most important molecular descriptors. Mathematical models were established and the best models were further validated by leave-on-out (LOO) technique as well as by the calculation of the statistical parameters. Statistically significant models were established.

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Molecular mechanism of retention in reversed-phase high-performance liquid chromatography and classification of modern stationary phases by using quantitative structure–retention relationships

Cited by 197 publications

References 36 publications

Lipophilicity Measurement of Drugs by Reversed Phase HPLC over Wide pH Range Using an Alkaline-Resistant Silica-Based Stationary Phase, XBridgeTM Shield RP18

Lipophilicity Measurement of Drugs by Reversed Phase HPLC over Wide pH Range Using an Alkaline-Resistant Silica-Based Stationary Phase, XBridgeTM Shield RP18

New Support for High-Performance Liquid Chromatography Based on Silica Coated with Alumina Particles

QSRR Analysis in Characterization of Some Benzimidazole Derivatives

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