Computational Chemical Analysis of the Retention of Acidic Drugs on a Pentyl-Bonded Silica Gel in Reversed-Phase Liquid Chromatography

Hanai, Toshihiko; Miyazaki, Rie; A, Koseki; Kinoshita, Toshio

doi:10.1093/chromsci/42.7.354

Cited by 10 publications

(2 citation statements)

References 8 publications

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“…However, the alkyl bonded phase is dense; therefore, it was suitable for the analysis of the retention times of flat molecules such as phenolic compounds [39]. An alkyl-bonded poly silicone dioxide phase was constructed and applied to analyze phenolic compounds [40,41], acidic drugs [42], basic drugs [43], and aromatic acids as well as chromatographic behavior of steroids in normal-phase (nonaqueous HILIC) [44]. Furthermore, a large sp 3 atom, lead, was used to build a model homogeneous phase, and the mew model phases were used to analyze the retention data of acidic drugs measured using a pentyl-and an octyl-bonded silica gels was analyzed.…”

Section: Mihb = Hb (Molecule A) + Hb (Molecule B) -Hb (Molecule a Andmentioning

confidence: 99%

Fundamental Properties of Packing Materials for Liquid Chromatography

Hanai¹

2019

Separations

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The high performance of chemically-modified silica gel packing materials is based on the utilization of pure silica gels. Earlier silica gels used to be made from inorganic silica; however, nowadays, silica gels are made from organic silanes. The surface smoothness and lack of trace metals of new silica gels permits easy surface modifications (chemical reactions) and improves the reproducibility and stability. Sharpening peak symmetry is based on developing better surface modification methods (silylation). Typical examples can be found in the chromatography of amitriptyline for silanol testing and that of quinizarin for trace metal testing. These test compounds were selected and demonstrated sensitive results in the measurement of trace amounts of either silanol or trace metals. Here, we demonstrate the three-dimensional model chemical structures of bonded-phase silica gels with surface electron density for easy understanding of the molecular interaction sites with analytes. Furthermore, a quantitative explanation of hydrophilic and hydrophobic liquid chromatographies was provided. The synthesis methods of superficially porous silica gels and their modified products were introduced.

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Section: Mihb = Hb (Molecule A) + Hb (Molecule B) -Hb (Molecule a Andmentioning

confidence: 99%

Fundamental Properties of Packing Materials for Liquid Chromatography

Hanai¹

2019

Separations

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“…However, the alkyl bonded phase is dense; therefore, it supported for flat molecules such as phenolic compounds [21] . The alkyl-bonded polysiloxane support [16,22] was applied to analyze retention times in reversed-phase liquid chromatography of phenolic compounds [23] , acidic drugs [24] , basic drugs [25] and aromatic acids [26] , and in normal-phase liquid chromatography [27] .…”

Section: Introductionmentioning

confidence: 99%

In Silico Chromatography: Modeling a New Support for Alkyl-Bonded Phases and a Solvent Phase

Hanai¹,

Internationals²

2017

JABST

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Chromatography is a tool to measure molecular interactions, and computational chemistry is a tool to explain molecular interactions. Therefore, reversed-phase liquid chromatography of acidic drugs using a pentyl- and an octyl-bonded silica gels was quantitatively analyzed in silico. A model pentyl- and an octyl-bonded silica gel and a methanol phases were constructed for docking with acidic drugs. Molecular interaction energy values based on van der Waals energy were obtained after docking an acidic drug into the model pentyl- or octyl-phases. Solvent effects, hydrogen bonding, and electrostatic energy values were obtained after docking an acidic drug onto the model methanol phase. Chromatographically measured log k values were correlated with the sum of van der Waals, hydrogen bonding, and electrostatic energy values. The correlation coefficient between the log k values measured using the pentyl-bonded silica gel phase and the molecular interaction energy values was 0.95 (n = 20); that between the log k values measured using the octyl-bonded silica gel and the molecular interaction energy values was 0.95 (n = 20).

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Chromatography in silico, basic concept in reversed-phase liquid chromatography

Hanai

2005

Anal Bioanal Chem

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Basic phenomena in reversed-phase liquid chromatography have been quantitatively analyzed using a computational chemical calculation. Pyridine interacted with an ionized silica surface under neutral conditions. Alkyl-chain length affected the contact surface area with an analyte. Steric hindrance was demonstrated using a model graphitic carbon phase and unsaturated alkenes. Quantitative structure-retention relationships in reversed-phase liquid chromatography were demonstrated for phenolic compounds and acidic and basic drugs. The correlations between predicted and measured retention factors were satisfactory. Dissociation constants were derived from the atom partial charge and used to predict retention factors of partially ionized compounds.

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Computational Chemical Analysis of the Retention of Acidic Drugs on a Pentyl-Bonded Silica Gel in Reversed-Phase Liquid Chromatography

Cited by 10 publications

References 8 publications

Fundamental Properties of Packing Materials for Liquid Chromatography

Fundamental Properties of Packing Materials for Liquid Chromatography

In Silico Chromatography: Modeling a New Support for Alkyl-Bonded Phases and a Solvent Phase

Chromatography in silico, basic concept in reversed-phase liquid chromatography

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