Deactivated hydrocarbonaceous silica and immobilized artificial membrane stationary phases in high-performance liquid chromatographic determination of hydrophobicities of organic bases: relationship to log P and CLOGP

Kaliszan, Roman; Kaliszan, Anna; Wainer, Irving W.

doi:10.1016/0731-7085(93)80164-v

Cited by 56 publications

(12 citation statements)

References 17 publications

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“…In addition, the lifetime of the IAM columns was significantly shorter than that usually seen for the coated reversed-phase columns, the chromatography deteriorating after 2 3 months of use with both peak fronting and tailing increasing markedly during this time. Similar observations regarding the stability of IAM phases have been reported [32] and these are thought to be associated with stripping of the PC moiety from the stationary phase resulting in increased interactions of analytes with aliphatic chains bound to the aminopropyl silica surface [32].…”

Section: Comparison Between the Iam And Dynamically Coated Phasesmentioning

confidence: 57%

Biomembrane lipids as components of chromatographic phases: Comparative chromatography on coated and bonded phases

et al. 2000

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SummaryPreparation of biomembrane lipid based stationary phases has been achieved by recycling 1 mM solutions of the appropriate lipid (soybean lecithin phosphatidylcholine, SLPC; phosphatidylcholine, sphingomyelin, phosphatidylethanolamine or phosphatidylserine) in methanol:water (80:20 v/v) through reversed-phase (C8) HPLC columns for 18 hours at 0.25 mL min 1.The chromatographic characteristics (retention, peak symmetry and reproducibilily and phase stabilily) have been assessed and compared with f,,vo commercially available bonded Immobilized Artificial Membrane (IAM) phases (IAM.PC.MG and IAM.PC.DD) by examination of the retention properties of a range of structurally diverse analytes (n = 119). The application of the SLPC phase for prediction of analyte hpophilicily (log Poctanol/water) is shown to be comparable to the IAM.PC.MG and superior to the IAM.PC.DD bonded phases. Cross-phase comparison of analyte retention characteristics on four different lipid phases indicate that such phases may provide a rapid evaluation of analyte-lipid interactions. The dynamic coating methodology is economically viable for the small laboratory, rapid and reproducible, resulting in phase surfaces which are stable over longer periods of time than those of the commercially available bonded phases.

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Section: Comparison Between the Iam And Dynamically Coated Phasesmentioning

confidence: 57%

Biomembrane lipids as components of chromatographic phases: Comparative chromatography on coated and bonded phases

et al. 2000

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“…Generally, the mobile phase employed is a mixture of H 2 O and an organic modifier (MeOH or MeCN), and isocratic log k, at a fixed percentage, or extrapolated log k w values (obtained by extrapolation to 100% H 2 O from five isocratic log k values) are used to determine the log P oct of an unknown solute using the equation established for a series of reference compounds with a specific stationary phase and mobile phase. Even if isocratic log k values, at a fixed percentage, present the advantage to drastically improve the throughput, it was demonstrated that log k w give better correlations [4] [5].…”

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confidence: 97%

Lipophilicity Determination of Highly Lipophilic Compounds by Liquid Chromatography

Guillot¹,

Henchoz²,

Moccand³

et al. 2009

Chemistry & Biodiversity

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Different experimental strategies using short columns in both conventional liquid chromatography (HPLC) and ultra-high pressure liquid chromatography (UHPLC) were evaluated to allow, for the first time with these techniques, the lipophilicity determination of compounds with log P>5. Various organic modifiers, stationary phases, and elution modes were tested on 14 rigid compounds with a CLogP between 5 and 8, and 38 compounds with log P(oct) from 0 to 5. The best results in HPLC were obtained with the 20-mm Discovery RP Amide C16 stationary phase in isocratic mode using MeOH as organic modifier. To improve analysis time, the UHPLC approach was then evaluated. Consequently, a generic method was developed with a 30-mm Acquity BEH Shield RP18 column in gradient mode using MeOH as organic modifier, allowing a fourfold gain of time compared to the HPLC method, for the highly lipophilic compounds tested. Finally, the most rapid and accurate results were obtained with a 10-mm Hypersil GOLD Javelin HTS stationary phase in UHPLC, enabling an eightfold gain of time compared to the HPLC method.

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“…In general, the correlations between logarithms of retention factor determined on the IAM columns, log k IAM , and the reference parameter of hydrophobicity, log P, are not high (Kaliszan et al, 1993;Abraham et al, 1997;Ducarme et al, 1997). On the other hand, the hydrophobicity parameter determined on the IAM columns appeared to be a better predictor of bioactivity than log P for several classes of drugs.…”

Section: Introductionmentioning

confidence: 81%

Retention of barbituric acid derivatives on immobilized artificial membrane stationary phase and its correlation with biological activity

Kępczyńska¹,

Bojarşki

Haber

et al. 2000

Biomed. Chromatogr.

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A series of 30 barbituric acid derivatives were subjected to high-performance liquid chromatography (HPLC) on the 'immobilized artificial membrane' (IAM) column with acetonitrile buffer mobile phase. The retention parameter log k(IAM) was related to the logarithms of partition coefficients determined in octanol-water partition system, log P, to a thin-layer chromatographic (TLC) parameter from partition TLC, R(m0), to an adsorption HPLC retention parameter, log k(0), and to a solubility parameter, delta. It was demonstrated that log k(IAM) correlated significantly to the other parameters of barbiturates determined in partition systems but not to delta. However, log k(IAM) appeared to be a distinctive descriptor of hydrophobicity of barbiturates as compared to the standard log P parameters. The parameter log k(IAM) was shown to correlate with bioactivity data of the agents studied.

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Deactivated hydrocarbonaceous silica and immobilized artificial membrane stationary phases in high-performance liquid chromatographic determination of hydrophobicities of organic bases: relationship to log P and CLOGP

Cited by 56 publications

References 17 publications

Biomembrane lipids as components of chromatographic phases: Comparative chromatography on coated and bonded phases

Biomembrane lipids as components of chromatographic phases: Comparative chromatography on coated and bonded phases

Lipophilicity Determination of Highly Lipophilic Compounds by Liquid Chromatography

Retention of barbituric acid derivatives on immobilized artificial membrane stationary phase and its correlation with biological activity

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