Prediction of retention time of phenols in liquid chromatography

Hanai, Toshihiko; Hubert, J.

doi:10.1002/jhrc.1240060105

Cited by 39 publications

(6 citation statements)

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“…As an important parameter for estimating the hydrophobicity of a compound, LogP also be used to describe the tendency for distribution from aqueous phase into hydrophobic phase. Compounds with a high LogP would have long retention time on reverse phase high performance liquid chromatography [ 31 , 32 ]. Considering that 1,2,3,9-tetrahydropyrrolo [2,1-b] quinazolin-2,3-diol had a smaller LogP value (0.45, calculated by ChemBioDraw Ultra 12.0) than 1,2,3,9-tetrahydropyrrolo [2,1-b] quinazolin-3,9-diol (LogP = 1.02), M3-1 could be determined as 1,2,3,9-tetrahydropyrrolo [2,1-b] quinazolin-2,3-diol and M3-3 as 1,2,3,9-tetrahydropyrrolo [2,1-b] quinazolin-3,9-diol.…”

Section: Resultsmentioning

confidence: 99%

In Vitro and In Vivo Metabolism and Inhibitory Activities of Vasicine, a Potent Acetylcholinesterase and Butyrylcholinesterase Inhibitor

et al. 2015

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Vasicine (VAS), a potential natural cholinesterase inhibitor, exhibited promising anticholinesterase activity in preclinical models and has been in development for treatment of Alzheimer’s disease. This study systematically investigated the in vitro and in vivo metabolism of VAS in rat using ultra performance liquid chromatography combined with electrospray ionization quadrupole time-of-flight mass spectrometry. A total of 72 metabolites were found based on a detailed analysis of their 1H- NMR and 13C NMR data. Six key metabolites were isolated from rat urine and elucidated as vasicinone, vasicinol, vasicinolone, 1,2,3,9-tetrahydropyrrolo [2,1-b] quinazolin-3-yl hydrogen sulfate, 9-oxo-1,2,3,9-tetrahydropyrrolo [2,1-b] quinazolin-3-yl hydrogen sulfate, and 1,2,3,9-tetrahydropyrrolo [2,1-b] quinazolin-3-β-D-glucuronide. The metabolic pathway of VAS in vivo and in vitro mainly involved monohydroxylation, dihydroxylation, trihydroxylation, oxidation, desaturation, sulfation, and glucuronidation. The main metabolic soft spots in the chemical structure of VAS were the 3-hydroxyl group and the C-9 site. All 72 metabolites were found in the urine sample, and 15, 25, 45, 18, and 11 metabolites were identified from rat feces, plasma, bile, rat liver microsomes, and rat primary hepatocyte incubations, respectively. Results indicated that renal clearance was the major excretion pathway of VAS. The acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activities of VAS and its main metabolites were also evaluated. The results indicated that although most metabolites maintained potential inhibitory activity against AChE and BChE, but weaker than that of VAS. VAS undergoes metabolic inactivation process in vivo in respect to cholinesterase inhibitory activity.

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Section: Resultsmentioning

confidence: 99%

In Vitro and In Vivo Metabolism and Inhibitory Activities of Vasicine, a Potent Acetylcholinesterase and Butyrylcholinesterase Inhibitor

et al. 2015

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“…The list of potential surrogate chromatographic models, identified as just described, together with the source for the original chromatographic data is assembled in Table 3. [32][33][34][35][36][37][38][39][40][41][42][43][44][45][46][47][48][49][50][51] The systems are ranked in descending order by the sum of the system constant differences and the list length restricted to the 10 closest fits for any individual biopartitioning process. To achieve diversity in the selection process (near) duplicate systems were eliminated, for example, all the bile salts have similar system constant ratios and can be substituted for each other without much impact on the ranking.…”

Section: Resultsmentioning

confidence: 99%

Systematic search for surrogate chromatographic models of biopartitioning processes

Cimpean

Poole

2002

Analyst

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A systematic approach for identifing surrogate chromatographic models for biopartitioning processes is described. The method is based on a comparison of the system constant ratios of the solvation parameter model for biopartitioning processes and a database of system constant ratios for reversed-phase liquid chromatographic and micellar electrokinetic chromatographic systems compiled from literature sources. An acceptance filter of < or = 0.2 is applied for each difference in system constant ratio for the compared systems to provide a reasonable probability of success without outputting too many systems with limited predictive properties. Surrogate chromatographic models identified for the non-specific toxicity of neutral organic compounds to the fathead minnow and the soil-water distribution constant are tested by construction of a correlation model for the characteristic property of the biological process and the chromatographic retention factors for a structurally varied group of compounds. Although these models are not the best that could be obtained based on ranking of the differences in system constant ratios the predictive ability of the correlation models is suitable for typical applications and similar to the accepted uncertainty in the measurements of the biological property. Retention factors on the immobilized artificial membrane column (IAM PC DD 2) with 10% (v/v) methanol-water as mobile phase are able to estimate non-specific toxicity to the fathead minnow with a standard error (SE) of 0.22 log units and coefficient of determination (r2) of 0.97 for 31 compounds. Retention factors on a Bakerbond DIOL column with 20% (v/v) acetonitrile-water as mobile phase are able to estimate the soil-water distribution constant with an SE of 0.38 log units and r2 = 0.88 for 59 compounds. Other potential surrogate chromatographic models are identified for non-specific toxicity to the guppy, tadpole, Vibrio fischeri and Terahymena pyriformis as well as the plant cuticle matrix-water distribution constant. On the other hand reversed-phase chromatographic systems seem poorly suited for estimating intestinal absorption and the blood-brain distribution constant.

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“…From Table I it is apparent that resolution of solutes 1,5,8,9,12,25, and 26 by tetrahydrofuran is very poor. The chromatographer cannot, therefore, expect complete resolution of the tested mixture by use of this modifier.…”

Section: Resultsmentioning

confidence: 99%

“…[25,26], was for 24 compounds of diverse polarity (aliphatic and aromatic hydrocarbons, alcohols, and chlorobenzenes) chromatographed on a 150 mm x 4.6 mm Develosil ODS-5 column with acetonitrile-water mobile phases containing 60, 70, 80, 85, 90, and 95% acetonitrile and with tetrahydrofuran-water mobile phases containing 50 and 70% tetrahydrofuran, and on a 100 mm x 6 mm YMC phenyl column with acetonitrile-water mobile phases containing 50, 60, 70, and 80% acetonitrile and with tetrahydrofuran-water mobile phases containing 50 and 60% tetrahydrofuran. [25,26], was for 24 compounds of diverse polarity (aliphatic and aromatic hydrocarbons, alcohols, and chlorobenzenes) chromatographed on a 150 mm x 4.6 mm Develosil ODS-5 column with acetonitrile-water mobile phases containing 60, 70, 80, 85, 90, and 95% acetonitrile and with tetrahydrofuran-water mobile phases containing 50 and 70% tetrahydrofuran, and on a 100 mm x 6 mm YMC phenyl column with acetonitrile-water mobile phases containing 50, 60, 70, and 80% acetonitrile and with tetrahydrofuran-water mobile phases containing 50 and 60% tetrahydrofuran.…”

Section: Rg • 100mentioning

confidence: 99%

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Towards the optimization of complementary systems in reversed-phase liquid chromatography

Vivó-Truyols

Torres-Lapası́o

Garcı́a-Alvarez-Coque

2002

Chromatographia

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Previously reported optimization methodology, which seeks complementary mobile phases (CMP) in isocratic chromatography, has been extended to include more than one system simultaneously (i.e. more than one organic solvent ancl/or column). In the literature the benefits of complementarity are not usually fully exploited -few working conditions giving rise to interactions as different as possible are examined, without developing a fully linked optimization. The proposed approach is compared criticallywith use of a single mobile phase orCMP which consider one system only. The strategy greatly expands the capability of isocratic chromatography in the analysis of complex samples that cannot be resolved by use of conventional methods.

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Prediction of retention time of phenols in liquid chromatography

Cited by 39 publications

References 20 publications

In Vitro and In Vivo Metabolism and Inhibitory Activities of Vasicine, a Potent Acetylcholinesterase and Butyrylcholinesterase Inhibitor

In Vitro and In Vivo Metabolism and Inhibitory Activities of Vasicine, a Potent Acetylcholinesterase and Butyrylcholinesterase Inhibitor

Systematic search for surrogate chromatographic models of biopartitioning processes

Towards the optimization of complementary systems in reversed-phase liquid chromatography

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