Comparative modelling study on enantioresolution of structurally unrelated compounds with amylose-based chiral stationary phases in reversed phase liquid chromatography-mass spectrometry conditions

Pérez-Baeza, Mireia; Escuder-Gilabert, Laura; Martı́n-Biosca, Yolanda; Sagrado, S.; Medina-Hernández, M.J.

doi:10.1016/j.chroma.2020.461281

Cited by 7 publications

(5 citation statements)

References 32 publications

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“…In a more recent study [93] this group performed a modelling study of R s C with DPLS1 using 53 structurally unrelated compounds on three amylose-based CSP: ADMPC, amylose tris-(5-chloro-2methylphenylcarbamate) and ACMPC. The experiments were carried out in RPLC mode and only ADMPC and ACMPC results were used to build the models, because amylose tris-(5-chloro-2methylphenylcarbamate) showed less good separations.…”

Section: Datasetmentioning

confidence: 99%

Modelling approaches for chiral chromatography on polysaccharide-based and macrocyclic antibiotic chiral selectors: A review

Gauquier

Vanommeslaeghe

Heyden

et al. 2022

Analytica Chimica Acta

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Section: Datasetmentioning

confidence: 99%

Modelling approaches for chiral chromatography on polysaccharide-based and macrocyclic antibiotic chiral selectors: A review

Gauquier

Vanommeslaeghe

Heyden

et al. 2022

Analytica Chimica Acta

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“…Separations were performed at a flow rate of 1 mL·min –1 and a temperature of 25 °C. Most of the data were taken from previous papers, ,, except those corresponding to CSPs A1 and A3 with MPs containing more than 80% acetonitrile and all methanol MPs, which were obtained experimentally in this work. All experiments for compounds N = 29, 34, 37, 51, and 56 with CSPs A1 and A3; and for compounds N = 4 and 26 with C2, C3, C4, and C5 cellulose, CSPs were also performed in this work, as well as experiments for omeprazole and tebuconazole (external test compounds).…”

Section: Experimental Sectionmentioning

confidence: 99%

“…Alternatively, quantitative structure-enantioselective retention relationships (QSERR) have emerged as a useful sustainable strategy to select a suitable CSP/MP combination in chiral HPLC optimization processes . For polysaccharide-based CSPs, QSERR have been constructed using chemometric tools, which allow the prediction of enantioselective parameters. − …”

Section: Introductionmentioning

confidence: 99%

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Intelligent Recommendation Systems Powered by Consensus Neural Networks: The Ultimate Solution for Finding Suitable Chiral Chromatographic Systems?

Sagrado,

Pardo-Cortina,

Escuder-Gilabert

et al. 2024

Anal. Chem.

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The selection of suitable combinations of chiral stationary phases (CSPs) and mobile phases (MPs) for the enantioresolution of chiral compounds is a complex issue that often requires considerable experimental effort and can lead to significant waste. Linking the structure of a chiral compound to a CSP/MP system suitable for its enantioseparation can be an effective solution to this problem. In this study, we evaluate algorithmic tools for this purpose. Our proposed consensus model, which uses multiple optimized artificial neural networks (ANNs), shows potential as an intelligent recommendation system (IRS) for ranking chromatographic systems suitable for the enantioresolution of chiral compounds with different molecular structures. To evaluate the IRS potential in a proof-of-concept stage, 56 structural descriptors for 56 structurally unrelated chiral compounds across 14 different families are considered. Chromatographic systems under study comprise 7 cellulose and amylose derivative CSPs and acetonitrile or methanol aqueous MPs (14 chromatographic systems in all). The ANNs are optimized using a fit-for-purpose version of the chaotic neural network algorithm with competitive learning (CCLNNA), a novel approach not previously applied in the chemical domain. CCLNNA is adapted to define the inner ANN complexity and perform feature selection of the structural descriptors. A customized target function evaluates the correctness of recommending the appropriate CSP/MP system. The ANN-consensus model exhibits no advisory failures and requires only an experimental attempt to verify the IRS recommendation for complete enantioresolution. This outstanding performance highlights its potential to effectively resolve this problem.

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“…CSPs were a common approach to chiral chromatographic separation, and polysaccharide-based CSPs derived from cellulose and amylose are the most commonly used CSP in HPLC [19][20][21][22]. To separate the two enantiomers of TDF, we investigated the effects of three chromatographic columns and different mobile phases on the separation of (R)tenofovir and (S)-enantiomer.…”

Section: Optimization Of Chromatographic Conditionsmentioning

confidence: 99%

Study on Quality Control of Tenofovir Disoproxil Fumarate Enantiomers by High-Performance Liquid Chromatography–Mass Spectrometry

Lin

Huang

et al. 2023

Chromatographia

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This study aims at developing a high-performance liquid chromatography–mass spectrometry (LC–MS) method to analyze tenofovir disoproxil fumarate (TDF) and its pharmaceutical preparations. Several cyclodextrin mobile-phase additives were applied to reversed-phase and normal-phase chromatography, and the effects of three chiral stationary phases on the TDF separation were investigated in this study. The R-type and S-type of TDF tablets were quantitatively analyzed in the single ion monitoring (SIM) scanning mode with a Unichiral CMD column. This method has been successfully applied to the separation and quantification of TDF and its isomers. The linear ranges of (R)-TDF and (S)-enantiomer were 1–20 and 0.2–16 μg/mL, respectively. The limit of detection for (R)-TDF and (S)-enantiomer was 0.0015 and 0.0012 μg/mL, respectively. (S)-enantiomer was not detected in the formulas from all the seven manufacturers, and the drug content of each took more than 98.5% of the labeled amount, which complies with the regulations. The method shows its advantages on high sensitivity, low detection limit, good practicability, and repeatability. The proposed method may provide a novel platform for separation of TDF enantiomers and quality control of TDF raw materials and preparations.

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Comparative modelling study on enantioresolution of structurally unrelated compounds with amylose-based chiral stationary phases in reversed phase liquid chromatography-mass spectrometry conditions

Cited by 7 publications

References 32 publications

Modelling approaches for chiral chromatography on polysaccharide-based and macrocyclic antibiotic chiral selectors: A review

Modelling approaches for chiral chromatography on polysaccharide-based and macrocyclic antibiotic chiral selectors: A review

Intelligent Recommendation Systems Powered by Consensus Neural Networks: The Ultimate Solution for Finding Suitable Chiral Chromatographic Systems?

Study on Quality Control of Tenofovir Disoproxil Fumarate Enantiomers by High-Performance Liquid Chromatography–Mass Spectrometry

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