Analytical separation of four stereoisomers of luliconazole using supercritical fluid chromatography: Thermodynamic aspects and simulation study with chiral stationary phase

Pandya, Pranav A.; Shah, Priyanka A.; Shrivastav, Pranav S.

doi:10.1016/j.chroma.2020.461299

Cited by 19 publications

(7 citation statements)

References 29 publications

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“…2 Schematic representation of Chiralpak columns based on amylose and cellulose derivatives immobilized on silica gel using QuEChERS (Quick, Easy, Cheap, Effective, Rugged, Safe) technique was performed on an immobilized amylose tris((S)-α-methylbenzylcarbamate)-based Chiralpak IH column [35]. The same column was selected for the separation of four stereoisomers of the antifungal agent luliconazole by supercritical fluid chromatography (SFC) [36]. Five different columns based on both derivatized cyclofructans (Larihc CF6-RN and Larihc CF6-P columns) and teicoplanin glycopeptide (Chirobiotic T column) were tested for enantioseparation of zopiclone, a drug used to treat insomnia.…”

Section: Polysaccharide-based Stationary Phasesmentioning

confidence: 99%

An overview of chiral separations of pharmaceutically active substances by HPLC (2018–2020)

Grybinik

Bosáková

2021

Monatsh Chem

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Graphic abstract This review provides a brief survey of chiral separation of pharmaceutically active substances published over the last 3 years (2018–2020). Chiral separation of drugs is an important area of research. The control of enantiomeric purity and determination of individual enantiomeric drug molecules is a necessity especially for clinical, analytical, and regulatory purposes. Among chromatographic resolution methods, high-performance liquid chromatography based on chiral stationary phases remains the most popular and effective method used for chiral separation of various drugs. In this review, attention is paid to several classes of chiral stationary phases that have been the most frequently used for drug enantioseparation during this period.

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Section: Polysaccharide-based Stationary Phasesmentioning

confidence: 99%

An overview of chiral separations of pharmaceutically active substances by HPLC (2018–2020)

Grybinik

Bosáková

2021

Monatsh Chem

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“…The enantioseparation mechanism was studied by computational chemistry according to Pandya et al and Ali et al , Briefly, the 2D structures of R -penflufen, S -penflufen, and cellulose tris-(3-chloro-4-methylphenylcarbamate) [OZ-3 column chiral stationary phase (CSP)] are shown in Figure S1. The conformation search and force field optimization of R -penflufen, S -penflufen, and cellulose tris-(3-chloro-4-methylphenylcarbamate) were conducted using Maestro Materials Science 2018-4 (Schrödinger), obtaining 3D structures.…”

Section: Methodsmentioning

confidence: 99%

“…It had been reported that the binding energy was correlated with the elution order, and the more negative the binding energy, the more the retention of the enantiomer. 20 The binding energy was related to the nature and type of interaction between the penflufen enantiomer and cellulose tris-(3-chloro-4-methylphenylcarbamate) (the CSP of the OZ-3 column). Table 1 shows the binding energies and types of intermolecular interactions such as the hydrogen bond with the bond length.…”

Section: Enantioseparation Of Penflufen Enantiomersmentioning

confidence: 99%

Evaluation of Chiral Fungicide Penflufen in Legume Vegetables: Enantioseparation and Its Mechanism, Enantioselective Behaviors, and Risk Assessment

Zhao

Liu

et al. 2022

J. Agric. Food Chem.

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Illustrating the enantioselective behaviors of the novel chiral fungicide penflufen was extremely important for ecological safety and human health. For penflufen enantiomers, an excellent separation method including a short analysis time (4 min), a high sensitivity (2 ng/g), and lesser consumption of an organic solvent was first established through supercritical fluid chromatography–tandem mass spectrometry. The enantioseparation mechanism was explained by computational chemistry, and the stronger binding ability of S-(+)-penflufen with cellulose tris-(3-chloro-4-methylphenylcarbamate) (the chiral stationary phase OZ-3 column) contributed to the posterior elution. In legume vegetables, penflufen dissipation was the fastest in Pisum sativum Linn plants (half-life, 1 day) and the slowest in Glycine max plants (half-lives, 11.3–12.9 days). After 30, 50, and 40 days, the rac-penflufen residues were lower than the maximum residue level value in the Electronic Code of Federal Regulations (10 ng/g) in G. max, P. sativum Linn, and Vigna unguiculata, respectively. Abundant S-(+)-penflufen was found in these plants with stereoisomeric excess (se) changes being >10% in the initial stage, so the risk assessment might be driven by S-(+)-penflufen. However, the se changes were <10% in V. unguiculata plants, and the risk assessment might be calculated based on rac-penflufen. Moreover, penflufen enantiomers could be transferred from legume vegetables to soils, and the concentrations increased with time. The high persistence and medium mobility of penflufen in soils might lead to potential groundwater contamination, which was noteworthy. These results could contribute to a more accurate risk assessment of penflufen in legume vegetables.

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“…3 In the current clinical application, the imdazole drugs, accompanied with the advantages of higher therapy and lower toxicity properties, play an indispensable role in achieving the treatment of the topical fungal infections of the skin. [4][5][6] According to the reports in several literatures, 1% rac-isoconazole nitrate cream as imidazole topical antimycotic drug is available to the treatment of a wide range of dermatomycoses caused by varieties of dermatophytes, yeasts, and so forth. [7][8][9] Isoconazole, (RS)-1-[2-[(2, 6-dichlorobenzyl) oxy]-2-(2, 4-dichlorobenzyl) ethyl]-1H-imidazole), contains one chiral center and thus possesses a pair of enantiomers (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

“…Dermatophyte infections are estimated to affect over 20–25% of the world's population and contribute a significant public health issue because of the high incidence in recent years 3 . In the current clinical application, the imdazole drugs, accompanied with the advantages of higher therapy and lower toxicity properties, play an indispensable role in achieving the treatment of the topical fungal infections of the skin 4–6 . According to the reports in several literatures, 1% rac ‐isoconazole nitrate cream as imidazole topical antimycotic drug is available to the treatment of a wide range of dermatomycoses caused by varieties of dermatophytes, yeasts, and so forth 7–9 …”

Section: Introductionmentioning

confidence: 99%

Development of a novel HPLC‐ESI‐MS/MS method to analyze the stereoselective pharmacokinetics and tissue distribution of isoconazole enantiomers in rats

Zhu

Wang²,

Guo³

et al. 2022

Chirality

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Isoconazole with an asymmetrical carbon is a broad‐spectrum antimicrobial imidazole, but there is still lack of relevant report about the potential enantioselectivity in biological samples. The object of this research was to develop and validate a sensitive and effective high performance liquid chromatography‐electrospray ionization coupled with tandem mass spectrometry (HPLC‐ESI‐MS/MS) method for stereoselective separation and determination of isoconazole enantiomers in Sprague‐Dawley (SD) rat plasma and tissues. The greater enantioseparation of isoconazole enantiomers was obtained on a Chiralpak IC column with a mobile phase consisted of acetonitrile‐10 mM aqueous ammonium acetate (90:10, v/v) under the reversed‐phase mode. Subsequently, the studied compounds and internal standard (IS) were detected on a multiple reaction monitoring (MRM) mode with positive electrospray ionization source. The experimental and theoretical Electronic Circular Dichroism (ECD) spectra were employed to confirm the absolute configuration of isoconazole enantiomers. Eventually, after full method validation, the newly developed method was successfully applied to the study of enantioselectivity in plasma and tissues in SD rats. Results illustrated that the enantioselective differences in plasma were observed for the evidence that the concentrations of S‐(−)‐isoconazole were always higher than R‐(+)‐isomer. In terms of tissue distribution, liver, kidney, lung, spleen, and small intestine were the mainly distributed tissues and then followed by heart and muscle. This is the first study to reveal the stereoselective behavior of isoconazole enantiomers in vivo, which also provides reliable and valuable reference for further elucidating the enantioselective metabolisms of isoconazole enantiomers.

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Analytical separation of four stereoisomers of luliconazole using supercritical fluid chromatography: Thermodynamic aspects and simulation study with chiral stationary phase

Cited by 19 publications

References 29 publications

An overview of chiral separations of pharmaceutically active substances by HPLC (2018–2020)

An overview of chiral separations of pharmaceutically active substances by HPLC (2018–2020)

Evaluation of Chiral Fungicide Penflufen in Legume Vegetables: Enantioseparation and Its Mechanism, Enantioselective Behaviors, and Risk Assessment

Development of a novel HPLC‐ESI‐MS/MS method to analyze the stereoselective pharmacokinetics and tissue distribution of isoconazole enantiomers in rats

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