Investigation of fusidic acid as a chiral selector in capillary electrophoresis

Zhang, Qi; Ren, Siru; Xue, Song

doi:10.1016/j.seppur.2020.116768

Cited by 19 publications

(12 citation statements)

References 31 publications

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“…One possible explanation is that the enantiomers with a rigid planar structure can induce a strong steric hindrance effect when interacting with the unique chair-boat-chair conformation fusidic acid. Among the five β-blockers, only propranolol contains a rigid planar structure (because of its naphthyloxy group); as expected, split peaks were obtained only in the case of propranolol using fusidic acid as CS ( Figure 11 ) [ 77 ].…”

Section: Antibiotics As Css In Cementioning

confidence: 77%

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The Use of Antibiotics as Chiral Selectors in Capillary Electrophoresis: A Review

Hancu¹,

Papp²,

Szekely-Szentmiklosi³

et al. 2022

Molecules

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Chirality is becoming an essential issue in modern pharmaceutical research as regulatory agencies emphasize the safety and efficiency of enantiomers in drug development. The development of efficient and reliable chiral separation methods became a necessity in the last 30 years, and capillary electrophoresis (CE), due to its relatively low costs and “green” features, is attracting increased attention. Cyclodextrin (CD) and their derivatives are the most frequently used chiral selectors (CSs) in CE, however, the use of antibiotics as CSs represents an interesting alternative. Various classes of antibiotics (aminoglycosides, ansamycins, glycopeptides, lincosamides, macrolides, tetracyclines) have been used more or less successfully for the enantio-separation of pharmaceuticals. Antibiotics offer the possibility of a multitude of potential interactions (electrostatic, inclusion, hydrogen bonding, etc.) due to their chemical diversity, allowing the enantio-separation of analytes with a wide range of structural characteristics. This article aims to review the application of various classes of antibiotics in the CE enantio-separation of pharmaceuticals. Antibiotic physiochemical characteristics, variables impacting enantio-separation, advantages, and disadvantages when certain antibiotics are used as CSs in CE are also explored.

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Section: Antibiotics As Css In Cementioning

confidence: 77%

“…It has a pKa of 5.35, a neutral or basic BGE would be preferable for its CE use, as the ionization of the carboxyl group might enable complexation between fusidic acid and enantiomers through electrostatic interactions. It is insoluble in water (its sodium salt is soluble in water) but soluble in organic solvents [ 77 ].…”

Section: Antibiotics As Css In Cementioning

confidence: 99%

The Use of Antibiotics as Chiral Selectors in Capillary Electrophoresis: A Review

Hancu¹,

Papp²,

Szekely-Szentmiklosi³

et al. 2022

Molecules

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“…The authors suggested its special effective enantiodiscrimination power for chiral analytes containing rigid planar structures. The authors expected the finding to open the door for investigating other structurally similar steroids for possible enantioseparation power [ 78 ].…”

Section: Chiral Capillary Electrokinetic Chromatography Principle and Selectorsmentioning

confidence: 99%

Chiral Capillary Electrokinetic Chromatography: Principle and Applications, Detection and Identification, Design of Experiment, and Exploration of Chiral Recognition Using Molecular Modeling

et al. 2021

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This work reviews the literature of chiral capillary electrokinetic chromatography from January 2016 to March 2021. This is done to explore the state-of-the-art approach and recent developments carried out in this field. The separation principle of the technique is described and supported with simple graphical illustrations, showing migration under normal and reversed polarity modes of the separation voltage. The most relevant applications of the technique for enantioseparation of drugs and other enantiomeric molecules in different fields using chiral selectors in single, dual, or multiple systems are highlighted. Measures to improve the detection sensitivity of chiral capillary electrokinetic chromatography with UV detector are discussed, and the alternative aspects are explored, besides special emphases to hyphenation compatibility to mass spectrometry. Partial filling and counter migration techniques are described. Indirect identification of the separated enantiomers and the determination of enantiomeric migration order are mentioned. The application of Quality by Design principles to facilitate method development, optimization, and validation is presented. The elucidation and explanation of chiral recognition in molecular bases are discussed with special focus on the role of molecular modeling.

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“…Fusidic Acid (Fus) is a steroid-antibiotic and contains many chiral centers and functional group structures. These properties may enable it to enantiospecific interactions with chiral compounds, as well as being in the literature as a suitable potential for chiral separations with its easy availability and cheapness [215]. Streptomycin, one of the aminoglycoside antibiotics, has been used in the past for enantiomeric separations by coating the capillary column chirally with Diethylaminoethyl (DEAE) dextran hydrochloride [216].…”

Section: Antibiotics As Chiral Selectorsmentioning

confidence: 99%

Chiral Separations by Capillary Electrophoresis and related Techniques with Different Chiral Selectors: A Review

Şarkaya

Göktürk

Yılmaz

et al. 2021

Hacettepe Journal of Biology and Chemistry

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A nalitik saflıkta ve büyük ölçekli üretim çalışmaları için çözüm yolları bulmaya çalışan farmakoloji ve doğa bilimleriyle ilgilenen araştırmacıların ilgisini kiral bileşiklerin tayin ve enantiyomerik olarak ayrımı konuları çekmiştir. Kapiler Elektroforez, kiral selektörlerin yüksek ayırım gücü ve verimliliği gibi üstün özellikleri nedeniyle enantiyomerik ayırımlar için en önemli analitik yaklaşımlardan biri haline gelmiştir. Yüksek ayırma gücü ve yüksek etkinlik gösterme gibi sahip olduğu üstün özelliklerden dolayı kapiler elektroforez, enantiyomerik ayırmalarda kullanılan en önemli analitik yaklaşımlardan biri haline gelmiştir. Kapiler Elektroforez temeline dayanan teknolojinin gelişim sürecine paralel olarak kiral seçicilerin farklı formlardaki gelişimide süremektedir. Bu derlemede, kapiler elektroforezde kullanılan teknikleri açıklayan bazı tanımlayıcı teorik bilgilere yer verilmiştir. Ayrıca son 10 yılda gerçekleştilen (2010-2020) ve moleküler baskılı polimerler, siklodekstrinler, metal-organik çerçeveler, iyonik sıvılar, nanopartiküller, monolitler gibi farklı kiral seçicilerin ve farklı kiral katkı maddelerin kullanıldığı kiral ayırmalara dayanan çalışmalarda incelenmiştir. Anahtar KelimelerKapiler Elektroforez, kiral selektörler, kiral katkı maddeleri, kiral ayırım.

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Investigation of fusidic acid as a chiral selector in capillary electrophoresis

Cited by 19 publications

References 31 publications

The Use of Antibiotics as Chiral Selectors in Capillary Electrophoresis: A Review

The Use of Antibiotics as Chiral Selectors in Capillary Electrophoresis: A Review

Chiral Capillary Electrokinetic Chromatography: Principle and Applications, Detection and Identification, Design of Experiment, and Exploration of Chiral Recognition Using Molecular Modeling

Chiral Separations by Capillary Electrophoresis and related Techniques with Different Chiral Selectors: A Review

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