Comparing cyclodextrin derivatives as chiral selectors for enantiomeric separation in capillary electrophoresis

Vescina, M.C.; Fermier, Adam M.; Guo, Yong

doi:10.1016/s0021-9673(02)01192-5

Cited by 49 publications

(29 citation statements)

References 20 publications

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“…Th e application of CDs as chiral and achiral selectors in CE has been reviewed by several authors [2,3,[7][8][9][10][11]. In this study -CD, -CD, HP--CD and RAMEB were tested for the separation of two fl uoroquinolones and for demonstration of inclusion complex formation, in diff erent experimental conditons.…”

Section: Discussionmentioning

confidence: 99%

Study of Cyclodextrin/Fluoroquinolone Inclusion Complexes by Capillary Electrophoresis

Székely-Szentmiklósi

Tőkés

2013

Acta Medica Marisiensis

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Introduction:In the present work we evaluated the complexation role of cyclodextrins toward fl uoroquinolones in an attempt to assess their potential as new formulation additives for more effi cient fl uoroquinolone delivery and as selectors in capillary electrophoresis. Material and method: Guest-host interactions of two second generation quinolones, ciprofl oxacin and norfl oxacin with four cyclodextrins, beta-cyclodextrin (-CD), gamma-cyclodextrin (-CD) and two beta-cyclodextrin derivatives, 2-hydroxypropyl beta-cyclodextrin (HP--CD) and randomly methylated beta-cyclodextrin (RAMEB), were tested by capillary electrophoresis in borate running buffer. Experimental parameters like buffer concentration, pH, organic modifi er, voltage and cyclodextrin concentration have been varied for a better resolution. Results: In capillary zone electrophoresis ciprofl oxacin and norfl oxacin are migrating together, a difference in their migration times and thus separation occured by the addition of cyclodextrins. Conclusion: Our results suggest formation of inclusion complexes between fl uoroquinolones and cyclodextrins. Differences in their affi nity to host molecules resulted in separation of the two fl uoroquinolones.

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Section: Discussionmentioning

confidence: 99%

Study of Cyclodextrin/Fluoroquinolone Inclusion Complexes by Capillary Electrophoresis

Székely-Szentmiklósi

Tőkés

2013

Acta Medica Marisiensis

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“…Dos vários seletores quirais utilizados, as ciclodextrinas (CD) e seus derivados são, reconhecidamente, os mais importantes. Estima-se que cerca de 80% das separações enantioméricas em CE são obtidas pelo uso de CDs 77,78 . Dessa forma, esses seletores quirais serão discutidos em detalhes.…”

Section: Separação De Enantiômeros Por Ceunclassified

Análise enantiosseletiva de fármacos: contribuições da cromatografia líquida de alta eficiência e eletroforese capilar

Bonato¹,

Jabor²,

Gaitani³

2005

Quím. Nova

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Recebido em 2/7/04; aceito em 6/10/04; publicado na web em 17/2/05 ENANTIOSELECTIVE ANALYSIS OF DRUGS: CONTRIBUTIONS OF HIGH-PERFORMANCE LIQUID CHROMATOGRAPHY AND CAPILLARY ELECTROPHORESIS. The demand for analytical methods suitable for accurate and reproducible determination of drug enantiomers has increased significantly in the last years. High-performance liquid chromatography (HPLC) using chiral stationary phases and capillary electrophoresis (CE) are the most important techniques used for this purpose. In this paper, the fundamental aspects of chiral separations using both techniques are presented. Some important aspects for the development of enantioselective methods, particularly for the analysis of drugs and metabolites in biological samples, are also discussed.Keywords: chiral drugs; high-performance liquid chromatography; capillary electrophoresis. INTRODUÇÃOPor razões econômicas e dificuldades de ordem prática nos processos de produção, a maioria dos fármacos quirais obtidos por vias sintéticas é comercializada como racemato, ou seja, mistura contendo quantidades iguais dos dois enantiômeros 1 . No entanto, existem inúmeros exemplos de fármacos que apresentam atividades farmacológicas estereosseletivas (propriedades farmacodinâmicas), conseqüência de interações com receptores biológi-cos, que são altamente específicas 2 . Um exemplo clássico que não pode ser esquecido é o da talidomida. Somente depois das investigações da contribuição das propriedades estereosseletivas desse fármaco, é que foi possível estabelecer que as propriedades teratogênicas da talidomida, que causaram deformidades físicas em recém nascidos cujas mães fizeram uso desse fármaco durante a gravidez, estavam relacionadas com o enantiômero (-)-(S)-3 . Infelizmente, em estudos posteriores foi constatada a inversão de configuração não apenas in vitro mas também in vivo da talidomida 4,5 , evidenciando que se o enantiômero (+)-(R)-puro tivesse sido administrado, teria sido parcialmente convertido no isômero responsável pelo efeito teratogênico. Exemplos menos drásticos que esse são bastante comuns, nos quais as diferenças existentes entre os dois enantiômeros podem ser qualitativas ou quantitativas, sendo que, nesse último caso, o enantiômero mais ativo é chamado de eutômero enquanto que ao outro dá-se o nome de distômero 6 . Estudos têm mostrado que β-bloqueadores, propranolol é um exemplo, se ligam estereosseletivamente a receptores β-adrenérgicos e que os enantiômeros (-)-são os principais responsáveis pela atividade β-bloqueadora dessa classe de fármacos 7 . Adicionalmente, quando um fármaco quiral é administrado como racemato, os dois enantiômeros podem apresentar os processos de absorção, distribuição, metabolização e excreção (disposição cinética) de forma estereosseletiva [8][9][10][11] . Desses processos, a estereosseletividade é mais significativa no metabolismo, devido ao envolvimento do sistema enzimático. Dentre os inúmeros exemplos, pode-se destacar o verapamil; o enantiômero ativo (-)-(S) é preferencialmente metabolizado ...

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“…A comparison of 26 CD derivatives from different commercial sources substituted with different functional groups and with different degree of substitution have been evaluated with regard to their effectiveness as chiral selectors in CE towards 35 basic compounds with large structural variation [53]. In a phosphate buffer pH 2.5, five CDs, highly sulfated b-CD, highly sulfated a-CD, Several studies centered on mechanistic aspects in order to gain some understanding how chiral interactions between selectors and analytes influence a chiral separation.…”

Section: Separation Of Drug Enantiomersmentioning

confidence: 99%

Pharmaceutical and biomedical applications of chiral capillary electrophoresis and capillary electrochromatography: An update

Scriba¹

2003

Electrophoresis

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Pharmaceutical and biomedical applications of chiral capillary electrophoresis and capillary electrochromatography: An updateCapillary electrophoresis is often considered an ideal method for the chiral analysis of compounds due to the high separation power of the technique and has therefore found widespread acceptance for the analysis of drugs and pharmaceuticals. In contrast, capillary electrochromatography is still more or less in an infancy state searching for its place among the analytical separation techniques although interesting applications have been published. The present review summarizes recent developments and applications of chiral pharmaceutical analysis by electromigration techniques published in 2002 and early 2003.

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Comparing cyclodextrin derivatives as chiral selectors for enantiomeric separation in capillary electrophoresis

Cited by 49 publications

References 20 publications

Study of Cyclodextrin/Fluoroquinolone Inclusion Complexes by Capillary Electrophoresis

Study of Cyclodextrin/Fluoroquinolone Inclusion Complexes by Capillary Electrophoresis

Análise enantiosseletiva de fármacos: contribuições da cromatografia líquida de alta eficiência e eletroforese capilar

Pharmaceutical and biomedical applications of chiral capillary electrophoresis and capillary electrochromatography: An update

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