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Cyclodextrin-modified Micellar Electrokinetic Chromatography for Enantioseparations

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Chiral Separations

Part of the book series: Methods in Molecular Biology ((MIMB,volume 970))

Abstract

The separation of enantiomers is one of the important fields of modern analytical chemistry, especially for agrochemical and pharmaceutical products because the stereochemistry has a significant influence on the biological activities of compounds. Cyclodextrin-modified micellar electrokinetic chromatography (CD-MEKC) has become an important capillary electrophoresis mode for enantioseparations. Here, we describe an example of a CD-MEKC method using hydroxypropyl-γ-cyclodextrin as chiral selector and sodium dodecyl sulfate as micellar solution for enantioseparation of triazole fungicides and the drug econazole.

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References

  1. Aboul-Enein HY, Ali I (2003) Chiral separation by liquid chromatography and related technologies. Marcel Dekker Inc, New York

    Book  Google Scholar 

  2. Wang P, Jiang S, Liu D, Wang P, Zhou Z (2005) Direct enantiomeric resolutions of chiral triazole pepticides by high-performance liquid chromatography. J Biochem Biophys Methods 62:219–230

    Article  PubMed  CAS  Google Scholar 

  3. Ali I, Aboul-Enein HY, Gaitonde VD, Singh P, Rawat MSM, Sharma B (2009) Chiral separations of imidazole antifungal drugs on amycoat RP column in HPLC. Chromatographia 70:223–227

    Article  CAS  Google Scholar 

  4. Fanali S, Cristalli M, Vespalec R, Bocek P (1994) Chiral separations in capillary electrophoresis. In: Chrambach A, Dunn MJ, Radola BJ (eds) Advances in Electrophoresis, vol 7. Weinheim, VCH Verlagsgesellschaft GmbH, pp 3–61

    Google Scholar 

  5. Chankvetadze B, Lindner W, Scriba GKE (2004) Enantiomer separations in capillary electrophoresis in the case of equal binding constants of the enantiomers with a chiral selector: commentary on the feasibility of the concept. Anal Chem 76:4256–4260

    Article  PubMed  CAS  Google Scholar 

  6. Wang Z, Ouyang J, Baeyens WRG (2008) Recent developments of enantioseparation techniques for adrenergic drugs using liquid chromatography and capillary electrophoresis: A Review. J Chromatogr B 862:1–14

    Article  CAS  Google Scholar 

  7. Terabe S, Otsuka K, Ichikawa K, Tsuchiya A, Ando T (1984) Electrokinetic separations with micellar solutions and open-tubular capillaries. Anal Chem 56:111–113

    Article  CAS  Google Scholar 

  8. Otsuka K, Terabe S (2000) Enantiomer separation of drugs by micellar electrokinetic chromatography using chiral surfactants. J Chromatogr A 875:163–178

    Article  PubMed  CAS  Google Scholar 

  9. Kodama S, Yamamoto A, Saitoh Y, Matsunaga A, Okamura K, Kizu R, Hayakawa K (2002) Enantioseparation of Vinclozolin by Cyclodextrin-Modified Micellar Electrokinetic Chromatography. J Agric Food Chem 50:1312–1317

    Article  PubMed  CAS  Google Scholar 

  10. Perez-Fernandez V, Garcia MA, Marina ML (2011) Chiral separation of fungicides. J Chromatogr A 1218:6561–6582

    Article  PubMed  CAS  Google Scholar 

  11. Otsuka K, Matsumura M, Kim JB, Terabe S (2003) On-line preconcentration and enantioselective separation of triadimenol by electrokinetic chromatography using cyclodextrins as chiral selectors. J Pharm Biomed Anal 30:1861–1867

    Article  PubMed  CAS  Google Scholar 

  12. Wan Ibrahim WA, Hermawan D, Sanagi MM (2007) On-line preconcentration and chiral separation of propiconazole by cyclodextrin-modified micellar electrokinetic chromatography. J Chromatogr A 1170:107–113

    Article  PubMed  CAS  Google Scholar 

  13. Wan Ibrahim WA, Hermawan D, Sanagi MM, Aboul-Enein HY (2009) Cyclodextrin-modified micellar electrokinetic chromatography method for chiral separation of hexaconazole, penconazole and myclobutanil. J Sep Sci 32(3):466–471

    Article  PubMed  Google Scholar 

  14. Wan Ibrahim WA, Warno SA, Aboul-Enein HY, Hermawan D, Sanagi MM (2009) Simultaneous enantioseparation of cyproconazole, bromuconazole, and diniconazole enantiomers by cyclodextrin-modified micellar electrokinetic chromatography. Electrophoresis 30:1976–1982

    Article  PubMed  Google Scholar 

  15. Wan Ibrahim WA, Hermawan D, Sanagi MM, Aboul-Enein HY (2010) Stacking and sweeping in cyclodextrin-modified MEKC for chiral separation of hexaconazole, penconazole and myclobutanil. Chromatographia 71:305–309

    Article  CAS  Google Scholar 

  16. Hermawan D, Wan Ibrahim WA, Sanagi MM, Aboul-Enein HY (2010) Chiral separation of econazole using micellar electrokinetic chromatography with hydroxypropyl-γ-cyclodextrin. J Pharm Biomed Anal 53(5):1244–1248

    Article  PubMed  CAS  Google Scholar 

  17. Antczak A, Ramstad T, Johnson R (2006) A CD-MEKC Method Utilizing a Neutral Surfactant for Enantiomeric Purity Determination of an Oxazolidinone Drug Candidate. Chromatographia 64:57–64

    Article  CAS  Google Scholar 

  18. Chu BL, Guo BY, Wang Z, Lin JM (2008) Enantioseparation of esbiothrin by cyclodextrin-modified microemulsion and micellar electrokinetic chromatography. J Sep Sci 31:3911–3920

    Article  PubMed  CAS  Google Scholar 

  19. Zhu C, Lin X, Wei Y (2002) Chiral separation of pemoline enantiomers by cyclodextrin-modified micellar capillary chromatography. J Pharm Biomed Anal 30:293–298

    Article  PubMed  CAS  Google Scholar 

  20. Drover VJ, Bottaro CS (2008) Determination of pharmaceuticals in drinking water by CD-modified MEKC: Separation optimization using experimental design. J Sep Sci 31:3740–3748

    Article  PubMed  CAS  Google Scholar 

  21. Eder AR, Chen JS, Arriaga EA (2006) Separation of doxorubicin and doxorubicinol by cyclodextrin-modified micellar electrokinetic capillary chromatography. Electrophoresis 27:3263–3270

    Article  PubMed  CAS  Google Scholar 

  22. Gotti R, El-Hady DA, Andrisano V, Bertucci C, El-Maali NA, Cavrini V (2004) Determination of the chiral and achiral related substances of methotrexate by cyclodextrin-modified micellar electrokinetic chromatography. Electrophoresis 25:2830–2837

    Article  PubMed  CAS  Google Scholar 

  23. Lantz AW, Rozhkov RV, Larock RC, Armstrong DW (2004) Enantiomeric separation of neutral hydrophobic dihydrofuroflavones by cyclodextrin-modified micellar capillary electrophoresis. Electrophoresis 25:2727–2734

    Article  PubMed  CAS  Google Scholar 

  24. Lin X, Hou W, Zhou C (2003) Enantiomer Separation of Miconazole by Capillary Electrophoresis with Dual Cyclodextrin Systems. Anal Sci 19:1509–1512

    Article  PubMed  CAS  Google Scholar 

  25. Lin CE, Chen KH, Hsiao YY, Liao WS, Chen CC (2002) Enantioseparation of phenothiazines in cyclodextrin-modified micellar electrokinetic chromatography. J Chromatogr A 971:261–266

    Article  PubMed  CAS  Google Scholar 

  26. Liu Y, Fu X, Ma C, Zhong J, Liao Y, Liu H (2009) Chiral separation of raltitrexed by cyclodextrin-modified micellar electrokinetic chromatography. Anal Bioanal Chem 393:321–326

    Article  PubMed  CAS  Google Scholar 

  27. Lucangioli SE, Hermida LG, Tripodi VP, Rodrıguez VG, Lopez EE, Rouge PD, Carducci CN (2000) Analysis of cis-trans isomers and enantiomers of sertraline by cyclodextrin-modified micellar electrokinetic chromatography. J Chromatogr A 871:207–215

    Article  PubMed  CAS  Google Scholar 

  28. Mbuna J, Kaneta T, Imasaka T (2010) Measurement of intracellular accumulation of anthracyclines in cancerous cells by direct injection of cell lysate in MEKC/LIF detection. Electrophoresis 31:1396–1404

    Article  PubMed  CAS  Google Scholar 

  29. Méndez SP, González EB, Sanz-Medel A (2000) Enantiomeric separation of selenoaminoacid derivatives by cyclodextrin-modified micellar electrokinetic chromatography using a mixed micellar system of sodium dodecyl sulphate and taurodeoxycholic acid. Anal Chim Acta 416:1–7

    Article  Google Scholar 

  30. Pérez-Fernández V, García MA, Marina ML (2010) Enantiomeric separation of cis-bifenthrin by CD-MEKC: Quantitative analysis in a commercial insecticide formulation. Electrophoresis 31:1533–1539

    Article  PubMed  Google Scholar 

  31. Polisel Jabor VA, Bonato PS (2001) Enantiomeric determination of praziquantel and its main metabolite trans-4-hydroxypraziquantel in human plasma by cyclodextrin-modified micellar electrokinetic chromatography. Electrophoresis 22:1399–1405

    Article  Google Scholar 

  32. Shang X, Yuan Z (2003) Determination of hydroxyanthraquinoids in Rhubarb by cyclodextrin-modified micellar electrokinetic chromatography using a mixed micellar system of sodium dodecyl sulfate and sodium cholate. J Pharm Biomed Anal 31:75–81

    Article  PubMed  CAS  Google Scholar 

  33. Shen J, Zhao S (2004) Enantiomeric separation of naphthalene-2,3-dicarboxaldehyde derivatized DL-3,4 dihydroxyphenylalanine and optical purity analysis of L-3,4-dihydroxyphenylalanine drug by cyclodextrin-modified micellar electrokinetic chromatography. J Chromatogr A 1059:209–214

    Article  PubMed  CAS  Google Scholar 

  34. Wang Z, Tang Z, Gu Z, Hu Z, Ma S, Kang J (2005) Enantioseparation of chiral allenic acids by micellar electrokinetic chromatography with cyclodextrins as chiral selector. Electrophoresis 26:1001–1006

    Article  PubMed  CAS  Google Scholar 

  35. Wang B, He J, Bianchi V, Shamsi SA (2009) Combined use of chiral ionic liquid and CD for MEKC: Part II. Determination of binding constants. Electrophoresis 30:2820–2828

    Article  PubMed  CAS  Google Scholar 

  36. Zhang W, Zhu C (2004) Separation of Uniconazole by Enantiomers Capillary Electrophoresis with Dual Cyclodextrin Systems. Canad J Anal Sci Spec 49:277–281

    CAS  Google Scholar 

  37. Zhang ZX, Zhang MZ, Zhang SS (2009) Online preconcentration and two-dimensional separation of cationic compounds via hyphenation of capillary zone electrophoresis with cyclodextrin-modified micellar electrokinetic capillary chromatography. Electrophoresis 30:1958–1966

    Article  PubMed  CAS  Google Scholar 

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Author information

Authors and Affiliations

  1. Separation Science and Technology Group (SepSTec), Department of Chemistry, Faculty of Science, Universiti Teknologi Malaysia, Johor, Malaysia

    Wan Aini Wan Ibrahim

  2. Department of Chemistry, Universiti Teknologi Malaysia, Johor, Malaysia

    Dadan Hermawan & Mohd Marsin Sanagi

Authors
  1. Wan Aini Wan Ibrahim
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  2. Dadan Hermawan
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  3. Mohd Marsin Sanagi
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Corresponding author

Correspondence to Wan Aini Wan Ibrahim .

Editor information

Editors and Affiliations

  1. , Department of Pharmaceutical Chemistry, Friedrich-Schiller-University Jena, Philosophenweg 14, Jena, 07743, Germany

    Gerhard K. E. Scriba

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Ibrahim, W.A.W., Hermawan, D., Sanagi, M.M. (2013). Cyclodextrin-modified Micellar Electrokinetic Chromatography for Enantioseparations. In: Scriba, G. (eds) Chiral Separations. Methods in Molecular Biology, vol 970. Humana Press, Totowa, NJ. https://doi.org/10.1007/978-1-62703-263-6_22

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  • DOI: https://doi.org/10.1007/978-1-62703-263-6_22

  • Published:

  • Publisher Name: Humana Press, Totowa, NJ

  • Print ISBN: 978-1-62703-262-9

  • Online ISBN: 978-1-62703-263-6

  • eBook Packages: Springer Protocols

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