Skip to main content
SpringerLink
Log in

Enantioseparations in Nonaqueous Capillary Electrophoresis Using Charged Cyclodextrins

  • Protocol
Chiral Separations

Part of the book series: Methods in Molecular Biology ((MIMB,volume 1985))

Abstract

The enantioseparation of acidic and basic compounds can be successfully achieved in nonaqueous capillary electrophoresis (NACE) using single-isomer charged β-cyclodextrin (β-CD) derivatives of opposite charge to that of the analytes. This chapter describes how to separate the enantiomers of three basic substances selected as model compounds, i.e., alprenolol, bupranolol, and terbutaline, using the negatively charged heptakis(2,3-di-O-acetyl-6-O-sulfo)-β-CD (HDAS-β-CD). The enantiomers of three acidic drugs (tiaprofenic acid, suprofen, and flurbiprofen) are resolved using a monosubstituted amino β-CD derivative, namely 6-monodeoxy-6-mono(3-hydroxy)propylamino-β-CD (PA-β-CD).

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Protocol
USD 49.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 169.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Hardcover Book
USD 219.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  1. Saz JM, Marina ML (2016) Recent advances on the use of cyclodextrins in the chiral analysis of drugs by capillary electrophoresis. J Chromatogr A 1467:79–94

    Article  CAS  Google Scholar 

  2. Kenndler E (2014) A critical overview of non-aqueous capillary electrophoresis. Part I: mobility and separation selectivity. J Chromatogr A 1335:16–30

    Article  CAS  Google Scholar 

  3. Kenndler E (2014) A critical overview of non-aqueous capillary electrophoresis. Part II: separation efficiency and analysis time. J Chromatogr A 1335:31–41

    Article  CAS  Google Scholar 

  4. Rizzi A (2001) Fundamental aspects of chiral separations by capillary electrophoresis. Electrophoresis 22:3079–3106

    Article  CAS  Google Scholar 

  5. Lämmerhofer M (2005) Chiral separations by capillary electromigration techniques in nonaqueous media. I. Enantioselective nonaqueous capillary electrophoresis. J Chromatogr A 1068:3–30

    Article  Google Scholar 

  6. Scriba GKE (2011) Fundamental aspects of chiral electromigration techniques and application in pharmaceutical and biomedical analysis. J Pharm Biomed Anal 55:688–701

    Article  CAS  Google Scholar 

  7. Chankvetadze B (2009) Separation of enantiomers with charged chiral selectors in CE. Electrophoresis 30:S211–S221

    Article  Google Scholar 

  8. Li S, Vigh G (2004) Single-isomer sulfated alpha-cyclodextrins for capillary electrophoresis. Part 2. Hexakis(6-O-sulfo)-alpha-cyclodextrin: synthesis, analytical characterization, and initial screening tests. Electrophoresis 25:1201–1210

    Article  CAS  Google Scholar 

  9. Vincent JB, Kirby DM, Nguyen TV, Vigh G (1997) A family of single-isomer chiral resolving agents for capillary electrophoresis. 2. Hepta-6-sulfato-beta-cyclodextrin. Anal Chem 69:4419–4428

    Article  CAS  Google Scholar 

  10. Zhu W, Vigh G (2003) A family of single-isomer, sulfated gamma-cyclodextrin chiral resolving agents for capillary electrophoresis: octa(6-O-sulfo)-gamma-cyclodextrin. Electrophoresis 24:130–138

    Article  CAS  Google Scholar 

  11. Li S, Vigh G (2004) Single-isomer sulfated alpha-cyclodextrins for capillary electrophoresis: hexakis(2,3-di-O-methyl-6-O-sulfo)-alpha-cyclodextrin, synthesis, analytical characterization, and initial screening tests. Electrophoresis 25:2657–2670

    Article  CAS  Google Scholar 

  12. Cai H, Nguyen TV, Vigh G (1998) A family of single-isomer chiral resolving agents for capillary electrophoresis. 3. Heptakis(2,3-dimethyl-6-sulfato)-beta-cyclodextrin. Anal Chem 70:580–589

    Article  CAS  Google Scholar 

  13. Cai H, Vigh G (1998) Capillary electrophoretic separation of weak base enantiomers using the single-isomer heptakis-(2,3-dimethyl-6-sulfato)-beta-cyclodextrin as resolving agent and methanol as background electrolyte solvent. J Pharm Biomed Anal 18:615–621

    Article  CAS  Google Scholar 

  14. Busby MB, Lim P, Vigh G (2003) Synthesis, analytical characterization and use of octakis(2,3-di-O-methyl-6-O-sulfo)-gamma-cyclodextrin, a novel, single-isomer, chiral resolving agent in low-pH background electrolytes. Electrophoresis 24:351–362

    Article  CAS  Google Scholar 

  15. Busby MB, Maldonado O, Vigh G (2002) Nonaqueous capillary electrophoretic separation of basic enantiomers using octakis(2,3-O-dimethyl-6-O-sulfo)-gamma-cyclodextrin, a new, single-isomer chiral resolving agent. Electrophoresis 23:456–461

    Article  CAS  Google Scholar 

  16. Li S, Vigh G (2003) Synthesis, analytical characterization and initial capillary electrophoretic use in acidic background electrolytes of a new, single-isomer chiral resolving agent: hexakis(2,3-di-O-acetyl-6-O-sulfo)-alpha-cyclodextrin. Electrophoresis 24:2487–2498

    Article  CAS  Google Scholar 

  17. Li S, Vigh G (2004) Use of the new, single-isomer, hexakis(2,3-diacetyl-6-O-sulfo)-alpha-cyclodextrin in acidic methanol background electrolytes for nonaqueous capillary electrophoretic enantiomer separations. J Chromatogr A 1051:95–101

    Article  CAS  Google Scholar 

  18. Vincent JB, Sokolowski AD, Nguyen TV, Vigh G (1997) A family of single-isomer chiral resolving agents for capillary electrophoresis.1. Heptakis(2,3-diacetyl-6-sulfato)-beta-cyclodextrin. Anal Chem 69:4226–4233

    Article  CAS  Google Scholar 

  19. Zhu W, Vigh G (2000) A family of single-isomer, sulfated gamma-cyclodextrin chiral resolving agents for capillary electrophoresis. 1. Octakis(2,3-diacetyl-6-sulfato)-gamma-cyclodextrin. Anal Chem 72:310–317

    Article  CAS  Google Scholar 

  20. Zhu W, Vigh G (2000) Enantiomer separations by nonaqueous capillary electrophoresis using octakis(2,3-diacetyl-6-sulfato)-gamma-cyclodextrin. J Chromatogr A 892:499–507

    Article  CAS  Google Scholar 

  21. Busby MB, Vigh G (2005) Synthesis of heptakis(2-O-methyl-3-O-acetyl-6-O-sulfo)-cyclomaltoheptaose, a single-isomer, sulfated beta-cyclodextrin carrying nonidentical substituents at all the C2, C3, and C6 positions and its use for the capillary electrophoretic separation of enantiomers in acidic aqueous and methanolic background electrolytes. Electrophoresis 26:1978–1987

    Article  CAS  Google Scholar 

  22. Busby MB, Vigh G (2005) Synthesis of a single-isomer sulfated beta-cyclodextrin carrying nonidentical substituents at all of the C2, C3, and C6 positions and its use for the electrophoretic separation of enantiomers in acidic aqueous and methanolic background electrolytes. Part 2: Heptakis(2-O-methyl-6-O-sulfo) cyclomaltoheptaose. Electrophoresis 26:3849–3860

    Article  CAS  Google Scholar 

  23. Servais AC, Fillet M, Abushoffa AM, Hubert P, Crommen J (2003) Synergistic effects of ion-pairing in the enantiomeric separation of basic compounds with cyclodextrin derivatives in nonaqueous capillary electrophoresis. Electrophoresis 24:363–369

    Article  CAS  Google Scholar 

  24. Servais AC, Fillet M, Chiap P, Dewe W, Hubert P, Crommen J (2004) Enantiomeric separation of basic compounds using heptakis(2,3-di-O-methyl-6-O-sulfo)-beta-cyclodextrin in combination with potassium camphorsulfonate in nonaqueous capillary electrophoresis: optimization by means of an experimental design. Electrophoresis 25:2701–2710

    Article  CAS  Google Scholar 

  25. Servais AC, Chiap P, Hubert P, Crommen J, Fillet M (2004) Determination of salbutamol enantiomers in human urine using heptakis(2,3-di-O-acetyl-6-O-sulfo)-beta-cyclodextrin in nonaqueous capillary electrophoresis. Electrophoresis 25:1632–1640

    Article  CAS  Google Scholar 

  26. Servais AC, Fillet M, Chiap P, Dewe W, Hubert P, Crommen J (2005) Influence of the nature of the electrolyte on the chiral separation of basic compounds in nonaqueous capillary electrophoresis using heptakis(2,3-di-O-methyl-6-O-sulfo)-beta-cyclodextrin. J Chromatogr A 1068:143–150

    Article  CAS  Google Scholar 

  27. Marini RD, Servais AC, Rozet E, Chiap P, Boulanger B, Rudaz S, Crommen J, Hubert P, Fillet M (2006) Nonaqueous capillary electrophoresis method for the enantiomeric purity determination of S-timolol using heptakis(2,3-di-O-methyl-6-O-sulfo)-beta-cyclodextrin: validation using the accuracy profile strategy and estimation of uncertainty. J Chromatogr A 1120:102–111

    Article  CAS  Google Scholar 

  28. Rousseau A, Chiap P, Oprean R, Crommen J, Fillet M, Servais AC (2009) Effect of the nature of the single-isomer anionic CD and the BGE composition on the enantiomeric separation of beta-blockers in NACE. Electrophoresis 30:2862–2868

    Article  CAS  Google Scholar 

  29. Rousseau A, Gillotin F, Chiap P, Crommen J, Fillet M, Servais AC (2010) Association of two single-isomer anionic CD in NACE for the chiral and achiral separation of fenbendazole, its sulphoxide and sulphone metabolites: application to their determination after in vitro metabolism. Electrophoresis 31:1482–1487

    CAS  PubMed  Google Scholar 

  30. Rousseau A, Florence X, Pirotte B, Varenne A, Gareil P, Villemin D, Chiap P, Crommen J, Fillet M, Servais AC (2010) Development and validation of a nonaqueous capillary electrophoretic method for the enantiomeric purity determination of a synthetic intermediate of new 3,4-dihydro-2,2-dimethyl-2H-1-benzopyrans using a single-isomer anionic cyclodextrin derivative and an ionic liquid. J Chromatogr A 1217:7949–7955

    Article  CAS  Google Scholar 

  31. Rousseau A, Gillotin F, Chiap P, Bodoki E, Crommen J, Fillet M, Servais AC (2011) Generic systems for the enantioseparation of basic drugs in NACE using single-isomer anionic CDs. J Pharm Biomed Anal 54:154–159

    Article  CAS  Google Scholar 

  32. Cucinotta V, Contino A, Giuffrida A, Maccarrone G, Messina M (2010) Application of charged single isomer derivatives of cyclodextrins in capillary electrophoresis for chiral analysis. J Chromatogr A 1217:953–967

    Article  CAS  Google Scholar 

  33. Fradi I, Servais AC, Pedrini M, Chiap P, Ivanyi R, Crommen J, Fillet M (2006) Enantiomeric separation of acidic compounds using single-isomer amino cyclodextrin derivatives in nonaqueous capillary electrophoresis. Electrophoresis 27:3434–3442

    Article  CAS  Google Scholar 

  34. Rousseau A, Pedrini M, Chiap P, Ivanyi R, Crommen J, Fillet M, Servais AC (2008) Determination of flurbiprofen enantiomers in plasma using a single-isomer amino cyclodextrin derivative in nonaqueous capillary electrophoresis. Electrophoresis 29:3641–3648

    Article  CAS  Google Scholar 

  35. Rousseau A, Chiap P, Ivanyi R, Crommen J, Fillet M, Servais AC (2008) Validation of a nonaqueous capillary electrophoretic method for the enantiomeric purity determination of R-flurbiprofen using a single-isomer amino cyclodextrin derivative. J Chromatogr A 1204:219–225

    Article  CAS  Google Scholar 

  36. Marini RD, Groom C, Doucet FR, Hawari J, Bitar Y, Holzgrabe U, Gotti R, Schappler J, Rudaz S, Veuthey JL, Mol R, Somsen GW, de Jong GJ, Ha PT, Zhang J, Van Schepdael A, Hoogmartens J, Brione W, Ceccato A, Boulanger B, Mangelings D, Vander Heyden Y, Van Ael W, Jimidar I, Pedrini M, Servais AC, Fillet M, Crommen J, Rozet E, Hubert P (2006) Interlaboratory study of a NACE method for the determination of R-timolol content in S-timolol maleate: assessment of uncertainty. Electrophoresis 27:2386–2399

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Laboratory for the Analysis of Medicines, Department of Pharmaceutical Sciences, CIRM, Quartier Hôpital, University of Liège, Liège, Belgium

    Anne-Catherine Servais & Marianne Fillet

Authors
  1. Anne-Catherine Servais
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Marianne Fillet
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Anne-Catherine Servais .

Editor information

Editors and Affiliations

  1. Department of Pharmaceutical Chemistry, University of Jena, Jena, Germany

    Gerhard K. E. Scriba

Rights and permissions

Reprints and permissions

Copyright information

© 2019 Springer Science+Business Media, LLC, part of Springer Nature

About this protocol

Cite this protocol

Servais, AC., Fillet, M. (2019). Enantioseparations in Nonaqueous Capillary Electrophoresis Using Charged Cyclodextrins. In: Scriba, G.K.E. (eds) Chiral Separations. Methods in Molecular Biology, vol 1985. Humana, New York, NY. https://doi.org/10.1007/978-1-4939-9438-0_21

Download citation

  • DOI: https://doi.org/10.1007/978-1-4939-9438-0_21

  • Publisher Name: Humana, New York, NY

  • Print ISBN: 978-1-4939-9437-3

  • Online ISBN: 978-1-4939-9438-0

  • eBook Packages: Springer Protocols

Publish with us

Policies and ethics

Search

Navigation