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Cyclodextrin modified gold nanoparticles-based open-tubular capillary electrochromatographic separations of polyaromatic hydrocarbons

  • Special Issue: Nanostructured Materials 2010
  • Published:
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Abstract

In this study, spherical gold nanoparticles (GNPs) of 14.7 nm diameter, prepared by citrate reduction of a gold(III) salt and characterized by UV–Vis absorption spectrometry and transmission electron microscopy, were modified by a covalent attachment of 6I-O-(3-mercaptopropyl)β-cyclodextrin (β-CD-SH) or per-6-deoxy-per-6-mercapto-β-cyclodextrin (β-CD-SH7). Subsequently, via three alternative approaches, β-CD-modified GNPs were immobilized onto the inner wall of the fused-silica (FS) capillaries and applied as special stationary phases for open-tubular capillary electrochromatography (OT-CEC). The first immobilization procedure was based on pre-derivatization of a FS capillary with (3-mercaptopropyl)trimethoxysilane (MPTMS) followed by subsequent reactions with GNPs and β-CD-SH or β-CD-SH7. The other two preparation protocols took advantage of sol–gel approach gaining a significant increase in the interaction surface for solutes. In both instances, the sol–gel created 3D structure was further covalently modified with GNPs. Serving that purpose, either β-CD-SH7 modified GNPs were used for the immobilization into the sol–gel matrix (“one-step sol–gel technique”) or native GNPs were immobilized first into the sol–gel matrix and subsequently modified with β-CD-SH7 (“two-step sol–gel technique”). The separation performance of CD-GNPs modified FS capillaries was tested by OT-CEC in reversed-phase mode applied to separation of a model mixture of five polyaromatic hydrocarbons. The highest separation efficiencies were obtained with the capillaries prepared by two-step sol–gel technique. However, with respect to the relatively low reproducibility of this method, the first of the above preparation procedures, i.e., a simple pre-derivatization of the FS capillary with MPTMS ensued with β-CD-SH7-GNPs immobilization seems to be more feasible approach providing decent separation efficiency.

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References

  • Daniel M-C, Astruc D (2004) Gold nanoparticles: assembly, supramolecular chemistry, quantum-size-related properties, and applications toward biology, catalysis, and nanotechnology. Chem Rev 104:293–346

    Article  CAS  Google Scholar 

  • Dios AS, Díaz-García ME (2010) Multifunctional nanoparticles: analytical prospects. Anal Chim Acta 666:1–22. doi:10.1016/j.aca.2010.03.038

    Article  Google Scholar 

  • Guihen E, Glennon JD (2003) Nanoparticles in separation science—recent developments. Anal Lett 36:3309–3336

    Article  CAS  Google Scholar 

  • Hongjun E, Yang Y, Su P, Zhang WD (2009) Preparation of stationary phases for open tubular capillary electrochromatography on the basis of sulfated beta-cyclodextrin intercalated in layered double hydroxides. J Anal Chem 64:393–397. doi:10.1134/S1061934809040133

    Article  Google Scholar 

  • Jung M, Mayer S, Schurig V (1994) Enantiomer Separation by Gc, Sfc, and Ce on Immobilized Polysiloxane-Bonded Cyclodextrins. Lc Gc. Mag Sep Sci 12:458

    CAS  Google Scholar 

  • Li YJ, Song CH, Zhang LY, Zhang WB, Fu HG (2010) Fabrication and evaluation of chiral monolithic column modified by beta-cyclodextrin derivatives. Talanta 80:1378–1384. doi:10.1016/j.talanta.2009.09.039

    Article  CAS  Google Scholar 

  • Lin B, Shi ZG, Zhang HJ, Ng SC, Feng YQ (2006) Perphenylcarbamoylated beta-cyclodextrin bonded-silica particles as chiral stationary phase for enantioseparation by pressure-assisted capillary electrochromatography. Electrophoresis 27:3057–3065. doi:10.1002/elps.200500906

    Article  CAS  Google Scholar 

  • Liu FK, Hsu YT, Wu CH (2005) Open tubular capillary electrochromatography using capillaries coated with films of alkanethiol-self-assembled gold nanoparticle layers. J Chromatogr A 1083:205–214

    Article  CAS  Google Scholar 

  • Mayer S, Schurig V (1992) Enantiomer separation by electrochromatography on capillaries coated with Chirasil-Dex. J High Resolut Chromatogr 15:129–131. doi:10.1002/jhrc.1240150216

    Article  CAS  Google Scholar 

  • Mayer S, Schurig V (1993) Enantiomer separation by electrochromatography in open tubular columns coated with Chirasil-Dex. J Liq Chromatogr 16:915–931. doi:10.1080/10826079308020943

    Article  CAS  Google Scholar 

  • Mayer S, Schurig V (1994) Enantiomer separation using mobile and immobile cyclodextrin derivatives with electromigration. Electrophoresis 15:835–841. doi:10.1002/elps.11501501118

    Article  CAS  Google Scholar 

  • Mayer S, Schleimer M, Schurig V (1994) Dual chiral recognition system involving cyclodextrin derivatives in capillary electrophoresis. J Microcolumn Sep 6:43–48. doi:10.1002/mcs.1220060109

    Article  CAS  Google Scholar 

  • O’Mahony T, Owens VP, Murrihy JP, Guihen E, Holmes JD, Glennon JD (2003) Alkylthiol gold nanoparticles in open-tubular capillary electrochromatography. J Chromatogr A 1004:181–193

    Article  Google Scholar 

  • Qu QS, Zhang XX, Shen M, Liu Y, Hu XY, Yang GJ, Wang CY, Zhang YK, Yan C (2008) Open-tubular capillary electrochromatography using a capillary coated with octadecylamine-capped gold nanoparticles. Electrophoresis 29:901–909

    Article  CAS  Google Scholar 

  • Qu Q, Liu D, Mangelings D, Yang C, Hu X (2010) Permanent gold nanoparticle coatings on polyelectrolyte multilayer modified capillaries for open-tubular capillary electrochromatography. J Chromatogr A 1217:6588–6594. doi:10.1016/j.chroma.2010.08.057

    Article  CAS  Google Scholar 

  • Řezanka P, Záruba K, Král V (2008) A change in nucleotide selectivity pattern of porphyrin derivatives after immobilization on gold nanoparticles. Tetrahedron Lett 49:6448–6453. doi:10.1016/j.tetlet.2008.08.099

    Article  Google Scholar 

  • Rojas MT, Königer R, Stoddart JF, Kaifer AE (1995) Supported monolayers containing preformed binding sites. Synthesis and interfacial binding properties of a thiolated beta-cyclodextrin derivative. J Am Chem Soc 117:336–343

    Article  CAS  Google Scholar 

  • Schurig V, Mayer S (2001) Separation of enantiomers by open capillary electrochromatography on polysiloxane-bonded permethyl-beta-cyclodextrin. J Biochem Biophys Methods 48:117–141. doi:10.1016/S0165-022X(01)00144-0

    Article  CAS  Google Scholar 

  • Schurig V, Jung M, Mayer S, Fluck M, Negura S, Jakubetz H (1995) Unified enantioselective capillary chromatography on a Chirasil-DEX stationary phase. Advantages of column miniaturization. J Chromatogr A 694:119–128. doi:10.1016/0021-9673(94)00662-S

    Article  CAS  Google Scholar 

  • Sekhon BS (2010) Enantioseparation of chiral drugs—an overview. Int J Pharm Technol Res 2:1584–1594

    CAS  Google Scholar 

  • Sýkora D, Kašička V, Mikšík I, Řezanka P, Záruba K, Matějka P, Král V (2010) Application of gold nanoparticles in separation sciences. J Sep Sci 33:372–387. doi:10.1002/jssc.200900677

    Article  Google Scholar 

  • Tian Y, Zhong C, Fu EQ, Zeng ZR (2009) Novel beta-cyclodextrin derivative functionalized polymethacrylate-based monolithic columns for enantioselective separation of ibuprofen and naproxen enantiomers in capillary electrochromatography. J Chromatogr A 1216:1000–1007. doi:10.1016/j.chroma.2008.12.014

    Article  CAS  Google Scholar 

  • Wang YC, Zeng ZR, Guan N, Cheng JK (2001) Sol–gel technique for the preparation of beta-cyclodextrin derivative stationary phase in open-tubular capillary electrochromatography. Electrophoresis 22:2167–2172. doi:10.1002/1522-2683(20017)

    Article  CAS  Google Scholar 

  • Wang Y, Xiao Y, Tan TTY, Ng SC (2009) Application of Click-chemistry-based perphenylcarbamated beta-CD chiral stationary phase in CEC. Electrophoresis 30:705–711. doi:10.1002/elps.200800424

    Article  CAS  Google Scholar 

  • Wistuba D, Schurig V (1999) Enantiomer separation by pressure-supported electrochromatography using capillaries packed with Chirasil-Dex polymer-coated silica. Electrophoresis 20:2779–2785. doi:10.1002/(SICI)1522-2683(19990901)

    Article  CAS  Google Scholar 

  • Wistuba D, Schurig V (2000) Enantiomer separation by capillary electrochromatography on a cyclodextrin-modified monolith. Electrophoresis 21:3152–3159. doi:10.1002/1522-2683(20000901)

    Article  CAS  Google Scholar 

  • Wistuba D, Cabrera K, Schurig V (2001) Enantiomer separation by nonaqueous and aqueous capillary electrochromatography on cyclodextrin stationary phases. Electrophoresis 22:2600–2605. doi:10.1002/1522-2683(200107)

    Article  CAS  Google Scholar 

  • Wistuba D, Banspach L, Schurig V (2005) Enantiomeric separation by capillary electrochromatography using monolithic capillaries with sol–gel-glued cyclodextrin-modified silica particles. Electrophoresis 26:2019–2026. doi:10.1002/elps.200410251

    Article  CAS  Google Scholar 

  • Yang L, Guihen E, Glennon JD (2005a) Alkylthiol gold nanoparticles in sol–gel-based open tubular capillary electrochromatography. J Sep Sci 28:757–766

    Article  CAS  Google Scholar 

  • Yang L, Guihen E, Holmes JD, Loughran M, O’Sullivan GP, Glennon JD (2005b) Gold nanoparticle-modified etched capillaries for open-tubular capillary electrochromatography. Anal Chem 77:1840–1846

    Article  CAS  Google Scholar 

  • Yang L, Chen CJ, Liu X, Shi J, Wang GA, Zhu LD, Guo LP, Glennon JD, Scully NM, Doherty BE (2010) Use of cyclodextrin-modified gold nanoparticles for enantioseparations of drugs and amino acids based on pseudostationary phase-capillary electrochromatography. Electrophoresis 31:1697–1705. doi:10.1002/elps.200900541

    Article  CAS  Google Scholar 

  • Zhang MQ, El Rassi Z (2000a) Enantiomeric separation by capillary electrochromatography—I. Chiral separation of dansyl amino acids and organochlorine pesticides on a diol-silica dynamically coated with hydroxypropyl-beta-cyclodextrin. Electrophoresis 21:3126–3134. doi:10.1002/1522-2683(20000901)

    Article  CAS  Google Scholar 

  • Zhang MQ, El Rassi Z (2000b) Enantiomeric separation by capillary electrochromatography—II. Chiral separation of dansyl amino acids and phenoxy acid herbicides on sulfonated silica having surface-bound hydroxypropyl-beta-cyclodextrin. Electrophoresis 21:3135–3140. doi:10.1002/1522-2683(20000901)

    Article  CAS  Google Scholar 

  • Zhou A, Lv X, Xie Y, Yan C, Gao R (2005) Chromatographic evaluation of perphenylcarbamoylated beta-cyclodextrin bonded stationary phase for micro-high performance liquid chromatography and pressurized capillary electrochromatography. Anal Chim Acta 547:158–164. doi:10.1016/j.aca.2005.05.043

    Article  CAS  Google Scholar 

Download references

Acknowledgments

Financial support from the Ministry of Education of the Czech Republic, No. MSMT6046137307 and from the Czech Science Foundation, No. 203/09/0675 is gratefully acknowledged.

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Authors and Affiliations

  1. Department of Analytical Chemistry, Institute of Chemical Technology, Technická 5, 166 28, Prague 6, Czech Republic

    Pavel Řezanka, Klára Navrátilová, Pavel Žvátora, David Sýkora, Pavel Matějka & Vladimír Král

  2. Institute of Physiology, Academy of Sciences of the Czech Republic, Vídeňská 1083, 142 20, Prague 4, Czech Republic

    Ivan Mikšík

  3. Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 166 10, Prague 6, Czech Republic

    Václav Kašička

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  1. Pavel Řezanka
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  2. Klára Navrátilová
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  3. Pavel Žvátora
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  8. Vladimír Král
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Correspondence to David Sýkora.

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Řezanka, P., Navrátilová, K., Žvátora, P. et al. Cyclodextrin modified gold nanoparticles-based open-tubular capillary electrochromatographic separations of polyaromatic hydrocarbons. J Nanopart Res 13, 5947–5957 (2011). https://doi.org/10.1007/s11051-011-0437-5

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