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A Cyclodextrin Self-Assembled Monolayer (SAM) Based Surface Plasmon Resonance (SPR) Sensor for Enantioselective Analysis of Thyroxine

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Abstract

Heptakis 6-deoxy-6-[12-(thiododecyl) undecanamido-β-cyclodextrin has been produced by reaction of Heptakis(6-deoxy-6-amino)-β-cyclodextrin and 12-(thiododecyl)undecanoic acid using O-Benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium tetrafluoroborate (TBTU) as activating agent. Self-assembled monolayers of this macrocycle have been used in a surface plasmon resonance (SPR) sensor; it has been shown that this system is suitable to discriminate between d and l enantiomers of thyroxine, with a greater affinity for the d-enantiomer.

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References

  1. J.L. Atwood J.W. Steed (Eds) (2004) Encyclopedia of Supramolecular Chemistry Marcel Dekker New York

    Google Scholar 

  2. J.M. Lehn (1995) Supramolecular Chemistry: Concepts and Perspectives VCH Weinheim

    Google Scholar 

  3. H.-J. Schneider A.K. Yatsimirsky (2000) Principles and Methods in Supramolecular Chemistry John Wiley and Sons Chichester

    Google Scholar 

  4. A.J. Stone (2002) The Theory of Intermolecular Forces Clarendon Press Oxford

    Google Scholar 

  5. M. Simonyi (1984) Med. Res. Rev. 4 359–413 Occurrence Handle6087043

    PubMed  Google Scholar 

  6. A.J. Hutt S.C. Tan (1996) Drugs 52 IssueIDSuppl 5 1–12

    Google Scholar 

  7. G. Subramanian (1994) A Practical Approach to Chiral Separations by Liquid Chromatography Weinheim VCH

    Google Scholar 

  8. V. Schurig (2002) Trends Anal Chem. 21 647–661 Occurrence Handle10.1016/S0165-9936(02)00808-7

    Article  Google Scholar 

  9. D. Wistuba V. Schürig (2000) J Chromatography A 875 255–276 Occurrence Handle10.1016/S0021-9673(00)00066-2

    Article  Google Scholar 

  10. S. Stanley C.J. Percival T. Morel A. Braithwaite M.I. Newton G. McHale W. Hayes (2003) Sens Actuator B 89 103–106 Occurrence Handle10.1016/S0925-4005(02)00449-5

    Article  Google Scholar 

  11. C.J. Percival S. Stanley M. Galle A. Braithwaite M.I. Newton G. McHale W. Hayes (2001) Anal. Chem. 73 4225–4228 Occurrence Handle10.1021/ac0155198 Occurrence Handle11569813

    Article  PubMed  Google Scholar 

  12. L. Cao X.C. Zhou S.F. Li (2001) Analyst 126 184–188 Occurrence Handle10.1039/b005750i Occurrence Handle11235101

    Article  PubMed  Google Scholar 

  13. K. Haupt K. Noworyta W. Kutner (1999) Anal. Commun. 36 391–393 Occurrence Handle10.1039/a907844d

    Article  Google Scholar 

  14. R. Paolesse D. Monti L. La Monica M. Venanzi A. Froiio S. Nardis C. Di Natale E. Martinelli A. D’Amico (2002) Chem. Eur. J. 8 2476–2483 Occurrence Handle10.1002/1521-3765(20020603)8:11<2476::AID-CHEM2476>3.0.CO;2-E

    Article  Google Scholar 

  15. M.I. Prodromidis T. Hirsch V.M. Mirsky O.S. Wolfbeis (2003) Electroanalysis 15 1795–1798 Occurrence Handle10.1002/elan.200302756

    Article  Google Scholar 

  16. B. Kieser C. Fietzek R. Schmidt G. Belge U. Weimar V. Schurig G. Gauglitz (2002) Anal.Chem. 74 3005–3012 Occurrence Handle10.1021/ac015689k Occurrence Handle12141658

    Article  PubMed  Google Scholar 

  17. J. Szejtli (1988) Cyclodextrin Technology Kluwer Dordrecht

    Google Scholar 

  18. E. Schneiderman A.M. Stalcup (2000) J. Chromoatogr., B 745 83–102

    Google Scholar 

  19. T. Auletta B. Dordi A. Mulder A. Sartori S. Onclin C.M. Bruinink M. Peter C.A. Nijhuis H. Beijleveld H. Schoenherr G.J. Vansco A. Casnati R. Ungaro B.J. Ravoo J. Huskens D.N. Reinhoudt (2004) Angew. Chem. Int. Ed. 43 369–373 Occurrence Handle10.1002/anie.200352767

    Article  Google Scholar 

  20. T. Auletta M.R. De Jong A. Mulder F.C.J.M. Van Veggel J. Huskens D.N. Reinhoudt S. Zou S. Zapotoczny H. Schoenherr G.J. Vansco L. Kuipers (2004) J. Am. Chem. Soc. 126 1577–1584 Occurrence Handle10.1021/ja0383569 Occurrence Handle14759218

    Article  PubMed  Google Scholar 

  21. J. Huskens M.A. Deij D.N. Reinhoudt (2002) Angew. Chem. Int. Ed 41 4467–4471 Occurrence Handle10.1002/1521-3773(20021202)41:23<4467::AID-ANIE4467>3.0.CO;2-C

    Article  Google Scholar 

  22. M.R. De Jong J. Huskens D.N. Reinhoudt (2001) Chem. Eur. J. 7 4164–4170 Occurrence Handle10.1002/1521-3765(20011001)7:19<4164::AID-CHEM4164>3.0.CO;2-Q

    Article  Google Scholar 

  23. M.W.J. Beulen J. Bugler B. Lammerink F.A.J. Geurts E.M.E.F. Biemond K.G.C. Van Leerdam F.C.J.M. Van Veggel J.F.J. Engbersen D.N. Reinhoudt (1998) Langmuir 14 6424–6429 Occurrence Handle10.1021/la980936+

    Article  Google Scholar 

  24. M.W.J. Beulen J. Bugler M.R. Jong ParticleDe B. Lammerink J. Huskens H. Schonherr G.J. Vancso B.A. Boukamp H. Wieder A. Offenhauser W. Knoll F.C.J.M. Van Veggel D.N. Reinhoudt (2000) Chem. Eur. J. 6 1176–1183 Occurrence Handle10.1002/(SICI)1521-3765(20000403)6:7<1176::AID-CHEM1176>3.3.CO;2-T

    Article  Google Scholar 

  25. J.H. Oppenheimer H.L. Schwartz C.N. Mariash W.B. Kinlaw N.C.W. Wong H.C. Freake (1987) Endocrin. Rev. 8 288–308

    Google Scholar 

  26. P.R. Ashton R. Königer J.F. Stoddart (1996) J. Org. Chem. 61 903–908 Occurrence Handle10.1021/jo951396d

    Article  Google Scholar 

  27. E.B. Troughton C.D. Bain G.M. Whitesides R.G. Nuzzo D.L. Allara M.D. Porter (1988) Langmuir 4 365–385 Occurrence Handle10.1021/la00080a021

    Article  Google Scholar 

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Authors and Affiliations

  1. Institute of Physics, University of Basel, Klingelbergstrasse 82, CH-4056, Basel, Switzerland

    Patrick Shahgaldian & Martin Hegner

  2. Fachhochschule beider Basel, Abteilung Chemie/Nano-Technologie, Gründenstrasse 40, CH-4132, Muttenz, Switzerland

    Patrick Shahgaldian & Uwe Pieles

Authors
  1. Patrick Shahgaldian
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  2. Martin Hegner
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  3. Uwe Pieles
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Correspondence to Patrick Shahgaldian.

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Received in final form: 6 January 2005

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Shahgaldian, P., Hegner, M. & Pieles, U. A Cyclodextrin Self-Assembled Monolayer (SAM) Based Surface Plasmon Resonance (SPR) Sensor for Enantioselective Analysis of Thyroxine. J Incl Phenom Macrocycl Chem 53, 35–39 (2005). https://doi.org/10.1007/s10847-005-0248-3

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  • DOI: https://doi.org/10.1007/s10847-005-0248-3

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