Peptoid Functions

Investigating rhodamine B-labeled peptoids: Scopes and limitations of its applications†

  1. Esther Birtalan1,
  2. Birgit Rudat1,2,
  3. Dominik K. Kölmel1,
  4. Daniel Fritz1,
  5. Sidonie B. L. Vollrath1,
  6. Ute Schepers3,
  7. Stefan Bräse1,*

Article first published online: 14 MAR 2011

DOI: 10.1002/bip.21617

Issue

Peptide Science

Peptide Science

Special Issue: Special issue on 7th Peptoid Summit

Volume 96, Issue 5, pages 694–701, 2011

Additional Information

How to Cite

Birtalan, E., Rudat, B., Kölmel, D. K., Fritz, D., Vollrath, S. B. L., Schepers, U. and Bräse, S. (2011), Investigating rhodamine B-labeled peptoids: Scopes and limitations of its applications. Biopolymers, 96: 694–701. doi: 10.1002/bip.21617

Author Information

  1. 1

    Institute of Organic Chemistry, Karlsruhe Institute of Technology, Fritz-Haber-Weg 6 D-76131 Karlsruhe, Germany

  2. 2

    Light Technology Institute, Karlsruhe Institute of Technology, Engesser Str. 13 D-76131 Karlsruhe, Germany

  3. 3

    Institute of Toxicology and Genetics, Karlsruhe Institute of Technology, Hermann-von-Helmholtz-Platz 1 D-76344 Eggenstein-Leopoldshafen, Germany

*Institute of Organic Chemistry, Karlsruhe Institute of Technology, Fritz-Haber-Weg 6 D-76131 Karlsruhe, Germany

  1. †

    This article was originally published online as an accepted preprint. The “Published Online” date corresponds to the preprint version. You can request a copy of the preprint by emailing the Biopolymers editorial office at biopolymers@wiley. com

Publication History

  1. Issue published online: 9 SEP 2011
  2. Article first published online: 14 MAR 2011
  3. Manuscript Accepted: 4 FEB 2011
  4. Manuscript Revised: 23 DEC 2010
  5. Manuscript Received: 25 OCT 2010

Funded by

  • The Center for Functional Nanostructures of the German Research Council
  • The German Business Foundation
  • The Karlsruhe School of Optics & Photonics (KSOP), the Karlsruhe Institute of Technology
  • The Fonds der Chemischen Industrie
  • The Evangelisches Studienwerk e.V. Villigst
  • The Landesgraduiertenförderung at the Karlsruhe Institute of Technology

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Keywords:

  • molecular transporter;
  • peptoid;
  • fluorescent marker;
  • rhodamine;
  • spirolactam formation

Abstract

The fluorophore rhodamine B is often used in biological assays. It is inexpensive, robust under a variety of reaction conditions, can be covalently linked to bioactive molecules, and has suitable spectral properties in terms of absorption and fluorescence wavelength. Nonetheless, there are some drawbacks: it can readily form a spirolactam compound, which is nonfluorescent, and therefore may not be the dye of choice for all fluorescence microscopy applications. Herein this spirolactam formation was observed by purifying such a labeled peptoid with high performance liquid chromatography (HPLC) and monitored in detail by making a series of analytical HPLC runs over time. Additionally, a small library of eight peptoids with rhodamine B as label was synthesized. Analysis of the absorption properties of these molecules demonstrated that the problem of fluorescence loss can be overcome by coupling secondary amines with rhodamine B. © 2011 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 96: 694–701, 2011.

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