Investigating Rhodamine B-Labeled Peptoids: Scopes and Limitations of Its Applications

被引:51
作者
Birtalan, Esther [1 ]
Rudat, Birgit [1 ,2 ]
Koelmel, Dominik K. [1 ]
Fritz, Daniel [1 ]
Vollrath, Sidonie B. L. [1 ]
Schepers, Ute [3 ]
Braese, Stefan [1 ]
机构
[1] Karlsruhe Inst Technol, Inst Organ Chem, D-76131 Karlsruhe, Germany
[2] Karlsruhe Inst Technol, Light Technol Inst, D-76131 Karlsruhe, Germany
[3] Karlsruhe Inst Technol, Inst Toxicol & Genet, D-76344 Eggenstein Leopoldshafen, Germany
关键词
molecular transporter; peptoid; fluorescent marker; rhodamine; spirolactam formation; FLUORESCENT; SPIROLACTAM; PEPTIDES; CARRIER; CELLS; DYES;
D O I
10.1002/bip.21617
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
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. (C) 2011 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 96: 694-701, 2011.
引用
收藏
页码:694 / 701
页数:8
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