| Zugriffsnummer | 39283 |
| Dokumenttyp | Zeitschriftenartikel |
| Peer Review | mit Peer Review |
| Sprache | Englisch |
| Titel | Heterobifunctional dyes: highly fluorescent linkers based on cyanine dyes |
| Autor(in); Institution |
Wycisk, V.; Institute of Chemistry and Biochemistry, Freie Universität Berlin, GERMANY
Achazi, K.; Institute of Chemistry and Biochemistry, Freie Universität Berlin, GERMANY
Hirsch, Ole; 8.3, Biomedizinische Optik, PTB-Berlin
Kuehne, C.; Institute of Laboratory Medicine, Clinical Chemistry and Pathobiochemistry, Charité-Universitätsmedizin Berlin, GERMANY
Dernedde, J.; Institute of Laboratory Medicine, Clinical Chemistry and Pathobiochemistry, Charité-Universitätsmedizin Berlin, GERMANY
Haag, R.; Institute of Chemistry and Biochemistry, Freie Universität Berlin, GERMANY
Licha, K.; Institute of Chemistry and Biochemistry, Freie Universität Berlin, GERMANY
|
| Quelle/Jahr | ChemistryOpen: 6 (2017), 3, 437 - 446 |
| ISSN | 2191-1355 (PRINT) ; 2191-1363 (ONLINE) |
| DOI | |
| Verlag | Weinheim: Wiley-VCH |
| Zusammenfassung | Herein, we present a new synthetic route to cyanine-based heterobifunctional dyes for application as fluorescent linkers between polymers and biomolecules. The synthesized compounds, designed in the visible spectral range, are equipped with two different reactive groups for highly selective conjugation under physiological conditions. By applying indolenine precursors with functionalized benzenes, we achieved water-soluble asymmetric cyanine dyes in a 3-step synthesis bearing maleimido and N-hydroxysuccinimidyl (NHS) functionalities. Spectroscopic characterization revealed good molar absorption coefficients and moderate fluorescence quantum yields. Further reaction with poly(ethyleneglycol) (PEG) yielded dye-polymer-conjugates which were subsequently coupled to the antibody cetuximab (ctx) often applied in cancer therapy. Successful coupling was confirmed by mass shifts detected by gel electrophoresis. Receptor binding studies and live cell imaging revealed that labeling did not alter the biological function. In sum, we have provided a successful synthetic pathway to rigid heterobifunctional cyanine dyes that are applicable as fluorescent linkers, for example, for connecting antibodies with macromolecules. Our approach contributes to the field of bioconjugation chemistry, such as for antibody-drug conjugates by combining diagnostic and therapeutic approaches. |
| Kostenfreier Zugang | Open Access Gold |
| Rechteinformation | Original article under: ACS AuthorChoice License, which permits copying and redistribution of the article or any adaptations for non-commercial purposes |