Heterobifunctional Dyes: Highly Fluorescent Linkers Based on Cyanine Dyes
Abstract: Herein, we present a new synthetic route to cyanine‐based heterobifunctional dyes and their 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 bearing maleimido and N‐hydroxysuccinimidyl functionalities in a three‐step synthesis. Spectroscopic characterization revealed good molar absorption coefficients and moderate fluorescence quantum yields. Further reaction with polyethylene glycol yielded dye–polymer conjugates that were subsequently coupled to the antibody cetuximab, 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 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 antibody–drug conjugates by combining diagnostic and therapeutic approaches.
- Standort
-
Deutsche Nationalbibliothek Frankfurt am Main
- Umfang
-
Online-Ressource
- Sprache
-
Englisch
- Erschienen in
-
Heterobifunctional Dyes: Highly Fluorescent Linkers Based on Cyanine Dyes ; volume:6 ; number:3 ; year:2017 ; pages:437-446 ; extent:10
ChemistryOpen ; 6, Heft 3 (2017), 437-446 (gesamt 10)
- Urheber
-
Wycisk, Virginia
Achazi, Katharina
Hirsch, Ole
Kuehne, Christian
Dernedde, Jens
Haag, Rainer
Licha, Kai
- DOI
-
10.1002/open.201700013
- URN
-
urn:nbn:de:101:1-2022100606065916154654
- Rechteinformation
-
Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Letzte Aktualisierung
-
04.04.2025, 08:02 MESZ
Datenpartner
Deutsche Nationalbibliothek. Bei Fragen zum Objekt wenden Sie sich bitte an den Datenpartner.
Beteiligte
- Wycisk, Virginia
- Achazi, Katharina
- Hirsch, Ole
- Kuehne, Christian
- Dernedde, Jens
- Haag, Rainer
- Licha, Kai
Ähnliche Objekte (12)
Fluorescent Dyes and Quenchers with Rigid Linkers
Synthesen, Strukturen und Reaktionen hochgespannter Acepentalenvorläufer : das Dilithiumacepentalendiid
Stereochemistry‐Controlled Supramolecular Architectures of New Tetrahydroxy‐Functionalised Amphiphilic Carbocyanine Dyes
Die Forcierung der klassischen Beteiligungsfinanzierung der Kreditgenossenschaft
Systematic Screening of Different Polyglycerin‐Based Dienophile Macromonomers for Efficient Nanogel Formation through IEDDA Inverse Nanoprecipitation
Functional Fluorescent Dyes and their Polymer Conjugates
Mechanically tunable organogels from highly charged polyoxometalate clusters loaded with fluorescent dyes
Dyes
Macroscopic Air-Based Molecular Communication using Fluorescent Dyes
Synthesis of pH-degradable polyglycerol-based nanogels by iEDDA-mediated crosslinking for encapsulation of asparaginase using inverse nanoprecipitation
Polyglycerol‐Based Biomedical Matrix for Immunomagnetic Circulating Tumor Cell Isolation and Their Expansion into Tumor Spheroids for Drug Screening
Responsive Emulsions for Sequential Multienzyme Cascades
Fluorescent Dyes and Quenchers with Rigid Linkers
Synthesen, Strukturen und Reaktionen hochgespannter Acepentalenvorläufer : das Dilithiumacepentalendiid
Stereochemistry‐Controlled Supramolecular Architectures of New Tetrahydroxy‐Functionalised Amphiphilic Carbocyanine Dyes
Die Forcierung der klassischen Beteiligungsfinanzierung der Kreditgenossenschaft
Systematic Screening of Different Polyglycerin‐Based Dienophile Macromonomers for Efficient Nanogel Formation through IEDDA Inverse Nanoprecipitation
Functional Fluorescent Dyes and their Polymer Conjugates
Mechanically tunable organogels from highly charged polyoxometalate clusters loaded with fluorescent dyes
Dyes
Macroscopic Air-Based Molecular Communication using Fluorescent Dyes
Synthesis of pH-degradable polyglycerol-based nanogels by iEDDA-mediated crosslinking for encapsulation of asparaginase using inverse nanoprecipitation
Polyglycerol‐Based Biomedical Matrix for Immunomagnetic Circulating Tumor Cell Isolation and Their Expansion into Tumor Spheroids for Drug Screening
Responsive Emulsions for Sequential Multienzyme Cascades
Fluorescent Dyes and Quenchers with Rigid Linkers
Synthesen, Strukturen und Reaktionen hochgespannter Acepentalenvorläufer : das Dilithiumacepentalendiid
Stereochemistry‐Controlled Supramolecular Architectures of New Tetrahydroxy‐Functionalised Amphiphilic Carbocyanine Dyes
Die Forcierung der klassischen Beteiligungsfinanzierung der Kreditgenossenschaft
Systematic Screening of Different Polyglycerin‐Based Dienophile Macromonomers for Efficient Nanogel Formation through IEDDA Inverse Nanoprecipitation
Functional Fluorescent Dyes and their Polymer Conjugates
Mechanically tunable organogels from highly charged polyoxometalate clusters loaded with fluorescent dyes
Dyes
Macroscopic Air-Based Molecular Communication using Fluorescent Dyes
Synthesis of pH-degradable polyglycerol-based nanogels by iEDDA-mediated crosslinking for encapsulation of asparaginase using inverse nanoprecipitation
Polyglycerol‐Based Biomedical Matrix for Immunomagnetic Circulating Tumor Cell Isolation and Their Expansion into Tumor Spheroids for Drug Screening