ArticleJournal of the American Chemical Society2023
Method To Diversify Cyanine Chromophore Functionality Enables Improved Biomolecule Tracking and Intracellular Imaging.
Article in Journal of the American Chemical Society, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 28 papers.
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Who cites it
28 citing papers in PubMed.
- Decoupling Photophysical Brightness and Cellular Imaging Efficiency in 4-ANI-Based Fluorophores: The Critical Role of Sterically Hindered N-Substituents.Chembiochem : a European journal of chemical biology · 2026Article
- More Than a Glow: How Cyanine Dyes Shape Tracer Pharmacokinetics.Angewandte Chemie (International ed. in English) · 2026Review
- π-Extended COUPY Fluorophores for Targeted Near-Infrared Fluorescence and Lifetime Imaging in Live Cells.Angewandte Chemie (International ed. in English) · 2026Article
- C1'-Substituted Penta- and Heptamethine Cyanines: Synthetic Scope and Properties.The Journal of organic chemistry · 2026Article
- Near-Infrared and Shortwave Infrared Building Blocks for Activity-Based Sensors in Animals.Bioconjugate chemistry · 2026Review
- A first-in-class precision antibody conjugate targeting EGFR, mTOR, and PI3K to treat head and neck cancers.Research square · 2026Article
- Recent advances of cyanine dyes in tumor theranostics: molecular modification, delivery strategies, and synergistic mechanisms.RSC advances · 2026Review
- Enhanced Fluorescence of Near-Infrared Anti-CEA Antibodies for Visualizing Colorectal Cancers Using Modified Heptamethine Cyanines.Molecular imaging and biology · 2026Article
- In vivo Fluorescent Molecular Imaging Using Nanobodies Labeled with Next-Generation FNIR-Tag-Dyes.Research square · 2026Article
- Fluorogenic Imaging Enables the Identification of Phosphoramidate Antibody-Drug Conjugate Linkers.Bioconjugate chemistry · 2026Article
- Cell wash-free fluorescent probes based on phenothiazine and phenoxazine with high photostability and large stokes shifts for targeted imaging of subcellular organelles.Materials today. Bio · 2025Article
- Above the Energy Gap Law: Heavy Chalcogenide Substitution in NIR II-Emissive Diradicaloid Qubits.ACS central science · 2025Article
- Through every lens: assessing the impact of chemical modifications on antibody-conjugates using in vivo imaging.Npj imaging · 2025Review
- Visualizing the chronicle of multiple cell fates using a near-IR dual-RNA/DNA-targeting probe.Science advances · 2025Article
- Tracking the Fate of Therapeutic Proteins Using Ratiometric Imaging of Responsive Shortwave Infrared Probes.Journal of the American Chemical Society · 2025Article
- Harnessing Cyanine-like Properties to Develop Bright Fluorogenic Probes Based on Viscosity-Sensitive Molecular Rotors.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Benzyl Ammonium Carbamates Undergo Two-Step Linker Cleavage and Improve the Properties of Antibody Conjugates.Angewandte Chemie (International ed. in English) · 2025Article
- Divergent Syntheses of Near-Infrared Light-Activated Molecular Jackhammers for Cancer Cell Eradication.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Engineering Central Substitutions in Heptamethine Dyes for Improved Fluorophore Performance.JACS Au · 2024Article
- Mechanistic Insight into the Thermal "Blueing" of Cyanine Dyes.Journal of the American Chemical Society · 2024Article
Corrections and comments
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Authors and funding
10 authors.
Funding
Abstract
Heptamethine indocyanines are invaluable probes for near-infrared (NIR) imaging. Despite broad use, there are only a few synthetic methods to assemble these molecules, and each has significant limitations. Here, we report the use of pyridinium benzoxazole (PyBox) salts as heptamethine indocyanine precursors. This method is high yielding, simple to implement, and provides access to previously unknown chromophore functionality. We applied this method to create molecules to address two outstanding objectives in NIR fluorescence imaging. First, we used an iterative approach to develop molecules for protein-targeted tumor imaging. When compared to common NIR fluorophores, the optimized probe increases the tumor specificity of monoclonal antibody (mAb) and nanobody conjugates. Second, we developed cyclizing heptamethine indocyanines with the goal of improving cellular uptake and fluorogenic properties. By modifying both the electrophilic and nucleophilic components, we demonstrate that the solvent sensitivity of the ring-open/ring-closed equilibrium can be modified over a wide range. We then show that a chloroalkane derivative of a compound with tuned cyclization properties undergoes particularly efficient no-wash live cell imaging using organelle-targeted HaloTag self-labeling proteins. Overall, the chemistry reported here broadens the scope of accessible chromophore functionality, and, in turn, enables the discovery of NIR probes with promising properties for advanced imaging applications.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.