ArticleOrganic letters2015
Electrophile-integrating Smiles rearrangement provides previously inaccessible C4'-O-alkyl heptamethine cyanine fluorophores.
Article in Organic letters, 2015. 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.
- More Than a Glow: How Cyanine Dyes Shape Tracer Pharmacokinetics.Angewandte Chemie (International ed. in English) · 2026Review
- Ethoxy Meso-Modified Heptamethine Cyanine Fluorophores: Synthesis, Photophysical Properties and BSA Sensing Study.Molecules (Basel, Switzerland) · 2026Article
- Cyanines Substituted on the Polymethine Chain: Synthesis, Resulting Properties, and Application Use Cases.ChemPlusChem · 2025Review
- Evaluation of Indocyanine Green Derivatives with Sulfonic Acid and Carboxylic Acid Groups at the Benzoindolenine Moiety for Antibody-Based Tumor Imaging.Molecular imaging and biology · 2025Article
- Palladium-Catalyzed Functionalization of Shortwave Infrared Heptamethine Fluorophores Expands Their In Vivo Utility.JACS Au · 2025Article
- Method To Diversify Cyanine Chromophore Functionality Enables Improved Biomolecule Tracking and Intracellular Imaging.Journal of the American Chemical Society · 2023Article
- Modified norcyanines enable ratiometric pH imaging beyond 1000 nm.Biosensors & bioelectronics · 2022Article
- Repurposing Cyanine Photoinstability To Develop Near-Infrared Light-Activatable Nanogels for In Vivo Cargo Delivery.Journal of the American Chemical Society · 2022Article
- Cyanine Masking: A Strategy to Test Functional Group Effects on Antibody Conjugate Targeting.Bioconjugate chemistry · 2022Article
- Targeted Dual-Modal PET/SPECT-NIR Imaging: From Building Blocks and Construction Strategies to Applications.Cancers · 2022Review
- Not so innocent: Impact of fluorophore chemistry on the in vivo properties of bioconjugates.Current opinion in chemical biology · 2021Review
- Preferential Light-Chain Labeling of Native Monoclonal Antibodies Improves the Properties of Fluorophore Conjugates.Tetrahedron letters · 2021Article
- Explorations into the Effect of meso-Substituents in Tricarbocyanine Dyes: A Path to Diverse Biomolecular Probes and Materials.Angewandte Chemie (International ed. in English) · 2021Review
- Visible-to-NIR-Light Activated Release: From Small Molecules to Nanomaterials.Chemical reviews · 2020Article
- Cyanine Nanocages Activated by Near-Infrared Light for the Targeted Treatment of Traumatic Brain Injury.Frontiers in chemistry · 2020Article
- A Biliary Tract-Specific Near-Infrared Fluorescent Dye for Image-Guided Hepatobiliary Surgery.Molecular pharmaceutics · 2019Article
- A Nonaggregating Heptamethine Cyanine for Building Brighter Labeled Biomolecules.ACS chemical biology · 2019Article
- Site-Specific Labeling of Proteins with Near-IR Heptamethine Cyanine Dyes.Molecules (Basel, Switzerland) · 2018Article
- A chemically stable fluorescent marker of the ureter.Bioorganic & medicinal chemistry letters · 2018Article
- Shortwave infrared fluorescence imaging with the clinically approved near-infrared dye indocyanine green.Proceedings of the National Academy of Sciences of the United States of America · 2018Article
Corrections and comments
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Authors and funding
4 authors.
Funding
Abstract
New synthetic methods to rapidly access useful fluorophores are needed to advance modern molecular imaging techniques. A new variant of the classical Smiles rearrangement is reported that enables the efficient synthesis of previously inaccessible C4'-O-alkyl heptamethine cyanines. The key reaction involves N- to O-transposition with selective electrophile incorporation on nitrogen. A representative fluorophore exhibits excellent resistance to thiol nucleophiles, undergoes productive bioconjugation, and can be used in near-IR fluorescence 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.