ArticleACS central science2021
Defining the Basis of Cyanine Phototruncation Enables a New Approach to Single-Molecule Localization Microscopy.
Article in ACS central science, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 40 papers.
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Who cites it
40 citing papers in PubMed.
- Light-Induced Selective Control of Excitonic States in Supramolecular Nanotubes.Journal of the American Chemical Society · 2026Article
- Annulated cationic tetramethyl indo(di)carbocyanine dyes exhibit potent dark cytotoxicity in cancer cells.Dyes and pigments : an international journal · 2026Article
- Photochemical modification of two fluorene-based molecules with DNA intercalating and anti-methicillin resistant Staphylococcus aureus activity.The Journal of biological chemistry · 2026Article
- Counterion-Enhanced Brightness of Fluorous-Soluble Heptamethine Cyanine Dyes for Near- and Shortwave Infrared Fluorescence Imaging.Chemical & biomedical imaging · 2026Article
- Experimental Study Redefines the Mechanism of Heptamethine Cyanine Phototruncation.Journal of the American Chemical Society · 2026Article
- Article
- Photophysics of Organic Fluorophore Photobluing and Its Applications in Fluorescence and Super-Resolution Microscopy.Accounts of chemical research · 2026Article
- Single-Molecule Localization Expansion Nanoscopy via Spontaneously Blinking Fluorophores.Chemical & biomedical imaging · 2026Article
- "Blebbing" of a Gold Nanocluster by Dioxygen Insertion into Thiolate Staples during Self-Photooxidation.The journal of physical chemistry. A · 2025Article
- Cyanines Substituted on the Polymethine Chain: Synthesis, Resulting Properties, and Application Use Cases.ChemPlusChem · 2025Review
- Synthetic fluorophores for live-cell fluorescence microscopy and biosensing.Nature chemical biology · 2025Review
- Advancing Single-Molecule Biophysics: Next-Generation Organic Fluorophores with Tailored Labeling Strategies.Chemical & biomedical imaging · 2025Review
- High-Resolution Multicolor Shortwave Infrared DynamicJournal of the American Chemical Society · 2025Article
- Fluorescent labeling strategies for molecular bioimaging.Biophysical reports · 2025Review
- Super-photostable organic dye for long-term live-cell single-protein imaging.Nature methods · 2025Article
- Red light excitation: illuminating photocatalysis in a new spectrum.Beilstein journal of organic chemistry · 2025Review
- Indocarbocyanine-Indodicarbocyanine (sCy3-sCy5) Absorptive Interactions in Conjugates and DNA Duplexes.Molecules (Basel, Switzerland) · 2024Article
- Expedient Synthesis and Characterization of π-Extended Luciferins.The Journal of organic chemistry · 2024Article
- Recent advances in self-immobilizing fluorescent probes for in vivo imaging.Smart molecules : open access · 2024Review
- Thermal Truncation of Heptamethine Cyanine Dyes.Journal of the American Chemical Society · 2024Article
Corrections and comments
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Authors and funding
8 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The light-promoted conversion of extensively used cyanine dyes to blue-shifted emissive products has been observed in various contexts. However, both the underlying mechanism and the species involved in this photoconversion reaction have remained elusive. Here we report that irradiation of heptamethine cyanines provides pentamethine cyanines, which, in turn, are photoconverted to trimethine cyanines. We detail an examination of the mechanism and substrate scope of this remarkable two-carbon phototruncation reaction. Supported by computational analysis, we propose that this reaction involves a singlet oxygen-initiated multistep sequence involving a key hydroperoxycyclobutanol intermediate. Building on this mechanistic framework, we identify conditions to improve the yield of photoconversion by over an order of magnitude. We then demonstrate that cyanine phototruncation can be applied to super-resolution single-molecule localization microscopy, leading to improved spatial resolution with shorter imaging times. We anticipate these insights will help transform a common, but previously mechanistically ill-defined, chemical transformation into a valuable optical tool.
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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.