ArticleJournal of the American Chemical Society2015
Rapid Macrocycle Threading by a Fluorescent Dye-Polymer Conjugate in Water with Nanomolar Affinity.
Article in Journal of the American Chemical Society, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 25 papers.
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Who cites it
25 citing papers in PubMed.
- Chiral macrocycles forming high-affinity host-guest homoternary complexes for chiral discrimination and amplified circularly polarized luminescence.Nature communications · 2025Article
- Switchable protection and exposure of a sensitive squaraine dye within a redox active rotaxane.Communications chemistry · 2024Article
- Steric protection of near-infrared fluorescent dyes for enhanced bioimaging.Journal of materials chemistry. B · 2024Review
- Cucurbit[7]uril Complexation of Near-Infrared Fluorescent Azobenzene-Cyanine Conjugates.Molecules (Basel, Switzerland) · 2022Article
- Recent Advances in the Applications of Water-soluble Resorcinarene-based Deep Cavitands.ChemistryOpen · 2022Review
- Supramolecular Mitigation of the Cyanine Limit Problem.The Journal of organic chemistry · 2022Article
- Switchable bifunctional molecular recognition in water using a pH-responsive Endo-functionalized cavity.Nature communications · 2022Article
- When Molecules Meet in Water-Recent Contributions of Supramolecular Chemistry to the Understanding of Molecular Recognition Processes in Water.ChemistryOpen · 2022Review
- Supramolecular capture of highly polar amidosquaraine dye in water with nanomolar affinity and large turn-on fluorescence.Chemical communications (Cambridge, England) · 2021Article
- Panchromatic Fluorescence Emission from Thienosquaraines Dyes: White Light Electrofluorochromic Devices.Molecules (Basel, Switzerland) · 2021Article
- A contorted nanographene shelter.Nature communications · 2021Article
- High affinity threading of a new tetralactam macrocycle in water by fluorescent deep-red and near-infrared squaraine dyes.Chemical communications (Cambridge, England) · 2019Article
- A biomimetic receptor for glucose.Nature chemistry · 2019Article
- Molecular recognition using tetralactam macrocycles with parallel aromatic sidewalls.Beilstein journal of organic chemistry · 2019Review
- New tetralactam hosts for squaraine dyes.Organic & biomolecular chemistry · 2018Article
- Non-Covalently Pre-Assembled High-Performance Near-Infrared Fluorescent Molecular Probes for Cancer Imaging.Chemistry (Weinheim an der Bergstrasse, Germany) · 2018Article
- Fluorescent Thienothiophene-Containing Squaraine Dyes and Threaded Supramolecular Complexes with Tunable Wavelengths between 600⁻800 nm.Molecules (Basel, Switzerland) · 2018Article
- Non-Covalent Assembly Method that Simultaneously Endows a Liposome Surface with Targeting Ligands, Protective PEG Chains, and Deep-Red Fluorescence Reporter Groups.Chemistry (Weinheim an der Bergstrasse, Germany) · 2017Article
- Synthetic mimics of biotin/(strept)avidin.Chemical Society reviews · 2017Review
- Preassembled Fluorescent Multivalent Probes for the Imaging of Anionic Membranes.Bioconjugate chemistry · 2017Article
Corrections and comments
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Authors and funding
7 authors.
Funding
Abstract
A macrocyclic tetralactam host is threaded by a highly fluorescent squaraine dye that is flanked by two polyethylene glycol (PEG) chains with nanomolar dissociation constants in water. Furthermore, the rates of bimolecular association are very fast with k(on) ≈ 10(6)-10(7) M(-1) s(-1). The association is effective under cell culture conditions and produces large changes in dye optical properties including turn-on near-infrared fluorescence that can be imaged using cell microscopy. Association constants in water are ∼1000 times higher than those in organic solvents and strongly enthalpically favored at 27 °C. The threading rate is hardly affected by the length of the PEG chains that flank the squaraine dye. For example, macrocycle threading by a dye conjugate with two appended PEG2000 chains is only three times slower than threading by a conjugate with triethylene glycol chains that are 20 times shorter. The results are a promising advance toward synthetic mimics of streptavidin/biotin.
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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.