ArticleBiochemistry2017
The Cation-π Interaction Enables a Halo-Tag Fluorogenic Probe for Fast No-Wash Live Cell Imaging and Gel-Free Protein Quantification.
Article in Biochemistry, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 30 papers.
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Who cites it
30 citing papers in PubMed, 85 citations in OpenAlex.
- Navigating condensate micropolarity to enhance small-molecule drug targeting.Nature chemical biology · 2026Article
- A general one-step protocol to generate impermeable fluorescent HaloTag substrates for in situ live cell application and super-resolution imaging.Nature communications · 2026Article
- Rapid and Wash-free Live Cell Labeling with BenzoTag.Methods in molecular biology (Clifton, N.J.) · 2026Article
- Investigating the Site-Specific Impact of Fluorine Substitution on Aromatic Interactions in a Tryptophan Zipper Peptide.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Experimental Approaches to Visualize Effector Protein Translocation During Host-Pathogen Interactions.BioEssays : news and reviews in molecular, cellular and developmental biology · 2025Review
- BenzoHTag, a fluorogenic self-labeling protein developed using molecular evolution.bioRxiv : the preprint server for biology · 2024Article
- Micropolarity governs the structural organization of biomolecular condensates.Nature chemical biology · 2024Article
- Engineered fluorogenic HaloTag ligands for turn-on labelling in live cells.Chemical communications (Cambridge, England) · 2023Article
- Supramolecular Click Chemistry for Surface Modification of Quantum Dots Mediated by Cucurbit[7]uril.ACS nano · 2023Article
- Choosing the Probe for Single-Molecule Fluorescence Microscopy.International journal of molecular sciences · 2022Review
- Visualizing the Multistep Process of Protein Aggregation in Live Cells.Accounts of chemical research · 2022Article
- HaloTag Engineering for Enhanced Fluorogenicity and Kinetics with a Styrylpyridium Dye.Chembiochem : a European journal of chemical biology · 2021Article
- Oxime as a general photocage for the design of visible light photo-activatable fluorophores.Chemical science · 2021Article
- Inside a Shell-Organometallic Catalysis Inside Encapsulin Nanoreactors.Angewandte Chemie (International ed. in English) · 2021Article
- Kinetic and Structural Characterization of the Self-Labeling Protein Tags HaloTag7, SNAP-tag, and CLIP-tag.Biochemistry · 2021Article
- Engineering a Metathesis-Catalyzing Artificial Metalloenzyme Based on HaloTag.ACS catalysis · 2021Article
- HaloTag Forms an Intramolecular Disulfide.Bioconjugate chemistry · 2021Article
- Imaging living obligate anaerobic bacteria with bilin-binding fluorescent proteins.Current research in microbial sciences · 2020Article
- Visualizing and Manipulating Biological Processes by Using HaloTag and SNAP-Tag Technologies.Chembiochem : a European journal of chemical biology · 2020Review
- Tetrazine as a general phototrigger to turn on fluorophores.Chemical science · 2020Article
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Authors and funding
8 authors at 2 institutions in 1 country.
Funding
Abstract
The design of fluorogenic probes for a Halo tag is highly desirable but challenging. Previous work achieved this goal by controlling the chemical switch of spirolactones upon the covalent conjugation between the Halo tag and probes or by incorporating a "channel dye" into the substrate binding tunnel of the Halo tag. In this work, we have developed a novel class of Halo-tag fluorogenic probes that are derived from solvatochromic fluorophores. The optimal probe, harboring a benzothiadiazole scaffold, exhibits a 1000-fold fluorescence enhancement upon reaction with the Halo tag. Structural, computational, and biochemical studies reveal that the benzene ring of a tryptophan residue engages in a cation-π interaction with the dimethylamino electron-donating group of the benzothiadiazole fluorophore in its excited state. We further demonstrate using noncanonical fluorinated tryptophan that the cation-π interaction directly contributes to the fluorogenicity of the benzothiadiazole fluorophore. Mechanistically, this interaction could contribute to the fluorogenicity by promoting the excited-state charge separation and inhibiting the twisting motion of the dimethylamino group, both leading to an enhanced fluorogenicity. Finally, we demonstrate the utility of the probe in no-wash direct imaging of Halo-tagged proteins in live cells. In addition, the fluorogenic nature of the probe enables a gel-free quantification of fusion proteins expressed in mammalian cells, an application that was not possible with previously nonfluorogenic Halo-tag probes. The unique mechanism revealed by this work suggests that incorporation of an excited-state cation-π interaction could be a feasible strategy for enhancing the optical performance of fluorophores and fluorogenic sensors.
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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.