ArticleJournal of the American Chemical Society2013
Thioamide quenching of fluorescent probes through photoinduced electron transfer: mechanistic studies and applications.
Article in Journal of the American Chemical Society, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 36 papers.
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Who cites it
36 citing papers in PubMed.
- Thioimidate Protection Enables Amide, Thioamide, and Amidine Installation at Aspartic Acid Residues.The Journal of organic chemistry · 2026Article
- Playing with Structural Parameters in the Design of Ruthenium(II)-Inorganic chemistry · 2025Article
- Fluorescent Antibiotics: Bridging Diagnostic and Therapy in the Fight against Bacterial Infections.Small science · 2025Review
- Thioamides in medicinal chemistry and as small molecule therapeutic agents.European journal of medicinal chemistry · 2024Review
- Complementary Strategies for Installation of Thioimidates into Peptide Backbones.The Journal of organic chemistry · 2024Article
- Thioimidate Solutions to Thioamide Problems during Thionopeptide Deprotection.Organic letters · 2024Article
- The potential of fluorogenicity for single molecule FRET and DyeCycling.QRB discovery · 2024Review
- Thioimidates provide general access to thioamide, amidine, and imidazolone peptide-bond isosteres.Methods in enzymology · 2024Article
- Critical assessment of selenourea as an efficient small molecule fluorescence quenching probe to monitor protein dynamics.Chemical science · 2023Article
- A review of the current research on in vivo and in vitro detection for alpha-synuclein: a biomarker of Parkinson's disease.Analytical and bioanalytical chemistry · 2023Review
- Continuous Histone Deacylase Activity Assays.Methods in molecular biology (Clifton, N.J.) · 2023Article
- Site-Selective Amide Functionalization by Catalytic Azoline Engrafting.ACS catalysis · 2022Article
- Hydrogen Bond and Geometry Effects of Thioamide Backbone Modifications.The Journal of organic chemistry · 2021Article
- Rational design of thioamide peptides as selective inhibitors of cysteine protease cathepsin L.Chemical science · 2021Article
- Side-chain thioamides as fluorescence quenching probes.Biopolymers · 2021Article
- Incorporating thioamides into proteins by native chemical ligation.Methods in enzymology · 2021Article
- Studies of Thioamide Effects on Serine Protease Activity Enable Two-Site Stabilization of Cancer Imaging Peptides.ACS chemical biology · 2020Article
- Sensing mechanism of a ratiometric near-infrared fluorescent chemosensor for cysteine hydropersulfide: Intramolecular charge transfer.Scientific reports · 2020Article
- Single-Atom Fluorescence Switch: A General Approach toward Visible-Light-Activated Dyes for Biological Imaging.Journal of the American Chemical Society · 2019Article
- Microwave-assisted iodine-catalyzed oxidative coupling of dibenzyl(difurfuryl)disulfides with amines: a rapid and efficient protocol for thioamides.RSC advances · 2019Article
Corrections and comments
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Authors and funding
4 authors.
Funding
Abstract
Previously we have shown that thioamides can be incorporated into proteins as minimally perturbing fluorescence-quenching probes to study protein dynamics, folding, and aggregation. Here, we show that the spontaneity of photoinduced electron transfer between a thioamide and an excited fluorophore is governed by the redox potentials of each moiety according to a Rehm-Weller-type model. We have used this model to predict thioamide quenching of various common fluorophores, and we rigorously tested more than a dozen examples. In each case, we found excellent agreement between our theoretical predictions and experimental observations. In this way, we have been able to expand the scope of fluorophores quenched by thioamides to include dyes suitable for microscopy and single-molecule studies, including fluorescein, Alexa Fluor 488, BODIPY FL, and rhodamine 6G. We describe the photochemistry of these systems and explore applications that demonstrate the utility of thioamide quenching of fluorescein to studying protein folding and proteolysis.
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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.