ArticleACS chemical biology2020
Studies of Thioamide Effects on Serine Protease Activity Enable Two-Site Stabilization of Cancer Imaging Peptides.
Article in ACS chemical biology, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. An erratum has been issued. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed, 25 citations in OpenAlex.
- Stabilized thioamide peptide agonists of the neuropeptide Y type 2 receptor for targeted cancer imaging.RSC chemical biology · 2026Article
- Thioimidate Protection Enables Amide, Thioamide, and Amidine Installation at Aspartic Acid Residues.The Journal of organic chemistry · 2026Article
- 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
- Thioimidates provide general access to thioamide, amidine, and imidazolone peptide-bond isosteres.Methods in enzymology · 2024Article
- Thioamide Analogues of MHC I Antigen Peptides.Journal of the American Chemical Society · 2023Article
- An amide to thioamide substitution improves the permeability and bioavailability of macrocyclic peptides.Nature communications · 2023Article
- Chemoselective Transamidation of Thioamides by Transition-Metal-Free N-C(S) Transacylation.Angewandte Chemie (International ed. in English) · 2022Article
- A Urinary Drug-Disposing Approach as an Alternative to Intravesical Chemotherapy for Treating Nonmuscle Invasive Bladder Cancer.Cancer research · 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
- Modular Synthesis of Peptide-Based Single- and Multimodal Targeted Molecular Imaging Agents.ACS applied bio materials · 2021Article
- Side-chain thioamides as fluorescence quenching probes.Biopolymers · 2021Article
- Incorporating thioamides into proteins by native chemical ligation.Methods in enzymology · 2021Article
- Light-Emitting Probes for Labeling Peptides.Cell reports. Physical science · 2020Article
- Rosetta Machine Learning Models Accurately Classify Positional Effects of Thioamides on Proteolysis.The journal of physical chemistry. B · 2020Article
Corrections and comments
- Erratum issued
Authors and funding
9 authors at 2 institutions in 2 countries.
Funding
Abstract
Thioamide substitutions in peptides can be used as fluorescence quenchers in protease sensors and as stabilizing modifications of hormone analogs. To guide these applications in the context of serine proteases, we here examine the cleavage of several model substrates, scanning a thioamide between the P3 and P3' positions, and identify perturbing positions for thioamide substitution. While all serine proteases tested were affected by P1 thioamidation, certain proteases were also significantly affected by other thioamide positions. We demonstrate how these findings can be applied by harnessing the combined P3/P1 effect of a single thioamide on kallikrein proteolysis to protect two key positions in a neuropeptide Y-based imaging probe, increasing its serum half-life to >24 h while maintaining potency for binding to Y1 receptor expressing cells. Such stabilized peptide probes could find application in imaging cell populations in animal models or even in clinical applications such as fluorescence-guided surgery.
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Registered trials
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