ArticleAngewandte Chemie (International ed. in English)2022
Commonly Used Alkylating Agents Limit Persulfide Detection by Converting Protein Persulfides into Thioethers.
Article in Angewandte Chemie (International ed. in English), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 23 papers.
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Who cites it
23 citing papers in PubMed.
- Defining and refining the cysteine redoxome through sulfur chemical biology.Nature chemical biology · 2026Review
- Thiosulfonate-Derived BODIPY "Stick and Glue" Strategy for Fluorescent Thiol Labeling.Angewandte Chemie (International ed. in English) · 2026Article
- Best practices for cysteine analysis.Ferroptosis and oxidative stress · 2026Article
- Simultaneous and sensitive quantification of protein and low molecular weight persulfides, polysulfides and HNature communications · 2025Article
- HAdvanced science (Weinheim, Baden-Wurttemberg, Germany) · 2025Article
- Profiling the landscape of cysteine posttranslational modifications in brain aging and neurodegeneration.Neurotherapeutics : the journal of the American Society for Experimental NeuroTherapeutics · 2025Review
- Advancing Covalent Ligand and Drug Discovery beyond Cysteine.Chemical reviews · 2025Review
- Detection of Protein Polysulfidation Using a β-(4-Hydroxyphenyl)ethyl Iodoacetamide-Derived Biotin Tag HPB.Analytical chemistry · 2025Article
- Serendipitous Discovery of Photolytic Thiosulfoxide Formation: Application for Visible-Light-Inducible Manipulation of Supersulfide Level in Biological Systems.Journal of the American Chemical Society · 2025Article
- Polysulfides promote protein disulfide bond formation in microorganisms growing under anaerobic conditions.Applied and environmental microbiology · 2025Article
- Arylsulfonothioates: Thiol-Activated Donors of Hydropersulfides which are Excreted to Maintain Cellular Redox Homeostasis or Retained to Counter Oxidative Stress.Journal of the American Chemical Society · 2025Article
- Ten "Cheat Codes" for Measuring Oxidative Stress in Humans.Antioxidants (Basel, Switzerland) · 2024Review
- 50 shades of oxidative stress: A state-specific cysteine redox pattern hypothesis.Redox biology · 2023Article
- Thioxobimanes.The Journal of organic chemistry · 2023Article
- Sensing and regulation of reactive sulfur species (RSS) in bacteria.Current opinion in chemical biology · 2023Review
- Supersulfide catalysis for nitric oxide and aldehyde metabolism.Science advances · 2023Article
- Emerging Chemical Biology of Protein Persulfidation.Antioxidants & redox signaling · 2023Review
- Thiol redox proteomics: Characterization of thiol-based post-translational modifications.Proteomics · 2023Review
- 3-Mercaptopyruvate sulfur transferase is a protein persulfidase.Nature chemical biology · 2023Article
- Increased intracellular persulfide levels attenuate HlyU-mediated hemolysin transcriptional activation inbioRxiv : the preprint server for biology · 2023Article
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Authors and funding
6 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Protein persulfides (R-S-SH) have emerged as a common post-translational modification. Detection and quantitation of protein persulfides requires trapping with alkylating agents. Here we show that alkylating agents differ dramatically in their ability to conserve the persulfide's sulfur-sulfur bond for subsequent detection by mass spectrometry. The two alkylating agents most commonly used in cell biology and biochemistry, N-ethylmaleimide and iodoacetamide, are found to be unsuitable for the purpose of conserving persulfides under biologically relevant conditions. The resulting persulfide adducts (R-S-S-Alk) rapidly convert into the corresponding thioethers (R-S-Alk) by donating sulfur to ambient nucleophilic acceptors. In contrast, certain other alkylating agents, in particular monobromobimane and N-t-butyl-iodoacetamide, generate stable alkylated persulfides. We propose that the nature of the alkylating agent determines the ability of the disulfide bond (R-S-S-Alk) to tautomerize into the thiosulfoxide (R-(S=S)-Alk), and/or the ability of nucleophiles to remove the sulfane sulfur atom from the thiosulfoxide.
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