Academic Journal
Thiosulfonate-Derived BODIPY "Stick and Glue" Strategy for Fluorescent Thiol Labeling.
| Τίτλος: | Thiosulfonate-Derived BODIPY "Stick and Glue" Strategy for Fluorescent Thiol Labeling. |
|---|---|
| Συγγραφείς: | Šálková L; Institute of Organic Chemistry and Biochemistry of the CAS, Flemingovo náměstí 542, Prague, 160 00, Czech Republic.; Department of Organic Chemistry, University of Chemistry and Technology Prague, Technická 5, Prague 6, 166 28, Czech Republic., Dunlop D; Institute of Organic Chemistry and Biochemistry of the CAS, Flemingovo náměstí 542, Prague, 160 00, Czech Republic.; Department of Inorganic Chemistry, Faculty of Science, Charles University, Hlavova 2030, Prague 2, 128 40, Czech Republic., Tütüncü BB; Institute of Organic Chemistry and Biochemistry of the CAS, Flemingovo náměstí 542, Prague, 160 00, Czech Republic.; Department of Organic Chemistry, Faculty of Science, Charles University, Hlavova 2030, Prague 2, 128 40, Czech Republic., Knejzlík Z; Institute of Organic Chemistry and Biochemistry of the CAS, Flemingovo náměstí 542, Prague, 160 00, Czech Republic., Slanina T; Institute of Organic Chemistry and Biochemistry of the CAS, Flemingovo náměstí 542, Prague, 160 00, Czech Republic. |
| Πηγή: | Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2026 Feb 02; Vol. 65 (6), pp. e15338. Date of Electronic Publication: 2025 Nov 02. |
| Τύπος έκδοσης: | Journal Article; Research Support, Non-U.S. Gov't |
| Γλώσσα: | English |
| Στοιχεία περιοδικού: | Publisher: Wiley-VCH Country of Publication: Germany NLM ID: 0370543 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1521-3773 (Electronic) Linking ISSN: 14337851 NLM ISO Abbreviation: Angew Chem Int Ed Engl Subsets: MEDLINE |
| Imprint Name(s): | Publication: <2004-> : Weinheim : Wiley-VCH Original Publication: Weinheim/Bergstr. : New York, : Verlag Chemie ; Academic Press, c1962- |
| Ιατρικοί όροι (MeSH): | Boron Compounds*/chemistry , Fluorescent Dyes*/chemistry , Sulfhydryl Compounds*/chemistry , Thiosulfates*/chemistry, Molecular Structure ; Humans |
| Περίληψη: | Fluorescent thiol labeling is a powerful technique for investigating peptide and protein functions, interactions, and cellular localization, offering minimal structural disruption due to the low natural abundance of cysteine residues. The high nucleophilicity of cysteine thiol groups further facilitates efficient and selective labeling. However, existing thiol-labeling strategies, most commonly involving iodoacetamides, maleimides, or methanethiosulfonates (MTS), often suffer from limited selectivity, undesirable side reactions, and the instability of the resulting conjugates. To overcome these limitations, we developed three spectrally orthogonal MTS-derived fluorescent labeling agents based on coumarin and BODIPY photoremovable protecting groups and a BODIPY thiosulfate water-soluble analogue. Using conventional MTS chemistry, these agents form disulfide-linked conjugates with thiols, which are subsequently converted into stable thioethers upon light-induced sulfur extrusion. This two-step approach significantly improves the stability of labeled conjugates, providing a robust and permanent method for fluorescent labeling of small molecules, peptides, and proteins. Our findings offer a promising strategy for precise fluorescent labeling in biological applications. (© 2025 The Author(s). Angewandte Chemie International Edition published by Wiley‐VCH GmbH.) |
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| Grant Information: | 22-20319S Czech Science Foundation |
| Contributed Indexing: | Keywords: BODIPY; Fluorescent labels; Peptides; Rearrangement; Thiols |
| Substance Nomenclature: | 0 (Boron Compounds) 0 (Fluorescent Dyes) 0 (4,4-difluoro-4-bora-3a,4a-diaza-s-indacene) 0 (Sulfhydryl Compounds) 0 (Thiosulfates) |
| Entry Date(s): | Date Created: 20251103 Date Completed: 20260203 Latest Revision: 20260615 |
| Update Code: | 20260615 |
| PubMed Central ID: | PMC12865270 |
| DOI: | 10.1002/anie.202515338 |
| PMID: | 41178184 |
| Βάση Δεδομένων: | MEDLINE |
| ISSN: | 1521-3773 |
|---|---|
| DOI: | 10.1002/anie.202515338 |