Amine-Reactive Activated Esters of meso-CarboxyBODIPY: Fluorogenic Assays and Labeling of Amines, Amino Acids, and Proteins
| Autor: | Youngmi Kim, Jean Bouffard, Jeehyeon Bae, Tae-Il Kim, Sungjin Jeon, Hanyong Jin, Uisung Lee |
|---|---|
| Rok vydání: | 2020 |
| Předmět: |
chemistry.chemical_classification
Biomolecule General Chemistry 010402 general chemistry 01 natural sciences Biochemistry Fluorescence Combinatorial chemistry Catalysis 0104 chemical sciences Amino acid Hydrolysis Colloid and Surface Chemistry chemistry Fluorescence microscope Molecule Peptide bond Amine gas treating |
| Zdroj: | Journal of the American Chemical Society. 142:9231-9239 |
| ISSN: | 1520-5126 0002-7863 |
| DOI: | 10.1021/jacs.9b13982 |
| Popis: | Fluorescence-based amine-reactive dyes are highly valuable for the sensing of amines and the labeling of biomolecules. Although it would be highly desirable, large changes in emission spectra and intensity seldom accompany the conjugation of known amine-reactive dyes to their target molecules. On the contrary, amide bond formation between amines and the pentafluorophenyl (2-PFP) and succinimidyl (2-NHS) esters of meso-carboxyBODIPY results in significant changes in emission maxima (Δλ: 70-100 nm) and intensity (up to 3000-fold), enabling the fast (down to 5 min) and selective fluorogenic detection and labeling of amines, amino acids, and proteins. This approach further benefits from the demonstrated versatility and high reliability of activated ester chemistry, and background hydrolysis is negligible. The large "turn-on" response is a testament of the extreme sensitivity of meso-carboxyBODIPYs to the minimal changes in electronic properties that distinguish esters from amides. Applications to the detection of food spoilage, staining of proteins on electrophoretic gels or in living cells, and the expedited synthesis of organelle-specific fluorescence microscope imaging agents are further demonstrated. |
| Databáze: | OpenAIRE |
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