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Amine-Reactive Activated Esters of meso-CarboxyBODIPY: Fluorogenic Assays and Labeling of Amines, Amino Acids, and Proteins

Title
Amine-Reactive Activated Esters of meso-CarboxyBODIPY: Fluorogenic Assays and Labeling of Amines, Amino Acids, and Proteins
Authors
Jeon, SungjinKim, Tae-IlJin, HanyongLee, UisungBae, JeehyeonBouffard, JeanKim, Youngmi
Ewha Authors
Jean Bouffard
SCOPUS Author ID
Jean Bouffardscopus
Issue Date
2020
Journal Title
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
ISSN
0002-7863JCR Link

1520-5126JCR Link
Citation
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY vol. 142, no. 20, pp. 9231 - 9239
Publisher
AMER CHEMICAL SOC
Indexed
SCIE; SCOPUS WOS
Document Type
Article
Abstract
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 (Delta lambda: 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.
DOI
10.1021/jacs.9b13982
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자연과학대학 > 화학·나노과학전공 > Journal papers
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