Journal of the American Chemical Society, volume 142, issue 20, pages 9231-9239
Amine-Reactive Activated Esters of meso-CarboxyBODIPY: Fluorogenic Assays and Labeling of Amines, Amino Acids, and Proteins
Jeon Sungjin
1
,
Kim Tae Il
1
,
Jin Hanyong
2
,
Lee Uisung
1
,
BAE JEEHYEON
3
,
Bouffard Jean
4
,
Kim Youngmi
1
1
Department of Chemistry and Research Institute of Basic Sciences, Kyung Hee University, 26 Kyungheedae-ro, Dongdaemun-gu, Seoul 02447, Korea
|
2
Department of Life Science, Chung-Ang University, 84 Heukseok-ro, Dongjak-gu, Seoul 06974, Korea
|
3
School of Pharmacy, Chung-Ang University, 84 Heukseok-ro, Dongjak-gu, Seoul 06974, Korea
|
4
Department of Chemistry and Nanoscience (BK 21 Plus), Ewha Womans University, 52 Ewhayeodae-gil, Seodaemun-gu, Seoul, 03760, Korea
|
Publication type: Journal Article
Publication date: 2020-04-17
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 15
ISSN: 00027863, 15205126
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
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 (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.
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Jeon S. et al. Amine-Reactive Activated Esters of meso-CarboxyBODIPY: Fluorogenic Assays and Labeling of Amines, Amino Acids, and Proteins // Journal of the American Chemical Society. 2020. Vol. 142. No. 20. pp. 9231-9239.
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Jeon S., Kim T. I., Jin H., Lee U., BAE J., Bouffard J., Kim Y. Amine-Reactive Activated Esters of meso-CarboxyBODIPY: Fluorogenic Assays and Labeling of Amines, Amino Acids, and Proteins // Journal of the American Chemical Society. 2020. Vol. 142. No. 20. pp. 9231-9239.
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TY - JOUR
DO - 10.1021/jacs.9b13982
UR - https://doi.org/10.1021%2Fjacs.9b13982
TI - Amine-Reactive Activated Esters of meso-CarboxyBODIPY: Fluorogenic Assays and Labeling of Amines, Amino Acids, and Proteins
T2 - Journal of the American Chemical Society
AU - Jeon, Sungjin
AU - Kim, Tae Il
AU - Lee, Uisung
AU - Bouffard, Jean
AU - Kim, Youngmi
AU - Jin, Hanyong
AU - BAE, JEEHYEON
PY - 2020
DA - 2020/04/17 00:00:00
PB - American Chemical Society (ACS)
SP - 9231-9239
IS - 20
VL - 142
SN - 0002-7863
SN - 1520-5126
ER -
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@article{2020_Jeon,
author = {Sungjin Jeon and Tae Il Kim and Uisung Lee and Jean Bouffard and Youngmi Kim and Hanyong Jin and JEEHYEON BAE},
title = {Amine-Reactive Activated Esters of meso-CarboxyBODIPY: Fluorogenic Assays and Labeling of Amines, Amino Acids, and Proteins},
journal = {Journal of the American Chemical Society},
year = {2020},
volume = {142},
publisher = {American Chemical Society (ACS)},
month = {apr},
url = {https://doi.org/10.1021%2Fjacs.9b13982},
number = {20},
pages = {9231--9239},
doi = {10.1021/jacs.9b13982}
}
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MLA
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Jeon, Sungjin, et al. “Amine-Reactive Activated Esters of meso-CarboxyBODIPY: Fluorogenic Assays and Labeling of Amines, Amino Acids, and Proteins.” Journal of the American Chemical Society, vol. 142, no. 20, Apr. 2020, pp. 9231-9239. https://doi.org/10.1021%2Fjacs.9b13982.