Amine-Reactive Activated Esters of meso-CarboxyBODIPY: Fluorogenic Assays and Labeling of Amines, Amino Acids, and Proteins
- 주제(기타) Chemistry, Multidisciplinary
- 설명문(일반) [Bouffard, Jean] Ewha Womans Univ, Dept Chem & Nanosci BK 21 Plus, Seoul 03760, South Korea; [Jeon, Sungjin; Kim, Tae-Il; Lee, Uisung; Kim, Youngmi] Kyung Hee Univ, Dept Chem, Seoul 02447, South Korea; [Jeon, Sungjin; Kim, Tae-Il; Lee, Uisung; Kim, Youngmi] Kyung Hee Univ, Res Inst Basic Sci, Seoul 02447, South Korea; [Jin, Hanyong] Chung Ang Univ, Dept Life Sci, Seoul 06974, South Korea; [Bae, Jeehyeon] Chung Ang Univ, Sch Pharm, Seoul 06974, South Korea
- 등재 SCIE, SCOPUS
- 발행기관 AMER CHEMICAL SOC
- 발행년도 2020
- 총서유형 Journal
- URI http://www.dcollection.net/handler/ewha/000000169544
- 본문언어 영어
- Published As https://dx.doi.org/10.1021/jacs.9b13982
- PubMed https://pubmed.ncbi.nlm.nih.gov/32302126
초록/요약
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.
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