Readily Accessible and Brightly Fluorogenic BODIPY/NBD-Tetrazines via S N Ar Reactions

We describe S Ar reactions of some commercial amino-tetrazines and halo-dyes, which give efficiently quenched BODIPY/NBD-tetrazines ( < 0.01) in high yields and, importantly, with high purities affordable via simple silica gel chromatography only. The dyes exhibit large Stokes shifts, moderate en...

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Bibliographic Details
Published in:Journal of organic chemistry 2024-05, Vol.89 (9), p.6513-6519
Main Authors: Işık, Murat, Kısaçam, Mehmet Ali
Format: Article
Language:English
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Summary:We describe S Ar reactions of some commercial amino-tetrazines and halo-dyes, which give efficiently quenched BODIPY/NBD-tetrazines ( < 0.01) in high yields and, importantly, with high purities affordable via simple silica gel chromatography only. The dyes exhibit large Stokes shifts, moderate environmental sensitivity, and emission enhancements (up to 193-fold) upon Tz ligation with BCN─a strained dienophile. They successfully serve as labels for HSA protein premodified with BCN, resulting in bright blue-green emission upon ligation.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c02864