Readily Accessible and Brightly Fluorogenic BODIPY/NBD-Tetrazines via SNAr Reactions

Işık M., Kısaçam M. A.

Journal of Organic Chemistry, vol.89, no.9, pp.6513-6519, 2024 (SCI-Expanded, Scopus) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 89 Issue: 9
  • Publication Date: 2024
  • Doi Number: 10.1021/acs.joc.3c02864
  • Journal Name: Journal of Organic Chemistry
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, BIOSIS, Chemical Abstracts Core, Chimica, Compendex, MEDLINE
  • Page Numbers: pp.6513-6519
  • Hatay Mustafa Kemal University Affiliated: Yes

Abstract

We describe SNAr reactions of some commercial amino-tetrazines and halo-dyes, which give efficiently quenched BODIPY/NBD-tetrazines (ΦFl < 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.