BODIPY Catalyzes Proximity-Dependent Histidine Labelling

Keita Nakane, Tatsuya Niwa, Michihiko Tsushima, Shusuke Tomoshige, Hideki Taguchi, Hiroyuki Nakamura, Minoru Ishikawa, Shinichi Sato

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)


The novel function of BODIPY, a widely used fluorescent probe, as a catalyst for the chemical labelling of histidine is revealed. Singlet oxygen (1O2) produced by the photosensitizer property of BODIPY oxidises histidine residues, and the histidine oxidised by 1O2 is trapped by the nucleophile 1-methyl-4-arylurazole (MAUra). The simple chemical structure of BODIPY facilitates easier modification compared to other photosensitizer molecules and allows catalysis of protein/peptide-labelling with higher histidine selectivity compared to the ruthenium complex. Owing to the short life of 1O2, the reaction was selectively completed in close proximity with BODIPY. Site-selective functionalization of the target/antibody was successfully achieved using ligand-conjugated BODIPY.

Original languageEnglish
Article numbere202200077
Issue number9
Publication statusPublished - 2022 May 6


  • histidine labelling
  • photosensitizer
  • proximity labelling
  • singlet oxygen

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry


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