N’-acyl-N-methylphenylenediamine as a novel proximity labeling agent for signal amplification in immunohistochemistry

Shinichi Sato, Masaki Yoshida, Kensuke Hatano, Masaki Matsumura, Hiroyuki Nakamura

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)


We synthesized novel phenylenediamine derivatives and evaluated them as labeling agents to label proteins in close proximity to a single electron transfer catalyst. We found that N’-acyl-N-methylphenylenediamine labels tyrosine effectively in a model experiment using tris(bipyridine)ruthenium (Ru(bpy) 3 2+ ) as the single electron transfer catalyst. By changing the substituents on the nitrogen atom of the phenylenediamine derivatives, the electrochemical properties of the labeling agent can be drastically changed. On the other hand, horseradish peroxidase (HRP) also catalyzes the reaction with almost the same oxidation potential as Ru(bpy) 3 2+ (∼+1.1 V). HRP proximity labeling is applicable to signal amplification in immunohistochemistry. We evaluated the phenylenediamine derivatives as labeling agents for HRP proximity labeling and signal amplification, and found that N’-acyl-N-methylphenylenediamine is a novel and efficient agent for signal amplification using HRP in immunohistochemistry.

Original languageEnglish
Pages (from-to)1110-1118
Number of pages9
JournalBioorganic and Medicinal Chemistry
Issue number6
Publication statusPublished - 2019 Mar 15


  • Horseradish peroxidase
  • Protein labeling
  • Proximity labeling
  • Signal amplification
  • Single electron transfer


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