TY - JOUR
T1 - N’-acyl-N-methylphenylenediamine as a novel proximity labeling agent for signal amplification in immunohistochemistry
AU - Sato, Shinichi
AU - Yoshida, Masaki
AU - Hatano, Kensuke
AU - Matsumura, Masaki
AU - Nakamura, Hiroyuki
N1 - Funding Information:
This work was partially supported by Grants-in-Aid for ?Grant-in-Aid for Young Scientists (A) (15H05490 to S. Sato)? ?Homeostatic regulation by various types of cell death (15H01372 to S. Sato)? and ?Chemistry for Multimolecular Crowding Biosystems (18H04542 to H. Nakamura)? from MEXT, Japan. We would like to thank Prof. Hyun-Woo Rhee (Seoul National University) for donation of HRP-TM plasmid, and Prof. Nobuhiro Nishiyama and Dr. Makoto Matsui (Tokyo Institute of Technology) for donation of tissue sections of mouse brain.
Funding Information:
This work was partially supported by Grants-in-Aid for “Grant-in-Aid for Young Scientists (A) (15H05490 to S. Sato)”, “Homeostatic regulation by various types of cell death (15H01372 to S. Sato)”, and “Chemistry for Multimolecular Crowding Biosystems (18H04542 to H. Nakamura)” from MEXT , Japan. We would like to thank Prof. Hyun-Woo Rhee (Seoul National University) for donation of HRP-TM plasmid, and Prof. Nobuhiro Nishiyama and Dr. Makoto Matsui ( Tokyo Institute of Technology ) for donation of tissue sections of mouse brain.
Publisher Copyright:
© 2019 Elsevier Ltd
PY - 2019/3/15
Y1 - 2019/3/15
N2 - 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.
AB - 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.
KW - Horseradish peroxidase
KW - Protein labeling
KW - Proximity labeling
KW - Signal amplification
KW - Single electron transfer
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U2 - 10.1016/j.bmc.2019.01.036
DO - 10.1016/j.bmc.2019.01.036
M3 - Article
C2 - 30738654
AN - SCOPUS:85061039049
VL - 27
SP - 1110
EP - 1118
JO - Bioorganic and Medicinal Chemistry
JF - Bioorganic and Medicinal Chemistry
SN - 0968-0896
IS - 6
ER -