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Target Identification of Bioactive Compounds by Photoaffinity Labeling Using Diazido Probes

  • Suguru Yoshida
  • Takamitsu HosoyaEmail author
Chapter

Abstract

This chapter reviews a photoaffinity labeling (PAL) method which employs “diazido” probes bearing aromatic and aliphatic azido groups. Since our first report in 2004, the target molecules of various bioactive compounds have been identified by this method. It is a two-step target identification method involving the conjugation of the bioactive diazido probe with the target molecules through the selective photoreaction of the aromatic azido group and subsequent introduction of a detectable tag through a click reaction to the target molecules at the remaining aliphatic azido group. An overview of the history and recent progresses of this method, including facile methods for preparing diverse diazido building blocks, is presented, focusing mainly on the chemical aspects. The relevant methods using a bifunctional probe bearing photoreactive and bioorthogonal groups are also briefly summarized.

Keywords

Photoaffinity labeling Target identification Azide Diazirine Photoreaction Click reaction 

Abbreviations

9-BBN

9-Borabicyclo[3.3.1]nonane

AIBN

2,2′-Azobis(isobutyronitrile)

Boc

tert-Butyloxycarbonyl

CG

Connecting group

CuAAC

Copper-catalyzed azide–alkyne cycloaddition

DBU

1,8-Diazabicyclo[5.4.0]undec-7-ene

DIBAL–H

Diisobutylaluminum hydride

DPPA

Diphenylphosphoryl azide

dtbpy

4,4′-Di-tert-butyl-2,2′-bipyridyl

FG

Functional group

HDAC

Histone deacetylase

HMGR

Hydroxymethylglutaryl-coenzyme A reductase

HTS

High-throughput screening

MALDI

Matrix-assisted laser desorption/ionization

MASCOT

Modular approach to software construction operation and test

MS

Mass spectrum

NBS

N-Bromosuccinimide

PAL

Photoaffinity labeling

pin

Pinacolato

RI

Radioisotope

SDS-PAGE

Sodium dodecyl sulfate-polyacrylamide gel electrophoresis

TBS

tert-Butyldimethylsilyl

TBTA

Tris[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]amine

THP

2-Tetrahydropyranyl

TMS

Trimethylsilyl

TOF

Time of flight

Ts

p-Toluenesulfonyl

Notes

Acknowledgments

This work was supported by Japan Agency for Medical Research and Development (AMED) under Grant Numbers JP18am0101098 (Platform Project for Supporting Drug Discovery and Life Science Research, BINDS) and JP18am0301024 (the Basic Science and Platform Technology Program for Innovative Biological Medicine); JSPS KAKENHI Grant Numbers JP15H03118 and JP18H02104 (B; T. H.), JP16H01133 and JP18H04386 (Middle Molecular Strategy; T. H.), JP17H06414 (Organelle Zone; T. H.), and JP26350971 (C; S. Y.); the Cooperative Research Project of Research Center for Biomedical Engineering; and the Naito Foundation (S. Y.).

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Copyright information

© Springer Nature Singapore Pte Ltd. 2019

Authors and Affiliations

  1. 1.Laboratory of Chemical Bioscience, Institute of Biomaterials and BioengineeringTokyo Medical and Dental University (TMDU)TokyoJapan

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