Development of a near infrared fluorescence labeling reagent: Synthesis of indole-functionalized indocyanine green derivatives

Takayuki Doi, Koya Oikawa, Jun Suzuki, Masahito Yoshida, Nobuhiko Iki

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

We have demonstrated a facile synthesis of functionalized indocyanine green (ICG) derivatives. Heteroatom-substituted indolenine was synthesized via S NAr reaction of 5-chloro-2,4-di-nitroanisole with 1,2-dimethyl-1-propenyl trimethylsilyl ether followed by reduction of the nitro groups. After the introduction of hydrophilic butanesulfonate moieties, homo- and heterocondensations with glutaconaldehyde dianilide provided symmetrical and unsymmetrical ICG derivatives, which exhibit near infrared (NIR) absorption and fluorescence emission similar to those of ICG. NIR fluorescence labeling reagent was synthesized using the amino group in the ICG derivative. The 1,3-dipolar cycloaddition with benzyl azide was performed utilizing copper nanoparticles toward a versatile method for the synthesis of NIR molecular imaging probes.

Original languageEnglish
Pages (from-to)306-310
Number of pages5
JournalSynlett
Issue number2
DOIs
Publication statusPublished - 2012 Jan 4

Keywords

  • cycloaddition
  • indocyanine green
  • indoles
  • near infrared fluorescence
  • nucleophilic aromatic substitution

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Development of a near infrared fluorescence labeling reagent: Synthesis of indole-functionalized indocyanine green derivatives'. Together they form a unique fingerprint.

  • Cite this