Synthesis and luminescence properties of biphenyl-type firefly luciferin analogs with a new, near-infrared light-emitting bioluminophore

Chihiro Miura, Masahiro Kiyama, Satoshi Iwano, Kazuto Ito, Rika Obata, Takashi Hirano, Shojiro Maki, Haruki Niwa

Research output: Contribution to journalArticlepeer-review

25 Citations (Scopus)

Abstract

New firefly luciferin analogs of the 4,4′-substituted biphenyl-type were synthesized. One analog with a 4′-dimethylamino group possessed bioluminescence activity, emitting near-infrared biological window light at 675 nm suitable for deep-site bioimaging of living animals. The chemiluminescence light-emission maximum of the corresponding methyl ester of the bioluminescence active analog was 500 nm, implying that biphenyl and thiazolinone rings in the light emitter might be placed in a coplanar conformation at the polar luciferase active site.

Original languageEnglish
Pages (from-to)9726-9734
Number of pages9
JournalTetrahedron
Volume69
Issue number46
DOIs
Publication statusPublished - 2013 Nov 18

Keywords

  • Biological window
  • Bioluminescence
  • Biphenyl-type
  • Chemiluminescence
  • Firefly luciferin analog
  • Near-infrared

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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