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 journalArticle

21 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
Externally publishedYes

Fingerprint

Firefly Luciferin
Bioluminescence
Luminescence
Infrared radiation
Light
Chemiluminescence
Light emission
Luciferases
Conformations
Esters
Animals
Catalytic Domain
diphenyl

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthesis and luminescence properties of biphenyl-type firefly luciferin analogs with a new, near-infrared light-emitting bioluminophore. / Miura, Chihiro; Kiyama, Masahiro; Iwano, Satoshi; Ito, Kazuto; Obata, Rika; Hirano, Takashi; Maki, Shojiro; Niwa, Haruki.

In: Tetrahedron, Vol. 69, No. 46, 18.11.2013, p. 9726-9734.

Research output: Contribution to journalArticle

Miura, Chihiro ; Kiyama, Masahiro ; Iwano, Satoshi ; Ito, Kazuto ; Obata, Rika ; Hirano, Takashi ; Maki, Shojiro ; Niwa, Haruki. / Synthesis and luminescence properties of biphenyl-type firefly luciferin analogs with a new, near-infrared light-emitting bioluminophore. In: Tetrahedron. 2013 ; Vol. 69, No. 46. pp. 9726-9734.
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