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

doi:10.1016/j.tet.2013.09.018

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 journal › Article › peer-review

35 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 language	English
Pages (from-to)	9726-9734
Number of pages	9
Journal	Tetrahedron
Volume	69
Issue number	46
DOIs	https://doi.org/10.1016/j.tet.2013.09.018
Publication status	Published - 2013 Nov 18
Externally published	Yes

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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10.1016/j.tet.2013.09.018

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

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.",

keywords = "Biological window, Bioluminescence, Biphenyl-type, Chemiluminescence, Firefly luciferin analog, Near-infrared",

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

note = "Funding Information: This work was supported by Grants-in-Aid for Exploratory Research ( No. 24650633 ) to S.M. from the Ministry of Education, Culture, Sports, Science and Technology , and Adaptable & Seamless Technology Transfer Program through Target-driven R&D (A-Step) (No. AS2321366E ) to S.M. from the Japan Science and Technology Agency . ",

year = "2013",

month = nov,

day = "18",

doi = "10.1016/j.tet.2013.09.018",

language = "English",

volume = "69",

pages = "9726--9734",

journal = "Tetrahedron",

issn = "0040-4020",

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TY - JOUR

T1 - Synthesis and luminescence properties of biphenyl-type firefly luciferin analogs with a new, near-infrared light-emitting bioluminophore

AU - Miura, Chihiro

AU - Kiyama, Masahiro

AU - Iwano, Satoshi

AU - Ito, Kazuto

AU - Obata, Rika

AU - Hirano, Takashi

AU - Maki, Shojiro

AU - Niwa, Haruki

N1 - Funding Information: This work was supported by Grants-in-Aid for Exploratory Research ( No. 24650633 ) to S.M. from the Ministry of Education, Culture, Sports, Science and Technology , and Adaptable & Seamless Technology Transfer Program through Target-driven R&D (A-Step) (No. AS2321366E ) to S.M. from the Japan Science and Technology Agency .

PY - 2013/11/18

Y1 - 2013/11/18

N2 - 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.

AB - 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.

KW - Biological window

KW - Bioluminescence

KW - Biphenyl-type

KW - Chemiluminescence

KW - Firefly luciferin analog

KW - Near-infrared

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U2 - 10.1016/j.tet.2013.09.018

DO - 10.1016/j.tet.2013.09.018

M3 - Article

AN - SCOPUS:84885189048

SN - 0040-4020

VL - 69

SP - 9726

EP - 9734

JO - Tetrahedron

JF - Tetrahedron

IS - 46

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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