Development of a fluorescent indicator for the bioimaging of nitric oxide

Hirotatsu Kojima; Kuniko Sakurai; Kazuya Kikuchi; Shigenori Kawahara; Yutaka Kirino; Hiroshi Nagoshi; Yasunobu Hirata; Takaaki Akaike; Hiroshi Maeda; Tetsuo Nagano

doi:10.1248/bpb.20.1229

Development of a fluorescent indicator for the bioimaging of nitric oxide

Hirotatsu Kojima, Kuniko Sakurai, Kazuya Kikuchi, Shigenori Kawahara, Yutaka Kirino, Hiroshi Nagoshi, Yasunobu Hirata, Takaaki Akaike, Hiroshi Maeda, Tetsuo Nagano

Research output: Contribution to journal › Article › peer-review

50 Citations (Scopus)

Abstract

Nitric oxide (NO) has been reported to play various roles as a signal transmitter. However, detailed functions of NO have yet to be clarified. We have developed a fluorescent indicator for NO imaging in living cells. The N- nitrosation of newly designed and synthesized 4-((3-amino-2- naphthyl)aminomethyl)benzoic acid (DAN-1) by NO yielded the highly fluorescent triazole-form. The membrane permeable ester derivative of DAN-1 (DAN-1 EE) was applied to the imaging of NO produced in activated rat aortic smooth muscle cells. After DAN-1 EE has been loaded into cells, the ester bond is hydrolyzed by intracellular esterase, yielding original DAN-1 with less permeability. The fluorescence intensity of the cells loaded with DAN-1 EE increased according to NO production. The imaging method with fluorescent indicators will be significant for the functional clarification of NO in vivo.

Original language	English
Pages (from-to)	1229-1232
Number of pages	4
Journal	Biological and Pharmaceutical Bulletin
Volume	20
Issue number	12
DOIs	https://doi.org/10.1248/bpb.20.1229
Publication status	Published - 1997
Externally published	Yes

Keywords

Diaminonaphthalene
Fluorescent indicator
Imaging
Nitric oxide
Vascular smooth muscle cell

ASJC Scopus subject areas

Pharmacology
Pharmaceutical Science

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10.1248/bpb.20.1229

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title = "Development of a fluorescent indicator for the bioimaging of nitric oxide",

abstract = "Nitric oxide (NO) has been reported to play various roles as a signal transmitter. However, detailed functions of NO have yet to be clarified. We have developed a fluorescent indicator for NO imaging in living cells. The N- nitrosation of newly designed and synthesized 4-((3-amino-2- naphthyl)aminomethyl)benzoic acid (DAN-1) by NO yielded the highly fluorescent triazole-form. The membrane permeable ester derivative of DAN-1 (DAN-1 EE) was applied to the imaging of NO produced in activated rat aortic smooth muscle cells. After DAN-1 EE has been loaded into cells, the ester bond is hydrolyzed by intracellular esterase, yielding original DAN-1 with less permeability. The fluorescence intensity of the cells loaded with DAN-1 EE increased according to NO production. The imaging method with fluorescent indicators will be significant for the functional clarification of NO in vivo.",

keywords = "Diaminonaphthalene, Fluorescent indicator, Imaging, Nitric oxide, Vascular smooth muscle cell",

author = "Hirotatsu Kojima and Kuniko Sakurai and Kazuya Kikuchi and Shigenori Kawahara and Yutaka Kirino and Hiroshi Nagoshi and Yasunobu Hirata and Takaaki Akaike and Hiroshi Maeda and Tetsuo Nagano",

year = "1997",

doi = "10.1248/bpb.20.1229",

language = "English",

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pages = "1229--1232",

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AU - Kojima, Hirotatsu

AU - Sakurai, Kuniko

AU - Kikuchi, Kazuya

AU - Kawahara, Shigenori

AU - Kirino, Yutaka

AU - Nagoshi, Hiroshi

AU - Hirata, Yasunobu

AU - Akaike, Takaaki

AU - Maeda, Hiroshi

AU - Nagano, Tetsuo

PY - 1997

Y1 - 1997

N2 - Nitric oxide (NO) has been reported to play various roles as a signal transmitter. However, detailed functions of NO have yet to be clarified. We have developed a fluorescent indicator for NO imaging in living cells. The N- nitrosation of newly designed and synthesized 4-((3-amino-2- naphthyl)aminomethyl)benzoic acid (DAN-1) by NO yielded the highly fluorescent triazole-form. The membrane permeable ester derivative of DAN-1 (DAN-1 EE) was applied to the imaging of NO produced in activated rat aortic smooth muscle cells. After DAN-1 EE has been loaded into cells, the ester bond is hydrolyzed by intracellular esterase, yielding original DAN-1 with less permeability. The fluorescence intensity of the cells loaded with DAN-1 EE increased according to NO production. The imaging method with fluorescent indicators will be significant for the functional clarification of NO in vivo.

AB - Nitric oxide (NO) has been reported to play various roles as a signal transmitter. However, detailed functions of NO have yet to be clarified. We have developed a fluorescent indicator for NO imaging in living cells. The N- nitrosation of newly designed and synthesized 4-((3-amino-2- naphthyl)aminomethyl)benzoic acid (DAN-1) by NO yielded the highly fluorescent triazole-form. The membrane permeable ester derivative of DAN-1 (DAN-1 EE) was applied to the imaging of NO produced in activated rat aortic smooth muscle cells. After DAN-1 EE has been loaded into cells, the ester bond is hydrolyzed by intracellular esterase, yielding original DAN-1 with less permeability. The fluorescence intensity of the cells loaded with DAN-1 EE increased according to NO production. The imaging method with fluorescent indicators will be significant for the functional clarification of NO in vivo.

KW - Diaminonaphthalene

KW - Fluorescent indicator

KW - Imaging

KW - Nitric oxide

KW - Vascular smooth muscle cell

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Development of a fluorescent indicator for the bioimaging of nitric oxide

Abstract

Keywords

ASJC Scopus subject areas

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