Design and synthesis of a novel fluorescence probe for Zn2+ based on the spirolactam ring-opening process of rhodamine derivatives

Hiromi Sasaki; Kenjiro Hanaoka; Yasuteru Urano; Takuya Terai; Tetsuo Nagano

doi:10.1016/j.bmc.2010.05.074

Design and synthesis of a novel fluorescence probe for Zn²⁺ based on the spirolactam ring-opening process of rhodamine derivatives

Hiromi Sasaki, Kenjiro Hanaoka, Yasuteru Urano, Takuya Terai, Tetsuo Nagano

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

62 Citations (Scopus)

Abstract

The spirolactam ring-opening process of rhodamine derivative is one of the most useful mechanisms for controlling fluorescence properties. However, the open/closed equilibrium reaction of rhodamine spirolactam has not been well characterized. Therefore, we examined the relationship between the spirolactam ring-opening process of rhodamine derivatives and the structure of the xanthene moiety. Based on the results of this investigation, we selected a candidate xanthene moiety for a Zn²⁺ sensor, and successfully developed a new fluorescence probe for Zn²⁺.

Original language	English
Pages (from-to)	1072-1078
Number of pages	7
Journal	Bioorganic and Medicinal Chemistry
Volume	19
Issue number	3
DOIs	https://doi.org/10.1016/j.bmc.2010.05.074
Publication status	Published - 2011 Feb 1
Externally published	Yes

Keywords

Fluorescence
Rhodamine
Sensors
Zinc ion

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

Access to Document

10.1016/j.bmc.2010.05.074

Cite this

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title = "Design and synthesis of a novel fluorescence probe for Zn2+ based on the spirolactam ring-opening process of rhodamine derivatives",

abstract = "The spirolactam ring-opening process of rhodamine derivative is one of the most useful mechanisms for controlling fluorescence properties. However, the open/closed equilibrium reaction of rhodamine spirolactam has not been well characterized. Therefore, we examined the relationship between the spirolactam ring-opening process of rhodamine derivatives and the structure of the xanthene moiety. Based on the results of this investigation, we selected a candidate xanthene moiety for a Zn2+ sensor, and successfully developed a new fluorescence probe for Zn2+.",

keywords = "Fluorescence, Rhodamine, Sensors, Zinc ion",

author = "Hiromi Sasaki and Kenjiro Hanaoka and Yasuteru Urano and Takuya Terai and Tetsuo Nagano",

note = "Funding Information: This work was supported in part by the Ministry of Education, Culture, Sports, Science and Technology of the Japan (Grant Nos. 20689001 , 19890047 and 21659024 to K.H., 19205021 and 20117003 to Y.U., and 21750135 to T.T.), and by a grant from the Industrial Technology Development Organization (NEDO) of Japan (to T.T.). K.H. was also supported by The Mochida Memorial Foundation for Medical Pharmaceutical Research, and Sankyo Foundation of Life Science. ",

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AU - Sasaki, Hiromi

AU - Hanaoka, Kenjiro

AU - Urano, Yasuteru

AU - Terai, Takuya

AU - Nagano, Tetsuo

N1 - Funding Information: This work was supported in part by the Ministry of Education, Culture, Sports, Science and Technology of the Japan (Grant Nos. 20689001 , 19890047 and 21659024 to K.H., 19205021 and 20117003 to Y.U., and 21750135 to T.T.), and by a grant from the Industrial Technology Development Organization (NEDO) of Japan (to T.T.). K.H. was also supported by The Mochida Memorial Foundation for Medical Pharmaceutical Research, and Sankyo Foundation of Life Science.

PY - 2011/2/1

Y1 - 2011/2/1

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AB - The spirolactam ring-opening process of rhodamine derivative is one of the most useful mechanisms for controlling fluorescence properties. However, the open/closed equilibrium reaction of rhodamine spirolactam has not been well characterized. Therefore, we examined the relationship between the spirolactam ring-opening process of rhodamine derivatives and the structure of the xanthene moiety. Based on the results of this investigation, we selected a candidate xanthene moiety for a Zn2+ sensor, and successfully developed a new fluorescence probe for Zn2+.

KW - Fluorescence

KW - Rhodamine

KW - Sensors

KW - Zinc ion

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