Development of a potassium ion-selective fluorescent sensor based on 3-styrylated BODIPY

Tomoya Hirata; Takuya Terai; Toru Komatsu; Kenjiro Hanaoka; Tetsuo Nagano

doi:10.1016/j.bmcl.2011.08.056

Development of a potassium ion-selective fluorescent sensor based on 3-styrylated BODIPY

Tomoya Hirata, Takuya Terai, Toru Komatsu, Kenjiro Hanaoka, Tetsuo Nagano

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

31 Citations (Scopus)

Abstract

We have developed a red-emitting fluorescent K ⁺ probe, B3TAC, which also shows a wavelength shift upon binding to K ⁺. The probe was synthesized by conjugating a cryptand-based chelator, 2-triazacryptand [2,2,3-1-(2-methoxyethoxy)benzene (TAC), to position 3 of the BODIPY fluorophore through a styryl linker. In water-acetonitrile mixed solvent, it responded to K ⁺ in the physiological concentration range with high selectivity over Na ⁺ and other metal ions. B3TAC is potentially useful for measuring cellular K ⁺ ion concentration, as well as for simple, naked-eye detection of K ⁺ in solution.

Original language	English
Pages (from-to)	6090-6093
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	21
Issue number	20
DOIs	https://doi.org/10.1016/j.bmcl.2011.08.056
Publication status	Published - 2011 Oct 15
Externally published	Yes

Keywords

BODIPY
Fluorescent probe
Potassium ion

ASJC Scopus subject areas

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

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10.1016/j.bmcl.2011.08.056

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title = "Development of a potassium ion-selective fluorescent sensor based on 3-styrylated BODIPY",

abstract = "We have developed a red-emitting fluorescent K + probe, B3TAC, which also shows a wavelength shift upon binding to K +. The probe was synthesized by conjugating a cryptand-based chelator, 2-triazacryptand [2,2,3-1-(2-methoxyethoxy)benzene (TAC), to position 3 of the BODIPY fluorophore through a styryl linker. In water-acetonitrile mixed solvent, it responded to K + in the physiological concentration range with high selectivity over Na + and other metal ions. B3TAC is potentially useful for measuring cellular K + ion concentration, as well as for simple, naked-eye detection of K + in solution.",

keywords = "BODIPY, Fluorescent probe, Potassium ion",

author = "Tomoya Hirata and Takuya Terai and Toru Komatsu and Kenjiro Hanaoka and Tetsuo Nagano",

note = "Funding Information: This work was supported in part by the Ministry of Education, Culture, Sports, Science and Technology of Japan (Grant Nos. 22000006 to T.N., 21659024 to K.H. and 21750135 to T.T.), and by a grant from the New Energy and Industrial Technology Development Organization (NEDO) of Japan (to T.T.). T.T. was also supported by the Cosmetology Research Foundation, Japan. ",

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doi = "10.1016/j.bmcl.2011.08.056",

language = "English",

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AU - Hirata, Tomoya

AU - Terai, Takuya

AU - Komatsu, Toru

AU - Hanaoka, Kenjiro

AU - Nagano, Tetsuo

N1 - Funding Information: This work was supported in part by the Ministry of Education, Culture, Sports, Science and Technology of Japan (Grant Nos. 22000006 to T.N., 21659024 to K.H. and 21750135 to T.T.), and by a grant from the New Energy and Industrial Technology Development Organization (NEDO) of Japan (to T.T.). T.T. was also supported by the Cosmetology Research Foundation, Japan.

PY - 2011/10/15

Y1 - 2011/10/15

N2 - We have developed a red-emitting fluorescent K + probe, B3TAC, which also shows a wavelength shift upon binding to K +. The probe was synthesized by conjugating a cryptand-based chelator, 2-triazacryptand [2,2,3-1-(2-methoxyethoxy)benzene (TAC), to position 3 of the BODIPY fluorophore through a styryl linker. In water-acetonitrile mixed solvent, it responded to K + in the physiological concentration range with high selectivity over Na + and other metal ions. B3TAC is potentially useful for measuring cellular K + ion concentration, as well as for simple, naked-eye detection of K + in solution.

AB - We have developed a red-emitting fluorescent K + probe, B3TAC, which also shows a wavelength shift upon binding to K +. The probe was synthesized by conjugating a cryptand-based chelator, 2-triazacryptand [2,2,3-1-(2-methoxyethoxy)benzene (TAC), to position 3 of the BODIPY fluorophore through a styryl linker. In water-acetonitrile mixed solvent, it responded to K + in the physiological concentration range with high selectivity over Na + and other metal ions. B3TAC is potentially useful for measuring cellular K + ion concentration, as well as for simple, naked-eye detection of K + in solution.

KW - BODIPY

KW - Fluorescent probe

KW - Potassium ion

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Development of a potassium ion-selective fluorescent sensor based on 3-styrylated BODIPY

Abstract

Keywords

ASJC Scopus subject areas

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