A Novel, Cell-Permeable, Fluorescent Probe for Ratiometric Imaging of Zinc Ion

Maruyama, Satofumi; Kikuchi, Kazuya; Hirano, Tomoya; Urano, Yasuteru; Nagano, Tetsuo

doi:10.1021/ja026442n

Cited by 300 publications

(120 citation statements)

References 23 publications

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“…1 Hence the development of selective zinc chemosensors is of great importance for tracking the Zn 2+ status in biological systems. 2 Fluorescence chemosensors based on photoinduced electron transfer (PET), 3 intramolecular charge transfer (ICT), 4 excited-state intramolecular proton transfer (ESIPT), 5 and fluorescence resonance energy transfer (FRET) mechanisms have been developed for this purpose in the past years. 2,[6][7][8][9][10] Nevertheless, none of them completely satisfies the criteria for a biosystemoriented chemosensor.…”

Section: Introductionmentioning

confidence: 99%

A phenol-based compartmental ligand as a potential chemosensor for zinc(ii) cations

Chen¹,

Cao²,

Wang³

et al. 2009

J. Braz. Chem. Soc.

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O ligante compartimental 2,6-bis(2-hidroxibenzil-2-hidroxietilamino) metil-4-metilfenol (L) foi sintetizado como um sensor químico em potencial para íons Zn 2+ . A base L coordena dois cátions Zn 2+ em metanol-água, formando um complexo dinuclear cuja formulação foi confirmada por espectrometria de massas com ionização por "electrospray" (ESI-MS) e pelo gráfico de Job. A fluorescência de L é notavelmente aumentada por Zn 2+ em comparação com os íons K + , Ca 2+ , Mg 2+ , Cu 2+ , Pb 2+ , Mn 2+ , Fe 3+ , Fe 2+ , Co 2+ , Cd 2+ e Ni 2+ . Isto se deve ao fato de que a complexação do íon Zn 2+ a L interrompe o processo de transferência eletrônica fotoinduzida e aumenta a rigidez do esqueleto molecular de L. Observou-se ainda que a fluorescência de L é fortemente dependente da acidez e da polaridade dos solventes. Este composto poderá ser utilizado como uma sonda sensível a íons Zn 2+ em solventes polares próticos, após uma modificação estrutural adequada.An "end-off"-type compartmental Lewis base, 2,6-bis(2-hydroxybenzyl-2-hydroxyethylamino) methyl-4-methylphenol (L), was synthesized as a potential chemosensor for Zn 2+ ions. L coordinates two Zn 2+ cations in methanol-water solution, forming a dinuclear complex whose formulation was confirmed by ESI-MS spectroscopy and Job's plot. The fluorescence of L is remarkably enhanced by Zn 2+ as compared with K + , Ca 2+ , Mg 2+ , Cu 2+ , Pb 2+ , Mn 2+ , Fe 3+ , Fe 2+ , Co 2+ , Cd 2+ and Ni 2+ ions. The fluorescence enhancement is attributed to the complexation of Zn 2+ with L, which interrupts the photoinduced electron transfer process and rigidifies the molecular skeleton of L. The fluorescence of L is greatly dependent on the acidity and polarity of the solvents. This compound may be used as a probe to sense Zn 2+ ion in polar protic solvents after proper modification.Keywords: chemosensor, fluorescence mechanism, phenol derivative, solvent effects, zinc(II) IntroductionZinc(II) ions play vital roles in a wide range of physiological processes. Deficiency or imbalance of Zn 2+ within the human body can lead to a variety of diseases. 1 Hence the development of selective zinc chemosensors is of great importance for tracking the Zn 2+ status in biological systems. 2 Fluorescence chemosensors based on photoinduced electron transfer (PET), 3 intramolecular charge transfer (ICT), 4 excited-state intramolecular proton transfer (ESIPT), 5 and fluorescence resonance energy transfer (FRET) mechanisms have been developed for this purpose in the past years. 2,6-10 Nevertheless, none of them completely satisfies the criteria for a biosystemoriented chemosensor. Therefore, efforts to design novel zinc probes are still needed.Structural factors, such as molecular rigidity, could produce significant influence on the fluorescence efficiency of a chemosensor. An increase in planarity and a decrease in torsion may benefit the chemosensor to enhance its fluorescence. 11 As a metal ion binds to a chemosensor, the molecular rigidity is enhanced and the above mentioned transfer processes are poss...

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Section: Introductionmentioning

confidence: 99%

A phenol-based compartmental ligand as a potential chemosensor for zinc(ii) cations

Chen¹,

Cao²,

Wang³

et al. 2009

J. Braz. Chem. Soc.

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“…This characteristic is unique to fluorescence agents and many researchers have been interested in the development of various molecular designs. Thanks to their efforts, more flexible design strategies, such as Förster resonance energy transfer, 45,46 photoinduced electron transfer, 45,47 spirocyclization 48 and charge transfer, 49 than those for other modalities have been developed and applied to various target molecules. However, the molecular size of both types of optical imaging agents is larger than those used for PET/SPECT, so the agents often suffer from lower affinity, cell membrane permeability and catalytic constants.…”

Section: Optical Imaging Technologiesmentioning

confidence: 99%

In Vivo Molecular Imaging for Biomedical Analysis and Therapies

Ogawa

Takakura

2018

ANAL. SCI.

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In vivo molecular imaging is a powerful tool to analyze the human body. Precision medicine is receiving high attention these days, and molecular imaging plays an important role as companion diagnostics in precision medicine. Nuclear imaging with PET or SPECT and optical imaging technologies are used for in vivo molecular imaging. Nuclear imaging is superior for quantitative imaging, and whole-body analysis is possible even for humans. Optical imaging is superior due to its ease of use, and highly targeted specific imaging is possible with activatable agents. However, with optical imaging using fluorescence, it is difficult to obtain a signal from deep tissue and quantitation is difficult due to the attenuation and scattering of the fluorescent signal. Recently, to overcome these issues, optoacoustic imaging has been used in in vivo imaging. In this article, we review in vivo molecular imaging with nuclear and optical imaging and discuss their utility for precision medicine.

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“…Fluorescent probes for measuring biologically important ions such as Ca 2C , Mg 2C , and Zn 2C have been developed in many research groups [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16]. The fluorescence intensity of these metal probes changes mainly based on the differences of fluorescent properties between free form of the probe molecule and its metal complex.…”

Section: Introductionmentioning

confidence: 99%

Photochemical and complexation studies for new fluorescent and colored chelator

Ohshima

Momotake

Arai

2005

Science and Technology of Advanced Materials

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The photo-induced intramolecular proton (or hydrogen atom) transfer (ESIPT) and metal binding properties of Oxa-ester were studied in methanol solution. The dissociation constant between Oxa-ester and the metal ion was highly dependent with the metal ion and was determined by Hill plots or iterative least squares fitting to be 447 mM, 14.9 mM, and 290 nM for Ca 2C , Zn 2C , and Cu 2C , respectively, in methanol. The fluorescence intensity of Oxa-ester greatly increased with increasing concentration of Zn 2C , while the fluorescence intensity decreased with the addition of Ca 2C and Cu 2C . Transient absorption spectroscopy revealed that Oxa-ester underwent ESIPT to give Z-NH isomer in the excited state in benzene, while Oxa did not undergo ESIPT probably due to the hydrogen bonding with solvent water. q

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A Novel, Cell-Permeable, Fluorescent Probe for Ratiometric Imaging of Zinc Ion

Cited by 300 publications

References 23 publications

A phenol-based compartmental ligand as a potential chemosensor for zinc(ii) cations

A phenol-based compartmental ligand as a potential chemosensor for zinc(ii) cations

In Vivo Molecular Imaging for Biomedical Analysis and Therapies

Photochemical and complexation studies for new fluorescent and colored chelator

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