Novel Zinc Fluorescent Probes Excitable with Visible Light for Biological Applications

Hirano, Tomoya; Kikuchi, Kazuya; Urano, Yasuteru; Higuchi, T.; Nagano, Tetsuo

doi:10.1002/(sici)1521-3773(20000317)39:6<1052::aid-anie1052>3.0.co;2-5

Cited by 203 publications

(108 citation statements)

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“…The fluorescence of L was evaluated by recording its changes after addition of the metal ion to the methanol-water solution of L. To avoid possible hydrolysis and ensure the main reaction, the metal ion solution was added dropwise to L and the mixture was left for 5 min to reach the equilibrium. As Figure 9 shows, the alkali metal cation K + and the alkaline earth metal cations Ca 2+ and Mg 2+ hardly interfere with the fluorescence of L at high concentration (5 mmol L -1 ) due to their poor complexation with L. However, the metal cations Pb 2+ , Mn 2+ , Co 2+ , Ni 2+ , and especially Cu 2+ , Fe 3+ , and Fe 2+ , reduce the fluorescence of L at relatively low concentration (0.5 mmol L -1 ), probably due to an electron or energy transfer between metal cation and L. 12,27,28 Interestingly, Cd 2+ , that has the same d 10 electronic configuration as Zn 2+ , does not enhance the fluorescence of L. These observations indicate that L may selectively signal the presence of Zn 2+ in methanolwater solution. …”

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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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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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“…4). The PHD is important for the selectivity of Fllip for PIP 3 . If the PHD is replaced with domains that bind lipid messengers other than PIP 3 , such as diacylglycerol, phosphatidylinositol 3,4-bisphosphate, and phosphatidylinositol 4,5-bisphosphate, this allows us to change the selectivity of the indicator.…”

Section: Fluorescent Indicators For Lipid Second Messengersmentioning

confidence: 99%

“…2 In addition to Fura-2 for Ca 2þ , synthetic fluorescent indicators have been developed for several ions and small molecules, including Na þ , K þ , Zn 2þ , and nitric oxide. 3,4 However, I felt a limitation of the organic synthesisbased approach to the development of fluorescent indicators when I was a Ph.D. course student. Biomolecules that regulate physiological and/or pathophysiological processes in the cell, such as proteins, lipids, and sugar chains, have structures that are too complicated to develop indicators using organic synthesis.…”

Section: Introductionmentioning

confidence: 99%

Genetically Encoded Fluorescent Indicators to Visualize Molecular Processes in Living Cells

Sato¹

2008

Bulletin of the Chemical Society of Japan

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Fluorescence imaging could be the most powerful technique available for observing spatial and temporal dynamics of molecular processes in living cells, if fluorescent indicators for the relevant molecular processes become available. Therefore, we have been developing fluorescent indicators for a variety of cellular signaling processes, including second messengers and protein phosphorylation reactions. Using the indicators, we have visualized spatial and temporal dynamics of these molecular events in single living cells. The present fluorescent indicators are becoming an indispensable tool for understanding the complex mechanism of the signal transduction in living cells and for screening pharmaceuticals that inhibit or promote molecular processes in the cell.

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“…Rational design incorporates the use of fundamental knowledge of fluorophore properties, quantum-chemical calculations and chemical intuition, and is limited to small numbers of designed molecules and by the availability of prior knowledge of a fluorophore. [2][3][4] The diversity-oriented fluorescence library approach (DOFLA), a combinatorial approach which creates a diverse library of fluorophores by systematically varying the substituents attached to a core scaffold, has emerged as a general alternative in fluorophore design. [5] Such DOFLA-generated molecules have found wide applications as bioimaging sensors in a variety of analyses including those of DNA, [6] RNA, [7] nucleotides, [8] peptides, [9] proteins, [10][11][12] and polysaccharides, [13] thus demonstrating the universal applicability of this approach.…”

Section: Introductionmentioning

confidence: 99%

Quantitative Structure‐Fluorescence Property Relationship Analysis of a Large BODIPY Library

Schüller

Goh

Kim

et al. 2010

Molecular Informatics

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A quantitative structure‐fluorescence property relationship (QSPR) analysis of a large 288‐membered library based on a single fluorescent BODIPY scaffold is presented for the first time. BODIPY is a versatile fluorescent scaffold with outstanding photophysical properties. Absorption (λabs) and fluorescence emission (λem) wavelength maxima were modeled with help of stepwise multiple linear regression (MLR) and support vector regression (SVR). The models were rigorously validated by 10‐times 10‐fold cross‐validation (CV), y‐scrambling CV and with an external validation set. Non‐linear SVR models (R2=0.92 and Q2=0.71 for λabs; R2=0.89 and Q2=0.69 for λem) performed significantly better than linear models. A small root mean squared error (RMSE) of 5.62 nm and 11.07 nm was achieved for λabs and λem, respectively, and confirmed by external validation. A novel intramolecular charge transfer descriptor was developed based on the QSPR analysis and its inclusion in the modeling significantly improved models of λem. We conclude that QSPR is a useful tool for modeling λabs and λem of BODIPY fluorophores and suggest QSPR as an ideal partner for the design of compounds with tailored fluorescence properties in a diversity‐oriented fluorescence library approach (DOFLA).

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Novel Zinc Fluorescent Probes Excitable with Visible Light for Biological Applications

Cited by 203 publications

References 0 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

Genetically Encoded Fluorescent Indicators to Visualize Molecular Processes in Living Cells

Quantitative Structure‐Fluorescence Property Relationship Analysis of a Large BODIPY Library

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