An Azacrowned Phthalimide as a Metal‐Ion Sensitive and Solvatofluorochromic Fluorophore: Fluorescence Properties and a Mimic Integrated Logic Operation.

Okamoto, Hideki; Kohno, Mami; Satake, Kyosuke; Kimura, Masao

doi:10.1002/chin.200611027

Cited by 3 publications

(3 citation statements)

References 1 publication

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“…Another potential application for the API system lies in the finding that aminophthalimides display solvatofluorochromism (i.e., altered emission wavelength in response to polarity changes) (22). Although not explored in this study, it is envisaged that API-based investigations could yield valuable information regarding the total quantity of labels within cells (determined chemiluminometrically) and its distribution within distinct microenvironments (e.g., lipid bodies c/o cytosol), determined fluorometrically.…”

Section: Discussionmentioning

confidence: 99%

The Use of 3-Aminophthalimide as a Pro-Chemiluminescent Label in Chemiluminescence and Fluorescence-Based Cellular Assays

et al. 2009

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We present a labeling system for direct chemiluminescence-based cellular bioassays using the stable pro-chemiluminescent, luminol precursor, 3-aminophthalimide (API). API-coupled reporter molecules are detected chemiluminometrically after treatment with hydrazine, which converts the API label to luminol. API derivatives containing a variety of functional groups are readily synthesized, allowing for ease of coupling via the imide nitrogen to a host of reporter molecules. The fluorescent nature of APIs further allows for dual fluorescence and chemiluminescence studies. To highlight the utility of this label, we show that API-labeled insulin can be successfully utilized in cellular binding and transport assays and that an API-coupled mitochondrial probe (API-triphenylphosphonium(+)) can be used to both fluorescently and chemiluminometrically investigate mitochondrial function. We also assess the use of API as a polysaccharide and nucleic acid label, and we show that API-labeled palmitic acid undergoes cellular transport and lipid metabolism.

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Section: Discussionmentioning

confidence: 99%

The Use of 3-Aminophthalimide as a Pro-Chemiluminescent Label in Chemiluminescence and Fluorescence-Based Cellular Assays

et al. 2009

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“…[17] Moreover, upon increasing solvent H-bond donor ability the fluorescence of 4-aminophthalimide is quenched. [18] Due to its high values of fluorescence quantum yield, 4-aminophthalimides were used in the cation [19] and anion sensing, [20,21,22] design of logic gates, [23] or for the labelling of nucleosides for the study of DNA-protein interactions. [24] Herein, we present the spectral and photophysical characterization of 4-amino-N-adamantylphthalimide (1), and its use in fluorescence microscopy.…”

Section: Introductionmentioning

confidence: 99%

Application of 4-amino-N-adamantylphthalimide solvatochromic dye for fluorescence microscopy in selective visualization of lipid droplets and mitochondria

Benčić

Mandić

Džeba

et al. 2019

Sensors and Actuators B: Chemical

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4-Amino-N-adamantylphthalimide (1) is a dye with moderate absorptivity (in CH3CN ε363 = 4200 M-1 cm-1) and high quantum yield of fluorescence (ΦF = 0.15-0.80) that exhibits fluorosolvatochromic properties. The dye can be excited at 405 nm and the position of fluorescence maximum and the Stokes shift are well correlated with the ET(30) parameter. The excitation in the near-visible part of the spectrum and low cytotoxicity allow use of the dye in live cell microscopy. Due to its amphiphilic character, the dye stains artificial membranes in liposomes. Using confocal microscopy on two human cancer cell lines, we have shown that 1 binds primarily to intracellular lipid droplets. Colocalization experiments with different organelle markers indicated that 1 additionally binds to mitochondrial membranes. The fluorosolvatochromism of 1 allows the simultaneous visualization of mitochondria and intracellular lipid droplets in two separate emission channels, which has a potential use in cells and tissues exhibiting intense oxidative metabolism of lipids.

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“…Chromogenic and fluorogenic materials responding to the microscopic environment of a medium have been extensively studied 1,2 because of their potential for application to biological probes, [3][4][5][6] chemosensors for ionic species and ion-pairs [7][8][9][10][11][12][13] as well as molecular logic circuits. [14][15][16][17] Apart from such application studies, fundamental research has been conducted to reveal the interactions between the fluorophores and specific solvents, namely the polar protic ones (e.g. hydrogen bonding effects), [18][19][20][21] and to monitor photochemical reactions, such as photochemical uncaging.…”

Section: Introductionmentioning

confidence: 99%

Solvent-induced multicolour fluorescence of amino-substituted 2,3-naphthalimides studied by fluorescence and transient absorption measurements

Fujii

Namba

Yamaji

et al. 2016

Photochem Photobiol Sci

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A series of amino-2,3-naphthalimide derivatives having the amino functionality at 1-, 5- and 6-positions (, and , respectively) were prepared, and their photophysical properties were systematically investigated based on the measurements of steady-state absorption and fluorescence spectra, fluorescence lifetimes as well as transient absorption spectra. The s efficiently fluoresced in solution, and the emission spectra appreciably shifted depending on the solvent polarity. displayed only a slight fluorescence red-shift upon increasing the solvent polarity. In contrast, and showed marked positive solvatofluorochromism with large Stokes shifts displaying multicolour fluorescence; the fluorescence colours of and varied from violet-blue in hexane to orange-red in methanol. and , thus, serve as micro-environment responding fluorophores. In methanol, the intensity of the fluorescence emission band of and significantly reduced. Based on the fluorescence quantum yields and lifetimes, and transient absorption measurements, it has been revealed that internal conversion from the S1 state of s to the ground state was accelerated by the protic medium, resulting in a reduction in their fluorescence efficiency, while intersystem crossing from the S1 state to a triplet state was not responsible for the decrease of fluorescence intensity.

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An Azacrowned Phthalimide as a Metal‐Ion Sensitive and Solvatofluorochromic Fluorophore: Fluorescence Properties and a Mimic Integrated Logic Operation.

Cited by 3 publications

References 1 publication

The Use of 3-Aminophthalimide as a Pro-Chemiluminescent Label in Chemiluminescence and Fluorescence-Based Cellular Assays

The Use of 3-Aminophthalimide as a Pro-Chemiluminescent Label in Chemiluminescence and Fluorescence-Based Cellular Assays

Application of 4-amino-N-adamantylphthalimide solvatochromic dye for fluorescence microscopy in selective visualization of lipid droplets and mitochondria

Solvent-induced multicolour fluorescence of amino-substituted 2,3-naphthalimides studied by fluorescence and transient absorption measurements

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