Structural characteristics and optical properties of a series of solvatochromic fluorescent dyes displaying long-wavelength emission

Ando, Yosuke; Homma, Yuya; Hiruta, Yuki; Citterio, Daniel; Suzuki, Kôji

doi:10.1016/j.dyepig.2009.04.008

Cited by 36 publications

(23 citation statements)

References 27 publications

(40 reference statements)

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“…Here, we report the synthesis of a new nucleotide bearing an acetophenyl‐thienyl‐aniline (ATA) label for construction of solvatochromic fluorescence light‐up DNA probes. The ATA (KSD‐4) fluorophore [11] and its related furane analogues [12] were previously reported to exert high solvatofluorochromism and large Stokes shifts. ATA (KSD‐4) is excitable by blue visible light, but to the best of our knowledge, it was not used for labelling of biomolecules.…”

Section: Methodsmentioning

confidence: 99%

Acetophenyl‐thienyl‐aniline‐Linked Nucleotide for Construction of Solvatochromic Fluorescence Light‐Up DNA Probes Sensing Protein‐DNA Interactions

Güixens-Gallardo

Hocek

2021

Chemistry A European J

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The synthesis of 2'-deoxycytidine and its 5'-Otriphosphate bearing solvatochromic acetophenyl-thienylaniline fluorophore was developed using the Sonogashira cross-coupling reaction as the key step. The triphosphate was used for polymerase synthesis of labelled DNA. The labelled nucleotide or DNA exerted weak red fluorescence when excited at 405 nm, but a significant colour change (to yellow or green) and light-up (up to 20 times) was observed when the DNA probes interacted with proteins or lipids.

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Section: Methodsmentioning

confidence: 99%

Acetophenyl‐thienyl‐aniline‐Linked Nucleotide for Construction of Solvatochromic Fluorescence Light‐Up DNA Probes Sensing Protein‐DNA Interactions

Güixens-Gallardo

Hocek

2021

Chemistry A European J

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“…Although absorption spectra showed only a slight bathochromic shift ( Figure 1B), emission spectra displayed an strong positive solvatochromism from toluene (439 nm) to methanol (558 nm) representing a 119 nm bathochromic shift ( Figure 1C) which is in accordance with structurally close reported fluorophores. 52,53 Additionally, DAF showed a linear relationship between its maximum emission wavelength and the solvent polarity with a slope of 5.7 nm per ET (30) unit (Figure 2A). Interestingly, whereas DAF is efficiently excited by the commonly used 405 nm laser (lowest: 70% efficiency), it is virtually non-excitable by common light sources dedicated to the green channels, typically 488 nm.…”

Section: Spectroscopic Studiesmentioning

confidence: 99%

Probing Polarity and Heterogeneity of Lipid Droplets in Live Cells Using a Push–Pull Fluorophore

et al. 2018

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Lipid droplets (LDs) are organelles composed of a lipid core surrounded by a phospholipid monolayer. Lately, LDs attracted a considerable attention due to recent studies demonstrating their role in a variety of physiological processes as well as diseases. Herein we synthesized a push-pull molecule named DAF (Dimethyl Aniline Furaldehyde) that possesses a strong positive solvatochromism in emission of 119 nm from toluene to methanol. Its impressive fluorogenic properties from water to oil (2000fold) as well as its high quantum yields (up to 0.97) led us to investigate its ability to sense the distribution of polarity in live cells by fluorescence ratiometric imaging. When added to live cells and excited at 405 nm, DAF immediately and brightly stain lipid droplets using a blue channel (410-500 nm) and cytoplasm in a red channel (500-600 nm). DAF also proved to be compatible with fixation thus allowing 3D imaging of LDs in their cytoplasm environment. Taking advantage of DAF emission in two distinct channels, ratiometric imaging was successfully performed and led to the polarity mapping of the cell unraveling some heterogeneity in polarity within LDs of the same cell.

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“…Fluorescent dyes1 are vital analytical reagents and are widely used in molecular cell biology. Fluorophores that respond in a well‐defined way by changing their photophysical properties to the change in environmental factors, such as pH,2, 3 temperature,4, 5 gases,6, 7 organic8–10 and inorganic11, 12 analytes, and solvent polarity,13, 14 are of special interest. One of the most important groups is the so‐called solvatochromic dyes, the emission properties (emission maximum, quantum yield, fluorescent lifetime) of which are highly dependent upon the polarity of the surrounding environment.…”

Section: Introductionmentioning

confidence: 99%

Solvatochromic Study of Highly Fluorescent Alkylated Isocyanonaphthalenes, Their π‐Stacking, Hydrogen‐Bonding Complexation, and Quenching with Pyridine

et al. 2014

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Mono- and dialkylated derivatives of 1-amino-5-isocyanonaphthalene (ICAN) were studied as new members of a multifunctional, easy-to-prepare fluorophore family, which showed excellent solvatochromic properties. The monoallyl derivative and the starting ICAN exhibited strong fluorescence quenching in the presence of small amounts of pyridine. The formation of a hydrogen-bonded ground-state pyridine complex was detected; however, analysis of quantum chemical calculations suggested the presence of an additional π-stacked pyridine complex. The Stern-Volmer plot of the quenching process exhibited a downward curvature and after reaching a minimum the fluorescence intensity increased back to a significant level at high pyridine concentrations. Significant fluorescence was observed even in pure pyridine. A new mechanism and a simple mathematical equation were derived to explain the downward curvature and the remaining fluorescence by the formation of a fluorescent π-stacked complex.

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Structural characteristics and optical properties of a series of solvatochromic fluorescent dyes displaying long-wavelength emission

Cited by 36 publications

References 27 publications

Acetophenyl‐thienyl‐aniline‐Linked Nucleotide for Construction of Solvatochromic Fluorescence Light‐Up DNA Probes Sensing Protein‐DNA Interactions

Acetophenyl‐thienyl‐aniline‐Linked Nucleotide for Construction of Solvatochromic Fluorescence Light‐Up DNA Probes Sensing Protein‐DNA Interactions

Probing Polarity and Heterogeneity of Lipid Droplets in Live Cells Using a Push–Pull Fluorophore

Solvatochromic Study of Highly Fluorescent Alkylated Isocyanonaphthalenes, Their π‐Stacking, Hydrogen‐Bonding Complexation, and Quenching with Pyridine

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