2,6,8‐Trisubstituted 3‐Hydroxychromone Derivatives as Fluorophores for Live‐Cell Imaging

Dyrager, Christine; Friberg, Annika; Dahlén, Kristian; Fridén-Saxin, Maria; Börjesson, Karl; Wilhelmsson, L. Marcus; Smedh, Maria; Grøtli, Morten; Luthman, Kristina

doi:10.1002/chem.200900279

Cited by 30 publications

(16 citation statements)

References 43 publications

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“…5,22,23 3-Hydroxychromone (3HC) derivatives show exceptional solvatochromism of their dual emission, 24,25 due to an Excited-State Intramolecular Proton Transfer (ESIPT), but suffer from poor photostability. 26 This class of dyes found a variety of applications for probing biomembranes and protein interactions as well as for cellular imaging, 7,10,[27][28][29] and so we were particularly interested to design photostable fluorescent dyes based on these chromophores. It has been shown that the nature of photodegradation of 3HCs is photo-oxidation 26 and/or re-arrangement 30 in the tautomer state (T*) of the dye, which is an ESIPT product of the normal S1 excited state (N*).…”

Section: Introductionmentioning

confidence: 99%

Dipolar 3-methoxychromones as bright and highly solvatochromic fluorescent dyes

Kucherak

Richert

Mély

et al. 2012

Phys. Chem. Chem. Phys.

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Herein, three environment-sensitive (solvatochromic) fluorescent dyes presenting a strong electron acceptor 3-methoxychromone unit and varied electron donor 2-aryl were developed. All three dyes showed remarkable polarity-dependent shifts of the emission maximum, which increase with extension of the dye conjugation. For the 3-methoxychromone bearing a 7-(diethylamino)-9,9-dimethylfluoren-2-yl donor group the difference between the excited and the ground state dipole moments, estimated from the Lippert-Mataga expression, reached 20 D, which is among the largest reported for neutral dipolar fluorophores. Moreover, the new dyes are characterized by significant two-photon absorption cross-section (up to 450 GM) and large fluorescence quantum yields. The strong decrease in the fluorescence quantum yields of the dyes in polar protic solvents was observed together with the increase in the non-radiative deactivation rates, which can originate from twisted intramolecular charge transfer and intermolecular proton transfer phenomena. In comparison to the parent 3-hydroxychromone derivatives, the new dyes presented significantly improved photostability, which confirms that photodegradation of 3-hydroxychromones occurs from a product of the excited-state intramolecular proton transfer (phototautomer). Finally, an application of the new dyes for probing local binding site polarity of serum albumin was shown. This new class of fluorescent dyes may serve as attractive building blocks for future molecular sensors utilizing environment-sensitive fluorophores.

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Section: Introductionmentioning

confidence: 99%

Dipolar 3-methoxychromones as bright and highly solvatochromic fluorescent dyes

Kucherak

Richert

Mély

et al. 2012

Phys. Chem. Chem. Phys.

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“…Various dihalogenated chalcones have been of interest as intermediates in the synthesis of flavones and chromones 23 , 24 . Halogenated chalcones ( II–X , Figure 1 ) have been reported to exhibit high cytotoxic activity 25–28 .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and biological evaluation of halogenated phenoxychalcones and their corresponding pyrazolines as cytotoxic agents in human breast cancer

Halim

Hassan

Mohamed

et al. 2021

Journal of Enzyme Inhibition and Medicinal Chemistry

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Novel halogenated phenoxychalcones 2a–f and their corresponding N -acetylpyrazolines 3a–f were synthesised and evaluated for their anticancer activities against breast cancer cell line (MCF-7) and normal breast cell line (MCF-10a), compared with staurosporine. All compounds showed moderate to good cytotoxic activity when compared to control. Compound 2c was the most active, with IC 50 = 1.52 µM and selectivity index = 15.24. Also, chalcone 2f showed significant cytotoxic activity with IC 50 = 1.87 µM and selectivity index = 11.03. Compound 2c decreased both total mitogen activated protein kinase (p38α MAPK) and phosphorylated enzyme in MCF-7 cells, suggesting its ability to decrease cell proliferation and survival. It also showed the ability to induce ROS in MCF-7 treated cells. Compound 2c exhibited apoptotic behaviour in MCF-7 cells due to cell accumulation in G2/M phase and elevation in late apoptosis 57.78-fold more than control. Docking studies showed that compounds 2c and 2f interact with p38alpha MAPK active sites.

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Section: Introductionmentioning

confidence: 99%

“…Many natural products containing the flavone and isoflavone scaffolds have been reported to exhibit fluorescence, albeit with low fluorescence quantum yields. ,− Efforts have therefore focused on the development of chromone-derived fluorescent scaffolds with improved fluorescence. Luthman and co-workers demonstrated that 3-hydroxyflavone-derived fluorophores with improved fluorescence quantum yield could be used in various applications (Φ = 0.48 in EtOH) . Our group have a long-standing interest in this area, and we recently described the development of a new fluorescent moiety, 3-alkyl-6-methoxy-7-hydroxy-chromone (AMHC), which exhibited a medium fluorescence quantum yield (Φ = 0.48 in 0.1 M Tris–HCl buffer, pH 8.0) starting from the readily available natural product 7-hydroxyisoflavone (Figure ).…”

Section: Introductionmentioning

confidence: 99%

Determining Essential Requirements for Fluorophore Selection in Various Fluorescence Applications Taking Advantage of Diverse Structure–Fluorescence Information of Chromone Derivatives

Chen

Gao

et al. 2020

J. Med. Chem.

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Herein, we report our work exploring the essential requirements for fluorophore selection during the development of various fluorescence applications. We assembled a library of chromone-derived fluorophores with diverse structure−fluorescence properties, which allowed us to choose the fluorophore pairs with similar structures but differing fluorescence properties and compared the performance of the selected fluorophore pairs in three types of commonly used fluorescence applications. We found that the selection standard of a suitable fluorophore is variable depending on the application. (1) In fluorescence imaging, fluorophores with strong and constant fluorescence under various conditions, such as a large pH range, are preferred. Notably, (2) in the detection of bioactive species, fluorophores with relatively lower fluorescence quantum yield favor the detection sensitivity. Furthermore, (3) in enzymatic assays employing fluorescence, the key parameter is the binding affinity between the fluorophore and the enzyme.

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2,6,8‐Trisubstituted 3‐Hydroxychromone Derivatives as Fluorophores for Live‐Cell Imaging

Cited by 30 publications

References 43 publications

Dipolar 3-methoxychromones as bright and highly solvatochromic fluorescent dyes

Dipolar 3-methoxychromones as bright and highly solvatochromic fluorescent dyes

Synthesis and biological evaluation of halogenated phenoxychalcones and their corresponding pyrazolines as cytotoxic agents in human breast cancer

Determining Essential Requirements for Fluorophore Selection in Various Fluorescence Applications Taking Advantage of Diverse Structure–Fluorescence Information of Chromone Derivatives

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