Environment-sensitive fluorogens based on a GFP chromophore structural motif

Perfilov, Maxim M.; Zaitseva, Elvira R.; Smirnov, Alexander Yu.; Mikhaylov, Andrey А.; Балеева, Надежда С.; Myasnyanko, Ivan N.; Mishin, Alexander S.; Баранов, Михаил С.

doi:10.1016/j.dyepig.2021.110033

Cited by 18 publications

(16 citation statements)

References 41 publications

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“…The detailed experimental procedures and spectral data, copies of 1 H and 13 C NMR spectra are available in the Supporting Information. The authors have cited additional references within the Supporting Information [38–42] …”

Section: Supporting Informationmentioning

confidence: 99%

Synthesis of Spiro[imidazole‐4,3′‐pyrrolo[1,2‐a]quinolin]‐ 5‐ones via 1,3‐Dipolar Cycloaddition of Quinolinium Ylides with Arylydeneimidazol‐4‐ones

Molchanova,

Ikonnikova,

Smirnov

et al. 2024

ChemistrySelect

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Design of spirocyclic scaffolds, which are able for direct interaction with biological targets, is a developing trend in medicinal chemistry. In continuation of the previous work on HIV‐1 inhibitors, a synthetic approach towards spiro[imidazole‐4,3′‐pyrrolo[1,2‐a]quinolin]‐5‐ones via 1,3‐dipolar cycloaddition of quinolinium ylides with arylydeneimidazol‐4‐ones was outlined. Derivatives with various substitution pattern were prepared in 42–86 % yields. Use of 2,2,2‐trifluoroethanol as a solvent is crucial for successful preparation of the derivatives, its role is sought as prolonging lifetime of the cycloadducts.

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Section: Supporting Informationmentioning

confidence: 99%

Synthesis of Spiro[imidazole‐4,3′‐pyrrolo[1,2‐a]quinolin]‐ 5‐ones via 1,3‐Dipolar Cycloaddition of Quinolinium Ylides with Arylydeneimidazol‐4‐ones

Molchanova,

Ikonnikova,

Smirnov

et al. 2024

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“…Unlike conventional labels, fluorogens do not have their own pronounced fluorescence in a free form in an aqueous medium. However, they are capable of acquiring it upon binding to various target structures such as proteins [ 7 , 8 , 9 , 10 , 11 , 12 , 13 ], nucleotides [ 14 , 15 , 16 , 17 ], or even whole organelles [ 18 , 19 , 20 , 21 , 22 ]. Various methine dyes [ 20 , 23 ], including diverse arylidene-azolones [ 14 , 15 ] and derivatives of fluorescent protein chromophores [ 7 , 8 , 9 , 11 , 12 , 18 , 19 , 22 ], are widely used as such labels.…”

Section: Introductionmentioning

confidence: 99%

Meta-CF3-Substituted Analogues of the GFP Chromophore with Remarkable Solvatochromism

Perfilov

Zaitseva

Балеева

et al. 2023

IJMS

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In this work, we have shown that the introduction of a trifluoromethyl group into the me-ta-position of arylidene imidazolones (GFP chromophore core) leads to a dramatic increase in their fluorescence in nonpolar and aprotic media. The presence of a pronounced solvent-dependent gradation of fluorescence intensity makes it possible to use these substances as fluorescent polarity sensors. In particular, we showed that one of the created compounds could be used for selective labeling of the endoplasmic reticulum of living cells.

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“…Structural color is a kind of color effect produced by optical effects such as interference, diffraction, and scattering through its special structure (X. Li It presents a unique and deep color and has characteristics such as being bright and vivid, never fading, and also very friendly to the environment (Fu et al 2021;Per lov et al 2022). Structural color is mainly used in photochromic, infrared stealth, medical, alcohol detection, and textile applications (Fu et Fang et al 2021).…”

Section: Introductionmentioning

confidence: 99%

Self-assembly P(St-BA-MAA)@PGA-Fe 3+ photonic composites ink on cotton fabric for non-iridescent structure color

Qi,

Chen,

Huang

et al. 2023

Preprint

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Vat dyeing is the mainstream process of cotton fabric dyeing at present, but the high toxicity of the reducing agent and the high cost of dyeing waste liquid treatment make the process no longer meet the requirements of green and sustainable development of society. The photonic crystal structure color, which is made of nanoscale colloidal microspheres arranged in an orderly manner as structural units, is expected to be a new printing and dyeing technology, that provides a new way of thinking for dyeing cotton fabrics. However, the practical applications of photonic crystal structural colors on textile fabrics are hampered by their inadequate stability, muted color saturation, and weak mechanical properties. In this study, P(St-BA-MAA) nanospheres with a hard-core-soft-shell structure were prepared by soapless emulsion polymerization, and then P(St-BA-MAA)@PGA-Fe3+ photonic composite inks were prepared by forming a dark-colored coating film on the surface of the microspheres through the complexation of gallic acid with Fe3+. It was found that the performance of the prepared P(St-BA-MAA)@PGA-Fe3+ photonic composite ink was stable, and the dark metallic-polyphenol network film enabled the formation of vibrant non-iridescent structured colors on cotton fabrics, the soft shell of the seeded microspheres also significantly improved the adhesion between the ink and the fabrics, and the structural color fastness was greatly improved compared with the PS microspheres. The preparation of this photonic composite ink is facile, low-cost, and produces a bright color, providing practical value for the development of textile products that construct structural color effects on textile substrates.

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Environment-sensitive fluorogens based on a GFP chromophore structural motif

Cited by 18 publications

References 41 publications

Synthesis of Spiro[imidazole‐4,3′‐pyrrolo[1,2‐a]quinolin]‐ 5‐ones via 1,3‐Dipolar Cycloaddition of Quinolinium Ylides with Arylydeneimidazol‐4‐ones

Synthesis of Spiro[imidazole‐4,3′‐pyrrolo[1,2‐a]quinolin]‐ 5‐ones via 1,3‐Dipolar Cycloaddition of Quinolinium Ylides with Arylydeneimidazol‐4‐ones

Meta-CF3-Substituted Analogues of the GFP Chromophore with Remarkable Solvatochromism

Self-assembly P(St-BA-MAA)@PGA-Fe 3+ photonic composites ink on cotton fabric for non-iridescent structure color

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