Studies on the synthesis of fluorescein-5-isothiocyanate: A fluorescent nanomarker for biosensors

Glushko, V. N.; Blokhina, L. I.; Sadovskaya, N. Yu.

doi:10.1134/s1070363215100412

Cited by 6 publications

(7 citation statements)

References 3 publications

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“…olorants 2023, 2, FOR PEER REVIEW 3 [6]. When considering the synthesis scheme developed in our study, it became clear that the authors of the earlier cited works certainly obtained mixtures of different reaction products.…”

Section: Resultsmentioning

confidence: 81%

“…The synthesis was carried out according to the classical method by fusing resorcinol with 3-nitrophthalic acid (Scheme 1). The pathway from 2 to 5 is a standard procedure [6]. When considering the synthesis scheme developed in our study, it became clear that the authors of the earlier cited works certainly obtained mixtures of different reaction products.…”

Section: Resultsmentioning

confidence: 84%

“…Normally, they are prepared by reduction of the corresponding nitro derivatives. The latter are obtained by condensation of 4-nitrophthalic acid with resorcinol and separating the 4and 5 -nitro isomers [1,2,6]. However, to the best of our knowledge, there is no information on 3 -aminofluorescein in the literature.…”

Section: Introductionmentioning

confidence: 99%

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3′-Nitro- and 3′-Aminofluoresceins: Appearance of Previously Missing Dyes

Shekhovtsov,

Omelchenko,

Shishkina

et al. 2023

Colorants

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Contrary to the 4′- and 5′-nitro- and aminofluoresceins, the corresponding 3′-derivatives are practically unexplored. In this paper, we describe the synthesis and spectral properties of 3′-nitrofluorescein and 3′-aminofluorescein, as well as their methyl esters. Among other methods, X-ray analysis, 13C NMR spectroscopy, and ESI mass spectrometry made it possible to establish the molecular structure of the target compounds as well as intermediates and by-products. Some unexpected products, though in small amounts, were revealed within the course of study. Whereas the fluorescence of the double-charged R2− ion of 3′-nitrofluorescein in both aqueous and organic solvents is weak, the R2− anion of 3′-aminofluorescein in a non-hydrogen bonding donor solvent, but not in water, exhibits intensive fluorescence, analogous to the case of 4′- and 5′-aminofluoresceins. Interestingly, the λmax values in water of the R2− ions bearing an NO2 group in the 3′- and 6′-positions are 7 to 10 nm higher than those of the 4′- and 5′-nitro derivatives. The difference was also observed in dimethyl sulfoxide. This correlates with the angles between the xanthene and phthalic planes of the dyes. The dye 3′-aminofluorescein could be used as a fluorescent indicator sensitive to hydrogen bonding ability of the solvent. It could also serve as a platform for synthesizing fluorescent molecular probes for biochemical research, analogous to the very popular application of 4′- and 5′-amino derivatives.

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Section: Resultsmentioning

confidence: 81%

Section: Resultsmentioning

confidence: 84%

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3′-Nitro- and 3′-Aminofluoresceins: Appearance of Previously Missing Dyes

Shekhovtsov,

Omelchenko,

Shishkina

et al. 2023

Colorants

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“…The isomers 4′- and 5′-aminofluorescein (98% main compound) were purchased from Sigma-Aldrich and were used as received. 4′-Nitrofluorescein was synthesized according to the recently published procedure and purified by the accepted method using diacetate. , The 1 H NMR spectrum in (CD 3 ) 2 SO confirms this identity of the target compound; δ/ppm: 10.194 (2H, s, OH), 8.622 (1H, d, J = 2.2 Hz, 3′ ), 8.529 (1H, dd, J = 8.5 Hz, J = 2.2 Hz, 5′ ), 7.536 (1H, d, J = 8.5 Hz, 6′ ), 6.667 (2H, d, J = 2.3 Hz, 4 , 5 ), 6.636 (2H, d, J = 8.7 Hz, 1 , 8 ), 6.516 (2H, dd, J = 8.7 Hz, J = 2.3 Hz, 2 , 7 ).…”

Section: Methodsmentioning

confidence: 78%

Aminofluoresceins Versus Fluorescein: Peculiarity of Fluorescence

et al. 2019

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In this article, we examined the fluorescent properties of 4′- and 5′-aminofluorescein, unsubstituted fluorescein, and its 4′-nitro derivative in a set of solvent systems. Fluorescence lifetimes, quantum yields, time-resolved fluorescence spectra, and quantum chemical calculations allowed clarifying the reasons of the emitting properties in this dye series. In water, the dianions R2– of aminofluoresceins are practically nonfluorescent; in alcohols, the quantum yields are low. In dimethylsulfoxide (DMSO), acetonitrile, and other non-hydrogen bond donor solvents, the bright fluorescence of R2– ions is quenched either on adding small amounts of water which hydrate the carboxylate group or under conditions of protonation of this group (COO– → COOH). The last observation is possible owing to the peculiarities of the tautomerism of the 5′-aminofluorescein monoanion, HR–, which exists in DMSO as an equilibrium mixture of a colorless lactone and colored “phenolate” tautomer with an ionized xanthene moiety and unionized carboxylic group. In contrast, the R2– anion of 4′-nitrofluorescein demonstrates spectral behavior different from that of the amino derivatives. It practically does not emit in aprotic solvents; however, in alcohols or water media, its quantum yield increases to some extent. Such changing spectral properties are explained in terms of the excited-state interfragmental charge transfer.

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“…Developing methods for synthesizing thiocarbamoyl fluorides from readily available, safe, and cheap starting materials would enable their use as practical and available building blocks. Isothiocyanates are important building blocks which have been ubiquitously used in organic synthesis, materials science, biological, and pharmaceutical fields, and many isothiocyanates themselves show significant biological activities . Traditional methods for preparation of isothiocyanates involve highly toxic and/or highly electrophilic reagents such as thiophosgene, CS 2 , phosgene, thiocarbonyldiimidazole, or dipyridylthionocarbonate (DPT) .…”

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confidence: 99%

Synthesis of Thiocarbamoyl Fluorides and Isothiocyanates Using CF₃SiMe₃ and Elemental Sulfur or AgSCF₃ and KBr with Amines

2019

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Reactions of thiocarbonyl fluoride derived from cheap, readily available, and widely used CF 3 SiMe 3 , elemental sulfur, and KF with secondary amines and primary amines at room temperature in THF provided a wide variety of thiocarbamoyl fluorides and isothiocyanates in moderate to excellent yields, respectively. The two reactions show broad substrate scope and good functional group tolerance. Moreover, AgSCF 3 reacts with secondary/primary amines under KBr at room temperature, affording quantitative thiocarbamoyl fluorides/isothiocyanates, which feature late-stage application.

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Studies on the synthesis of fluorescein-5-isothiocyanate: A fluorescent nanomarker for biosensors

Cited by 6 publications

References 3 publications

3′-Nitro- and 3′-Aminofluoresceins: Appearance of Previously Missing Dyes

3′-Nitro- and 3′-Aminofluoresceins: Appearance of Previously Missing Dyes

Aminofluoresceins Versus Fluorescein: Peculiarity of Fluorescence

Synthesis of Thiocarbamoyl Fluorides and Isothiocyanates Using CF₃SiMe₃ and Elemental Sulfur or AgSCF₃ and KBr with Amines

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Studies on the synthesis of fluorescein-5-isothiocyanate: A fluorescent nanomarker for biosensors

Cited by 6 publications

References 3 publications

3′-Nitro- and 3′-Aminofluoresceins: Appearance of Previously Missing Dyes

3′-Nitro- and 3′-Aminofluoresceins: Appearance of Previously Missing Dyes

Aminofluoresceins Versus Fluorescein: Peculiarity of Fluorescence

Synthesis of Thiocarbamoyl Fluorides and Isothiocyanates Using CF3SiMe3 and Elemental Sulfur or AgSCF3 and KBr with Amines

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Synthesis of Thiocarbamoyl Fluorides and Isothiocyanates Using CF₃SiMe₃ and Elemental Sulfur or AgSCF₃ and KBr with Amines