Aminofluoresceins Versus Fluorescein: Peculiarity of Fluorescence

Mchedlov‐Petrossyan, Nikolay O.; Cheipesh, Tatyana A.; Roshal, Alexander D.; Shekhovtsov, Sergey V.; Moskaeva, Elena; Omelchenko, Irina V.

doi:10.1021/acs.jpca.9b05812

Cited by 14 publications

(8 citation statements)

References 45 publications

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“…The addition of even small amounts of water quenches the fluorescence. These observations completely match those made for 4 -nitrofluorescein and 4 -and 5 -aminofluoresceins in water and non-aqueous solvents [32,33]. The visible absorption and fluorescence spectra of the dianionic forms of the target dyes, R 2− are presented in Figure 6 and Table 4.…”

Section: Atomsupporting

confidence: 80%

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: Atomsupporting

confidence: 80%

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

Shekhovtsov,

Omelchenko,

Shishkina

et al. 2023

Colorants

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“…In alcohols, the quantum yield, φ , is quite low. In dimethylsulfoxide (DMSO), acetone and other hydrogen bond donor solvents, φ values approach dianionic values [ 77 ]. Its sodium salt form finds wide use in angiography [ 78 , 79 ] and glioma studies [ 80 ].…”

Section: Fluorescent Probes In Ocular Applicationsmentioning

confidence: 99%

Fluorescent Nanosystems for Drug Tracking and Theranostics: Recent Applications in the Ocular Field

et al. 2022

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The greatest challenge associated with topical drug delivery for the treatment of diseases affecting the posterior segment of the eye is to overcome the poor bioavailability of the carried molecules. Nanomedicine offers the possibility to overcome obstacles related to physiological mechanisms and ocular barriers by exploiting different ocular routes. Functionalization of nanosystems by fluorescent probes could be a useful strategy to understand the pathway taken by nanocarriers into the ocular globe and to improve the desired targeting accuracy. The application of fluorescence to decorate nanocarrier surfaces or the encapsulation of fluorophore molecules makes the nanosystems a light probe useful in the landscape of diagnostics and theranostics. In this review, a state of the art on ocular routes of administration is reported, with a focus on pathways undertaken after topical application. Numerous studies are reported in the first section, confirming that the use of fluorescent within nanoparticles is already spread for tracking and biodistribution studies. The first section presents fluorescent molecules used for tracking nanosystems’ cellular internalization and permeation of ocular tissues; discussions on the classification of nanosystems according to their nature (lipid-based, polymer-based, metallic-based and protein-based) follows. The following sections are dedicated to diagnostic and theranostic uses, respectively, which represent an innovation in the ocular field obtained by combining dual goals in a single administration system. For its great potential, this application of fluorescent nanoparticles would experience a great development in the near future. Finally, a brief overview is dedicated to the use of fluorescent markers in clinical trials and the market in the ocular field.

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“…In most of the cases, the newly formed or reinforced HB in the excited state leads to significant quenching of fluorescence due to the formation additional nonradiative pathways. For example, significant fluorescence quenching of a series of different probes in aqueous medium due the HB formation leads to the development of trace water detection systems for aprotic organic solvents. − Even, fluorescence quenching of novel carbon quantum dots due to the formation of CO---O–H bond with phenol is reported to detect trace amount phenol as organic pollutant . On the other hand, fluorescence enhancement of organic molecules is also noted mostly because of facile crystallization and/or generation of aggregation induced emission in HB medium. , …”

Section: Introductionmentioning

confidence: 99%

Deciphering Spectroscopic and Structural Insights into the Photophysical Behavior of 2,2′-Dipyridylamine: An Efficient Environment Sensitive Fluorescence Probe

et al. 2021

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Excited state deactivation properties and the effects of solvent hydrogen bonding (HB) on the photophysical behavior of 2,2′-dypyridylamine (DPyA) were investigated by steady state and time-resolved fluorescence experiments, molecular docking, and density functional theory (DFT) calculations. In addition to the polarity effect, the contributions of solvent HB donation (HBD) acidity and HB acceptance (HBA) basicity to modulate the solvatochromic spectral properties were estimated from multiparametric linear regression analysis using Kamlet–Taft (KT) and Catalán formalisms. The importance of C–N bond torsion, leading to the trans → cis conversion, was manifested by substantial increase in DPyA fluorescence yield in the presence of cyclodextrin (CD) and glycerol. The unusually low fluorescence yield in aqueous medium was explained on the basis of synergistic effect of solvent hydrogen bonding combined with excited state conformational isomerization, which renders DPyA to be an excellent environment sensitive fluorescence reporter. The experimental results were verified with structural insights obtained from DFT calculations at B3LYP/6-311++G(d,p) level and construction of potential energy surface (PES) in the ground state as well as in the excited states.

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Aminofluoresceins Versus Fluorescein: Peculiarity of Fluorescence

Cited by 14 publications

References 45 publications

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

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

Fluorescent Nanosystems for Drug Tracking and Theranostics: Recent Applications in the Ocular Field

Deciphering Spectroscopic and Structural Insights into the Photophysical Behavior of 2,2′-Dipyridylamine: An Efficient Environment Sensitive Fluorescence Probe

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