Synthesis, photophysical properties and systematic evaluations of new phenanthroimidazole fluorescent probe for bioimaging: Experimental and theoretical study

Krawczyk, Przemysław; Jędrzejewska, Beata; Pietrzak, Marek; Janek, Tomasz

doi:10.1016/j.jphotobiol.2016.11.008

Cited by 24 publications

(14 citation statements)

References 97 publications

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“…The fluorescence emission bands are broad in nature and shows wide spectral visible region from 500 to 650 nm for RHB1, from 520 to 650 nm for RHB2, and from 540 to 650 nm for RHB3 in a variety of solvent. 3 Moreover, the fluorescence band is affected by changing the solvent polarity. S 0 electronic transition.…”

Section: Resultsmentioning

confidence: 99%

“…[1][2][3] The common structural feature in several fluorophores is a conjugated πsystem and having both electrons donating and withdrawing group. For the qualifying conditions in the selection of organic dyes as a fluorescent probe, it must display the finest fluorescence response when it irradiated in the visible range and less lethal to the living cells and tissues.…”

Section: Introductionmentioning

confidence: 99%

“…During the past decade, fluorescent probes are used for the selective detection of chemical species in the environmental contaminants and labels of targeting molecules. For the qualifying conditions in the selection of organic dyes as a fluorescent probe, it must display the finest fluorescence response when it irradiated in the visible range and less lethal to the living cells and tissues . The common structural feature in several fluorophores is a conjugated π‐ system and having both electrons donating and withdrawing group .…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Studies on Photophysical Properties of Rhodamine Derivatives for Bioimaging Applications

Vanjare

Mahajan

Dige

et al. 2019

Bulletin Korean Chem Soc

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Rhodamine derivatives have been persistently used as fluorescent/solvatochromic dyes in various areas. For example, they are used as a labeling agent in biotechnology and a chemosensor. Also, rhodamine derivatives are used for cell imaging experiment. Herein, we report on the synthesis of fluorescent derivatives based on rhodamine B (RHB1, RHB2, and RHB3). We confirmed the structures and purities of the synthesized probes i.e., RHB1, RHB2, and RHB3 by using analytical technique's viz. 1 H NMR, 13 C NMR, Mass and FT-IR followed by exploring spectroscopic properties by using fluorescence/UV absorption spectroscopy. The effect of solvents on the fluorescence and absorption properties of the synthesized compounds has been comprehensively studied using a series of solvent. In addition, synthesized RHB1, RHB2, and RHB3 were found to be non-toxic against the cancer cell (MDA-MB-231). It is clear from the result of the conventional fluorescence microscopy that probe RHB2 exhibits significant optical properties as compared with those of RHB1 and RHB3.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis and Studies on Photophysical Properties of Rhodamine Derivatives for Bioimaging Applications

Vanjare

Mahajan

Dige

et al. 2019

Bulletin Korean Chem Soc

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“…The electronic properties were characterized by computations of the vertical absorption and emission spectra, which were obtained using the timedependent density functional theory (TDDFT/PBE0) [31] and by including the state-specific (SS) corrected linear response (cLR) approach [32]. Due to the high compatibility of theoretical and experimental data [33][34][35][36], all spectroscopic calculations were performed using the PBE0 functional.…”

Section: Computational Detailsmentioning

confidence: 99%

“…Theoretical linear optical properties of analyzed markers are shown in Tables 1 and SI7. Due to the high compatibility of theoretical and experimental values obtained on the basis of PBE0 [33][34][35][36], the spectroscopic parameters were determined using this function. It also accurately predicts NH 2 values recorded experimentally.…”

Section: Linear Optical Propertiesmentioning

confidence: 99%

Modulation of benzofuran structure as a fluorescent probe to optimize linear and nonlinear optical properties and biological activities

Krawczyk

2020

J Mol Model

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The study presents the influence of structure modulation by introducing selected donor and acceptor substituents on optical properties of benzofuran used in biological imaging. As the starting form, 2-(5-formylbenzofuran-2-yl)acetamide described experimentally was used. This molecule contains an aldehyde group as reactive site, through which conjugation with protein occurs. Structure modulation was carried out by attaching additional electron-donating and electron-withdrawing substituents to the amino group, namely -NH2, -NHCH3, -NO2, -OH, and -OCH3. Studies have shown that the -NH2, -NHCH3, -OH, and -OCH3 substituents do not induce a significant change in the position of maximum absorption and fluorescence relative to each other. They also do not change the parameters describing the nonlinear response. Only the presence of the -NO2 substituent results in significant solvatochromic shifts. Changing substituents also does not significantly affect the LD50 value, and all tested fluorescent probes should not be considered toxic to humans. Modulation of the benzofuran derivative structure also does not change the active center in which the biocomplex with the protein is formed. In each case, the conjugation takes place via LYS114. In addition, the study was prompted to analyze the linear and nonlinear optical properties of conjugates formed after the reaction with Concanavalin A. Graphical abstract

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Unveiling All‐Optical Switching Phenomenon in Anthracene Derivatives: A Comprehensive Study on Optical and Nonlinear Optical Multifunctionality

Szukalski,

Zajac,

Pardus

et al. 2024

Advanced Optical Materials

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In this study, it is considered three anthracene derivatives, characterized meticulously in terms of their chemical structure and product purity. Extensive quantum chemical calculations are conducted to elucidate their optical and nonlinear optical properties, shedding light on the mechanism of photoinduced conformational transformation, a pivotal discovery in this research. Experimental analyses encompassed fundamental optical properties and advanced nonlinear optical phenomena, including z‐scan experiments, second harmonic generation (SHG), and third harmonic generation (THG). Remarkably, a groundbreaking all‐optical switching phenomenon in these materials is experimentally validated, marking a significant advancement and contributing to their potential applications.

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Synthesis, photophysical properties and systematic evaluations of new phenanthroimidazole fluorescent probe for bioimaging: Experimental and theoretical study

Cited by 24 publications

References 97 publications

Synthesis and Studies on Photophysical Properties of Rhodamine Derivatives for Bioimaging Applications

Synthesis and Studies on Photophysical Properties of Rhodamine Derivatives for Bioimaging Applications

Modulation of benzofuran structure as a fluorescent probe to optimize linear and nonlinear optical properties and biological activities

Unveiling All‐Optical Switching Phenomenon in Anthracene Derivatives: A Comprehensive Study on Optical and Nonlinear Optical Multifunctionality

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