Fluorescence interactions of a novel chalcone derivative with membrane model systems and human serum albumin

Yildirim, Berat; Beşer, Burcu Meryem; Çolak, Nevin Ulaş; Altay, Ahmet; Yaşar, Ahmet

doi:10.1016/j.bpc.2022.106879

Cited by 5 publications

(6 citation statements)

References 40 publications

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“…If the value of light absorption remains constant when the concentration of a solution is changed, that wavelength is known as the isosbestic point. [28] The isosbestic points were observed at 534 nm and 536 nm for PyY and SfT, respectively, however, no isosbestic points were obtained for AcO and Fl.…”

Section: Resultsmentioning

confidence: 92%

“…We observed that the intensity of the absorption band of the acceptor increases with increasing concentration of the acceptor molecule (AcO), indicating a specific interaction with high affinity between donor and acceptor (Figure 2). If the value of light absorption remains constant when the concentration of a solution is changed, that wavelength is known as the isosbestic point [28] . The isosbestic points were observed at 534 nm and 536 nm for PyY and SfT, respectively, however, no isosbestic points were obtained for AcO and Fl.…”

Section: Resultsmentioning

confidence: 99%

“…Chalcone derivative was synthesized by the reaction of 2‐hydroxyacetophenone with 2‐pyridinecarboxaldehyde in a yield of 67 %. Then, the reaction mixture was stirred in a microwave oven (800 watt) at 70 °C for 4 min using hydrazine hydrate to obtain the final product [28] . Characterization of PYDP was carried out using FTIR, 1 H NMR, and 13 C NMR spectroscopy.…”

Section: Methodsmentioning

confidence: 99%

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Exploring Biological Interactions: A New Pyrazoline as a Versatile Fluorescent Probe for Energy Transfer and Cell Staining Applications

Beşer,

Yildirim

2023

ChemistryOpen

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Fluorescent dyes are used in biological systems, because they are highly sensitive and selective. In this work, we investigated the fluorescent probe properties of 2‐(5‐(pyridin‐2‐yl)‐1H‐pyrazol‐3‐yl) phenol (PYDP) in two media [sodium dodecyl sulfate (SDS) and human serum albumin (HSA)]. Energy transfer parameters, photophysical and thermodynamic parameters of probe were determined. We investigated cytotoxicity of PYDP against colorectal adenocarcinoma cell lines (HT‐29), breast cancer cell lines (MCF‐7) and 3T3‐L1 adipocytes (3T3 L1) cells. The cell staining property of PYDP was monitored using a confocal microscope. The results showed that PYDP binds to HSA, bindings are due to electrostatic/ionic interactions, and the binding process is spontaneous. PYDP was found to exhibit negligible cytotoxicity at high concentrations, and confocal microscope images showed that PYDP stained the cytoplasm of MCF‐7 cells.

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Section: Resultsmentioning

confidence: 92%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Exploring Biological Interactions: A New Pyrazoline as a Versatile Fluorescent Probe for Energy Transfer and Cell Staining Applications

Beşer,

Yildirim

2023

ChemistryOpen

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“… Comparison between previously studied strategies for red‐shifting absorption and emission bands in xanthene dyes and the molecular design used in the current study for decoupling the ground and excited states to increase the Stokes shift (the colored fields match the colors of the absorption and emission bands of each compound) [11c–e] …”

Section: Introductionmentioning

confidence: 99%

Central Ring Puckering Enhances the Stokes Shift of Xanthene Dyes

Dunlop,

Horváth,

Klán

et al. 2024

Chemistry A European J

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Small‐molecule dyes are generally designed based on well‐understood electronic effects. However, steric hindrance can promote excited‐state geometric relaxation, increasing the difference between the positions of absorption and emission bands (the Stokes shift). Accordingly, we hypothesized that sterically induced central ring puckering in xanthene dyes could be used to systematically increase their Stokes shift. Through a combined experimental/quantum‐chemical approach, we screened a group of (9‐acylimino)‐pyronin dyes with a perturbed central ring geometry. Our results showed that an atom with sp3 hybridization in position 10 of (9‐acylimino)‐pyronins induces central ring puckering and facilitates excited‐state geometric relaxation, thereby markedly enhancing their Stokes shifts (by up to ~2000 cm−1). Thus, we prepared fluorescent (9‐acylimino)‐pyronin pH sensors, which showed a Stokes shift disparity between acid and base forms of up to ~8700 cm−1. Moreover, the concept of ring puckering‐enhanced Stokes shift can be applied to a wide range of xanthene analogues found in the literature. Therefore, central ring puckering may be reliably used as a strategy for enhancing Stokes shifts in the rational design of dyes.

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“…On the other hand, chalcones are a class of organic compounds that contain a central α,β-unsaturated carbonyl system, which has attracted significant attention, due to their diverse applications in the fields of medicine, material science, and optics . Moreover, the chalcones due to the π-conjugated system and the two aromatic rings that act as donors and acceptors provide a reasonable fluorescence quantum yield, efficient stabilization of charge-transfer processes in the excited state, long-wavelength emission (λ em ), and large Stokes shifts, which means that they have potential applications in fluorescence microscopy or bioimaging applications as they can improve image sensitivity by reducing the interference caused by self-absorption or autofluorescence. − …”

Section: Introductionmentioning

confidence: 99%

Synthesis, Photophysical Properties, Theoretical Studies, and Living Cancer Cell Imaging Applications of New 7-(Diethylamino)quinolone Chalcones

Insuasty,

Mutis,

Trilleras

et al. 2024

ACS Omega

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In this article, three unsymmetrical 7-(diethylamino)quinolone chalcones with D-π–A-D and D-π–A-π-D type push–pull molecular arrangements were synthesized via a Claisen–Schmidt reaction. Using 7-(diethylamino)quinolone and vanillin as electron donor (D) moieties, these were linked together through the α,β-unsaturated carbonyl system acting as a linker and an electron acceptor (A). The photophysical properties were studied, revealing significant Stokes shifts and strong solvatofluorochromism caused by the ICT and TICT behavior produced by the push–pull effect. Moreover, quenching caused by the population of the TICT state in THF–H2O mixtures was observed, and the emission in the solid state evidenced a red shift compared to the emission in solution. These findings were corroborated by density functional theory (DFT) calculations employing the wb97xd/6-311G(d,p) method. The cytotoxic activity of the synthesized compounds was assessed on BHK-21, PC3, and LNCaP cell lines, revealing moderate activity across all compounds. Notably, compound 5b exhibited the highest activity against LNCaP cells, with an LC50 value of 10.89 μM. Furthermore, the compounds were evaluated for their potential as imaging agents in living prostate cells. The results demonstrated their favorable cell permeability and strong emission at 488 nm, positioning them as promising candidates for cancer cell imaging applications.

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Fluorescence interactions of a novel chalcone derivative with membrane model systems and human serum albumin

Cited by 5 publications

References 40 publications

Exploring Biological Interactions: A New Pyrazoline as a Versatile Fluorescent Probe for Energy Transfer and Cell Staining Applications

Exploring Biological Interactions: A New Pyrazoline as a Versatile Fluorescent Probe for Energy Transfer and Cell Staining Applications

Central Ring Puckering Enhances the Stokes Shift of Xanthene Dyes

Synthesis, Photophysical Properties, Theoretical Studies, and Living Cancer Cell Imaging Applications of New 7-(Diethylamino)quinolone Chalcones

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