Fluorescence properties of aurone derivatives: an experimental and theoretical study with some preliminary biological applications

Espinosa‐Bustos, Christian; Cortés‐Arriagada, Diego; Soto-Arriaza, Marco; Robinson‐Duggon, José; Pizarro, Nancy; Cabrera, A. L.; Fuentealba, Denis; Salas, Cristian O.

doi:10.1039/c7pp00078b

Cited by 19 publications

(23 citation statements)

References 32 publications

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“…In addition to their significant biological activities, chalcones, and aurones display attracting spectroscopic properties and potential application . Thus, the UV–Vis spectra of chalcones and aurones have been the subject of experimental and theoretical investigation. To the best of our knowledge, however, no experimental data about the UV–Vis spectra are available for all the studied compounds except for CH4 .…”

Section: Resultsmentioning

confidence: 99%

Antioxidant and spectral properties of chalcones and analogous aurones: Theoretical insights

Xue

Liu

Zhang

et al. 2018

Int J of Quantum Chemistry

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Density functional theory (DFT) and time-dependent DFT (TD-DFT) have been employed to elucidate the radical scavenging capacity and the UV-Vis spectral property of several chalcones and analogous aurones. Three main antioxidant mechanisms, hydrogen atom transfer (HAT), electron transfer followed by proton transfer (SET-PT) and sequential proton loss electron transfer (SPLET) were investigated. The results indicate that all the studied compounds adopt a fully planar conformation in their neutral, radical, cationic as well as anionic forms. 2 0 -OH plays important role in the stabilization of phenolic radicals due to the formation of intramolecular hydrogen bonds (IHBs). Introduction of electron-donating substituent on B-ring is helpful for improving the activity. For the considered compounds, HAT is proposed as the thermodynamically favored mechanism in gas phase and nonpolar environment, while SPLET is preferred in polar media. The results confirmed the crucial role of hydroxyl group on A-ring, especially on position 5 0 /5, in terms of the radical scavenging ability. The absorption spectra of title compounds were successfully simulated and the lowest energy transitions predominantly correspond to the π-π* transitions from HOMO to LUMO with charge transfer (CT) character. K E Y W O R D Saurones, chalcones, density functional theory, mechanism, radical scavenging activity

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Section: Resultsmentioning

confidence: 99%

Antioxidant and spectral properties of chalcones and analogous aurones: Theoretical insights

Xue

Liu

Zhang

et al. 2018

Int J of Quantum Chemistry

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“…were prepared following the procedure described in literature. [37] The size of the liposomes was determined by dynamic light scattering (DLS), and the absorption and fluorescence spectra were measured, as well as decays of fluorescence. An average nanoparticle size with the size distribution percentage of more than 80% confirmed the homogeneous liposomes in DPPC concentrations used ( Fig.…”

Section: Photophysical Propertiesmentioning

confidence: 99%

Application of 4-amino-N-adamantylphthalimide solvatochromic dye for fluorescence microscopy in selective visualization of lipid droplets and mitochondria

Benčić

Mandić

Džeba

et al. 2019

Sensors and Actuators B: Chemical

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4-Amino-N-adamantylphthalimide (1) is a dye with moderate absorptivity (in CH3CN ε363 = 4200 M-1 cm-1) and high quantum yield of fluorescence (ΦF = 0.15-0.80) that exhibits fluorosolvatochromic properties. The dye can be excited at 405 nm and the position of fluorescence maximum and the Stokes shift are well correlated with the ET(30) parameter. The excitation in the near-visible part of the spectrum and low cytotoxicity allow use of the dye in live cell microscopy. Due to its amphiphilic character, the dye stains artificial membranes in liposomes. Using confocal microscopy on two human cancer cell lines, we have shown that 1 binds primarily to intracellular lipid droplets. Colocalization experiments with different organelle markers indicated that 1 additionally binds to mitochondrial membranes. The fluorosolvatochromism of 1 allows the simultaneous visualization of mitochondria and intracellular lipid droplets in two separate emission channels, which has a potential use in cells and tissues exhibiting intense oxidative metabolism of lipids.

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“…The test compounds consisted of 82 aurone derivatives (symbols A1 to A82) collected from scientific papers investigating the biological effects of aurone derivatives [10,[15][16][17][18][19][20]. The 2D structures of these compounds were drawn by ISIS Draw 2.5 program and formatted in the MOL file.…”

Section: Ligandmentioning

confidence: 99%

AURONE AS PROMISING HUMAN PANCREATIC LIPASE INHIBITORS THROUGH <em>IN SILICO</em> STUDY

Nguyen

Huynh

Tran

2019

Proceedings of the 23rd International Electronic Conference on Synthetic Organic Chemistry

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In this study, 82 aurone compounds, a subclass of flavonoids were investigated towards to human pancreatic lipase inhibitory activity. Molecular docking of the aurones was done successfully into the catalytic position of lipase (Pdb: 1LPB) using AutoDock Vina software 1.5.7.rc1. The results showed that 62 compounds interacted well with residues in the catalytic trial Ser152-Asp176-His263 and Phe77 of protein 1LPB. In particular, A32 was selected as the best binding compound (docking score: -10.6 kcal.mol -1 ) and suitable for oral drug following the 5-Lipinski rule. Combining the results of docking and molecular dynamics simulation of A32-protein complex during 10 ns, this study performed that the A32 compound bound well and formed a stable complex with 1LPB protein. Therefore, the A32 compound was considered as the lead compound which could be synthesized and tested for pancreatic lipase inhibitor.Obesity is considered as a complex disease, with a variety of factors and causes, in which the most commonly is an unreasonable diet and unhealthy lifestyle leading to an imbalance between energy supplement and energy consumption in the body [1]. It opens up the way for for the obesity drug research, which is the inhibition of fat hydrolysis of human pancreatic lipase (HPL). Cause, HPL along with co-factors Colipase and Ca2+, play a main role in the process digestion and absorption of fat. HPL hydrolyzes 50 -70% of the total fat from the food, so inhibiting HPL will significantly reduce the amount of absorbed fat [2,3].Nowadays, many in silico models are being applied to finding potential bioactive compounds for the treatment of obesity [2,4,[5][6][7]. These models made the new drug research more clearly oriented and helped to save both cost and time. Besides that, there is a need to develop new drugs having fewer side effects and more safety, specifically taking from natural compounds for HPL inhibitory activities. The results have discovered natural compounds belonging to many different groups of structures such as saponins, alkaloids, carotenoids, flavonoids that inhibited HPL enzyme [2,4]. In particular, flavonoids with subclasses such as flavone, flavonole, chalcone have been extensively studied and the researches obtained many good HPL inhibition results with the IC50 values determined as Licochalcone A (IC50 35 µg/ml) [5], Galangin (IC50 48.20 mg/ml) [6], Hesperidin (IC50

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Fluorescence properties of aurone derivatives: an experimental and theoretical study with some preliminary biological applications

Cited by 19 publications

References 32 publications

Antioxidant and spectral properties of chalcones and analogous aurones: Theoretical insights

Antioxidant and spectral properties of chalcones and analogous aurones: Theoretical insights

Application of 4-amino-N-adamantylphthalimide solvatochromic dye for fluorescence microscopy in selective visualization of lipid droplets and mitochondria

AURONE AS PROMISING HUMAN PANCREATIC LIPASE INHIBITORS THROUGH <em>IN SILICO</em> STUDY

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