(<i>E</i>)-1-(3-Bromophenyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one

Escobar, Carlos A.; Trujillo, Alexander; Howard, Judith A. K.; Fuentealba, Mauricio

doi:10.1107/s1600536812006836

Cited by 8 publications

(3 citation statements)

References 10 publications

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“…The potential cytotoxic effect of the compounds CH1 and CH2 ( Figure 2 a) [ 26 , 27 ] were measured in HepG2, HuH-7 and HepM cells. As shown in Figure 2 b–d, both chalcones had a cytotoxic effect only in HCC (HuH-7 and HepG2) cells, whereas cytotoxic effects were not observed in mouse hepatocytes ( Figure 2 e).…”

Section: Resultsmentioning

confidence: 99%

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Chalcone-Induced Apoptosis through Caspase-Dependent Intrinsic Pathways in Human Hepatocellular Carcinoma Cells

Ramírez-Tagle

Escobar

Romero

et al. 2016

IJMS

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Hepatocellular carcinoma (HCC) is one of the most commonly diagnosed cancers worldwide. Chemoprevention of HCC can be achieved through the use of natural or synthetic compounds that reverse, suppress or prevent the development of cancer progression. In this study, we investigated the antiproliferative effects and the mechanism of action of two compounds, 2,3,4′-trimethoxy-2′-hydroxy-chalcone (CH1) and 3′-bromo-3,4-dimethoxy-chalcone (CH2), over human hepatoma cells (HepG2 and Huh-7) and cultured mouse hepatocytes (HepM). Cytotoxic effects were observed over the HepG2 and Huh-7, and no effects were observed over the HepM. For HepG2 cells, treated separately with each chalcone, typical apoptotic laddering and nuclear condensation were observed. Additionally, the caspases and Bcl-2 family proteins activation by using Western blotting and immunocytochemistry were studied. Caspase-8 was not activated, but caspase-3 and -9 were both activated by chalcones in HepG2 cells. Chalcones also induced reactive oxygen species (ROS) accumulation after 4, 8 and 24 h of treatment in HepG2 cells. These results suggest that apoptosis in HepG2 was induced through: (i) a caspase-dependent intrinsic pathway; and (ii) by alterations in the cellular levels of Bcl-2 family proteins, and also, that the chalcone moiety could be a potent candidate as novel anticancer agents acting on human hepatomas.

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Section: Resultsmentioning

confidence: 99%

“…We have previously described the synthesis of the following compounds: 2,3,4′-trimethoxy-2′-hydroxy-chalcone (CH1) [ 26 ] which was obtained as orange crystals (58%), mp. 129–130 °C; and 3′-bromo-3,4-dimethoxy-chalcone (CH2) [ 27 ] obtained as yellow crystals (73%), mp. 117–120 °C ( Figure 1 a).…”

Section: Methodsmentioning

confidence: 99%

Chalcone-Induced Apoptosis through Caspase-Dependent Intrinsic Pathways in Human Hepatocellular Carcinoma Cells

Ramírez-Tagle

Escobar

Romero

et al. 2016

IJMS

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“…129-130°C; 2,4-dimethoxy-2'-hydroxy-chalcone (2) 1,7,24 obtained as yellow crystals (58%), mp. 107 -109.8 °C; 3´-bromo-3,4-dimethoxy-chalcone (3) 25 obtained as yellow crystals (73%), mp.117-120 °C; The following compounds were prepared as previously reported in the literature. Spectroscopic data were identical to those previously reported: 2,5,4´-trimethoxy-2'-hydroxy-chalcone (4) 9 obtained as orange crystals (75%) mp.…”

Section: Synthesis Of Chalcones General Methodologymentioning

confidence: 99%

Interaction of Chalcones With Ct-Dna by Spectrophotometric Analysis and Theoreticalsimulations

et al. 2016

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publicado na web em 08/07/2016 Chalcones are open chain molecules precursors of flavonoids and isoflavonoids, found spread in edible plants. Because they are easily accessible trough Claisen Shmidt condensation, a great variety of derivatives are available. They have also shown potential in pharmacological and biological applications. It is known that chalcone derivatives display a role in the treatment of complex diseases such as cancer, among others, where the DNA is considered as the target for the action of these kinds of compounds. This action is commonly explained as the inhibition of the DNA replications and transcriptions through interactions. However, not conclusive associations between these DNA-Drug interactions and toxicity have been found. This research focuses on the capacity of a chalcone`s family to interact with DNA. Therefore, the binding constants for each compounds with Calf Thymus DNA [CT-DNA] were determined by spectrophotometric titration at room temperature. In addition, the effect of increasing the chalcone`s concentration over the relative viscosity of CT-DNA at room temperature was assessed. On the other hand, with the aim to find the optimal DNAchalcone configurations, as well as consistently predict their binding, a computational work was undertaken. To accomplish these goals within a reasonable time framework, an empirical scoring function (AScore) and a docking engine (ShapeDock) were performed using the ArgusLab package. The results of viscosity and docking measurement provided structural insights which suggest that chalcones bind with DNA via interaction as well as intercalation. The presence of interactions is also evidenced by the spectrophotometric study which showed luminescence quenching of the chalcones upon interaction with CT-DNA.

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Crystal structure and Hirshfeld surface analysis of (2E)-3-(3-chlorophenyl)-1-(3,4-dimethoxyphenyl)prop-2-en-1-one

et al. 2018

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(E)-1-(3-Bromophenyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one

Abstract: The molecular structure of the title compound, C17H15BrO3, consists of a bromophenyl and a 3,4-dimethoxyphenyl group linked through a prop-2-en-1-one spacer. The C=C double bond displays an E conformation, while the carbonyl group shows an S-cis conformation relative to the double bond.

Cited by 8 publications

References 10 publications

Chalcone-Induced Apoptosis through Caspase-Dependent Intrinsic Pathways in Human Hepatocellular Carcinoma Cells

Chalcone-Induced Apoptosis through Caspase-Dependent Intrinsic Pathways in Human Hepatocellular Carcinoma Cells

Interaction of Chalcones With Ct-Dna by Spectrophotometric Analysis and Theoreticalsimulations

Crystal structure and Hirshfeld surface analysis of (2E)-3-(3-chlorophenyl)-1-(3,4-dimethoxyphenyl)prop-2-en-1-one

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