Chalcone derivative cytotoxicity activity against MCF-7 human breast cancer cell QSAR study

Dimić, Dušan; Mercader, Andrew G.; Castro, Eduardo A.

doi:10.1016/j.chemolab.2015.06.011

Cited by 11 publications

(5 citation statements)

References 31 publications

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“…A retrospective QSAR study also proved that more robust models can be built by using the QuBiLS‐MIDAS 3D‐MDs, due to the fact that statistically superior outcomes were achieved with respect to 11 alignment‐dependent (or alignment‐free) QSAR methods reported in the literature . Finally, it is important to remark that the QuBiLS‐MIDAS 3D‐MDs have been successfully applied in prospective QSAR modeling …”

Section: Introductionmentioning

confidence: 80%

“…The QuBiLS‐MIDAS 3D‐MDs are calculated either from a user‐specified configuration in the graphical interface of the software or from projects previously created. However, once these 3D‐MDs are employed in cheminformatics studies (e.g., QSAR studies), it is necessary to directly compute them to use or corroborate the studies performed . Thus, a new module to compute a pool of QuBiLS‐MIDAS 3D‐MDs from their headings was developed.…”

Section: Novel Implementations and Resultsmentioning

confidence: 99%

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Distributed and multicore QuBiLS‐MIDAS software v2.0: Computing chiral, fuzzy, weighted and truncated geometrical molecular descriptors based on tensor algebra

et al. 2020

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Advances to the distributed, multi-core and fully cross-platform QuBiLS-MIDAS software v2.0 (http://tomocomd.com/qubils-midas) are reported in this article since the v1.0 release. The QuBiLS-MIDAS software is the only one that computes atom-pair and alignment-free geometrical MDs (3D-MDs) from several distance metrics other than the Euclidean distance, as well as alignment-free 3D-MDs that codify structural information regarding the relations among three and four atoms of a molecule. The most recent features added to the QuBiLS-MIDAS software v2.0 are related (a) to the calculation of atomic weightings from indices based on the vertex-degree invariant (e.g., Alikhanidi index); (b) to consider central chirality during the molecular encoding; (c) to use measures based on clustering methods and statistical functions to codify structural information among more than two atoms; (d) to the use of a novel method based on fuzzy membership functions to spherically truncate inter-atomic relations; and (e) to the use of weighted and fuzzy aggregation operators to compute global 3D-MDs according to the importance and/or interrelation of the atoms of a molecule during the molecular encoding. Moreover, a novel module to compute

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Section: Introductionmentioning

confidence: 80%

Section: Novel Implementations and Resultsmentioning

confidence: 99%

Distributed and multicore QuBiLS‐MIDAS software v2.0: Computing chiral, fuzzy, weighted and truncated geometrical molecular descriptors based on tensor algebra

et al. 2020

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“…In this work, we chose the training validation and test set compounds following the procedure developed in our previous study, one which has been applied elsewhere [21,33]. This methodology is based on the k-means cluster analysis (k-MCA) method [34].…”

Section: Model Validationmentioning

confidence: 99%

Quantitative structure–property relationship analysis for the retention index of fragrance-like compounds on a polar stationary phase

Rojas

Duchowicz

Tripaldi

et al. 2015

Journal of Chromatography A

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“…Chalcones (1,3-diaryl-2-propen-1-ones), or α,β-unsaturated carbonyl compounds, the bioprecursors of flavonoids, are an interesting class of compounds that engross medicinal [ 1 , 2 ], synthetic [ 3 ], and material chemists [ 4 , 5 , 6 ] with their diverse applications. Considerable evidence has shown that chalcones have immense chemotherapeutic importance, such as anti-inflammatory [ 7 , 8 ], antimicrobial [ 9 , 10 ], antileishmanial [ 11 ], anticancer [ 12 , 13 ], antimalarial [ 14 , 15 , 16 ] activities. Moreover, radiolabeled chalcones have been used as PET imaging agents for in vivo imaging of the β-amyloid plaques of Alzheimer’s disease [ 17 , 18 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Evaluation of Antiplasmodial Activity of 2,2,2-Trifluoroethoxychalcones and 2-Fluoroethoxy Chalcones against Plasmodium falciparum in Culture

et al. 2018

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A new class of compounds comprising two series of chalcones with 2,2,2-trifluoroethoxy group and 2-fluoroethoxy groups were synthesized and screened for in vitro antiplasmodial activity against Plasmodium falciparum (3D7) using the [3H] hypoxanthine incorporation inhibition assay. Chalcones with 2,2,2-trifluoroethoxy groups substituted on the p- and m-positions of the 1-phenyl ring showed weak antiplasmodial activity, while compounds substituted on the o-position of the 1-phenyl ring displayed enhanced antiplasmodial activity, thus indicating that 2,2,2-trifluoroethoxy groups on the 1-phenyl ring of chalcones show position-dependent antiplasmodial activity. Of the 34 compounds synthesized, chalcones 3a and 3f exhibited significant inhibitory effects, with IC50 values of 3.0 μg/mL and 2.2 μg/mL, respectively. Moreover, these compounds 3a and 3f showed profound antiplasmodial activity in combination with artemisinin in vitro. The most active molecules, 3a, and 3f, were further assessed for their cytotoxicity towards mammalian Vero cells and the selectivity index (SI) values are 8.6, and 8.2 respectively, being considered non-toxic. We also studied the antiplasmodial activity of 2-fluoroethoxychalcones to discern the effect of the number of fluorine atoms in the fluoroethoxy group. Our results showed that chalcones with 2-fluoroethoxy group on the 1-phenyl ring exhibited more enhanced inhibitory effects on the growth of parasites than their trifluoro analogues, which reveals that monofluoroethoxy group is generally more effective than trifluoroethoxy group in the inhibition of parasite growth. Thus o-2,2,2-trifluoroethoxychalcones (Series 3) and 2-fluoroethoxychalcones may serve as good antiplasmodial candidates for future further development.

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Chalcone derivative cytotoxicity activity against MCF-7 human breast cancer cell QSAR study

Cited by 11 publications

References 31 publications

Distributed and multicore QuBiLS‐MIDAS software v2.0: Computing chiral, fuzzy, weighted and truncated geometrical molecular descriptors based on tensor algebra

Distributed and multicore QuBiLS‐MIDAS software v2.0: Computing chiral, fuzzy, weighted and truncated geometrical molecular descriptors based on tensor algebra

Quantitative structure–property relationship analysis for the retention index of fragrance-like compounds on a polar stationary phase

Synthesis and Evaluation of Antiplasmodial Activity of 2,2,2-Trifluoroethoxychalcones and 2-Fluoroethoxy Chalcones against Plasmodium falciparum in Culture

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