Synthesis, cytotoxic and antioxidant evaluations of amino derivatives from perezone

Lozada, M. Concepción; Soria‐Arteche, Olivia; Apan, Ma. Teresa Ramírez; Nieto‐Camacho, Antonio; Enríquez, Raúl G.; Izquierdo, Teresa; Jiménez-Corona, Arturo

doi:10.1016/j.bmc.2012.07.027

Cited by 31 publications

(23 citation statements)

References 29 publications

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“…This molecule has been the target of many chemical studies, it has also been used as a pigment showing in addition several pharmacological effects, vg the release of mitochondrial Ca 2+ . In addition, perezone and some of its derivatives are able to produce cytotoxic activity …”

Section: Introductionmentioning

confidence: 99%

Computational Characterization of Perezone, Isoperezone and their Sulfur‐Derivatives: Anti‐inflammatory Activity.

et al. 2019

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Using DFT and in silico methods a theoretical study, to verify the spectroscopically characterization, this in addition to determine the anti‐inflammatory activity of a set of eight sulfur derivatives of perezone and isoperezone was performed. In this sense, conformational studies for the target sulfurs were carried out, in order to obtain the corresponding minimum energy structures. Also, the vibrational frequencies analysis, the magnitude of 1H NMR and 13C NMR spectra for perezone, isoperezone, and its sulfur‐derivatives, obtained by the DFT/B3LYP/6‐311++G(d,p) method correlated satisfactorily with the experimental data. Moreover, the calculation of physicochemical properties, and the prediction of the anti‐inflammatory activity, employing both PASS predictor and docking studies towards COX‐2 for the target compounds, showed that Benzy perezone is a good candidate as a therapeutic agent; finally, the anti‐inflammatory activity of Benzy perezone was evaluated in vivo, showing a similar naproxen activity.

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Section: Introductionmentioning

confidence: 99%

Computational Characterization of Perezone, Isoperezone and their Sulfur‐Derivatives: Anti‐inflammatory Activity.

et al. 2019

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“…The molecule has been the focus of many chemical, structural and biological studies [ 3 , 4 , 5 , 6 , 7 , 8 ]. It has also been used in an interesting green route for the production of various derivatives [ 9 ] and many of its pharmacological effects have been also reported [ 10 , 11 , 12 , 13 , 14 ].…”

Section: Introductionmentioning

confidence: 99%

In silico Study of the Pharmacologic Properties and Cytotoxicity Pathways in Cancer Cells of Various Indolylquinone Analogues of Perezone

et al. 2017

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Several indolylquinone analogues of perezone, a natural sesquiterpene quinone, were characterized in this work by theoretical methods. In addition, some physicochemical, toxicological and metabolic properties were predicted using bioinformatics software. The predicted physicochemical properties are in agreement with the solubility and cLogP values, the penetration across the cell membrane, and absorption values, as well as with a possible apoptosis-activated mechanism of cytotoxic action. The toxicological predictions suggest no mutagenic, tumorigenic or reproductive effects of the four target molecules. Complementarily, the results of a performed docking study show high scoring values and hydrogen bonding values in agreement with the cytotoxicity IC50 value ranking, i.e., indolylmenadione > indolylperezone > indolylplumbagine > indolylisoperezone. Consequently, it is possible to suggest an appropriate apoptotic pathway for each compound. Finally, potential metabolic pathways of the molecules were proposed.

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“…The cytotoxic activity of the synthesized compounds was evaluated employing the Sulforhodamine B assay against five human cancer cell lines: U-251 MG (glioblastoma), PC-3 (human prostatic), HCT-15 (human colorectal), K562 (human chronic myelogenous leukemia), and SKLU-1 (non-small cell lung cancer). Curcumin ( 1 ) and its derivatives 2 – 11 were screened at 50 µM concentration [ 31 ]. The results of growth inhibition for the five cell lines tested are shown in Table 1 .…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Curcuminoids and Evaluation of Their Cytotoxic and Antioxidant Properties

et al. 2017

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Curcumin (1) and ten derivatives (2–11) were synthesized and evaluated as cytotoxic and antioxidant agents. The results of primary screening by Sulforhodamine B assay against five human cancer cell lines (U-251 MG, glioblastoma; PC-3, human prostatic; HCT-15, human colorectal; K562, human chronic myelogenous leukemia; and SKLU-1, non-small cell lung cancer) allowed us to calculate the half maximal inhibitory concentration (IC50) values for the more active compounds against HCT-15 and K562 cell lines. Compounds 2 and 10 were the most active against both cell lines and were more active than curcumin itself. Thiobarbituric acid reactive substances (TBARS) assay showed that 7 has potent activity; even stronger than curcumin, α-tocopherol, and quercetin.

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Synthesis, cytotoxic and antioxidant evaluations of amino derivatives from perezone

Cited by 31 publications

References 29 publications

Computational Characterization of Perezone, Isoperezone and their Sulfur‐Derivatives: Anti‐inflammatory Activity.

Computational Characterization of Perezone, Isoperezone and their Sulfur‐Derivatives: Anti‐inflammatory Activity.

In silico Study of the Pharmacologic Properties and Cytotoxicity Pathways in Cancer Cells of Various Indolylquinone Analogues of Perezone

Synthesis of Curcuminoids and Evaluation of Their Cytotoxic and Antioxidant Properties

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