6′-Benzyloxy-4-bromo-2′-hydroxychalcone is cytotoxic against human leukaemia cells and induces caspase-8- and reactive oxygen species-dependent apoptosis

Saavedra, Ester; Rosario, Henoc del; Brouard, Ignacio; Quintana, José; Estévez, Francisco

doi:10.1016/j.cbi.2018.12.010

Cited by 10 publications

(7 citation statements)

References 42 publications

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“…SK-MEL-1 is a human melanoma cell line growing singly or in clumps (occasional giant, polynucleated cell) in suspension. Cells were cultured in RPMI 1640 medium containing 10% ( v / v ) heat-inactivated fetal bovine serum, 100 μg/mL streptomycin, and 100 U/mL penicillin, incubated at 37 °C in a humidified atmosphere containing 5% CO 2 as described [ 19 ]. The doubling times of the cell lines were 24 h in HL-60, 30 h in U-937, U-937/Bcl-2, 40 h in MOLT-3 and NALM-6, and several days in SK-MEL-1 cells.…”

Section: Methodsmentioning

confidence: 99%

Guanidine Derivatives Containing the Chalcone Skeleton Are Potent Antiproliferative Compounds against Human Leukemia Cells

Estévez-Sarmiento

Saavedra

Brouard

et al. 2022

IJMS

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In this study, we investigated the effects of eleven synthetic guanidines containing the 1,3-diphenylpropenone core on the viabilities of six human cancer cells. The most cytotoxic compound against human cancer cells of this series contains a N-tosyl group and a N-methylpiperazine moiety 6f. It was cytotoxic against leukemia cells (U-937, HL-60, MOLT-3, and NALM-6) with significant effects against Bcl-2-overexpressing U-937/Bcl-2 cells as well as the human melanoma SK-MEL-1 cell line. It exhibited low cytotoxicity against quiescent or proliferating human peripheral blood mononuclear cells. The IC50 value for the leukemia U-937 cells was 1.6 ± 0.6 µM, a similar value to that in the antineoplastic agent etoposide. The guanidine containing a N-phenyl substituent 6i was also as cytotoxic as the guanidine containing the N-tosyl substituent and the N-methylpiperazine group 6f against human U-937 leukemia cells and both synthetic guanidines were potent apoptotic inducers. Cell death was mediated by the activation of the initiator caspase-9 and the executioner caspase-3, and associated with the release of cytochrome c. These synthetic guanidines are potent cytotoxic compounds against several human leukemia cells and even the human melanoma cell line SK-MEL-1 and might be useful in the development of new strategies in the fight against cancer.

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Section: Methodsmentioning

confidence: 99%

Guanidine Derivatives Containing the Chalcone Skeleton Are Potent Antiproliferative Compounds against Human Leukemia Cells

Estévez-Sarmiento

Saavedra

Brouard

et al. 2022

IJMS

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“…U-937/Bcl-2 cells were kindly provided by Dr. Jacqueline Bréard (INSERM U749, Faculté de Pharmacie Paris-Sud, Châtenay-Malabry, France). Cells were cultured in RPMI 1640 medium containing 10% (v/v) fetal bovine serum, 100 μg/mL streptomycin and 100 U/mL penicillin, incubated at 37 • C in a humidified atmosphere containing 5% CO 2 as described [40]. Human peripheral blood mononuclear cells (PBMC) were isolated from blood anticoagulated with heparin of healthy donors by centrifugation with Ficoll-Paque Plus (GE Healthcare Bio-Sciences AB, Uppsala, Sweden).…”

Section: Cell Culturementioning

confidence: 99%

Structure-activity relationships reveal a 2-furoyloxychalcone as a potent cytotoxic and apoptosis inducer for human U-937 and HL-60 leukaemia cells

Rosario

Saavedra

Brouard

et al. 2022

Bioorganic Chemistry

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“…Halogenated chalcones ( II–X , Figure 1 ) have been reported to exhibit high cytotoxic activity 25–28 . They were also reported to be effective against leukaemia cell lines 15 , 29 and against breast cancer cell line 15 , 30–32 .…”

Section: Introductionmentioning

confidence: 99%

“…Many chalcones have the ability to inhibit tumour proliferation by a variety of mechanisms as inhibition of tubulin 20 , epidermal growth factor receptor (EGFR) 33 , vascular endothelial growth factor receptor-2 (VEGFR-2) 5 , 15 and mitogen-activated protein kinase (MAPK) 29 , 34 .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and biological evaluation of halogenated phenoxychalcones and their corresponding pyrazolines as cytotoxic agents in human breast cancer

Halim

Hassan

Mohamed

et al. 2021

Journal of Enzyme Inhibition and Medicinal Chemistry

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Novel halogenated phenoxychalcones 2a–f and their corresponding N -acetylpyrazolines 3a–f were synthesised and evaluated for their anticancer activities against breast cancer cell line (MCF-7) and normal breast cell line (MCF-10a), compared with staurosporine. All compounds showed moderate to good cytotoxic activity when compared to control. Compound 2c was the most active, with IC 50 = 1.52 µM and selectivity index = 15.24. Also, chalcone 2f showed significant cytotoxic activity with IC 50 = 1.87 µM and selectivity index = 11.03. Compound 2c decreased both total mitogen activated protein kinase (p38α MAPK) and phosphorylated enzyme in MCF-7 cells, suggesting its ability to decrease cell proliferation and survival. It also showed the ability to induce ROS in MCF-7 treated cells. Compound 2c exhibited apoptotic behaviour in MCF-7 cells due to cell accumulation in G2/M phase and elevation in late apoptosis 57.78-fold more than control. Docking studies showed that compounds 2c and 2f interact with p38alpha MAPK active sites.

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6′-Benzyloxy-4-bromo-2′-hydroxychalcone is cytotoxic against human leukaemia cells and induces caspase-8- and reactive oxygen species-dependent apoptosis

Cited by 10 publications

References 42 publications

Guanidine Derivatives Containing the Chalcone Skeleton Are Potent Antiproliferative Compounds against Human Leukemia Cells

Guanidine Derivatives Containing the Chalcone Skeleton Are Potent Antiproliferative Compounds against Human Leukemia Cells

Structure-activity relationships reveal a 2-furoyloxychalcone as a potent cytotoxic and apoptosis inducer for human U-937 and HL-60 leukaemia cells

Synthesis and biological evaluation of halogenated phenoxychalcones and their corresponding pyrazolines as cytotoxic agents in human breast cancer

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