Antitumor effects of curcumin and structurally β-diketone modified analogs on multidrug resistant cancer cells

Daniele, Simona; Rizzi, Michele; Rondanin, Riccardo; Baruchello, Riccardo; Marchetti, Paolo; Invidiata, Francesco Paolo; Labbozzetta, Manuela; Poma, Paola; Carina, Valeria; Notarbartolo, Monica; Alaimo, Alessandra; D’Alessandro, Natale

doi:10.1016/j.bmcl.2007.11.021

Cited by 78 publications

(56 citation statements)

References 23 publications

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“…In HepG2 cells, it was reported that curcumin-induced apoptotic cell death with IC 50 of 17.5 lM and 20 lM of curcumin reduced cell viability by *80% [34]. Curcumin also inhibited the cell growth of hepatocellular carcinoma HA22T/VGH cells with IC 50 of 17.4 lM [35]. These values for IC 50 are similar to those of the inhibitory effects of curcumin on ecto-ATPase activity (Fig.…”

Section: Discussionsupporting

confidence: 85%

Inhibition of ecto-ATPase activity by curcumin in hepatocellular carcinoma HepG2 cells

et al. 2011

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Effects of curcumin, a major constituent of turmeric, on ecto-nucleotidases have not been clarified. Here, we investigated whether curcumin affects ecto-nucleotidase activities in human hepatocellular carcinoma HepG2 cells. In the cells, high levels of Mg(2+)-dependent activity of ecto-nucleotidases were observed in the presence of 1 mM adenosine triphosphate (ATP). The activity was inhibited by ecto-ATPase inhibitors such as suramin, ZnCl(2) and 4,4'-diisothiocyanatostilbene-2,2'-disulfonic acid. On the other hand, the activity was significantly decreased at alkaline pH (pH 9) and was not inhibited by levamisole, an inhibitor of alkaline phosphatase. In the presence of ATP, curcumin inhibited the activity in a concentration-dependent manner (IC(50) = 6.2 μM). In contrast, curcumin had no effects on ecto-nucleotidase activity in the presence of ADP (1 mM) or AMP (1 mM). The K (m) value for ATP hydrolysis of curcumin-sensitive ecto-ATPase was similar to the value of NTPDase2, an isoform of ecto-nucleoside triphosphate diphosphohydrolase. These results suggest that curcumin is a potent inhibitor of ecto-ATPase and may affect extracellular ATP-dependent responses.

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Section: Discussionsupporting

confidence: 85%

Inhibition of ecto-ATPase activity by curcumin in hepatocellular carcinoma HepG2 cells

et al. 2011

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“…To circumvent this limitation, several approaches were carried out, including the synthesis of curcumin analogues [4,12,13]. Curcumin derivatives were synthesised in order to overcome the pharmacokinetics limitations, with the hope to preserve the same safety profile.…”

Section: Introductionmentioning

confidence: 99%

PAC, a novel curcumin analogue, has anti-breast cancer properties with higher efficiency on ER-negative cells

Al-Hujaily

Mohamed

Al-Sharif

et al. 2010

Breast Cancer Res Treat

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We have investigated here the anti-breast cancer properties of two novel curcumin analogues, EAC and PAC. Apoptosis was assessed by the annexin V/propidium iodide (PI) assay on different breast cancer and normal cells. Immunoblotting analysis determined the effects of these agents on different apoptotic and oncogenic proteins. Furthermore, flow cytometry and Elispot were utilised to investigate the effects on the cell cycle and the production of cytokines, respectively. Breast cancer tumour xenografts were developed in nude mice. Finally, (18)F-radiolabeled PAC and curcumin were produced to study their bioavailability and tissue biodistribution in mice. PAC is five times more efficient than curcumin and EAC in inducing apoptosis, mainly via the internal mitochondrial route. This effect was 10-fold higher against ER-negative as compared to ER-positive cells, and ectopic expression of ERα rendered ER-negative breast cancer cells more resistant to PAC. In addition, PAC delayed the cell cycle at G2/M phase with a stronger effect on ER-negative cells. Moreover, PAC exhibited strong capacity as an immuno-inducer through reducing the secretion of the two major Th2 cytokines IL-4 and IL-10. Importantly, PAC significantly reduced tumour size, and triggered apoptosis in vivo. Furthermore, PAC inhibited survivin, NF-kB and its downstream effectors cyclin D1 and Bcl-2, and strongly up-regulated p21(WAF1) both in vitro and in tumours. Besides, PAC exhibited higher stability in blood and greater biodistribution and bioavailability than curcumin in mice. These results indicate that PAC could constitute a powerful, yet not toxic, new chemotherapeutic agent against ER-negative breast tumours.

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“…The crude product 2.1.3. General procedure for the synthesis of isoxazol derivatives (14,15) To a solution of 3,4,5-trimethoxy benzaldoxime (8.00 mmol) in ethanol:water 1:1, chloramine-T (16.00 mmol) was added in small portions. This solution was slowly added in portions to compound 12 or 13 (4.00 mmol) dissolved in ethanol:water 1:1 and the reaction mixture was heated at 40 8C for 4 h. Then, the solution was evaporated and the residue was purified.…”

Section: Chemistrymentioning

confidence: 99%

“…In addition, an isoxazole derivative from curcumin has been reported as a good antioxidant and COX inhibitory agent [13] and showed greater activity against both MCF-7 and MCF-7R cell lines than its natural product precursor [14]. Promising properties as a heat Biomedicine & Pharmacotherapy 68 (2014) [847][848][849][850][851][852][853][854] shock protein 90 (HSP90) inhibitor have been reported for a diaryl resorcinylic isoxazole amide derivative, with antiproliferative potency quite similar to the clinical drug 17-AAG [15].…”

Section: Introductionmentioning

confidence: 99%

Differential effect of heterocyclic d-ribofuranoside derivatives on human prostate cancer cell viability and cell cycle progression

Gueron

Avanzo

Schuster

et al. 2014

Biomedicine & Pharmacotherapy

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Antitumor effects of curcumin and structurally β-diketone modified analogs on multidrug resistant cancer cells

Cited by 78 publications

References 23 publications

Inhibition of ecto-ATPase activity by curcumin in hepatocellular carcinoma HepG2 cells

Inhibition of ecto-ATPase activity by curcumin in hepatocellular carcinoma HepG2 cells

PAC, a novel curcumin analogue, has anti-breast cancer properties with higher efficiency on ER-negative cells

Differential effect of heterocyclic d-ribofuranoside derivatives on human prostate cancer cell viability and cell cycle progression

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