Design, synthesis, biological evaluation and molecular docking of curcumin analogues as antioxidant, cyclooxygenase inhibitory and anti-inflammatory agents

Selvam, Chelliah; Jachak, Sanjay M.; Thilagavathi, Ramasamy; Chakraborti, Asit K.

doi:10.1016/j.bmcl.2005.02.039

Cited by 284 publications

(142 citation statements)

References 20 publications

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“…On the other hand, clearly, the antitumor effects of curcumin may not depend solely on influences on gene transcription, but can also involve other mechanisms, including direct interactions with specific target molecules; there are also some cases [like that, e.g., concerning COX-2 (26)] in which the agent can affect both the function and the expression of a given molecule. With reference to this, it has been recently reported that MR 39 produces significantly higher direct inhibition of the COX-2 catalytic activity than curcumin (27), an interesting finding that may fit well with our observations.…”

Section: Discussionsupporting

confidence: 91%

The antitumor activities of curcumin and of its isoxazole analogue are not affected by multiple gene expression changes in an MDR model of the MCF-7 breast cancer cell line: Analysis of the possible molecular basis

Poma

Notarbartolo²,

Labbozzetta³

et al. 2007

Int J Mol Med

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Abstract.We examined the effects of curcumin and of its isoxazole analogue MR 39 in the MCF-7 breast cancer cell line and in its multidrug-resistant (MDR) variant MCF-7R. In comparison with MCF-7, MCF-7R lacks estrogen receptor α (ERα) and overexpressess P-glycoprotein (P-gp), different IAPs (inhibitory of apoptosis proteins) and COX-2. Through analyses of the effects on cell proliferation, cycling and death, we have observed that the antitumor activity of curcumin and of the more potent (approximately two-fold) MR 39 is at least equal in the MDR cell line compared to the parental MCF-7. Similar results were observed also in an MDR variant of HL-60 leukemia. RT-PCR evaluations performed in MCF-7 and MCF-7R showed that curcumin or MR 39 produced early modifications in the amounts of relevant gene transcripts, which, however, were mostly diverse (i.e. represented by decreases in IAPs and COX-2 in MCF-7R versus reductions in Bcl-2 and Bcl-X L as well as increases in the Bcl-X S /Bcl-X L ratio in MCF-7) in the two cell lines. These results could not be explained by an involvement of NF-κB (p65 subunit) or STAT3, since the low nuclear levels of these transcription factors present in MCF-7 were only slightly, though significantly, elevated in MCF-7R; moreover, curcumin or MR 39 caused minor changes in NF-κB or STAT3 activation. Overall, these data underline that curcumin or MR 39 antitumor activities are not hampered by P-gp expression or lack of ERα in breast cancer cells. Remarkably, the agents appeared to modify their molecular effects according to the diverse gene expression patterns existing in the MDR and in the parental MCF-7. Clearly, the structure and properties of curcumin can form the basis for the development of antitumor compounds that are more effective against both chemosensitive and MDR cells.

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Section: Discussionsupporting

confidence: 91%

The antitumor activities of curcumin and of its isoxazole analogue are not affected by multiple gene expression changes in an MDR model of the MCF-7 breast cancer cell line: Analysis of the possible molecular basis

Poma

Notarbartolo²,

Labbozzetta³

et al. 2007

Int J Mol Med

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“…So CUR causes cancer prevention through interfering with the activity of NF-κB (Huang et al, 1991) and suppression of expression of the enzyme in COX-2 (Plummer et al, 1999). Selvam (Selvam et al, 2005) designed an experiment which pyrazole analogues (including HZC) of CUR were synthesized and evaluated for COX-2 inhibitory, antioxidant and antiinflammatory activities. They found that HZC significantly enhanced COX-2 selectivity and possessed significant anti-inflammatory activity in carrageenan induced rat paw edema assay compared with CUR.…”

Section: Discussionmentioning

confidence: 99%

Preventive Effect of Hydrazinocurcumin on Carcinogenesis of Diethylnitrosamine-induced Hepatocarcinoma in Male SD Rats

Zhao¹,

Peng²,

Chen³

et al. 2014

Asian Pacific Journal of Cancer Prevention

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The purpose of the present study was to evaluate the preventive effects of hydrazinocurcumin (HZC) on diethylnitrosamine (DEN)-induced hepatocarcinogenesis in a male Sprague Dawley (SD) rat model. One hundred and twenty male SD rats used in this study were divided into six groups. Those receiving DEN with curcumin (CUR) or HZC were studied compared with the DEN-alone group. The study demonstrated that DEN induced severe histological and immunohistochemical changes in liver tissues, significantly increasing the levels of liver marker enzymes (alanine aminotransferase (ALT), aspartate aminotransferase (AST), alkaline phosphatase (ALP), γ-glutamyltransferase (GGT) and total bilirubin level (TBL)). The hepatocarcinoma incidences were 100.0%, 36.7% and 20.0% in the DEN-alone, DEN-CUR and DEN-HZC groups, respectively. Although macroscopic and microscopic features suggested that both CUR and HZC were effective in inhibiting DENinduced hepatocarcinogenesis, HZC was exerted a stronger influence. Immunohistochemical analysis with PCNA demonstrated significantly differences among the groups (all P < 0.05). Taken together, the results suggested application of CUR and HZC could prevent the occurrence of carcinogenesis and HZC may be a more potent compound for prevention of DEN-induced hepatocarcinogenesis in rats than CUR.

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“…Curcumin, a natural polyphenol isolated from the rhizome of Curcuma longa Linn, exerts a number of pharmacological activities such as anti-inflammatory 16 , anti-oxidant 17 , anti-bacterial 18 , anti-HIV 19 , and anticancer activities 20 . However, its poor aqueous solubility limits its effective use as a therapeutic agent 21 .…”

Section: Introductionmentioning

confidence: 99%

Influence of Lipid Composition, pH, and Temperature on Physicochemical Properties of Liposomes with Curcumin as Model Drug

et al. 2016

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Design, synthesis, biological evaluation and molecular docking of curcumin analogues as antioxidant, cyclooxygenase inhibitory and anti-inflammatory agents

Cited by 284 publications

References 20 publications

The antitumor activities of curcumin and of its isoxazole analogue are not affected by multiple gene expression changes in an MDR model of the MCF-7 breast cancer cell line: Analysis of the possible molecular basis

The antitumor activities of curcumin and of its isoxazole analogue are not affected by multiple gene expression changes in an MDR model of the MCF-7 breast cancer cell line: Analysis of the possible molecular basis

Preventive Effect of Hydrazinocurcumin on Carcinogenesis of Diethylnitrosamine-induced Hepatocarcinoma in Male SD Rats

Influence of Lipid Composition, pH, and Temperature on Physicochemical Properties of Liposomes with Curcumin as Model Drug

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