Effect of Curcumin on the Aryl Hydrocarbon Receptor and Cytochrome P450 1A1 in MCF-7 Human Breast Carcinoma Cells

Ciolino, Henry P.; Daschner, Phillip J.; Wang, Thomas T.Y.; Yeh, Grace Chao

doi:10.1016/s0006-2952(98)00143-9

Cited by 218 publications

(153 citation statements)

References 28 publications

Supporting

Mentioning

145

Contrasting

Unclassified

Order By: Relevance

“…Among them, resveratrol and curcumin have been reported to show antagonist activity on AhR. 10,12) As they also had inhibitory effects in this present assay system, it is suggested that they are candidate prophylactic agents for the prevention of dioxin toxicity. Figure 3 depicts the molecular models obtained as the minimum energy conformation of TCDD and the five compounds that inhibited the TCDD-induced AhR activation (apigenin, resveratrol, emodin, brevifolincarboxylic acid, and piperine).…”

Section: Resultsmentioning

confidence: 83%

See 1 more Smart Citation

Screening of the Inhibitory Effect of Vegetable Constituents on the Aryl Hydrocarbon Receptor-Mediated Activity Induced by 2,3,7,8-Tetrachlorodibenzo-p-dioxin

Amakura

Tsutsumi

Sasaki

et al. 2003

Biological & Pharmaceutical Bulletin

View full text Add to dashboard Cite

Section: Resultsmentioning

confidence: 83%

“…on the binding of TCDD to AhR, and it was found that these components exert antagonistic activity. [8][9][10][11][12] However, fundamental studies on the relationship between the AhR pathway and food constituents are still limited.…”

mentioning

confidence: 99%

Screening of the Inhibitory Effect of Vegetable Constituents on the Aryl Hydrocarbon Receptor-Mediated Activity Induced by 2,3,7,8-Tetrachlorodibenzo-p-dioxin

Amakura

Tsutsumi

Sasaki

et al. 2003

Biological & Pharmaceutical Bulletin

View full text Add to dashboard Cite

“…We speculate that such arylation of AhR by 1,2-NQ may promote the conformational change in AhR involved in its activation. In our preliminary study, we found that non-classical ligands for AhR such as curcumin (Ciolino et al, 1998) were able to bind to proteins as determined by a BPM assay, whereas little appreciable chemical modification of carbaryl (Denison et al, 1998) and oltipraz (Miao et al, 2003) was seen, even at concentrations of 100 μM (Abiko et al, unpublished observation). Further studies are needed to understand the association of the modification capacity of non-classical ligands for AhR with its activation.…”

Section: Discussionmentioning

confidence: 97%

“…A number of structure activity relationship studies with polycyclic aromatic hydrocarbons suggest that the size of the hydrocarbon is important to be able to fit the binding pocket of AhR, which has a size of 14 × 12 × 5 Å (Waller and McKinney, 1995). Conversely, kynurenine, and curcumin, which are non-classical ligands for AhR, are electrophilic and can modify protein nucle-ophiles and are known to induce cytochrome P450 1A1 (CYP1A1) through AhR activation (Opitz et al, 2011;Quattrochi and Tukey, 1993;Ciolino et al, 1998). These findings suggest that there may be ligand-independent electrophiles that can activate AhR.…”

Section: Introductionmentioning

confidence: 99%

Covalent binding of quinones activates the Ah receptor in Hepa1c1c7 cells

2015

View full text Add to dashboard Cite

-Highly reactive quinone species produced by photooxidation and/or metabolic activation of mono-or bi-aromatic hydrocarbons modulate cellular homeostasis and electrophilic signal transduction pathways through the covalent modification of proteins. Polycyclic aromatic hydrocarbons, but not mono-or bi-aromatic hydrocarbons, are well recognized as ligands for the aryl hydrocarbon receptor (AhR). However, quinone species produced from mono-and bi-aromatic hydrocarbons could potentially cause AhR activation. To clarify the AhR response to mono-and bi-aromatic hydrocarbon quinones, we studied Cyp1a1 (cytochrome P450 1A1) induction and AhR activation by these quinones. We detected Cyp1a1 induction during treatment with quinones in Hepa1c1c7 cells, but not their parent compounds. Nine of the twelve quinones with covalent binding capability for proteins induced Cyp1a1. Cyp1a1 induction mediated by 1,2-naphthoquinone (1,2-NQ), 1,4-NQ, 1,4-benzoquinone (1,4-BQ) and tert-butyl-1,4-BQ was suppressed by a specific AhR inhibitor and was not observed in c35 cells, which do not have a functional AhR. These quinones stimulated AhR nuclear translocation and interaction with the AhR nuclear translocator. Interestingly, 1,2-NQ covalently modified AhR, which was detected by an immunoprecipitation assay using a specific antibody against 1,2-NQ, resulting in enhancement of xenobiotic responsive element (XRE)-derived luciferase activity and binding of AhR to the Cyp1a1 promoter region. While mono-and bi-aromatic hydrocarbons are generally believed to be poor ligands for AhR and hence unable to induce Cyp1a1, our study suggests that the quinones of these molecules are able to modify AhR and activate the AhR/XRE pathway, thereby inducing Cyp1a1. Since we previously reported that 1,2-NQ and tert-butyl-1,4-BQ also activate NF-E2-related factor 2, it seems likely that some of quinones are bi-functional inducers for phase-I and phase-II reaction of xenobiotics.

show abstract

“…[9][10][11] The effects of green tea and its catechins, have also been examined, and the results indicated that they can compete with TCDD for binding to the AhR. 12) However, studies on foodstuffs themselves are limited.…”

mentioning

confidence: 99%

Preliminary Screening of the Inhibitory Effect of Food Extracts on Activation of the Aryl Hydrocarbon Receptor Induced by 2,3,7,8-Tetrachlorodibenzo-p-dioxin.

Amakura¹,

Tsutsumi²,

Nakamura

et al. 2002

Biological & Pharmaceutical Bulletin

View full text Add to dashboard Cite

A preliminary screening for the inhibitory effects on the activation of the aryl hydrocarbon receptor (AhR) by 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) by applying AhR-based bioassays for dioxins, the Ah-Immunoassay and CALUX assay, was attempted. Thirty-nine food extracts including vegetables, fruits, herbs, and teas were initially screened in vitro. We first examined the application of both bioassay methods using green tea extracts and (؊)-epigallocatechin gallate, reported antagonists of the AhR, since the results could reveal an inhibitory effect versus the control in both assays. Food extracts were then tested. Among the herbs, extracts of sage, among the vegetables, green leafy ones such as spinach, and among the fruit, citrus showed inhibitory effects on AhR activation by TCDD, although some tested samples did not show parallel behavior in both assays. Sage had a remarkable inhibitory effect (79% in the CALUX assay and 83% in the Ah-Immunoassay compared with control) and its effects were dose dependent. The results suggest that these assays might be applicable to the preliminary screening of antagonist activity against the AhR. Moreover, based on these results, the potential benefit of factors that function as dietary ligands of the AhR and are present in several foodstuffs is indicated.

show abstract

Effect of Curcumin on the Aryl Hydrocarbon Receptor and Cytochrome P450 1A1 in MCF-7 Human Breast Carcinoma Cells

Cited by 218 publications

References 28 publications

Screening of the Inhibitory Effect of Vegetable Constituents on the Aryl Hydrocarbon Receptor-Mediated Activity Induced by 2,3,7,8-Tetrachlorodibenzo-p-dioxin

Screening of the Inhibitory Effect of Vegetable Constituents on the Aryl Hydrocarbon Receptor-Mediated Activity Induced by 2,3,7,8-Tetrachlorodibenzo-p-dioxin

Covalent binding of quinones activates the Ah receptor in Hepa1c1c7 cells

Preliminary Screening of the Inhibitory Effect of Food Extracts on Activation of the Aryl Hydrocarbon Receptor Induced by 2,3,7,8-Tetrachlorodibenzo-p-dioxin.

Contact Info

Product

Resources

About