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Chemical Compound Review:

MCDF 1,3,8-trichloro-6-methyl- dibenzofuran

Synonyms: ACMC-1BUFR, AG-D-35864, SureCN1804174, LS-61096, CTK4A9135, ...

Liu, S. et al., Pearce, S.T. et al., Harper, N. et al., Santostefano, M. et al., Piskorska-Pliszczynska, J. et al., et al.

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Disease relevance of AIDS-105029

Like 6-methyl-1,3,8-trichlorodibenzofuran (MCDF), I-MCDF partially antagonized the induction by TCDD of microsomal aryl hydrocarbon hydroxylase (AHH) and ethoxyresorufin O-deethylase (EROD) activities in rat hepatoma H-4-II E cells and male Long-Evans rat liver [1].

High impact information on AIDS-105029

The polycyclic aromatic hydrocarbon 6-methyl-1,3,8-trichlorodibenzofuran (MCDF) is related to the industrial byproduct dioxin and is a weak agonist and partial antagonist at the aryl hydrocarbon receptor (AhR) [2].
Interaction of the aryl hydrocarbon receptor ligand 6-methyl-1,3,8-trichlorodibenzofuran with estrogen receptor alpha [2].
6-Methyl-1,3,8-trichlorodibenzofuran (MCDF) binds with moderate affinity to the aryl hydrocarbon (Ah) receptor protein (4.9 x 10(-8) M) but is a weak Ah receptor agonist [3].
AhR agonists including TCDD, benzo[a]pyrene (BaP) and 6-methyl-1,3,8-trichlorodibenzofuran, inhibited 32-47% of the E2-induced responses [4].
For a series of halogenated aromatics including 2,3,7,8- and 1,2,7,8-tetrachlorodibenzofuran, 1,3,7,8-TCDD and 6-methyl-1,3,8-trichlorodibenzofuran, their rank order potency for inhibiting E2-induced PR binding paralleled their rank order binding to the aryl hydrocarbon (Ah) receptor [5].

Biological context of AIDS-105029

This study also shows that the AhR agonists benzo[a]pyrene, 3,3',4,4'-tetrachlorobiphenyl, chrysin, 6-methyl-1,3,8-trichlorodibenzofuran, and 3,3'-diindolylmethane also induce ERalpha-dependent transactivation [6].

Anatomical context of AIDS-105029

The results of the present study indicate that 6-methyl-1,3,8-trichlorodibenzofuran (MCDF) effectively competes with [3H]TCDD for binding to the Ah receptor in rat liver cytosol [7].
In contrast, treatment of these cell lines with either alpha-naphthoflavone (alpha NF) or 6-methyl-1,3,8-trichlorodibenzofuran (MCDF) at concentrations as high as 10(-6) M resulted in only minimal induction of CYP1A1 mRNA levels or EROD activity [8].

Gene context of AIDS-105029

The results obtained from cotreatment of wt Hepa 1c1c7 cells with 10(-6) or 10(-7) M B[a]P and 5 x 10(-7) or 10(-7) M 6-methyl-1,3,8-trichlorodibenzofuran (MCDF) showed that MCDF inhibited the induction of EROD activity and Cyp1a-1 mRNA levels by B[a]P [9].
6-Methyl-1,3,8-trichlorodibenzofuran (MCDF) as an antiestrogen in human and rodent cancer cell lines: evidence for the role of the Ah receptor [10].
In contrast, the proteolytic clipping band shift assay showed that there were significant differences in the pattern of degraded protein-DNA products using nuclear AhR complexes derived from mouse Hepa 1c1c7 cells treated with TCDD or 6-methyl-1,3,8-trichlorodibenzofuran (MCDF) [11].

References

Mechanism of action of 2,3,7,8-tetrachlorodibenzo-p-dioxin antagonists: characterization of 6-[125I]methyl-8-iodo-1,3-dichlorodibenzofuran-Ah receptor complexes. Piskorska-Pliszczynska, J., Astroff, B., Zacharewski, T., Harris, M., Rosengren, R., Morrison, V., Safe, L., Safe, S. Arch. Biochem. Biophys. (1991) [Pubmed]
Interaction of the aryl hydrocarbon receptor ligand 6-methyl-1,3,8-trichlorodibenzofuran with estrogen receptor alpha. Pearce, S.T., Liu, H., Radhakrishnan, I., Abdelrahim, M., Safe, S., Jordan, V.C. Cancer Res. (2004) [Pubmed]
Partial antagonism of 2,3,7,8-tetrachlorodibenzo-p-dioxin-mediated induction of aryl hydrocarbon hydroxylase by 6-methyl-1,3,8-trichlorodibenzofuran: mechanistic studies. Harris, M., Zacharewski, T., Astroff, B., Safe, S. Mol. Pharmacol. (1989) [Pubmed]
Estrogen and aryl hydrocarbon receptor expression and crosstalk in human Ishikawa endometrial cancer cells. Wormke, M., Castro-Rivera, E., Chen, I., Safe, S. J. Steroid Biochem. Mol. Biol. (2000) [Pubmed]
Inhibition of estrogen-induced progesterone receptor in MCF-7 human breast cancer cells by aryl hydrocarbon (Ah) receptor agonists. Harper, N., Wang, X., Liu, H., Safe, S. Mol. Cell. Endocrinol. (1994) [Pubmed]
Aryl hydrocarbon receptor agonists directly activate estrogen receptor alpha in MCF-7 breast cancer cells. Liu, S., Abdelrahim, M., Khan, S., Ariazi, E., Jordan, V.C., Safe, S. Biol. Chem. (2006) [Pubmed]
6-Methyl-1,3,8-trichlorodibenzofuran as a 2,3,7,8-tetrachlorodibenzo-p-dioxin antagonist: inhibition of the induction of rat cytochrome P-450 isozymes and related monooxygenase activities. Astroff, B., Zacharewski, T., Safe, S., Arlotto, M.P., Parkinson, A., Thomas, P., Levin, W. Mol. Pharmacol. (1988) [Pubmed]
Mechanism of action of aryl hydrocarbon receptor antagonists: inhibition of 2,3,7,8-tetrachlorodibenzo-p-dioxin-induced CYP1A1 gene expression. Merchant, M., Morrison, V., Santostefano, M., Safe, S. Arch. Biochem. Biophys. (1992) [Pubmed]
Mechanism of benzo[a]pyrene-induced Cyp1a-1 gene expression in mouse Hepa 1c1c7 cells: role of the nuclear 6 s and 4 s proteins. Merchant, M., Wang, X., Kamps, C., Rosengren, R., Morrison, V., Safe, S. Arch. Biochem. Biophys. (1992) [Pubmed]
6-Methyl-1,3,8-trichlorodibenzofuran (MCDF) as an antiestrogen in human and rodent cancer cell lines: evidence for the role of the Ah receptor. Zacharewski, T., Harris, M., Biegel, L., Morrison, V., Merchant, M., Safe, S. Toxicol. Appl. Pharmacol. (1992) [Pubmed]
Characterization of the molecular and structural properties of the transformed and nuclear aryl hydrocarbon (Ah) receptor complexes by proteolytic digestion. Santostefano, M., Safe, S. Chem. Biol. Interact. (1996) [Pubmed]

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