Journal Article

Relation of structure of curcumin analogs to their potencies as inducers of Phase 2 detoxification enzymes

Albena T. Dinkova-Kostova and Paul Talalay

in Carcinogenesis

Volume 20, issue 5, pages 911-914
Published in print May 1999 | ISSN: 0143-3334
Published online May 1999 | e-ISSN: 1460-2180 | DOI:
Relation of structure of curcumin analogs to their potencies as inducers of Phase 2 detoxification enzymes

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A series of naturally occurring as well as synthetic structural analogs of the dietary constituent curcumin were examined in order to elucidate which portions of the molecule are critical for the ability to induce Phase 2 detoxification enzymes in murine hepatoma cells, and hence to assess the chemoprotective potential of these compounds. Two groups of compounds were studied: classical Michael reaction acceptors such as curcumin and related β-diketones such as dibenzoylmethane which lack direct Michael reactivity. The presence of two structural elements was found to be required for high inducer potency: (i) hydroxyl groups at ortho-position on the aromatic rings and (ii) the β-diketone functionality. All curcuminoids elevate the specific activity of quinone reductase in both wild type and mutant cells defective in either the aryl hydrocarbon (Ah) receptor or cytochrome P4501A1 activity. This indicates that neither binding to this receptor, nor metabolic activation by P4501A1 are required for the signaling process originating from this family of electrophiles and ultimately resulting in Phase 2 enzyme induction.

Keywords: Ah receptor, aryl hydrocarbon receptor; DMBA, 7,12-dimethylbenz[a]anthracene; NF-κB, nuclear factor κB; QR, quinone reductase; TPA, 12-O-tetradecanoylphorbol-13-acetate.

Journal Article.  3089 words.  Illustrated.

Subjects: Clinical Cytogenetics and Molecular Genetics

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