Dimethoxycurcumin
Like its parent compound, curcumin, this curcuminoid exhibits anticancer, antioxidative, anti-inflammatory, and antibacterial activities. In breast cancer cells, dimethoxycurcumin alters mitochondrial membrane potential, decreases ATP synthase activity, and induces DNA damage and apoptosis. In comparison to curcumin, dimethoxycurcumin is more stable and displays greater apoptosis-inducing activity in vitro. Additionally, dimethoxycurcumin is more effective in inhibition of NO production, iNOS expression, and NF-κB activation than curcumin. Dimethoxycurcumin exhibits pro-oxidative activity in cancer cells, increasing reactive oxygen species (ROS), but does not do so in normal cultured cells. This compound also inhibits the expression of pro-inflammatory cytokines such as IL-2, IL-6, and IFN-γ in vitro. Dimethoxycurcumin has phototoxic antibacterial activity against both gram-positive and gram-negative bacteria and binds the minor groove of DNA without intercalation.
References PubMed ID：:http://www.ncbi.nlm.nih.gov/pubmed/18875112
| Cas No. |
160096-59-3 |
|---|---|
| Purity |
≥98% |
| Formula |
C23H24O6 |
| Formula Wt. |
396.43 |
| IUPAC Name |
(1E,6E)-1,7-Bis(3,4-dimethoxyphenyl)-1,6-heptadiene-3,5-dione |
| Appearance |
Orange powder |
Kunwar A, Jayakumar S, Srivastava AK, et al. Dimethoxycurcumin-induced cell death in human breast carcinoma MCF7 cells: evidence for pro-oxidant activity, mitochondrial dysfunction, and apoptosis. Arch Toxicol. 2012 Apr;86(4):603-14. PMID: 22119759.
Patwardhan RS, Checker R, Sharma D, et al. Dimethoxycurcumin, a metabolically stable analogue of curcumin, exhibits anti-inflammatory activities in murine and human lymphocytes. Biochem Pharmacol. 2011 Sep 15;82(6):642-57. PMID: 21726543.
Kunwar A, Barik A, Sandur SK, et al. Differential antioxidant/pro-oxidant activity of dimethoxycurcumin, a synthetic analogue of curcumin. Free Radic Res. 2011 Aug;45(8):959-65. PMID: 21615275.
Kunwar A, Simon E, Singh U, et al. Interaction of a curcumin analogue dimethoxycurcumin with DNA. Chem Biol Drug Des. 2011 Apr;77(4):281-7. PMID: 21244640
Haukvik T, Bruzell E, Kristensen S, et al. A screening of curcumin derivatives for antibacterial phototoxic effects studies on curcumin and curcuminoids. XLIII. Pharmazie. 2011 Jan;66(1):69-74. PMID: 21391438.
Pae HO, Jeong SO, Kim HS, et al. Dimethoxycurcumin, a synthetic curcumin analogue with higher metabolic stability, inhibits NO production, inducible NO synthase expression and NF-kappaB activation in RAW264.7 macrophages activated with LPS. Mol Nutr Food Res. 2008 Sep;52(9):1082-91. PMID: 18481332.
Tamvakopoulos C, Dimas K, Sofianos ZD, et al. Metabolism and anticancer activity of the curcumin analogue, dimethoxycurcumin. Clin Cancer Res. 2007 Feb 15;13(4):1269-77. PMID: 17317839.
