160096-59-3
Chemical Structure
Dimethoxycurcumin
Synonym(s): DiMC; CHC 004; Di-O-methylcurcumin
- CAS No.: 160096-59-3
- Formula:C23H24O6
- Molecular Weight:396.43
IUPAC Name: (1E,6E)-1,7-bis(3,4-dimethoxyphenyl)hepta-1,6-diene-3,5-dione
InChIKey: HMJSBVCDPKODEX-NXZHAISVSA-N
SMILES: O=C(CC(/C=C/C1=CC=C(OC)C(OC)=C1)=O)/C=C/C2=CC=C(OC)C(OC)=C2
Biological Activity: Dimethoxycurcumin (DiMC) is a curcuminoid compound found in Curcuma longa. Dimethoxycurcumin is also an orally active thioredoxin reductase inhibitor (IC50 = 5.4 μM) and androgen receptor antagonist. Dimethoxycurcumin inhibits thioredoxin reductase, leading to oxidized thioredoxin accumulation, ROS production, DNA damage, glutathione depletion, mitochondrial membrane potential decrease, ATP depletion, S phase arrest, and apoptosis. Dimethoxycurcumin inhibits NF-κB, NADPH oxidase subunits, ATP synthase subunits, CDK4, cyclin-D1, FASN, ACC, and the IRS2-PI3K-Akt pathway, while activating AMPK, ERK, and JNK. Dimethoxycurcumin can be used for research on cancer, arsenic-induced hepatotoxicity, and tuberculosis[1][2][3][4][5][6][7][8][9][10][11][12].
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Dimethoxycurcumin | 98.48% | Dimethoxycurcumin (DiMC) is a curcuminoid compound found in Curcuma longa. Dimethoxycurcumin is also an orally active thioredoxin reductase inhibitor (IC50 = 5.4 μM) and androgen receptor antagonist. Dimethoxycurcumin inhibits thioredoxin reductase, leading to oxidized thioredoxin accumulation, ROS production, DNA damage, glutathione depletion, mitochondrial membrane potential decrease, ATP depletion, S phase arrest, and apoptosis. Dimethoxycurcumin inhibits NF-κB, NADPH oxidase subunits, ATP synthase subunits, CDK4, cyclin-D1, FASN, ACC, and the IRS2-PI3K-Akt pathway, while activating AMPK, ERK, and JNK. Dimethoxycurcumin can be used for research on cancer, arsenic-induced hepatotoxicity, and tuberculosis. | ||||||||||||||||||||
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Dimethoxycurcumin-d6 | Dimethoxycurcumin-d6 (DiMC-d6; CHC 004-d6; Di-O-methylcurcumin-d6) is the deuterated-labeled Dimethoxycurcumin (HY-100977). Dimethoxycurcumin (DiMC) is a curcuminoid compound found in Curcuma longa. Dimethoxycurcumin is also an orally active thioredoxin reductase inhibitor (IC50 = 5.4 μM) and androgen receptor antagonist. Dimethoxycurcumin inhibits thioredoxin reductase, leading to oxidized thioredoxin accumulation, ROS production, DNA damage, glutathione depletion, mitochondrial membrane potential decrease, ATP depletion, S phase arrest, and apoptosis. Dimethoxycurcumin inhibits NF-κB, NADPH oxidase subunits, ATP synthase subunits, CDK4, cyclin-D1, FASN, ACC, and the IRS2-PI3K-Akt pathway, while activating AMPK, ERK, and JNK. Dimethoxycurcumin can be used for research on cancer, arsenic-induced hepatotoxicity, and tuberculosis. | |||||||||||||||||||||
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References
- [1]. Miltonprabu S, et al. Dimethoxycurcumin potentially protects arsenic induced oxidative hepatic injury, inflammation and apoptosis via Nrf2-Keap1 signaling in rats. Biomedicine & Preventive Nutrition. 2014 Oct 1;4(4):561-77.
- [2]. Kunwar A, et al. Dimethoxycurcumin-induced cell death in human breast carcinoma MCF7 cells: evidence for pro-oxidant activity, mitochondrial dysfunction, and apoptosis. Archives of toxicology. 2012 Apr;86(4):603-14.
- [3]. Hatamipour M, et al. Demethoxycurcumin: A naturally occurring curcumin analogue with antitumor properties. Journal of cellular physiology. 2018 Dec;233(12):9247-9260.
- [4]. Patwardhan RS, et al. Dimethoxycurcumin, a metabolically stable analogue of curcumin, exhibits anti-inflammatory activities in murine and human lymphocytes. Biochemical pharmacology. 2011 Sep 15;82(6):642-57. [Content Brief]
- [5]. Zoi V, et al. Radiosensitization and Radioprotection by Curcumin in Glioblastoma and Other Cancers. Biomedicines. 2022 Jan 28;10(2):312.
- [6]. Jayakumar S, et al. Dimethoxycurcumin, a metabolically stable analogue of curcumin enhances the radiosensitivity of cancer cells: Possible involvement of ROS and thioredoxin reductase. Biochemical and biophysical research communications. 2016 Sep 09;478(1):446-454.
- [7]. Liu H, et al. Preparation, characterization, in vivo pharmacokinetics, and biodistribution of polymeric micellar dimethoxycurcumin for tumor targeting. International journal of nanomedicine. 2015;10:6395-410.
- [8]. Yoon MJ, et al. Stronger proteasomal inhibition and higher CHOP induction are responsible for more effective induction of paraptosis by dimethoxycurcumin than curcumin. Cell death & disease. 2014 Mar 13;5(3):e1112. [Content Brief]
- [9]. Nelen J, et al. Targeting Drug Resistance in Cancer: Dimethoxycurcumin as a Functional Antioxidant Targeting ABCC3. Antioxidants (Basel, Switzerland). 2025 May 16;14(5):599.
- [10]. Tamvakopoulos C, et al. Metabolism and anticancer activity of the curcumin analogue, dimethoxycurcumin. Clinical cancer research : an official journal of the American Association for Cancer Research. 2007 Feb 15;13(4):1269-77.
- [11]. Zanetti TA, et al. Dimethoxycurcumin reduces proliferation and induces apoptosis in renal tumor cells more efficiently than demethoxycurcumin and curcumin. Chemico-biological interactions. 2021 Apr 01;338:109410.
- [12]. Changtam C, et al. Isoxazole analogs of curcuminoids with highly potent multidrug-resistant antimycobacterial activity. European journal of medicinal chemistry. 2010 Oct;45(10):4446-57.
