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| Other Sizes |
| Targets |
Bisdemethoxycurcumin acts as an inhibitor of human pancreatic α-amylase. It is also an activator of HMOX1 (heme oxygenase 1), an agonist of NLRP3, and a stimulator of Nrf2. It inhibits wnt activity through activation of WIF-1. It induces demethylation through DNA methyltransferase 1 inhibition. BDMC-induced apoptosis is mediated by a combinatory inhibition of cytoprotective proteins, such as Bcl2 and heme oxygenase-1, and increased generation of reactive oxygen species.
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| ln Vitro |
Bisdemethoxycurcumin (BDMC) is a demethoxy derivative of curcumin, which is a natural substance found in the turmeric root. In a dose-dependent manner, BDMC slows the growth of the SGC 7901 gastric cancer cells. Since BDMC prevents cells from progressing to S phase and finishing the cycle, cell growth is stopped in G1 phase[2].
In vitro, Bisdemethoxycurcumin regulates anti-inflammatory and anti-proliferative responses through a ROS-independent mechanism. It suppresses MCF-7 cells proliferation by inducing ROS accumulation and modulating senescence-related pathways. It differentially inhibits cancer cell invasion through the down-regulation of MMPs and uPA. BDMC (10 µM) with DTX (10 nM) is effective in inhibiting PC3 and LNCaP cell growth and inducing apoptosis as well as G2/M arrest. BDMC significantly reduces cell viability and induces cell apoptosis in GBM 8401/luc2 cells. |
| ln Vivo |
Through modulating mitochondria, BDMC may encourage tumor apoptosis. In a xenograft model of gastric adenoadenocarcinoma, BDMC inhibits tumor growth and increases body weight[2].
In vivo, Bisdemethoxycurcumin (0.5% in diet; 15 weeks) significantly reduces both final body weight and body weight gain in HFD-induced obese mice. It has been shown to inhibit lipid accumulation in adipocytes. BDMC augments docetaxel efficacy for treatment of prostate cancer in vivo. BDMC induces cell apoptosis and inhibits human brain glioblastoma GBM 8401/Luc2 cell xenograft tumor in subcutaneous nude mice. In models of ulcerative colitis, BDMC demonstrated anti-inflammatory effects. |
| Enzyme Assay |
The cells are grown in a humid environment with 5% CO2 at 37°C. As a positive control, DAC is used to assess the hypomethylation effect of bisdemethoxycurcumin. Before use, stock solutions of curcumin, DMC, BDMC, and DAC (20 mM) in dimethyl sulfoxide (DMSO) are prepared and diluted in sterile-filtered media. In 6-well culture plates, 1×105 cells are seeded. Following a 24-hour culture period, the cells are given a 72-hour treatment with curcumin, DMC, BDMC (0-100 μM) or DAC (20 μM).
For non-cellular enzyme assays, the compound's inhibitory activity against MMP-2, MMP-9, and collagenase can be assessed using zymography or fluorometric substrate cleavage assays. Pancreatic α-amylase inhibition is measured using starch-iodine or chromogenic substrate-based assays. DNA methyltransferase 1 inhibition can be assessed using in vitro methylation assays. |
| Cell Assay |
For in vitro cell-based assays, cancer cells such as MCF-7, PC3, LNCaP, or GBM 8401/luc2 are cultured and treated with Bisdemethoxycurcumin. Cell proliferation is assessed using MTT assays, and apoptosis is evaluated by Annexin V/PI staining. Cell cycle analysis is performed via flow cytometry using PI staining. Protein expression (Bax, Bcl-2, caspase, PARP, cyclin B1, CDK1) is assayed by Western blot. Cell invasion is assessed using Transwell assays.
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| Animal Protocol |
In vivo studies are conducted in mouse models. For obesity studies, BDMC is administered in diet at 0.5% for 15 weeks. For cancer studies, xenograft models in nude mice are used. For ulcerative colitis models, BDMC is administered and inflammatory markers are assessed. For prostate cancer, BDMC is combined with docetaxel to evaluate efficacy. Tumor growth, apoptosis, and cell cycle markers are evaluated.
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| ADME/Pharmacokinetics |
Metabolism / Metabolites
The known metabolites of bisdemethoxycurcumin include bisdemethoxycurcumin and 4-O-glucuronide. Pharmacokinetic properties include solubility in DMSO. The molecular weight is 308.33. Purity is >98%. It is a natural derivative of curcumin. For in vivo studies, it can be administered in diet or via intraperitoneal injection. Storage conditions typically involve -20°C for long-term stability. |
| Toxicity/Toxicokinetics |
As a natural curcuminoid, toxicity is generally low. BDMC has antioxidant activities and reduces oxidative stress. No significant toxicity has been reported in preclinical studies at efficacious doses. It induces apoptosis in activated HSCs, but not in hepatocytes. The compound is considered safe for research applications.
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| References | |
| Additional Infomation |
Bisdemethoxycurcumin is a β-diketone with a methane structure in which two hydrogen atoms are replaced by 4-hydroxycinnamoyl groups. It is a metabolite and an EC 3.2.1.1 (α-amylase) inhibitor. It is a β-diketone, polyphenol, enone, and diarylheptane compound. Its function is related to 4-coumaric acid. Bisdemethoxycurcumin has been reported in turmeric (Curcuma xanthorrhiza), Guangxi turmeric (Curcuma kwangsiensis), and other organisms with relevant data.
Bisdemethoxycurcumin (BDMC; (E,E)-Curcumin III) is a natural derivative of curcumin with anti-inflammatory and anti-cancer activities. It inhibits wnt activity through activation of WIF-1 and induces demethylation through DNA methyltransferase 1 inhibition. It augments docetaxel efficacy for treatment of prostate cancer and inhibits ovarian cancer via reducing oxidative stress mediated MMPs expressions. Its antiulcer effect might be due to its properties of decreasing gastric acid secretion and enhancing the mucosal defensive mechanism through suppression of iNOS-mediated inflammation. |
| Molecular Formula |
C₁₉H₁₆O₄
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| Molecular Weight |
308.33
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| Exact Mass |
308.104
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| CAS # |
33171-05-0
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| Related CAS # |
Bisdemethoxycurcumin-d8;2470233-08-8
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| PubChem CID |
5315472
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| Appearance |
Yellow to orange solid
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
551.3±45.0 °C at 760 mmHg
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| Melting Point |
221-223ºC
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| Flash Point |
301.3±25.2 °C
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| Vapour Pressure |
0.0±1.5 mmHg at 25°C
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| Index of Refraction |
1.680
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| LogP |
3.39
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
23
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| Complexity |
408
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| Defined Atom Stereocenter Count |
0
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| SMILES |
OC1C=CC(=CC=1)/C=C/C(CC(/C=C/C1=CC=C(C=C1)O)=O)=O
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| InChi Key |
PREBVFJICNPEKM-YDWXAUTNSA-N
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| InChi Code |
InChI=1S/C19H16O4/c20-16-7-1-14(2-8-16)5-11-18(22)13-19(23)12-6-15-3-9-17(21)10-4-15/h1-12,20-21H,13H2/b11-5+,12-6+
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| Chemical Name |
(1E,6E)-1,7-bis(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione
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| Synonyms |
Bisdemethoxycurcumin; Curcumin III
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO: ~62 mg/mL (201.1 mM)
Ethanol: ~25 mg/mL (~81.1 mM) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (8.11 mM) (saturation unknown) in 10% DMSO + 40% PEG300 +5% Tween-80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 + to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.2433 mL | 16.2164 mL | 32.4328 mL | |
| 5 mM | 0.6487 mL | 3.2433 mL | 6.4866 mL | |
| 10 mM | 0.3243 mL | 1.6216 mL | 3.2433 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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