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Curcumin (Diferuloylmethane; NSC32982; Turmeric Yellow; curcumin I) is a naturally occurring diarylheptanoid diarylheptanoid with diverse pharmacologic effects including anti-inflammatory, antioxidant, antiproliferative and antiangiogenic activities. It is the major curcuminoid of turmeric, a member of the ginger family (Zingiberaceae). Curcumin is an inhibitor of p300 histone acetylatransferase ((HATs)) and also shows inhibitory effects on NF-κB and MAPKs. Curcumin has the potential for treating various diseases, including multiple myeloma, pancreatic cancer, myelodysplastic syndromes, colon cancer, psoriasis, arthritis, major depressive disorder and Alzheimer's disease.
| ln Vitro |
Part of how curcumin works as a chemopreventive agent is via activating its antioxidant and phase II detoxifying enzymes, as well as nuclear factor (erythroid-2 related) factor 2 (Nrf2)[1]. With IC50s of 25, 19, and 17.5 μM for 24, 48, and 72-hour MTT experiments, respectively, curcumin suppresses the proliferation of T47D cells. For 24, 48, and 72 hours of exposure, the IC50s of the curcumin and silibinin mixture against T47D cells are 17.5, 15, and 12 μM, respectively[2]. AGS and HT-29 cell lines exhibit apoptotic cell death in response to curcumin (2.5-80 μM); the IC50 values for these cell lines are 21.9±0.1 and 40.7±0.5 μM, respectively. In AGS and HT-29 cells, caspase activity are necessary for curcumin-induced apoptosis. Curcumin causes mitochondrial Ca2+ overloading and ER Ca2+ decline[3]. Curcumin dose-dependently promotes LNCaP and PC-3 cells to enter the G2/M cell cycle arrest. Curcumin decreases the protein levels of c-Jun and AR while increasing the protein level of the NF-kappaB inhibitor IkappaBalpha[5].
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| ln Vivo |
Compared to the rats exposed to CMS, curcumin (10 mg/kg, po) significantly avoids declines in the percentage of sucrose consumption. When stressed rats are treated with curcumin, their levels of TNF-α and IL-6 are significantly prevented from rising[4]. In chronic constriction injury (CCI) rats, curcumin reduces the binding of p300/CREB-binding protein (CBP) at the brain-derived neurotrophic factor (BDNF) promoter at 20 mg/kg (ip), as well as the binding of P300/CBP at 40 mg/kg and the binding of all four proteins of p300/CBP and H3K9ac/H4K5ac at 60 mg/kg[6].
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| References |
[1]. Gao S, et al. Curcumin attenuates arsenic-induced hepatic injuries and oxidative stress in experimental mice through activation of Nrf2 pathway, promotion of arsenic methylation and urinary excretion. Food Chem Toxicol. 2013 Jul 18. pii: S0278-6915(13)004
[2]. Nasiri M, et al. Curcumin and Silibinin Inhibit Telomerase Expression in T47D Human Breast Cancer Cells. Asian Pac J Cancer Prev. 2013;14(6):3449-53. [3]. Cao A, et all. Curcumin induces apoptosis in human gastric carcinoma AGS cells and colon carcinoma HT-29 cells through mitochondrial dysfunction and endoplasmic reticulum stress. Apoptosis. 2013 Jul 24. [Epub ahead of print] [4]. Jiang H, et al. Antidepressant-like effects of curcumin in chronic mild stress of rats: Involvement of its anti-inflammatory action. Prog Neuropsychopharmacol Biol Psychiatry. 2013 Jul 20. pii: S0278-5846(13)00150-4. [5]. Guo H, et al. Curcumin induces cell cycle arrest and apoptosis of prostate cancer cells by regulating the expression of IkappaBalpha, c-Jun and androgen receptor. Pharmazie. 2013 Jun;68(6):431-4. [6]. Zhu X, et al. Curcumin alleviates neuropathic pain by inhibiting p300/CBP histone acetyltransferase activity-regulated expression of BDNF and cox-2 in a rat model. PLoS One. 2014 Mar 6;9(3):e91303. [7]. Balasubramanyam K, et al. Curcumin, a novel p300/CREB-binding protein-specific inhibitor of acetyltransferase, represses the acetylation of histone/nonhistone proteins and histone acetyltransferase-dependent chromatin transcription. J Biol Chem. 2004 Dec [8]. Jun Wan Shin, et al. Curcumin induces stabilization of Nrf2 protein through Keap1 cysteine modification. Biochem Pharmacol. 2020 Mar;173:113820 |
| Molecular Formula |
C21H20O6
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|---|---|
| Molecular Weight |
368.38
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| Exact Mass |
368.12599
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| CAS # |
458-37-7
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| Related CAS # |
Curcumin-d6;1246833-26-0
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| SMILES |
O=C(CC(/C=C/C1=CC=C(O)C(OC)=C1)=O)/C=C/C2=CC=C(O)C(OC)=C2
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| InChi Key |
VFLDPWHFBUODDF-FCXRPNKRSA-N
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| InChi Code |
InChI=1S/C21H20O6/c1-26-20-11-14(5-9-18(20)24)3-7-16(22)13-17(23)8-4-15-6-10-19(25)21(12-15)27-2/h3-12,24-25H,13H2,1-2H3/b7-3+,8-4+
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| Chemical Name |
(1E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione
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| Synonyms |
Turmeric Yellow NSC32982Diferuloylmethane NSC-32982Curcumincurcumin I C.I. 75300 Natural Yellow 3
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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 : ~100 mg/mL (~271.46 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 3 mg/mL (8.14 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 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 30.0 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. Solubility in Formulation 2: 3 mg/mL (8.14 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 30.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: 25 mg/mL (67.86 mM) in 1% (w/v) carboxymethylcellulose (CMC) (add these co-solvents sequentially from left to right, and one by one), Suspension solution; with ultrasonication. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.7146 mL | 13.5729 mL | 27.1459 mL | |
| 5 mM | 0.5429 mL | 2.7146 mL | 5.4292 mL | |
| 10 mM | 0.2715 mL | 1.3573 mL | 2.7146 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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