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| 25mg |
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Purity: ≥98%
DIM-C-pPhOCH3 is an agonist Nur77 (Nerve growth factor-induced Bα, abbreviated as NGFI-Bα or Nur77). Nur77 is an orphan nuclear receptor with no known endogenous ligands and was reported to be overexpressed in colon tumors compared with normal colon tissue. In RKO colon cancer cells, DIM-C-phOCH3 was able to reduce survival and trigger apoptosis; this was accompanied by an increase in the protein known as tumor necrosis factor-related apoptosis-inducing ligand (TRAIL). A small Nur77 inhibitory RNA (iNur77) greatly reduced the induction of TRAIL and apoptosis by DIM-C-pPhOCH3, but RNA interference studies clearly demonstrated that DIM-C-pPhOCH3 also induced Nur77-independent apoptosis. Microarray analysis of DIM-C-phOCH3-induced gene expression revealed a number of proapoptotic genes. Reverse transcription-PCR analysis conducted in the presence or absence of iNur77 revealed that induction of gene 1 for programmed cell death was dependent on Nur77, while induction of cystathionase and activating transcription factor 3 was independent of Nur77. Furthermore, in athymic nude mice with RKO cell xenografts, DIM-C-pPhOCH3 (25 mg/kg/d) inhibited tumor growth. These findings demonstrate that a novel class of anti-colon cancer medications, known as DIM-C-phOCH3, functions via both receptor-dependent and receptor-independent mechanisms.
| Targets |
Nur77
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|---|---|
| ln Vitro |
DIM-C-pPhOCH3 causes tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) protein to be produced in conjunction with a decrease in survival and an increase in apoptosis in RKO colon cancer cells. Apoptosis that is Nur77-independent is also induced by DIM-C-phOCH3. After treatment, DIM-C-pHOCH3 (10 μM) inhibits cell growth for 24, 48, or 72 hours. The maximum inhibitory response is seen after 72 hours, at which point there is a significant amount of dead cells and cell detachment. Following a 72-hour period, DIM-C-phOCH3 was shown to exhibit growth-inhibitory effects along with a number of apoptosis markers, such as PARP cleavage and cleavage of caspase-3, caspase-9, and caspase-8. Following DIM-C-pHOCH3 treatment of RKO cells for 48 hours, PARP cleavage is also seen[1].
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| ln Vivo |
DIM-C-pPhOCH3 (25 mg/kg/d) also prevents tumor growth in RKO cell xenografted athymic nude mice. In athymic nude mice carrying RKO cell xenografts, the effects of DIM-C-pPhOCH3 (25 mg/kg/d) on colon tumor growth are also examined. Tumor volumes and final tumor weights are significantly reduced after treatment with DIM-C-phOCH3 when compared to corn oil controls[1].
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| Cell Assay |
For two and six hours, RKO cells are exposed to either 12.5 μM DIM-C-pHOCH3 or DMSO. For the reverse transcription-PCR (RT-PCR) experiment, RNA is isolated, examined for gene expression, and three replicates are calculated for every time point and the DMSO control. An analysis is done on the microarray data[1].
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| Animal Protocol |
Mice: The mice used are male athymic nude mice (Foxn1nu, aged 7-8 weeks). The mice are kept in laminar flow cabinets with particular pathogen-free conditions. In vitro cultured RKO cells (5×106 per 150 μL) are injected subcutaneously into each mouse's flank to create a xenograft. Four days are given to tumor growth before they become palpable. After that, mice are divided into two groups of six mice each, and they are given oral gavage doses of either corn oil or 25 mg/kg/d DIM-C-phOCH3 for a period of 21 days. Both the tumor size and the mice's weight are determined[1].
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| References |
| Molecular Formula |
C24H20N2O
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|---|---|---|
| Molecular Weight |
352.43
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| Exact Mass |
352.158
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| Elemental Analysis |
C, 81.79; H, 5.72; N, 7.95; O, 4.54
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| CAS # |
33985-68-1
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| Related CAS # |
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| PubChem CID |
11371604
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| Appearance |
White to off-white solid powder
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| LogP |
5.838
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
1
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
27
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| Complexity |
457
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| Defined Atom Stereocenter Count |
0
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| SMILES |
COC1=CC=C(C(C2=CNC3=C2C=CC=C3)C4=CNC5=C4C=CC=C5)C=C1
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| InChi Key |
ZCCMKJAXOIFTHH-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C24H20N2O/c1-27-17-12-10-16(11-13-17)24(20-14-25-22-8-4-2-6-18(20)22)21-15-26-23-9-5-3-7-19(21)23/h2-15,24-26H,1H3
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| Chemical Name |
3-[1H-indol-3-yl-(4-methoxyphenyl)methyl]-1H-indole
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| Synonyms |
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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 |
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| 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) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.09 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 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. Solubility in Formulation 2: ≥ 2.5 mg/mL (7.09 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in 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 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. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.8374 mL | 14.1872 mL | 28.3744 mL | |
| 5 mM | 0.5675 mL | 2.8374 mL | 5.6749 mL | |
| 10 mM | 0.2837 mL | 1.4187 mL | 2.8374 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.
Inhibition of tumor growth by DIM-C-pPhOCH3.Cancer Res.2007 Jan 15;67(2):674-83. |
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Induction of gene expression by DIM-C-pPhOCH3.Cancer Res.2007 Jan 15;67(2):674-83. |
Nur77-dependent induction of TRAIL and apoptosis in RKO cells. Induction of TRAIL by DIM-C-pPhOCH3Cancer Res.2007 Jan 15;67(2):674-83. |
Nur77-active C-DIMs decrease cell proliferation and induce apoptosis in RKO cells and also act through nuclear Nur77DIM-C-pPhOCH3.Cancer Res.2007 Jan 15;67(2):674-83. |
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Nur77 expression and induced transactivation in colon cancer cells and tumors.Cancer Res.2007 Jan 15;67(2):674-83. |
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