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Purity: =98.93%
Indole-3-carbinol (I3C; 3-Indolemethanol) is natural product produced by the breakdown of the glucosinolate glucobrassicin, which can be found at relatively high levels in cruciferous vegetables. NF-κB activity, an AhR agonist, and an inhibitor of WWP1 (a WW domain-containing ubiquitin E3 ligase 1) are all inhibited by it.
| Targets |
NF-κB; AhR; Human Endogenous Metabolite
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| ln Vitro |
It has been discovered that indole-3-carbinol (I3C) has low toxicity toward healthy monocytes and inhibits the proliferation of THP-1 cells in a dose- and time-dependent manner. When exposed to indole-3-carbinol, the AhR target genes CYP1A1 and IL1β are overexpressed (p<0.05 to p<0.001). Indole-3-carbinol's antiproliferative properties are linked to its ability to program cell death. In THP-1 cells, indole-3-carbinol downregulates BCL2 while upregulating FasR (p<0.05 to p<0.001). Using flow cytometry, it is also possible to see G1 cell cycle arrest. Indole-3-carbinol treatment results in overexpression of G1-acting cell cycle genes (P21, P27, and P53) (p<0.05 to p<0.001) and downregulation of CDK2 (p<0.01 to p<0.001)[1].In pre-B acute lymphoblastic leukemia cells, Indole-3-carbinol inhibits NF-κB activity while promoting the p53 pathway[2].
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| Enzyme Assay |
B cell precursor acute lymphoblastic leukemia (BCP-ALL) is the most common type of cancer in children. Dramatic improvements in primary therapy for childhood ALL have led to an overall cure rate of 80 %, providing opportunities for innovative combined-modality strategies that would increase cure rates while reducing the toxic side effects of current intensive regimens. In this study, we report that indole-3-carbinol (I3C), a natural phytochemical found in cruciferous vegetables, had anti-leukemic properties in BCP-ALL NALM-6 cells. I3C induced cell growth inhibition by G1 cell cycle arrest and triggered apoptosis in a dose- and time-dependent manner. p53, p21, and Bax proteins showed increased expression after I3C treatment. Real-time PCR analysis of pro-apoptotic p53 target genes revealed up-regulation of PUMA, NOXA, and Apaf-1. I3C also suppressed constitutive nuclear factor-κB (NF-κB) activation and inhibited the protein expression of NF-kappa B-regulated antiapoptotic (IAP1, Bcl-xL, Bcl-2, XIAP) and proliferative (c-Myc) gene products. Coadministration of I3C with the topoisomerase II inhibitor, doxorubicin, potentiates cytotoxic effects compared with either agent alone. Apoptosis induction by the drug combination was associated with enhanced caspase-9 activation and PARP cleavage. Furthermore, I3C abolished doxorubicin-induced NF-κB activity as evidenced by decreased nuclear accumulation of p65, inhibition of IκBα phosphorylation and its degradation, and decreased NF-κB DNA-binding activity. Western blot analysis revealed that doxorubicin-induced Bcl-2 protein expression was inhibited by I3C. Overall, our results indicated that using nontoxic agents, such as I3C, in combination with anthracyclines might provide a new insight into the development of novel combination therapies in childhood BCP-ALL.[2]
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| Cell Assay |
In a fully humidified environment with 5% CO2, THP-1 cells are cultured in RPMI 1640 with 10% FBS, 100 U/mL penicillin, 100 mg/mL streptomycin, and 2 mM Glutamax. Six-well plates are seeded with cells (2-5×105 mL-1), and the cells are then resuspended in full growth medium. Then, 10 ng/mL phorbol 12-myristate 13-acetate is added to THP-1 monocyte cells as a tumor promoter to cause stable differentiation into adhering macrophage-like cells and overexpression of AhR. Following that, indole-3-carbinol (1, 10, 100μM, and 1 mM) is treated with various concentrations in the cells. In a 24-well plate with different concentrations of indole-3-carbinol, HP-1 cells and enriching normal monocytes are seeded at a density of 5 104 cells/well. After 24 and 48 hours, MTT assay is performed. Triplicates of the cells are incubated for 20 hours in a final volume of 200 mL of Phenol Red-free RPMI 1640. Each well is filled with an aliquot of 20 mL of MTT solution (5 mg/mL), which is then left to sit for 4 hours. Crystals of formazan grow. Then, as a cell lysis solution, 300 mL of DMSO is added to each well. Spectrophotometry at 570 nm is used to measure cell viability percentage[1].
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| Toxicity/Toxicokinetics |
rat LDLo subcutaneous 500 mg/kg
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| References |
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| Additional Infomation |
Indole-3-methanol is an indolyl alcohol carrying a hydroxymethyl group at position 3. It is a constituent of the cruciferous vegetables and had anticancer activity. It has a role as a plant metabolite and an antineoplastic agent.
Indole 3 Carbinol is under investigation in clinical trial NCT00033345 (Indole-3-Carbinol in Preventing Breast Cancer in Nonsmoking Women Who Are at High Risk For Breast Cancer). Indole-3-carbinol has been reported in Pinus sylvestris, Dalbergia, and other organisms with data available. Indole-3-Carbinol is a naturally occurring, orally available cleavage product of the glucosinolate glucobrassicanin, a natural compound present in a wide variety of plant food substances including members of the family Cruciferae with antioxidant and potential chemopreventive properties. Indole-3-carbinol scavenges free radicals and induces various hepatic cytochrome P450 monooxygenases. Specifically, this agent induces the hepatic monooxygenase cytochrome P4501A1 (CYP1A1), resulting in increased 2-hydroxylation of estrogens and increased production of the chemoprotective estrogen 2-hydroxyestrone. |
| Molecular Formula |
C9H9NO
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| Molecular Weight |
147.18
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| Exact Mass |
147.068
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| Elemental Analysis |
C, 73.45; H, 6.16; N, 9.52; O, 10.87
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| CAS # |
700-06-1
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| Related CAS # |
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| PubChem CID |
3712
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| Appearance |
White to off-white solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
360.6±17.0 °C at 760 mmHg
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| Melting Point |
96-99 °C(lit.)
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| Flash Point |
171.9±20.9 °C
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| Vapour Pressure |
0.0±0.8 mmHg at 25°C
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| Index of Refraction |
1.705
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| LogP |
0.96
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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 |
1
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| Heavy Atom Count |
11
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| Complexity |
138
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O([H])C([H])([H])C1=C([H])N([H])C2=C([H])C([H])=C([H])C([H])=C12
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| InChi Key |
IVYPNXXAYMYVSP-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C9H9NO/c11-6-7-5-10-9-4-2-1-3-8(7)9/h1-5,10-11H,6H2
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| Chemical Name |
1H-indol-3-ylmethanol
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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 (16.99 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 (16.99 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. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (16.99 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 6.7944 mL | 33.9720 mL | 67.9440 mL | |
| 5 mM | 1.3589 mL | 6.7944 mL | 13.5888 mL | |
| 10 mM | 0.6794 mL | 3.3972 mL | 6.7944 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.
| NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
| NCT00033345 | Completed | Other: Placebo Drug: Indole-3-carbinol |
Breast Cancer | University of Kansas Medical Center |
January 2002 | Phase 1 |
| NCT03687073 | Completed | Drug: Indole-3-Carbinol Drug: Silibinin |
Smoking | Masonic Cancer Center, University of Minnesota |
November 29, 2018 | Phase 1 |
| NCT00607932 | Completed | Procedure: adjuvant therapy Drug: indole-3-carbinol |
Prostate Cancer | Vanderbilt University | March 2005 | Not Applicable |
| NCT00033345 | Completed | Drug: Indole-3-carbinol Other: Placebo |
Breast Cancer | University of Kansas Medical Center |
January 2002 | Phase 1 |
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