I7256
Indole-3-carbinol
Sinónimos:
3-Indolemethanol
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Fórmula empírica (notación de Hill):
C9H9NO
Número CAS:
Peso molecular:
147.17
NACRES:
NA.25
PubChem Substance ID:
UNSPSC Code:
12352005
EC Number:
211-836-2
MDL number:
Quality level:
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Permítanos ayudarleQuality Level
mp
96-99 °C (lit.)
storage temp.
2-8°C
SMILES string
OCc1c[nH]c2ccccc12
InChI
1S/C9H9NO/c11-6-7-5-10-9-4-2-1-3-8(7)9/h1-5,10-11H,6H2
InChI key
IVYPNXXAYMYVSP-UHFFFAOYSA-N
General description
Indole-3-carbinol is a novel secondary plant metabolite produced in cruciferous vegetables, such as cabbage, cauliflower and brussels sprouts.
Application
Indole-3-carbinol has been used for encapsulation with poly-lactic-co-glycolic acid (PLGA), to study its in-vitro anti-cancerogenic effects on breast adenocarcinoma epithelial (MCF7), colon adenocarcinoma epithelial (Caco2), prostate carcinoma epithelial (PC3) cells. It has also been used as a cytochrome P4501A (CYP1A) inducer.
Biochem/physiol Actions
Indole-3-carbinol (I3C) activates aryl hydrocarbon receptor (AhR) and induces G1 cell cycle arrest and apoptosis. Thus, it acts as a potential anti-cancer agent. In addition, it induces estradiol metabolism by stimulating cytochrome P450 enzymes. Therefore, I3C is considered to be a potent chemotherapeutic for various types of cancer including, breast, prostate, colon cancer, and leukemia.
Inhibits cancinogenesis at the initiation stage. Has be shown to inhibit carcinogenesis in several animal species, but it enhances tumor incidence if administered at a post-initiation stage. Found in cruciferous vegetables.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2
Clase de almacenamiento
11 - Combustible Solids
ppe
dust mask type N95 (US), Eyeshields, Gloves
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PLGA encapsulation and radioiodination of indole-3-carbinol: investigation of anticancerogenic effects against MCF7, Caco2 and PC3 cells by in vitro assays
Yildiz G, et al.
J. Radioanal. Nucl. Chem., 311(2), 1043-1052 (2017)
Profiling the hepatic effects of flutamide in rats: a microarray comparison with classical aryl hydrocarbon receptor ligands and atypical CYP1A inducers
Coe KJ, et al.
Drug Metabolism and Disposition, 34(7), 1266-1275 (2006)
Stephen Safe et al.
Cancer letters, 269(2), 326-338 (2008-05-27)
Indole-3-carbinol (I3C) conjugates are phytochemicals expressed in brassica vegetables and have been associated with the anticancer activities of vegetable consumption. I3C and its metabolite bis(3'-indolyl)methane (DIM) induce overlapping and unique responses in multiple cancer cell lines and tumors, and these
Effects of dietary indole-3-carbinol on estradiol metabolism and spontaneous mammary tumors in mice
Bradlow HL, et al.
Carcinogenesis, 12(9), 1571-1574 (1991)
Chemoprevention of chemically-induced mammary carcinogenesis by indole-3-carbinol.
Grubbs CJ, et al.
Anticancer Research, 15(3), 709-716 (1995)
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