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![2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine](https://www.biomol.com/media/image/79/af/1a/Cay22590-1_600x600.png)
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2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) is a food-derived carcinogen that is found... more
Product information "2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine"
2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) is a food-derived carcinogen that is found in high temperature-cooked fish and meat. In humans, PhIP is metabolized by the cytochrome (CYP) P450 isoform CYP1A2 and conjugated by N-acetyltransferase or sulfotransferase to a metabolite that reacts with DNA to form adducts, which are directly correlated with increased risk of breast, colon, and prostate cancers. Chronic treatment (1 pM/L for 20 cycles) of MCF-10A cells with PhIP induces anchorage-independent cell growth and reduces cellular dependence on growth factors. It increases wild-type H-Ras gene and protein expression, which activates ERK signaling, MMP-2 and MMP-9 protein expression, and NOX1-driven production of reactive oxygen species (ROS) in vitro. In vivo, PhIP pre-treatment of MCF-10A cells increases tumor formation in a murine breast cancer xenograft model. In a CYP1A2 humanized rat model, PhIP induces formation of colon tumors with beta-catenin gene mutations that hyperactivate the Wnt signaling pathway, mimicking the phenotype observed in human tumor isolates. In vivo administration of PhIP (400 ppm/week for 52 weeks) also increases the occurrence of atypical hyperplasias and carcinomas in the ventral prostate and seminal vesicles of rats.Formal Name: 1-methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine. CAS Number: 105650-23-5. Synonyms: PhIP. Molecular Formula: C13H12N4. Formula Weight: 224.3. Purity: >98%. Formulation: (Request formulation change), A crystalline solid. Solubility: DMF: 10 mg/ml, DMSO: 10 mg/ml, Ethanol: 15 mg/ml, Ethanol:PBS (pH 7.2) (1:3): 0.25 mg/ml. lambdamax: 223 nm. SMILES: CN1C(N)=NC(C1=C2)=NC=C2C3=CC=CC=C3. InChi Code: InChI=1S/C13H12N4/c1-17-11-7-10(9-5-3-2-4-6-9)8-15-12(11)16-13(17)14/h2-8H,1H3,(H2,14,15,16). InChi Key: UQVKZNNCIHJZLS-UHFFFAOYSA-N.
Keywords: | PhIP, 1-methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine |
Supplier: | Cayman Chemical |
Supplier-Nr: | 22590 |
Properties
Application: | Cooked meat carcinogen |
MW: | 224.3 D |
Formula: | C13H12N4 |
Purity: | >98% |
Format: | Crystalline Solid |
Database Information
CAS : | 105650-23-5| Matching products |
Handling & Safety
Storage: | -20°C |
Shipping: | +20°C (International: -20°C) |
Signal Word: | Danger |
GHS Hazard Pictograms: |
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H Phrases: | H301, H315, H319, H335, H351 |
P Phrases: | P201, P202, P261, P264, P270, P271, P280, P312, P321, P330, P301+P310, P302+P352, P304+P340, P305+P351+P338, P308+P313, P332+P313, P337+P313, P362+P364, P405, P403+P233, P501 |
Caution
Our products are for laboratory research use only: Not for administration to humans!
Our products are for laboratory research use only: Not for administration to humans!
Information about the product reference will follow.
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