A food-derived carcinogen; metabolized by CYP1A2 and conjugated by N-acetyltransferase or sulfotransferase to a metabolite that reacts with DNA to form adducts; chronic treatment (1 pM/L for 20 cycles) of MCF-10A cells induces anchorage-independent cell growth and reduces cellular dependence on growth factors; increases wild-type H-Ras gene and protein expression which activates ERK signaling

2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine – 5 mg

Brand:
Cayman
CAS:
105650-23-5
Storage:
-20
UN-No:
De Minimis - 2811 / 6.1

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.{38226} 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.{38226,38227,38228} 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.{38226} 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 β-catenin gene mutations that hyperactivate the Wnt signaling pathway, mimicking the phenotype observed in human tumor isolates.{38228} 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.{38227}  

 

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Description

A food-derived carcinogen; metabolized by CYP1A2 and conjugated by N-acetyltransferase or sulfotransferase to a metabolite that reacts with DNA to form adducts; chronic treatment (1 pM/L for 20 cycles) of MCF-10A cells induces anchorage-independent cell growth and reduces cellular dependence on growth factors; 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 ROS in vitro; increases tumor formation in a murine breast cancer xenograft model; induces formation of colon tumors with β-catenin gene mutations that hyperactivate the Wnt signaling pathway in a CYP1A2 humanized rat model; 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

Synonyms:  PhIP

Molecular weight: 224.3

CAS: 105650-23-5

Purity: ≥98%

Formulation: A crystalline solid

Product Type|Biochemicals||Research Area|Cancer|Cell Migration & Metastasis||Research Area|Cancer|Cell Signaling|ERK/MAPK Signaling||Research Area|Cancer|Cell Signaling|Wnt Signaling||Research Area|Cancer|DNA Damage and Repair||Research Area|Cancer|Tumor Microenvironment||Research Area|Toxicology|Drug Metabolism|Cytochrome P450

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