A food-derived carcinogen
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2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine

Item No. 22590

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
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(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 10 mg/mlEthanol: 15 mg/mlEthanol:PBS (pH 7.2) (1:3): 0.25 mg/ml
λmax
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    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.1 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.1,2,3 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.1 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.3 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.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Choudhary, S., Sood, S., Donnell, R.L., et al. Intervention of human breast cell carcinogenesis chronically induced by 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine. Carcinogenesis 33(4), 876-885 (2012).

    2. Shirai, T., Sano, M., Tamano, S., et al. The prostate: A target for carcinogenicity of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) derived from cooked foods. Cancer Res. 57(2), 195-198 (1997).

    3. Wang, H., Zhou, H., Liu, A., et al. Genetic analysis of colon tumors induced by a dietary carcinogen PhIP in CYP1A humanized mice: Identification of mutation of β-catenin/Ctnnb1 as the driver gene for the carcinogenesis. Mol. Carcinog. 54(11), 1264-1274 (2015).