A carcinogenic PAH
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7,12-Dimethylbenz[a]anthracene

Item No. 30383

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
CAS Number
57-97-6
Synonyms
  • DMBA
Molecular Formula
C20H16
Formula Weight
256.3
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 10 mg/ml
λmax
212, 222, 264, 275, 285, 296 nm
SMILES
CC1=C2C=CC=CC2=C(C)C3=C4C(C=CC=C4)=CC=C13
InChi Code
InChI=1S/C20H16/c1-13-16-8-5-6-9-17(16)14(2)20-18(13)12-11-15-7-3-4-10-19(15)20/h3-12H,1-2H3
InChi Key
ARSRBNBHOADGJU-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    7,12-Dimethylbenz[a]anthracene (DMBA) is a polycyclic aromatic hydrocarbon (PAH) that has been found in tobacco smoke and diesel exhaust and has carcinogenic activity.1,2 It undergoes metabolic activation by numerous enzymes, including the cytochrome P450 (CYP450) isoform CYP1B1, as well as microsomal epoxide hydrolase (mEH), producing a variety of reactive metabolites that form DNA adducts in vivo, and it has been commonly used to induce tumor formation in various rodent models.2,3,1 DMBA increases proliferation and migration of, and induces epithelial-to-mesenchymal transition (EMT) in, MCF-10A breast cancer cells when used at a concentration of 5 µM.4 It also has immunosuppressant activity, inhibiting proliferation of isolated mouse splenic B- and T cells stimulated ex vivo with LPS or concanavalin A (Item No. 14951), respectively, when administered at doses of 50 and 100 mg/kg.5 Intragastric administration of DMBA (20 mg/animal) induces formation of mammary gland tumors in rats.6 DMBA (50 µg/animal), in combination with phorbol 12-myristate 13-acetate (TPA; Item No. 10008014), initiates papilloma formation in a rat two-stage model of skin carcinogenesis.7

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Rengarajan, T., Rajendran, P., Nandakumar, N., et al. Exposure to polycyclic aromatic hydrocarbons with special focus on cancer. Asian Pac. J. Trop. Biomed. 5(3), 182-189 (2015).

    2. Csiszar, A., Balasubramanian, B., Tarantini, S., et al. Chemically induced carcinogenesis in rodent models of aging: Assessing organismal resilience to genotoxic stressors in geroscience research. Geroscience 41(2), 209-227 (2019).

    3. Huberman, E., Chou, M.W., and Yang, S.K. Identification of 7,12-dimethylbenz[a]anthracene metabolites that lead to mutagenesis in mammalian cells. Proc. Natl. Acad. Sci. USA 76(2), 862-866 (1979).

    4. Kwon, Y.-J., Ye, D.-J., Baek, H.-S., et al. 7,12-Dimethylbenz[α]anthracene increases cell proliferation and invasion through induction of Wnt/β-catenin signaling and EMT process. Environ. Toxicol. 33(7), 729-742 (2018).

    5. Gao, J., Lauer, F.T., Dunaway, S., et al. Cytochrome P450 1B1 is required for 7,12-dimethylbenz(a)-anthracene (DMBA) induced spleen cell immunotoxicity. Toxicol. Sci. 86(1), 68-74 (2005).

    6. Barros, A.C.S.D., Muranaka, E.N.K., Mori, L.J., et al. Induction of experimental mammary carcinogenesis in rats with 7,12-dimethylbenz(a)anthracene. Rev. Hosp. Clin. Fac. Med. Sao Paulo 59(5), 257-261 (2005).

    7. Vähätupa, M., Pemmari, T., Junttila, I., et al. Chemical-Induced Skin Carcinogenesis Model Using Dimethylbenz[a]Anthracene and 12-O-Tetradecanoyl Phorbol-13-Acetate (DMBA-TPA). J. Vis. Exp. 154 (2019).