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Accessible (Haz class 3, 4, 5 or 8), International USD 200+
Chemical Structure| 57-97-6 Chemical Structure| 57-97-6

Structure of DMBA
CAS No.: 57-97-6

Chemical Structure| 57-97-6

DMBA

CAS No.: 57-97-6

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. 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. 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. It also has immunosuppressant activity, inhibiting proliferation of isolated mouse splenic B- and T cells stimulated ex vivo with LPS or concanavalin A, respectively, when administered at doses of 50 and 100 mg/kg. 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, initiates papilloma formation in a rat two-stage model of skin carcinogenesis.

Synonyms: 7,12-Dimethylbenz[a]anthracene; 7,12-DMBA; 7,12-Dimethylbenzanthracene

4.5 *For Research Use Only !

Cat. No.: A152001 Purity: 98%

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Boyao Zhang ; George-Eugen Maftei ; Bartosz Bartmanski ; Michael Zimmermann ;

Abstract: Organic carcinogens, in particular DNA-reactive compounds, contribute to the irreversible initiation step of tumorigenesis through introduction of genomic instability. Although carcinogen bioactivation and detoxification by human enzymes has been extensively studied, carcinogen biotransformation by human-associated bacteria, the microbiota, has not yet been systematically investigated. We tested the biotransformation of 68 mutagenic carcinogens by 34 bacterial species representative for the upper and lower human gastrointestinal tract and found that the majority (41) of the tested carcinogens undergo bacterial biotransformation. To assess the functional consequences of microbial carcinogen metabolism, we developed a pipeline to couple gut bacterial carcinogen biotransformation assays with Ames mutagenicity testing and liver biotransformation experiments. This revealed a bidirectional crosstalk between gut microbiota and host carcinogen metabolism, which we validated in gnotobiotic mouse models. Overall, the systematic assessment of gut microbiota carcinogen biotransformation and its interplay with host metabolism highlights the gut microbiome as an important modulator of exposome-induced tumorigenesis.

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Product Details of DMBA

CAS No. :57-97-6
Formula : C20H16
M.W : 256.34
SMILES Code : CC1=C(C2=CC=CC=C2C=C3)C3=C(C)C4=CC=CC=C41
Synonyms :
7,12-Dimethylbenz[a]anthracene; 7,12-DMBA; 7,12-Dimethylbenzanthracene
MDL No. :MFCD00003600
InChI Key :ARSRBNBHOADGJU-UHFFFAOYSA-N
Pubchem ID :6001

Safety of DMBA

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H301+H311+H331-H350-H370
Precautionary Statements:P201-P260-P280-P301+P310-P311
Class:6.1
UN#:2811
Packing Group:

Isoform Comparison

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

3.90mL

0.78mL

0.39mL

19.51mL

3.90mL

1.95mL

39.01mL

7.80mL

3.90mL

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