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MedKoo Cat#: 463372 | Name: DMBA
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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.

Chemical Structure

DMBA
DMBA
CAS#57-97-6

Theoretical Analysis

MedKoo Cat#: 463372

Name: DMBA

CAS#: 57-97-6

Chemical Formula: C20H16

Exact Mass: 256.1252

Molecular Weight: 256.35

Elemental Analysis: C, 93.71; H, 6.29

Price and Availability

Size Price Availability Quantity
100mg USD 285.00 2 Weeks
250mg USD 550.00 2 Weeks
1g USD 950.00 2 Weeks
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Related CAS #
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Synonym
DMBA; 7,12-Dimethylbenz[a]anthracene; 7,12 Dimethylbenz[a]anthracene; 7,12-DIMETHYLBENZANTHRACENE
IUPAC/Chemical Name
7,12-dimethyltetraphene
InChi Key
ARSRBNBHOADGJU-UHFFFAOYSA-N
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
SMILES Code
CC1=C2C=CC=CC2=C(C3=C4C(C=CC=C4)=CC=C13)C
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Certificate of Analysis
View CoA: current batch, Lot#C25M01C24
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction
Biological target:
DMBA has carcinogenic activity as a polycyclic aromatic hydrocarbon (PAH).
In vitro activity:
In this experiment, a profound reduction in MCF-7 cell growth, proliferation and invasion was ascertained following extensive downregulation of mTOR expression. NL-mTOR-siRNA suppressed tumour growth and restored morphological alterations of DMBA-induced breast cancer. Reference: Br J Cancer. 2022 Oct 19. https://pubmed.ncbi.nlm.nih.gov/36261586/
In vivo activity:
The present study was designed to investigate the anti-cancer effect of Canagliflozin (CNG) in an experimental model of DMBA-induced mammary carcinoma in female rats. Reference: Biomed Pharmacother. 2022 Nov;155:113675. https://pubmed.ncbi.nlm.nih.gov/36115110/
Solvent mg/mL mM
Solubility
DMF 20.0 78.02
DMSO 17.5 68.27
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 256.35 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Sahu R, Jha S, Pattanayak SP. Therapeutic silencing of mTOR by systemically administered siRNA-loaded neutral liposomal nanoparticles inhibits DMBA-induced mammary carcinogenesis. Br J Cancer. 2022 Oct 19. doi: 10.1038/s41416-022-02011-1. Epub ahead of print. PMID: 36261586. 2. El Makawy AI, Mabrouk DM, Mohammed SE, Abdel-Aziem SH, El-Kader HAA, Sharaf HA, Youssef DA, Ibrahim FM. The suppressive role of nanoencapsulated chia oil against DMBA-induced breast cancer through oxidative stress repression and tumor genes expression modulation in rats. Mol Biol Rep. 2022 Nov;49(11):10217-10228. doi: 10.1007/s11033-022-07885-1. Epub 2022 Sep 5. PMID: 36063350; PMCID: PMC9618492. 3. Sabaa M, Sharawy MH, El-Sherbiny M, Said E, Salem HA, Ibrahim TM. Canagliflozin interrupts mTOR-mediated inflammatory signaling and attenuates DMBA-induced mammary cell carcinoma in rats. Biomed Pharmacother. 2022 Nov;155:113675. doi: 10.1016/j.biopha.2022.113675. Epub 2022 Sep 15. PMID: 36115110.
In vitro protocol:
1. Sahu R, Jha S, Pattanayak SP. Therapeutic silencing of mTOR by systemically administered siRNA-loaded neutral liposomal nanoparticles inhibits DMBA-induced mammary carcinogenesis. Br J Cancer. 2022 Oct 19. doi: 10.1038/s41416-022-02011-1. Epub ahead of print. PMID: 36261586.
In vivo protocol:
1. El Makawy AI, Mabrouk DM, Mohammed SE, Abdel-Aziem SH, El-Kader HAA, Sharaf HA, Youssef DA, Ibrahim FM. The suppressive role of nanoencapsulated chia oil against DMBA-induced breast cancer through oxidative stress repression and tumor genes expression modulation in rats. Mol Biol Rep. 2022 Nov;49(11):10217-10228. doi: 10.1007/s11033-022-07885-1. Epub 2022 Sep 5. PMID: 36063350; PMCID: PMC9618492. 2. Sabaa M, Sharawy MH, El-Sherbiny M, Said E, Salem HA, Ibrahim TM. Canagliflozin interrupts mTOR-mediated inflammatory signaling and attenuates DMBA-induced mammary cell carcinoma in rats. Biomed Pharmacother. 2022 Nov;155:113675. doi: 10.1016/j.biopha.2022.113675. Epub 2022 Sep 15. PMID: 36115110.
1: Hendi AA, Elnagar DM, Awad MA, Ortashi KM, Alnamlah RA, Merghani NM. Green nanogold activity in experimental breast carcinoma in vivo. Biosci Rep. 2020 Nov 9:BSR20200115. doi: 10.1042/BSR20200115. Epub ahead of print. PMID: 33165619. 2: Herrera-Calderon O, Yepes-Pérez AF, Quintero-Saumeth J, Rojas-Armas JP, Palomino-Pacheco M, Ortiz-Sánchez JM, Cieza-Macedo EC, Arroyo-Acevedo JL, Figueroa-Salvador L, Peña-Rojas G, Andía-Ayme V. Carvacrol: An In Silico Approach of a Candidate Drug on HER2, PI3Kα, mTOR, hER-α, PR, and EGFR Receptors in the Breast Cancer. Evid Based Complement Alternat Med. 2020 Oct 26;2020:8830665. doi: 10.1155/2020/8830665. PMID: 33163084; PMCID: PMC7607278. 3: Ramu A, Ali D, Alarifi S, Hussain SAM, Ahmed BA. Reserpine inhibits DNA repair, cell proliferation, invasion and induces apoptosis in oral carcinogenesis via modulation of TGF-β signaling. Life Sci. 2020 Nov 5:118730. doi: 10.1016/j.lfs.2020.118730. Epub ahead of print. PMID: 33160994. 4: Wang J, Hu Y, Yuan J, Zhang Y, Wang Y, Yang Y, Alahmadi TA, Ali Alharbi S, Zhuang Z, Wu F. Chemomodulatory effect of neferine on DMBA-induced squamous cell carcinogenesis: Biochemical and molecular approach. Environ Toxicol. 2020 Nov 6. doi: 10.1002/tox.23051. Epub ahead of print. PMID: 33156559. 5: Pathak P, Rimac H, Grishina M, Verma A, Potemkin V. Design, synthesis, and computational study of hybrid quinazoline 1,3,5-triazines as epidermal growth factor receptor (EGFR) inhibitors with anticancer activity. ChemMedChem. 2020 Nov 5. doi: 10.1002/cmdc.202000646. Epub ahead of print. PMID: 33155373. 6: Nasti TH, Yusuf N, Sherwani MA, Athar M, Timares L, Elmets CA. Regulatory T cells play an important role in the prevention of murine melanocytic nevi and melanomas. Cancer Prev Res (Phila). 2020 Nov 4:canprevres.0360.2020. doi: 10.1158/1940-6207.CAPR-20-0360. Epub ahead of print. PMID: 33148679. 7: Rina YA, Schmidt JAR. Double Hydrophosphorylation of Nitriles Catalyzed by Rare-Earth-Metal Lanthanum. J Org Chem. 2020 Oct 30. doi: 10.1021/acs.joc.0c02016. Epub ahead of print. PMID: 33125235. 8: Rajendran P, Alzahrani AM, Rengarajan T, Veeraraghavan VP, Krishna Mohan S. Consumption of reused vegetable oil intensifies BRCA1 mutations. Crit Rev Food Sci Nutr. 2020 Oct 27:1-8. doi: 10.1080/10408398.2020.1837725. Epub ahead of print. PMID: 33107328. 9: Akhouri V, Kumari M, Kumar A. Therapeutic effect of Aegle marmelos fruit extract against DMBA induced breast cancer in rats. Sci Rep. 2020 Oct 22;10(1):18016. doi: 10.1038/s41598-020-72935-2. PMID: 33093498; PMCID: PMC7581526. 10: Metibemu DS, Akinloye OA, Akamo AJ, Okoye JO, Ojo DA, Morifi E, Omotuyi IO. Carotenoid isolates of Spondias mombin demonstrate anticancer effects in DMBA- induced breast cancer in Wistar rats through X-linked inhibitor of apoptosis protein (XIAP) antagonism and anti-inflammation. J Food Biochem. 2020 Oct 20:e13523. doi: 10.1111/jfbc.13523. Epub ahead of print. PMID: 33084091. 11: Pu Y, Hu S, Chen Y, Zhang Q, Xia C, Deng H, Wang Y, Hu Q. Thymoquinone loaded calcium alginate and polyvinyl alcohol carrier inhibits the 7,12-dimethylbenz[a]anthracene-induced hamster oral cancer via the down- regulation of PI3K/AKT/mTOR signaling pathways. Environ Toxicol. 2020 Oct 17. doi: 10.1002/tox.23040. Epub ahead of print. PMID: 33068063. 12: Dosumu OA, Rotimi SO, Adeleye OO, Akamo AJ, Osinuga KT, Taiwo OA, Omotosho OO, Sani LO. Vitamin K protects against 7,12-dimethylbenz(A)anthracene induced hepatotoxicity in Wistar rats. Environ Toxicol. 2020 Oct 16. doi: 10.1002/tox.23042. Epub ahead of print. PMID: 33063951. 13: Deng Y, Ma M, Guo G, Tang Z. Kirenol regulates the cell proliferative and inflammatory markers in DMBA-induced oral squamous cell carcinogenesis in hamster. Environ Toxicol. 2020 Oct 12. doi: 10.1002/tox.23039. Epub ahead of print. PMID: 33044773. 14: Kang MJ, Gong JE, Kim JE, Choi HJ, Bae SJ, Choi YJ, Lee SJ, Seo MS, Kim KS, Jung YS, Cho JY, Lim Y, Hwang DY. Correction to: Influence of three BALB/c substrain backgrounds on the skin tumor induction efficacy to DMBA and TPA cotreatment. Lab Anim Res. 2020 Oct 6;36:35. doi: 10.1186/s42826-020-00067-9. Erratum for: Lab Anim Res. 2020 Sep 3;36:30. PMID: 33042782; PMCID: PMC7542335. 15: Tan YT, Kesselheim AS. Implementing U.S. Covid-19 Testing: Regulatory and Infrastructural Challenges. J Law Med Ethics. 2020 Sep;48(3):606-612. doi: 10.1177/1073110520958889. PMID: 33021179. 16: Mehraban F, Mostafazadeh M, Sadeghi H, Azizi A, Akbartabar Toori M, Gramizadeh B, Barati V, Sadeghi H. Anticancer activity of Astragalus ovinus against 7, 12 dimethyl benz (a) anthracene (DMBA)-induced breast cancer in rats. Avicenna J Phytomed. 2020 Sep-Oct;10(5):533-545. PMID: 32995331; PMCID: PMC7508319. 17: Muqbil I, Fatima S, Azmi AS, Alsharidah AS, Khan SA, Aljaser F, Banu N. Restraint stress abates the antioxidant potential of melatonin on dimethyl benz (a) anthracene (DMBA) induced carcinogenesis. Med Oncol. 2020 Sep 29;37(10):96. doi: 10.1007/s12032-020-01422-5. PMID: 32990835; PMCID: PMC7522450. 18: Reis Conceição N, Nesterova OV, Rajnák C, Boča R, Pombeiro AJL, Guedes da Silva MFC, Nesterov DS. New members of the polynuclear manganese family: MnMn single-molecule magnets and MnMn antiferromagnetic complexes. Synthesis and magnetostructural correlations. Dalton Trans. 2020 Oct 20;49(40):13970-13985. doi: 10.1039/d0dt02652b. PMID: 32985628. 19: Mutlu EG, Baltaci SB. Zinc and melatonin supplementation ameliorates brain cortex tissue damage in DMBA-induced breast cancer in rats. Bratisl Lek Listy. 2020;121(10):749-752. doi: 10.4149/BLL_2020_122. PMID: 32955908. 20: Wickramasinghe PCK, Munafo JP Jr. Fermentation Dynamics and Benzylic Derivative Production in Ischnoderma resinosum Isolates. ACS Omega. 2020 Aug 24;5(35):22268-22277. doi: 10.1021/acsomega.0c02550. PMID: 32923784; PMCID: PMC7482237.