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3 methylcholanthrene 3 mc

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3-methylcholanthrene (3-MC) is a chemical compound used in laboratory research. It is a polycyclic aromatic hydrocarbon. 3-MC is a solid substance.

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Lab products found in correlation

Ch223191, by Merck Group (2 mentions) Dimethyl sulfoxide (dmso), by Merck Group (2 mentions) Neutral buffered 10 formalin solution, by Merck Group (1 mentions) 2 3 7 8 tetrachlorodibenzo p dioxin tcdd, by Merck Group (1 mentions) Mtp 810, by Corona Electric (1 mentions) Glycidol, by Fujifilm (1 mentions) Glyoxal, by Fujifilm (1 mentions) 1 methyl 3 nitro 1 nitrosoguanidine mnng, by Tokyo Chemical Industry (1 mentions) 7 12 dimethylbenz a anthracene dmba, by Tokyo Chemical Industry (1 mentions) Rifampicin, by Merck Group (1 mentions) Dexamethasone (dex), by Fujifilm (1 mentions) Omeprazole, by Fujifilm (1 mentions) Triiodothyronine t3, by Merck Group (1 mentions) P450 glotm cyp3a assay, by Promega (1 mentions) Luciferin ipa, by Promega (1 mentions)

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3-methylcholanthrene (21 citations)

7 protocols using 3 methylcholanthrene 3 mc

1

Hepatotoxicity Evaluation with 3-Methylcholanthrene

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For chemical treatments, a 100-mg vial of 3-methylcholanthrene (3MC) was purchased from Sigma-Aldrich (St. Louis, MO, USA) at an HPLC purity of >97.5%. Dimethyl sulfoxide (DMSO) and CH223191 were also purchased from Sigma-Aldrich. One-hundred percent pure corn oil (CO) was purchased from a local grocer. A 10 mg/mL stock of 3MC was made and this solution was made fresh before injection and disposed of after 30 days. Liver sections for H&E staining were preserved in neutral buffered 10% formalin solution (Sigma-Aldrich), and liver sections for Oil Red O were suspended in VWR® Clear Frozen Section Compound (Radnor, PA, USA) to embed tissues for cryosectioning. The Infinity™ ALT Liquid Stable Reagent was purchased from Fisher Diagnostics (Middletown, VA, USA) for use in the in vitro determination of ALT activity in mouse serum.
Cho T.E., Bott D., Ahmed S., Hutin D., Gomez A., Tamblyn L., Zhou A.C., Watts T.H., Grant D.M, & Matthews J. (2019). 3-Methylcholanthrene Induces Chylous Ascites in TCDD-Inducible Poly-ADP-Ribose Polymerase (Tiparp) Knockout Mice. International Journal of Molecular Sciences, 20(9), 2312.
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2

Synthesis and Purification of Chlorinated Biphenyls

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PCB 126 (3,3′,4,4′,5-pentachlorobiphenyl) was synthesized by Dr. Gregor Luthe using a modified Suzuki-coupling method as previously reported (Luthe et al. 2009 (link)), purified by aluminum oxide column and flash silica gel column chromatography, and recrystallized from methanol. The final product purity (> 99.8%) and identity were confirmed by GC–MS and 13C NMR. PCB 153 (2,2′,4,4′,5,5′-hexachorobiphenyl), PCB 154 (2,2′,4,4′,5,6′-hexachlorobiphenyl), PCB155 (2,2′,4,4′,6,6′-hexachlorobiphenyl), and PCB184 (2,2′,3,4,4′,6,6′-heptachlorobiphenyl) were generously provided by Dr. Hans-Joachim Lehmler (University of Iowa Superfund Research Program). 3-methylcholanthrene (3-MC) and 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) were purchased from Sigma-Aldrich (St. Louis, MO). All other reagents were obtained from Fisher Scientific (Pittsburgh, PA), if not stated otherwise, and were the highest purity available.
Shen H., Robertson L.W, & Ludewig G. (2015). Regulatory effects of dioxin-like and non-dioxin-like PCBs and other AhR ligands on the antioxidant enzymes paraoxonase 1/2/3. Environmental science and pollution research international, 23(3), 2108-2118.
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3

Assessing CYP1A1 Activity via EROD Assay

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Activity of cytochrome P450 1A1 enzyme was assessed using ethoxyresorufin-O-deethylase (EROD) assay as described previously32 (link). Briefly, 48 h before EROD assay, primary rat hepatocytes cultured either in cell fibers or in collagen-coated well-plates started to be treated with 3 mM of the CYP1A1 inducer, 3 methylcholanthrene (3-MC; Sigma-Aldrich), contained in DMEM with a final concentration of 0.1% of dimethylsulfoxide (DMSO; Sigma-Aldrich). The media containing inducers were changed daily during the treatment. In the procedures of EROD assay, inducer-treated primary rat hepatocytes were incubated with 25 µM of EROD substrate for 1 h and subsequently the absorbency of samples at 530 nm was measured by a microplate reader (MTP-810, Corona Electric, Japan).
Mazari-Arrighi E., Okitsu T., Teramae H., Aoyagi H., Kiyosawa M., Yano M., Chatelain F., Fuchs A, & Takeuchi S. (2022). In vitro proliferation and long-term preservation of functional primary rat hepatocytes in cell fibers. Scientific Reports, 12, 8813.
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4

Genotoxic Compound Acquisition for Research

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1-methyl-3-nitro-1-nitrosoguanidine (MNNG; CASRN. 70-25-7), methyl methanesulfonate (MMS; CASRN. 66-27-3), 4-nitroquinoline N-oxide (4NQO; CASRN. 56-57-5), propylene oxide (PO; CASRN. 75-56-9), 2-acetamidofluorene (2AAF; CASRN. 53-96-3) and 7,12-dimethylbenz[a]anthracene (DMBA; CASRN. 57-97-6) were purchased from Tokyo Chemical Industry Co. Ltd. (Tokyo, Japan). Glyoxal (CASRN. 107-22-2) and glycidol (CASRN. 556-52-5) were purchased from FUJIFILM Wako Pure Chemical Corporation (Osaka, Japan). Formaldehyde (FA; CASRN. 50-00-0), 2-aminoanthracene (2AA; CASRN. 613-13-8) and 3-methylcholanthrene (3MC; CASRN. 56-49-5) were purchased from Sigma-Aldrich (St. Louis, MO, USA).
Otsubo Y., Matsumura S., Ikeda N, & Morita O. (2021). Hawk-Seq™ differentiates between various mutations in Salmonella typhimurium TA100 strain caused by exposure to Ames test-positive mutagens. Mutagenesis, 36(3), 245-254.
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5

Preparation of Cytotoxic Compounds

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3-Methylcholanthrene (3MC) and CH223191 (1-Methyl-N-[2-methyl-4-[2-(2-methylphenyl)diazenyl]phenyl-1H-pyrazole-5-carboxamide) were purchased from Sigma-Aldrich (Milan, Italy). (3aS,4R,9bR)-4-(6-bromo-1,3-benzodioxol-5-yl)-3a,4,5,9b-3H-cyclopenta [c] quinolone (G15) and 1-[2,(3,5-dimethoxyphenyl) ethenyl]-2,4-dimethoxybenzene (TMS) were obtained from Tocris Bioscience (Space, Milan, Italy). Mithramycin A (MTM A) was purchased from Abcam (Euroclone, Milan, Italy). CH223191 and G15 were dissolved in dimethyl sulfoxide (DMSO), 3MC in toluene and MTM A in ethanol. All reagents were used at concentrations previously reported [61 (link)–63 (link)].
Cirillo F., Lappano R., Bruno L., Rizzuti B., Grande F., Guzzi R., Briguori S., Miglietta A.M., Nakajima M., Di Martino M.T, & Maggiolini M. (2019). AHR and GPER mediate the stimulatory effects induced by 3-methylcholanthrene in breast cancer cells and cancer-associated fibroblasts (CAFs). Journal of Experimental & Clinical Cancer Research : CR, 38, 335.
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6

Synthesis and Characterization of Methylated Benzimidazoles

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The structures of the 4-MeMBI, 5-MeMBI and MBI are shown in Fig. 1. 4(5)-MeMBI (CAS No. 53988-10-6) was supplied from Ohuchi Shinko Chemical Ind., Ltd. (Tokyo, Japan). 5-MeMBI (CAS No. 27231-36-3, PubChem CID: 712373), 3-methylcholanthrene (3-MC, CAS No. 56-49-5) and rifampicin (CAS No. 13292-46-1) were purchased from Sigma-Aldrich Co. LLC. (Merck KGaA, Darmstadt, Germany). 4-MeMBI (CAS No. 27231-33-0, PubChem CID: 3034478) was isolated from 4(5)-MeMBI by repeated fractional recrystallization [18 ]. MBI (CAS No. 583-39-1, PubChem CID: 707035), dexamethasone (CAS No. 50-02-2) and omeprazole (CAS No. 73590-58-69) were purchased from Wako Pure Chemical Industries (Osaka, Japan). These chemicals were dissolved in dimethyl sulfoxide (DMSO; final concentration 0.1 %) before the addition to the culture medium.

Structures of 4-methyl-2-mercaptobenzimidazole (4-MeMBI), 5-methyl-2-mercaptobenzimidazole (5-MeMBI) and 2-mercaptobenzimidazole (MBI). 4(or 5)-Methyl-MBI (4(5)-MeMBI) is not shown because it is a 1:1 mixture of 4-MeMBI and 5-MeMBI. Thioureylene structure is depicted in bold. Marvin was partly used for drawing the chemical structures [Marvin JS (19.11.0), 2019, ChemAxon (http://www.chemaxon.com)].

Fig. 1
Miyajima A., Kuroda Y., Sakemi-Hoshikawa K., Usami M., Mitsunaga K., Irie T., Ohno Y, & Sunouchi M. (2020). Inhibitory and inductive effects of 4- or 5-methyl-2-mercaptobenzimidazole, thyrotoxic and hepatotoxic rubber antioxidants, on several forms of cytochrome P450 in primary cultured rat and human hepatocytes. Toxicology Reports, 7, 979-985.
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7

Thyroid Hormone and CYP3A Interaction

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Triiodothyronine (T3) and 3-methylcholanthrene (3-MC) were purchased from Sigma-Aldrich (St. Louis, MO, USA). Thyroxine (T4) was purchased from Tokyo Chemical Industry Co., Ltd. (Tokyo, Japan). Dexamethasone (DEX) was purchased from Nacalai tesque (Kyoto, Japan). The P450-Glo TM CYP3A assay with Luciferin-IPA and Luciferin-MultiCYP were purchased from Promega (Fitchburg, WI, USA).
Mori J., Sanoh S., Kashiwagi K., Hanada H., Shigeta M., Suzuki K.T., Yamamoto T., Kotake Y., Sugihara K., Kitamura S., Kashiwagi A, & Ohta S. (2017). Developmental changes in drug-metabolizing enzyme expression during metamorphosis of Xenopus tropicalis. The Journal of toxicological sciences, 42(5).
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