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Type | HazMat fee for 500 gram (Estimated) |
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Structure of 90-94-8
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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*For Research Use Only !
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Systematic analysis of gut bacterial carcinogen metabolism and its functional consequences
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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Purchased from AmBeed: 446-86-6 ; 121-66-4 ; 607-35-2 ; 67-20-9 ; 105650-23-5 ; 59-87-0 ; 117-39-5 ; 57-97-6 ; 5131-60-2 ; 512-56-1 ; 62-44-2 ; 6959-48-4 ; 84-65-1 ; 137-17-7 ; 117-39-5 ; 153-78-6 ; 1614-12-6 ; 298-81-7 ; 404-86-4 ; 320-67-2 ; 99-55-8 ; 94-52-0 ; 2832-40-8 ; 101-61-1 ; 103-33-3 ; 114-83-0 ; 64091-91-4 ; 53-96-3 ; 3817-11-6 ; 90-94-8 ; 613-13-8 ; 56-57-5 ; 91-64-5 ; 26148-68-5 ; 101-80-4 ; 139-65-1 ; 366-70-1 ; 389-08-2 ; 99-59-2 ; 132-32-1 ; 394-69-4 ; 3544-23-8 ; 389-08-2 ; 320-67-2 ; 82-28-0 ; 2475-45-8 ; 129-15-7
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CAS No. : | 90-94-8 |
Formula : | C17H20N2O |
M.W : | 268.35 |
SMILES Code : | O=C(C1=CC=C(N(C)C)C=C1)C2=CC=C(N(C)C)C=C2 |
MDL No. : | MFCD00008312 |
InChI Key : | VVBLNCFGVYUYGU-UHFFFAOYSA-N |
Pubchem ID : | 7031 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H318-H341-H350 |
Precautionary Statements: | P201-P280-P305+P351+P338-P308+P313 |
Class: | 8(6.1) |
UN#: | 2923 |
Packing Group: | Ⅲ |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With n-butyllithium; In tetrahydrofuran; at 45℃; | 9-phenyl-9H-carbazole (1.0 g, 2.49 mmol, 1.0 eq) was dissolved in 35 ml of tetrahydrofuran, followed by the addition of bis (4- (dimethylamino) phenyl) methanone (1.6 g, 5.34 mmol, Was slowly added to a flask dissolved in 25 ml of tetrahydrofuran at 45 DEG C and stirred.After the reaction was completed, the reaction mixture was distilled under reduced pressure to remove the solvent. The solvent was distilled off with distilled H 2 O (100 ml × 3), dried over MgSO 4, filtered and dried to obtain 9-phenyl-9H-carbazole-3,6-diyl bis - (dimethylamino) phenyl) methanol (1.4 g). The solution was dissolved in a mixture of 35 ml of methanol and 35 ml of hydrogenchloride, followed by heating and stirring at 80 ° C for 2 hours. After the reaction was completed, the solvent was distilled off, and the solvent was removed. A small amount of distilled water was added thereto, and after work-up, water was removed with MgSO 4, filtered and dried to obtain G-3 (1.3 g, yield: 69.90percent |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With n-butyllithium; In tetrahydrofuran; at 45℃; | Dibromodibenzo [b, d] furan (1.0 g, 3.07 mmol, 1.0 eq) was dissolved in tetrahydrofuran (35 ml) followed by the addition of Tetrahydrofuran To a 25 ml flaskThe mixture was gradually added at 45 and stirred. After completion of the reaction, the reaction mixture was distilled under reduced pressure to remove the solvent. The solvent was distilled off (100 ml X 3), and the filtrate was dried over MgSO 4, filtered, and dried to obtain dibenzo [b, d] furan-2,8-diylbis ) Phenyl) methanol (1.7 g). The solution was dissolved in 35 ml of methanol and 35 ml of hydrogen chloride, followed by heating and stirring at 80 ° C for 2 hours. After the reaction was completed, the solvent was distilled off to remove the solvent, and then a small amount of distilled water was added thereto. After the work-up, water was removed with MgSO 4 and filtered to obtain G-4 (1.3 g, yield 63.17percent |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With n-butyllithium; In tetrahydrofuran; at 45℃; | 2,2'-dibromo-9,9'-spirobi [fluorene] (1.0 g, 2.11 mmol, 2.05 eq) was dissolved in 35 ml of tetrahydrofuran, 1.0 eq) was slowly added to a flask dissolved in 25 ml of tetrahydrofuran at 45 DEG C and stirred. After the completion of the reaction, the solvent was distilled off under reduced pressure to remove the solvent. After work-up with distilled water (100 ml X 3), water was removed with MgSO 4, and the product was filtered and dried. Thereafter, 9,9'- spirobi [fluorene] -3,6-diylbis (Dimethylamino) phenyl) methanol (1.5 g). The solution was dissolved in a mixture of 35 ml of methanol and 35 ml of hydrogenchloride, followed by heating and stirring at 80 ° C for 2 hours. After completion of the reaction, the reaction mixture was distilled under reduced pressure to remove the solvent and then added with a small amount of distilled water. After the work-up, water was removed with MgSO 4, filtered and dried to obtain G-8 (1.3 g, yield 75.26percent |