Benzo a pyrene

Manufactured by Merck Group

Sourced in United States, Germany, United Kingdom, Spain, Sao Tome and Principe, Macao, Canada, France

Benzo[a]pyrene is a polycyclic aromatic hydrocarbon commonly used as a reference compound in various laboratory applications. It serves as a standard for analytical techniques and is often employed in research, environmental monitoring, and regulatory compliance testing.

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Lab products found in correlation

153 protocols using benzo a pyrene

Polycyclic Aromatic Hydrocarbon Analysis

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For the experiments performed in the United States, fluoranthene (Flthn; purity 97.2%) was purchased from AccuStandard (New Haven, CT, USA), benzo[a]pyrene (B[a]P; purity ≥ 96%), dimethyl sulfoxide (DMSO) and Lucifer yellow from Sigma-Aldrich (St. Louis, MO, USA) and 1-methylanthracene (1-MeA; purity 99.5%) from Crescent Chemical (Islandia, NY, USA). All PAH stock solutions and forskolin (Sigma-Aldrich) and cyclic adenosine monophosphate (cAMP, Sigma-Aldrich) stock solutions were prepared in DMSO.
For the experiments performed in Germany, benzo[a]pyrene (99.9% purity) was purchased at Sigma-Aldrich (Taufkirchen, Germany), fluoranthene (98.6% purity) from AccuStandard (New Haven, CT, USA), and 1-methylanthracene (97.71% purity) from LGC Standards (Wesel, Germany). B[a]P-tetrol I-1 was purchased from Dr. Albrecht Seidel (BIU—Biochemical Institute for Environmental Carcinogens, Großhansdorf, Germany). The DNA adduct studies and cytochrome p450 studies were all conducted in Germany. All other studies were completed at the University of Colorado Anschutz.

Bauer A.K., Siegrist K.J., Wolff M., Nield L., Brüning T., Upham B.L., Käfferlein H.U, & Plöttner S. (2022). The Carcinogenic Properties of Overlooked yet Prevalent Polycyclic Aromatic Hydrocarbons in Human Lung Epithelial Cells. Toxics, 10(1), 28.

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Analytical Protocol for BaP and AzaBaP

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Benzo[a]pyrene (BaP) and 10-Azabenzo[a]pyrene (AzaBaP) were purchased from Sigma Aldrich (Madrid, Spain). SPE Silica cartridges were obtained from Phenomenex (Madrid, Spain). The solvents used (all purchased in HPLC-gradient grade) including ethyl acetate, n-hexane, water and acetonitrile (ACN) were from Sigma–Aldrich (Madrid, Spain). All the other chemicals were of analytical grade, and were purchased from local companies.

Rey-Salgueiro L., Martínez-Carballo E., Cid A, & Simal-Gándara J. (2017). Determination of kinetic bioconcentration in mussels after short term exposure to polycyclic aromatic hydrocarbons. Heliyon, 3(1), e00231.

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Murine Model of Benzo[a]pyrene-Induced Carcinogenesis

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Female A/J mice (6 to 7 weeks old) were purchased from the Institute of Medical Science (University of Tokyo, Tokyo, Japan). Mice were fed the AIN-93M diet and housed in pathogen-free animal quarters. Fresh food was provided every 2 to 3 days and the water bottles were changed twice weekly. The diet and drinking water were provided ad libitum. The mice were maintained at room temperature (20°C ± 2°C) at a relative humidity of 50% ± 10% with ≥ 10 to 15 air changes/hour under an alternating 12-hour/12-hour light/dark cycle. The study was approved by the Institutional Animal Care and Use Committees in Department of Laboratory Animal, St. Paul's Hospital, The Catholic University of Korea (SPH-20140207-01).
Benzo[a]pyrene (B[a]P, purity > 99%) and carboplatin were purchased from Sigma (St. Louis, MO, USA). carboplatin was dissolved in double-distilled water.

Lee H.Y., Kim I.K., Lee H.I., Lee H.Y., Kang H.S., Yeo C.D., Kang H.H., Moon H.S, & Lee S.H. (2017). Combination of carboplatin and intermittent normobaric hyperoxia synergistically suppresses benzo[a]pyrene-induced lung cancer. The Korean Journal of Internal Medicine, 33(3), 541-551.

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Benzo(a)pyrene Exposure Protocol

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Anhydrous DMSO, corn oil, benzo(a)pyrene [B(a)P, purity 99%] and actinomycin D were from Sigma-Aldrich. Benzo(a)pyren-7, 8-dihydrodiol-9, 10-epoxide (BPDE, 99.9%) was from MRIGlobal (MRIGlobal). BPDE was dissolved in DMSO at

4 millimolar

and stored at

negative 80 degrees Celsius

. B(a)P was dissolved in corn oil before use. All the vehicle control or cultures included an equal amount of DMSO (0.03%, v/v).

Dai M., Huang W., Huang X., Ma C., Wang R., Tian P., Chen W., Zhang Y., Mi C, & Zhang H. (2023). BPDE, the Migration and Invasion of Human Trophoblast Cells, and Occurrence of Miscarriage in Humans: Roles of a Novel lncRNA-HZ09. Environmental Health Perspectives, 131(1), 017009.

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Comparative Analysis of AhR Ligands

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The AhR ligands were obtained from: 2,3,7,8-TCDD (TCDD) (Sigma Aldrich, 48599), FICZ (Sigma Aldrich, SML1489), Vemurafenib (Vem, PLX4032) (Selleckchem, RG7204), Dabrafenib (Dab) (Santa Cruz Biotechnology, SC364477), PLX7904 (MedChem Express, HY-18997), PLX8394 (MedChem Express, HY-18972), CH-223191 (Selleckchem, S7711), L-Kynurenine (Sigma Aldrich, K8625), Resveratrol (RSV) (Selleckchem, S1396), StemRegenin 1 (SR1) (Selleckchem, S2858), and Benzo(a)pyrene (B(a)P) (Sigma Aldrich, B1760).

Corre S., Tardif N., Mouchet N., Leclair H.M., Boussemart L., Gautron A., Bachelot L., Perrot A., Soshilov A., Rogiers A., Rambow F., Dumontet E., Tarte K., Bessede A., Guillemin G.J., Marine J.C., Denison M.S., Gilot D, & Galibert M.D. (2018). Sustained activation of the Aryl hydrocarbon Receptor transcription factor promotes resistance to BRAF-inhibitors in melanoma. Nature Communications, 9, 4775.

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Synthesis of BaP and 3-NBA

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Benzo[a]pyrene (BaP, CAS number 50-32-8; purity ≥96%) was obtained from Sigma Aldrich (UK). 3-Nitrobenzanthrone (3-NBA, CAS number 17117-34-9) was prepared as previously reported (Arlt et al., 2005 (link)).

Bussolaro D., Wright S.L., Schnell S., Schirmer K., Bury N.R, & Arlt V.M. (2019). Co-exposure to polystyrene plastic beads and polycyclic aromatic hydrocarbon contaminants in fish gill (RTgill-W1) and intestinal (RTgutGC) epithelial cells derived from rainbow trout (Oncorhynchus mykiss). Environmental pollution (Barking, Essex : 1987), 248, 706-714.

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Synthesis and Characterization of Cyclodextrin-Based Polymer Composites

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β-cyclodextrin (>98%), poly(vinyl alcohol) (M_w ca. 13,000; 98.0–98.8 mol% hydrolysis), N,N-dimethyformamide (DMF; 99%), acetone (99.5%), methanol (HPLC grade), and chloroform (99%) were obtained from Sigma-Aldrich (Darmstadt, Germany). Maleic anhydride (MA; 99%) was supplied by Acros Organics (Geel, Belgium). Chitosan with acetylation degree (DA) of 15 mol% (average molecular weight 87 × 10³ g mol⁻¹) was purchased from Golden-Shell Biochemical (Yuhuan, China). Acetonitrile was purchased from Fisher Scientific (Loughborough, UK).
BTXs-Benzene (ben; >99.7%) and xylene (xyl; mixture of isomers; >97%) were purchased from Merck KGaA (Darmstadt, Germany), toluene (tol; >99.8%) were obtained from Lab-Scan (Gliwice, Poland). PAHs—Pyrene (pyr) gas chromatography (GC) grade (>97%), benzo(b)fluoranthene (B(b)F) HPLC grade (>98%), and benzo(a)pyrene (B(a)P; >96%) were purchased from Sigma-Aldrich (Darmstadt, Germany). Deionized water was obtained using a Millipore© system (Merck KGaA, Darmstadt, Germany). All reagents were used without further purification.

Filho C.M., Bueno P.V., Matsushita A.F., Vilsinski B.H., Rubira A.F., Muniz E.C., Murtinho D.M, & Valente A.J. (2020). Uncommon Sorption Mechanism of Aromatic Compounds onto Poly(Vinyl Alcohol)/Chitosan/Maleic Anhydride-β-Cyclodextrin Hydrogels. Polymers, 12(4), 877.

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Quantitative Analysis of Lipids and PAHs

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Standards of tocopherols, phytosterols and squalene were purchased from Sigma Aldrich (St. Louis, MO, USA). Triacylglycerols were obtained from J&K Scientific (Beijing, China). Target standard compounds of polycyclic aromatic hydrocarbons (PAHs, dissolved in acetonitrile, 200 μg/mL), including benzo(a)anthracene (BaA), chrysene (Chr), benzo(b)fluoranthene BbFlu, benzo(k)fluoranthene (BkFlu), benzo(a)pyrene (BaP), dibenzo(a.h)anthracene (DBahA), benzo(g.h.i)perylene (BghiP), and indeno(1,2,3-cd)pyrene (IP), were purchased from Sigma-Aldrich (St. Louis, MO, USA). Chemical solvents were of HPLC grade. Commercial detection kits of triglyceride (TG), total cholesterol (TC), low-density lipoprotein-cholesterol (LDL-C) and high-density lipoprotein-cholesterol (HDL-C) were obtained from Nanjing Jiancheng Bioengineering Institute (Nanjing, China).

Shen Y., Zheng L., Jin J., Li X., Fu J., Wang M., Guan Y, & Song X. (2018). Phytochemical and Biological Characteristics of Mexican Chia Seed Oil. Molecules, 23(12), 3219.

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Evaluation of Complex Petroleum Substance Toxicity

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Benzo[a]pyrene (BaP; CAS no. CAS No. 50–32–8), 5-fluorouracil (CAS no. 51–21-8) and 3,4-dichloroaniline (CAS no. 95–76-1) were purchased from Sigma-Aldrich (Zwijndrecht, The Netherlands). All stocks and dilutions of test compounds were prepared in dimethyl sulfoxide (DMSO) (Merck, Darmstadt, Germany).
DMSO extracts of the sixteen complex petroleum substances (Fig. 1) were tested, including a distillate (sample SN100-DIS, CAS No. 64741–50-0), an aromatic extract (sample SN100-AE, CAS No. 64742–05-8), waxy raffinates (samples SN100-WR and SN400-WR; CAS No. 64741–89-5), base oils (sample SN100-LBO, CAS. No 64742–65-0; sample SN500-LBO, CAS. No 64742–65-0; sample SN100-BO, CAS No. 64742–56-9), a technical white oil (sample SN100-TWO, CAS No. 8042–47-5), a medicinal white oil (sample SN100-MWO, CAS No. 8042–47-5), a slackwax (sample SN400-SW, CAS No.64742–61-6), a hard paraffin wax (sample SN400-HPW, CAS No. 8002–74-2), a highly refined hard paraffin wax (sample SN400-HPHPW, CAS No.64742–51-4), a waxy brightstock (sample WBS, CAS No. not available), a brightstock slackwax (sample BSSW, CAS No. not available), a microcrystalline wax (sample MCW, CAS No. 63231–60-7), and a hydrogenated microcrystalline wax (sample HGMCW, CAS No. 64742–60-5).

Fang J., Rietjens I.M., Carrillo J.C., Boogaard P.J, & Kamelia L. (2023). Evaluating the in vitro developmental toxicity potency of a series of petroleum substance extracts using new approach methodologies (NAMs). Archives of Toxicology, 98(2), 551-565.

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Fabrication and Characterization of Polymer-Based Hybrid Materials

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β-cyclodextrin (>98%), pectin from apple (M_V: 9000; 73.9% esterification), sulfuric acid (96.5%), poly(vinyl alcohol) (M_wca. 13 000; 98.0–98.8 mol% hydrolysis), dimethylformamide (DMF) (99%), acetone (99.7%) and dialysis tubing cellulose membrane (molecular weight cut-off: 14 000 Da MWCO) were obtained from Sigma-Aldrich (Germany). Chitosan with acetylation degree of 15 mol% (M_wA: 87 × 10³ g mol⁻¹) was purchased from Golden-Shell Biochemical (China). Benzyl alcohol (99%) was obtained from Merck KGaA (Germany).
Benzene (ben) (>99.7%) and xylene (xyl) (mixture of isomers >97%) were purchased from Merck KGaA (Germany) and toluene (tol) (>99.8%) was obtained from Lab-Scan (Poland). Pyrene (pyr) (GC grade > 97%), benzo(b)fluoranthene (B(b)F) (HPLC grade > 98%) and benzo(a)pyrene (B(a)P) (>96%) were purchased from Sigma-Aldrich (Germany).
Acetonitrile and methanol, HPLC grade, were purchased from Fisher Scientific (UK) and Sigma-Aldrich (Germany), respectively. Deionized water was obtained using a Millipore© system. All reagents were used without further purification.

Filho C.M., Bueno P.V., Matsushita A.F., Rubira A.F., Muniz E.C., Durães L., Murtinho D.M, & Valente A.J. (2018). Synthesis, characterization and sorption studies of aromatic compounds by hydrogels of chitosan blended with β-cyclodextrin- and PVA-functionalized pectin. RSC Advances, 8(26), 14609-14622.

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