Benzo[a]pyrene (3,4-Benzopyrene)

Benzo[a]pyrene (3,4-Benzopyrene) (BaP, B[a]P)は多環芳香族炭化水素であり、ピレンに縮合したベンゼン環で構成される^[1]。Benzo[a]pyrene (3,4-Benzopyrene)のジオールエポキシド代謝物であるBPDEは、DNAと反応し結合し、その結果、突然変異と発癌を起こした^[3]。Benzo[a]pyrene (3,4-Benzopyrene)は神経系、免疫系と発癌性には毒性を持つ^[3]。

体外で、Benzo[a]pyrene (3,4-Benzopyrene) (0.2µg/ml；24時間)はヒト乳腺上皮細胞の変形を誘発する^[4]。Benzo[a]pyrene (3,4-Benzopyrene) (1,5, 10μM；最大6日間)は、細菌感染に対する感受性を増強させる^[5]。Benzo[a]pyrene (3,4-Benzopyrene) (0.05-500μg/ml；24時間)による発癌は、イソフラボンビオカニンAによって回復することが可能である^[6]。

体内で、Benzo[a]pyrene (3,4-Benzopyrene) (300μg/kg；3日間；経口投与)投与の結果、NMDA NR2B受容体サブユニットのmRNA発見が減少し、よって子孫で皮質神経活動の老年期の障害を起こす^[7]。Benzo[a]pyrene (3,4-Benzopyrene) (150µg/kg；30日間、一日に一回；経口)も、肝臓ミクロソーム分画で、7-エトキシレゾルフィン-O-デエチラーゼの活性をも増やす^[8]。

References:
[1] Bukowska, Bożena et al. “Benzo[*a*]pyrene-Environmental Occurrence, Human Exposure, and Mechanisms of Toxicity.” *International journal of molecular sciences* vol. 23,11 6348. 6 Jun. 2022, doi:10.3390/ijms23116348
[2] Matter, Brock et al. “Formation of diastereomeric benzo[a]pyrene diol epoxide-guanine adducts in p53 gene-derived DNA sequences.” *Chemical research in toxicology* vol. 17,6 (2004): 731-41. doi:10.1021/tx049974l
[3] Fu, Chenghao et al. “Benzo(a)pyrene and cardiovascular diseases: An overview of pre-clinical studies focused on the underlying molecular mechanism.” *Frontiers in nutrition* vol. 9 978475. 4 Aug. 2022, doi:10.3389/fnut.2022.978475
[4] Stampfer, M R, and J C Bartley. “Induction of transformation and continuous cell lines from normal human mammary epithelial cells after exposure to benzo[a]pyrene.” *Proceedings of the National Academy of Sciences of the United States of America*vol. 82,8 (1985): 2394-8. doi:10.1073/pnas.82.8.2394
[5] Clark, Ryan S et al. “Validation of research trajectory 1 of an Exposome framework: Exposure to benzo(a)pyrene confers enhanced susceptibility to bacterial infection.” *Environmental research* vol. 146 (2016): 173-84. doi:10.1016/j.envres.2015.12.027
[6] Cassady, J M et al. “Use of a mammalian cell culture benzo(a)pyrene metabolism assay for the detection of potential anticarcinogens from natural products: inhibition of metabolism by biochanin A, an isoflavone from Trifolium pratense L.” *Cancer research* vol. 48,22 (1988): 6257-61.
[7] McCallister, Monique M et al. “Prenatal exposure to benzo(a)pyrene impairs later-life cortical neuronal function.” *Neurotoxicology* vol. 29,5 (2008): 846-54. doi:10.1016/j.neuro.2008.07.008
[8]Kang, Hwan Goo et al. “Changes of biomarkers with oral exposure to benzo(a)pyrene, phenanthrene and pyrene in rats.” *Journal of veterinary science*vol. 8,4 (2007): 361-8. doi:10.4142/jvs.2007.8.4.361