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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/01/13 08:42:46」(JST)

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Chemical structure of benzo[a]pyrene

Chemical structure of benzo[e]pyrene

A benzopyrene is an organic compound with the formula C₂₀H₁₂. Structurally speaking, the colorless isomers of benzopyrene are pentacyclic hydrocarbons and are fusion products of pyrene and a phenylene group. Two isomeric species of benzopyrene are benzo[a]pyrene and the less common benzo[e]pyrene. They belong to the chemical class of polycyclic aromatic hydrocarbons.

Related compounds include cyclopentapyrenes, dibenzopyrenes, indenopyrenes and naphthopyrenes. Benzopyrene is a component of pitch and occurs together with other related pentacyclic aromatic species such as picene, benzofluoranthenes, and perylene.^[1] It is naturally emitted by forest fires and volcanic eruptions and can also be found in coal tar, cigarette smoke, wood smoke, and burnt foods such as coffee. Fumes that develop from fat dripping on blistering charcoal are rich in benzopyrene, which can condense on grilled goods.^[2]

Benzopyrenes are problematic because they intercalate into DNA, interfering with transcription. They are considered pollutants and carcinogens. Especially the mechanism of action of benzo(a)pyrene-related DNA modification is well investigated and relates to the activity of cytochrome P450 subclass 1A1 (CYP1A1).^[3] Seemingly, the high activity of CYP1A1 in the intestinal mucosa prevents major amounts of ingested benzo(a)pyrene from entering portal blood and systemic circulation.^[4] The intestinal (but not hepatic) detoxification mechanism seems to depend on receptors that recognize bacterial surface components (TLR2).^[5]

Evidence exists to link benzo[a]pyrene to the formation of lung cancer.^[6]

References[edit]

^ W. D. Betts "Tar and Pitch" in Kirk‑Othmer Encyclopedia of Chemical Technology, 1997, John Wiley & Sons, New York. doi: 10.1002/0471238961.20011802052020.a01
^ Larsson, B. K.; Sahlberg, GP; Eriksson, AT; Busk, LA (1983). "Polycyclic aromatic hydrocarbons in grilled food". J Agric Food Chem. 31 (4): 867–873. doi:10.1021/jf00118a049. PMID 6352775.
^ Uno, S.; Dalton, TP; Dragin, N; Curran, CP et al. (2006). "Oral Benzo[a]pyrene in Cyp1 knockout mouse lines: CYP1A1 important in detoxication, CYP1B1 metabolism required for immune damage independent of total-body burden and clearance rate". Mol Pharmacol. 69 (4): 1103–1112. doi:10.1124/mol.105.021501. PMID 16377763.
^ Uno, S.; Dragin, N; Miller, ML; Dalton, TP et al. (2008). "Basal and inducible CYP1 mRNA quantitation and protein localization throughout the mouse gastrointestinal tract". Free Radic Biol Med. 44 (4): 570–83. doi:10.1016/j.freeradbiomed.2007.10.044. PMC 2754765. PMID 17997381.
^ Do, KN; Fink, LN; Jensen, TE; Gautier, L; Parlesak, A (2012). "TLR2 controls intestinal carcinogen detoxication by CYP1A1". In Lebedeva, Irina V. PLoS ONE 7 (3): e32309. doi:10.1371/journal.pone.0032309. PMC 3307708. PMID 22442665.
^ Denissenko, M. F.; Pao, A.; Tang, M.-s.; Pfeifer, G. P. (1996). "Preferential Formation of Benzo[a]pyrene Adducts at Lung Cancer Mutational Hotspots in P53". Science 274 (5286): 430–2. doi:10.1126/science.274.5286.430. PMID 8832894.

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1. 肺癌における喫煙およびその他の危険因子 cigarette smoking and other risk factors for lung cancer

English Journal

Enhanced aggressiveness of benzopyrene-induced squamous carcinomas in transgenic mice overexpressing the proprotein convertase PACE4 (PCSK6).

Bassi DE1,2, Cenna J1, Zhang J1, Cukierman E2, Klein-Szanto AJ1,2.
Molecular carcinogenesis.Mol Carcinog.2015 Oct;54(10):1122-31. doi: 10.1002/mc.22183. Epub 2014 May 21.
PACE4 (PCSK6) is a proprotein convertase (PC) capable of processing numerous substrates involved in tumor growth, invasion, and metastasis. Because of the human relevancy of the tobacco-associated carcinogen benzo[a]pyrene (B(a)P) we investigated whether transgenic mice in which this PC is targeted
PMID 24845697

2'-Hydroxyflavanone: A promising molecule for kidney cancer prevention.

Singhal SS1, Singhal J2, Figarola JL2, Riggs A2, Horne D3, Awasthi S4.
Biochemical pharmacology.Biochem Pharmacol.2015 Aug 1;96(3):151-8. doi: 10.1016/j.bcp.2015.04.022. Epub 2015 May 6.
Kidney cancer, also known as renal cell carcinoma (RCC), is one of the top 10 diagnosed cancers in the USA, and the incidence is rising. Despite major improvements in drug therapy strategies, RCC remains a deadly malignancy if not found and removed in its early stages. RCC is so highly drug-resistan
PMID 25957660

Dysfunction of methionine sulfoxide reductases to repair damaged proteins by nickel nanoparticles.

Feng PH1, Huang YL2, Chuang KJ3, Chen KY4, Lee KY5, Ho SC6, Bien MY7, Yang YL8, Chuang HC9; Taiwan CardioPulmonary Research Group.
Chemico-biological interactions.Chem Biol Interact.2015 Jul 5;236:82-9. doi: 10.1016/j.cbi.2015.05.003. Epub 2015 May 13.
BACKGROUND: Protein oxidation is considered to be one of the main causes of cell death, and methionine is one of the primary targets of reactive oxygen species (ROS). However, the mechanisms by which nickel nanoparticles (NiNPs) cause oxidative damage to proteins remain unclear.OBJECTIVES: The objec
PMID 25979628

Japanese Journal

遺伝子多型と口腔がん

産業医科大学雑誌 32(3), 221-236, 2010-09-01
NAID 110007700768

職業性が疑われた多発性ボーエン病の1例

Skin cancer : official organ of the Japanese Society for Skin Cancer = 皮膚悪性腫瘍研究会機関誌 22(3), 316-319, 2008-03-25
NAID 10022601517

「環境と健康」研究の諸課題

生物物理化学 = Journal of Electrophoresis 50(2), 49-52, 2006-06-15
NAID 10018150449

「ベンツピレン」

　　[★]

英: benzpyrene
関: ベンゾピレン benzoapyrene、benzopyrene

[show details]

ベンゾピレン : 約 5,650 件
ベンツピレン : 約 18,900 件
benzpyrene : 約 32,400 件
benzoapyrene : 約 517,000 件
benzopyrene : 約 47,700 件

含有物

タバコ

臨床関連

発癌と関連

肺癌

参考

1.

http://www.pharm.or.jp/dictionary/wiki.cgi?%E3%83%99%E3%83%B3%E3%83%84%E3%83%94%E3%83%AC%E3%83%B3

「7,8-dihydro-7,8-dihydroxybenzopyrene-9,10-oxide」

　　[★]

7,8-ジヒドロ-7,8-ジヒドロキシベンゾピレン-9,10-オキシド

発癌性物質

関: BPDE

「benzopyrene hydroxylase」

　　[★]

ベンゾピレン水酸化酵素、ベンゾピレンヒドロキシラーゼ

「dihydroxydihydrobenzopyrene」

　　[★]

ジヒドロキシジヒドロベンゾピレン

「benzopyrene diol epoxide」

　　[★] ベンツピレンジオールエポキシド

[1] W. D. Betts "Tar and Pitch" in Kirk‑Othmer Encyclopedia of Chemical Technology, 1997, John Wiley & Sons, New York. doi: 10.1002/0471238961.20011802052020.a01

[2] Larsson, B. K.; Sahlberg, GP; Eriksson, AT; Busk, LA (1983). "Polycyclic aromatic hydrocarbons in grilled food". J Agric Food Chem. 31 (4): 867–873. doi:10.1021/jf00118a049. PMID 6352775.

[3] Uno, S.; Dalton, TP; Dragin, N; Curran, CP et al. (2006). "Oral Benzo[a]pyrene in Cyp1 knockout mouse lines: CYP1A1 important in detoxication, CYP1B1 metabolism required for immune damage independent of total-body burden and clearance rate". Mol Pharmacol. 69 (4): 1103–1112. doi:10.1124/mol.105.021501. PMID 16377763.

[4] Uno, S.; Dragin, N; Miller, ML; Dalton, TP et al. (2008). "Basal and inducible CYP1 mRNA quantitation and protein localization throughout the mouse gastrointestinal tract". Free Radic Biol Med. 44 (4): 570–83. doi:10.1016/j.freeradbiomed.2007.10.044. PMC 2754765. PMID 17997381.

[5] Do, KN; Fink, LN; Jensen, TE; Gautier, L; Parlesak, A (2012). "TLR2 controls intestinal carcinogen detoxication by CYP1A1". In Lebedeva, Irina V. PLoS ONE 7 (3): e32309. doi:10.1371/journal.pone.0032309. PMC 3307708. PMID 22442665.

[6] Denissenko, M. F.; Pao, A.; Tang, M.-s.; Pfeifer, G. P. (1996). "Preferential Formation of Benzo[a]pyrene Adducts at Lung Cancer Mutational Hotspots in P53". Science 274 (5286): 430–2. doi:10.1126/science.274.5286.430. PMID 8832894.

リンク元	「ベンツピレン」
拡張検索	「7,8-dihydro-7,8-dihydroxybenzopyrene-9,10-oxide」「benzopyrene hydroxylase」「dihydroxydihydrobenzopyrene」「benzopyrene diol epoxide」

匿名

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案内

案内

benzopyrene