関: 4NQO

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any compound of oxygen with another element or a radical

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酸化物

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/12/15 23:38:18」(JST)

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4-Nitroquinoline 1-oxide (also known as 4-NQO, 4NQO, 4Nqo, NQO and NQNO) is a quinoline derivative and a tumorigenic compound used in the assessment of the efficacy of diets, drugs, and procedures in the prevention and treatment of cancer in animal models. It induces DNA lesions usually corrected by nucleotide excision repair.

General

4-nitroquinoline 1-oxide (4NQO) is a quinoline, a carcinogenic and mutagenic chemical. Quinolines, like 4NQO, possess a heterocyclic aromatic structure and the same basic chemical formula of C9H7N.^[1] 4NQO may naturally occur in the environment but is typically manufactured for research purposes.^[2] 4NQO is known to mimic the biological effects of ultraviolet light on various organisms.^[3] Both 4NQO and its reduced metabolite 4-hydroxyaminoquinoline 1-oxide (4HAQO) bind covalently to cellular macromolecules such as nucleic acids and proteins.^[4]

4NQO may induce DNA damage through the production of reactive oxygen species thought to arise from enzymatic reduction of its nitro group, although its exact mechanism is unknown.^[5] 4NQO’s reactive oxygen species may serve as a byproduct of DNA damage or signaling molecule from damage.^[6] In response to damage from 4NQO, cells attempt to repair and initiate a transcriptional response to detoxify the cell from 4NQO and its metabolites.^[7]

Technical

DNA damage by 4NQO is a potent model. 4NQO induces DNA lesions usually corrected by nucleotide excision repair. 4NQO’s four electron reduction product, 4-hydroxyaminoquinoline 1-oxide (4HAQO), is believed to be a carcinogenic metabolite of 4NQO. When 4NQO is metabolized to its electrophilic reactant, selyl-4HAQO, it reacts with DNA to form stable quinolone monoadducts considered responsible for its mutagenicity and genotoxicity.^[5]

The stable quinolone monoadducts oxidize to form 8-hydroxydeoxyguanosine (8OHdG), which, if left unrepaired, lead to transversions of guanines to thymines, which are nucleotides in DNA. Despite the direct mutagenic properties of 4HAQO, it is less toxic than 4NQO, indicating that metabolism of 4NQO produces other reactive chemicals such as anion radical metabolites.^[6]

Yeast species have been used to map polymorphic regions in response to 4NQO, identifying the polymorphic transcription factor Yrr1. Yrr1 confers 4NQO resistance to wild-type S. cerevisiae yeast, binding upstream from core genes well-known to regulation drug response.^[8] Yrr1 shifts cellular response in resistance to 4NQO and rates of respiration.^[6]

References

^ http://www.chemicalland21.com/industrialchem/organic/QUINOLINE.htm^{[full citation needed]}
^ LaVoie, Edmond J.; Adams, Elisabeth Ann; Shigematsu, Akemi; Hoffman, Dietrich (September 1983). "On the metabolism of quinoline and isoquinoline: possible molecular basis for differences in biological activities". Carcinogenesis. 4 (9): 1169–73. doi:10.1093/carcin/4.9.1169. PMID 6883639.
^ Ikenaga, Mituo; Ichikawa-Ryo, Haruko; Kondo, Sohei (1975). "The major cause of inactivation and mutation by 4-Nitroquinoline 1-Oxide in Escherichia coli: Excisable 4NQO-purine adducts". Journal of Molecular Biology. 92 (2): 341–56. doi:10.1016/0022-2836(75)90233-8. PMID 806692.
^ Tada, Mitsuhiko; Tada, Mariko (1975). "Seryl-tRNA synthetase and activation of the carcinogen 4-nitroquinoline 1-oxide". Nature. 255 (5508): 510–2. Bibcode:1975Natur.255..510T. doi:10.1038/255510a0. PMID 166317.
^ ^a ^b Arima, Yaeno; Nishigori, Chikako; Takeuchi, Toru; Oka, Shigenori; Morimoto, Kanehisa; Utani, Atsushi; Miyachi, Yoshiki (2006). "4-Nitroquinoline 1-Oxide Forms 8-Hydroxydeoxyguanosine in Human Fibroblasts through Reactive Oxygen Species". Toxicological Sciences. 91 (2): 382–92. doi:10.1093/toxsci/kfj161. PMID 16547075.
^ ^a ^b ^c Gallagher, Jennifer E. G.; Zheng, Wei; Rong, Xiaoqing; Miranda, Noraliz; Lin, Zhixiang; Dunn, Barbara; Zhao, Hongyu; Snyder, Michael P. (2014). "Divergence in a master variator generates distinct phenotypes and transcriptional responses". Genes & Development. 28 (4): 409–21. doi:10.1101/gad.228940.113. PMC 3937518. PMID 24532717.
^ Fry, Rebecca C.; Begley, Thomas J.; Samson, Leona D. (2005). "Genome-Wide Responses to DNA-Damaging Agents". Annual Review of Microbiology. 59: 357–77. doi:10.1146/annurev.micro.59.031805.133658. PMID 16153173.
^ Le Crom, Stéphane; Devaux, Frédéric; Marc, Philippe; Zhang, Xiaoting; Moye-Rowley, W. Scott; Jacq, Claude (2002). "New Insights into the Pleiotropic Drug Resistance Network from Genome-Wide Characterization of the YRR1 Transcription Factor Regulation System". Molecular and Cellular Biology. 22 (8): 2642–9. doi:10.1128/MCB.22.8.2642-2649.2002. PMC 133742. PMID 11909958.

UpToDate Contents

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English Journal

Genistein, isoflavonoids in soybeans, prevents the formation of excess radiation-induced centrosomes via p21 up-regulation.

Shimada M, Kato A, Habu T, Komatsu K.SourceDepartment of Genome Repair Dynamics, Radiation Biology Center, Kyoto University, Yoshida-konoe, Sakyo, Kyoto 606-8501, Japan.
Mutation research.Mutat Res.2011 Nov 1;716(1-2):27-32. Epub 2011 Aug 5.
The centrosome is a cytoplasmic organelle which duplicates once during each cell cycle, and the presence of excess centrosomes promote chromosome instability through chromosome missegregation following cytokinesis. Ionizing radiation (IR) can induce extra centrosomes by permitting the continuation o
PMID 21843532

Use of the in vivo skin comet assay to evaluate the DNA-damaging potential of chemicals applied to the skin.

Toyoizumi T, Ohta R, Nakagawa Y, Tazura Y, Kuwagata M, Noguchi S, Yamakage K.SourceHatano Research Institute, Food and Drug Safety Center (FDSC), 729-5 Ochiai, Hadano, Kanagawa 257-8523, Japan.
Mutation research.Mutat Res.2011 Sep 16. [Epub ahead of print]
The aim of the present study was to evaluate both sensitivity and specificity of an in vivo skin comet assay using chemically treated, hairless mouse dorsal skin as a model. N-methyl-N'-nitro-N-nitrosoguanidine (MNNG, 0.0125-0.2%), 4-nitroquinoline-1-oxide (4NQO, 0.01-0.25%), mitomycin C (MMC, 0.012
PMID 21944904

Japanese Journal

Introduction of a Normal Human Chromosome 8 Corrects Abnormal Phenotypes of Werner Syndrome Cells Immortalized by Expressing an hTERT Gene

ARIYOSHI Kentaro,SUZUKI Keiji,GOTO Makoto,OSHIMURA Mitsuo,ISHIZAKI Kanji,WATANABE Masami,KODAMA Seiji
Journal of radiation research 50(3), 253-259, 2009-05-16
… Here, we demonstrate that the abnormal WS phenotypes including cellular sensitivities to 4-nitroquinoline-1-oxide (4NQO) and hydroxy urea (HU), and chromosomal radiosensitivity at G2 phase are corrected by expression of the WRN gene mediated by introducing a chromosome 8. …
NAID 10025911840

4-nitroquinoline 1-oxide誘発ラット舌癌発生過程におけるp21^<WAF1/CIP1>の発現(大阪歯科大学大学院歯学研究科博士(歯学)学位論文内容要旨および論文審査結果要旨の公表)

松島由紀
歯科医学 71(2), 47-48, 2008-06-25
NAID 110006862119

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★リンクテーブル★

リンク元	「4NQO」「4-ニトロキノリン-1-オキシド」
関連記事	「oxide」

「4NQO」

4-Nitroquinoline 1-oxide
Names
	IUPAC name 4-Nitroquinoline 1-oxide
Identifiers
CAS Number	56-57-5
3D model (Jmol)	Interactive image
ChEBI	CHEBI:16907
ChEMBL	ChEMBL127655
ChemSpider	5740
ECHA InfoCard	100.000.256
KEGG	C03474
PubChem	5955
	InChI InChI=1S/C9H6N2O3/c12-10-6-5-9(11(13)14)7-3-1-2-4-8(7)10/h1-6H Key: YHQDZJICGQWFHK-UHFFFAOYSA-N ; InChI=1/C9H6N2O3/c12-10-6-5-9(11(13)14)7-3-1-2-4-8(7)10/h1-6H Key: YHQDZJICGQWFHK-UHFFFAOYAP ;
	SMILES [O-][N+](=O)c2c1c(cccc1)[n+]([O-])cc2 ;
Properties
Chemical formula	C9H6N2O3
Molar mass	190.16 g/mol
Appearance	yellow-brown crystals or powder
Melting point	26 to 28 °C (79 to 82 °F; 299 to 301 K)
Boiling point	237 to 243 °C (459 to 469 °F; 510 to 516 K)
Solubility in water	slightly
Hazards
Main hazards	DANGER: CANCER RISK, causes blood, liver, and thyroid injury; causes DNA adducts
Flash point	101 °C (214 °F; 374 K)
Autoignition; temperature	400 °C (752 °F; 673 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references