| Revision as of 18:21, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 443354675 of page 4-Nitroquinoline_1-oxide for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 14:06, 26 September 2024 edit JWBE (talk | contribs)Extended confirmed users10,126 edits removed Category:Nitro compounds; added Category:Nitroarenes using HotCat |
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{{Redirect|Nqo|the language with the ISO 639 code nqo|N'Ko language}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| Watchedfields = changed |
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| verifiedrevid = 443353363 |
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| verifiedrevid = 477223204 |
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|ImageFile=NQO structure.png |
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| ImageFile=NQO structure.png |
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|ImageSize=150px |
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| ImageSize=130 |
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|IUPACName=4-nitroquinoline 1-oxide |
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| ImageAlt = Structural formula of 4-nitroquinoline 1-oxide |
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|OtherNames= |
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| ImageFile1 = 4-Nitroquinoline 1-oxide 3D spacefill.png |
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|Section1= {{Chembox Identifiers |
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| ImageSize1 = 160 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ImageAlt1 = Space-filling model of the 4-nitroquinoline 1-oxide molecule |
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| IUPACName=4-Nitroquinoline 1-oxide |
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| OtherNames= |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 5740 |
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| ChemSpiderID = 5740 |
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| EINECS = 200-281-1 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C03474 |
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| KEGG = C03474 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo=56-57-5 |
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| CASNo=56-57-5 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| PubChem=5955 |
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| UNII = X5081510EV |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| PubChem=5955 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 16907 |
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| ChEBI = 16907 |
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| SMILES = (=O)c2c1c(cccc1)()cc2 |
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| SMILES = (=O)c2c1c(cccc1)()cc2 |
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|Section2= {{Chembox Properties |
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|Section2={{Chembox Properties |
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|C=9|H=6|N=2|O=3 |
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| C=9 | H=6 | N=2 | O=3 |
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| MolarMass=190.16 g/mol |
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| MolarMass=190.16 g/mol |
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| Appearance=yellow-brown crystals or powder |
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| MeltingPtC = 26 to 28 |
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| BoilingPtC = 237 to 243 |
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| Solubility=slightly |
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|Section3= {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| MainHazards= causes DNA adducts. lactobacillus is being investigated for antigenotoxocity it causes. |
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| MainHazards= DANGER: CANCER RISK, causes blood, liver, and thyroid injury; causes DNA adducts |
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| GHSPictograms = {{GHS08}} |
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| GHSSignalWord = Danger |
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| HPhrases = {{H-phrases|350}} |
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| PPhrases = {{P-phrases|201|202|281|308+313|405|501}} |
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| FlashPtC = 101 |
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| AutoignitionPtC = 400 |
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'''4-Nitroquinoline 1-oxide''' (also known as 4-NQO, 4NQO, 4Nqo, NQO and NQNO) is a ] derivative and a ] compound used in the assessment of the efficacy of ]s, ], and procedures in the prevention and treatment of ] in ]s. It induces DNA lesions usually corrected by ]. |
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==General== |
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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 C<sub>9</sub>H<sub>7</sub>N.<ref>{{Cite web | url=http://www.chemicalland21.com/industrialchem/organic/QUINOLINE.htm |title = Quinoline (Benzopyridine)}}</ref> 4NQO may naturally occur in the environment but is typically manufactured for research purposes.<ref>{{cite journal |last1=LaVoie |first1=Edmond J. |last2=Adams |first2=Elisabeth Ann |last3=Shigematsu |first3=Akemi |last4=Hoffman |first4=Dietrich |date=September 1983 |title=On the metabolism of quinoline and isoquinoline: possible molecular basis for differences in biological activities |journal=Carcinogenesis |volume=4 |issue=9 |pages=1169–73 |pmid=6883639 |doi=10.1093/carcin/4.9.1169}}</ref> 4NQO is known to mimic the biological effects of ultraviolet light on various organisms.<ref>{{cite journal |last1=Ikenaga |first1=Mituo |last2=Ichikawa-Ryo |first2=Haruko |last3=Kondo |first3=Sohei |year=1975 |title=The major cause of inactivation and mutation by 4-Nitroquinoline 1-Oxide in Escherichia coli: Excisable 4NQO-purine adducts |journal=Journal of Molecular Biology |volume=92 |issue=2 |pages=341–56 |pmid=806692 |doi=10.1016/0022-2836(75)90233-8}}</ref> Both 4NQO and its reduced metabolite 4-hydroxyaminoquinoline 1-oxide (4HAQO) bind covalently to cellular macromolecules such as nucleic acids and proteins.<ref>{{cite journal |last1=Tada |first1=Mitsuhiko |last2=Tada |first2=Mariko |year=1975 |title=Seryl-tRNA synthetase and activation of the carcinogen 4-nitroquinoline 1-oxide |journal=Nature |volume=255 |issue=5508 |pages=510–2 |pmid=166317 |bibcode=1975Natur.255..510T |doi=10.1038/255510a0|s2cid=4151802 }}</ref> |
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4NQO has been shown to trap topoisomerase I cleavage complexes.<ref>{{cite journal |last1=Miao |first1=Z.H. |title=4-nitroquinoline-1-oxide induces the formation of cellular topoisomerase I-DNA cleavage complexes |journal=Cancer Res |volume=66 |issue=13 |pages=6540–5 |doi=10.1158/0008-5472.CAN-05-4471 |pmid=16818625 |year=2006 |doi-access=free }}</ref> It may also 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.<ref name=pmid16547075>{{cite journal |last1=Arima |first1=Yaeno |last2=Nishigori |first2=Chikako |last3=Takeuchi |first3=Toru |last4=Oka |first4=Shigenori |last5=Morimoto |first5=Kanehisa |last6=Utani |first6=Atsushi |last7=Miyachi |first7=Yoshiki |year=2006 |title=4-Nitroquinoline 1-Oxide Forms 8-Hydroxydeoxyguanosine in Human Fibroblasts through Reactive Oxygen Species |journal=Toxicological Sciences |volume=91 |issue=2 |pages=382–92 |pmid=16547075 |doi=10.1093/toxsci/kfj161|doi-access=free }}</ref> 4NQO’s reactive oxygen species may serve as a byproduct of DNA damage or signaling molecule from damage.<ref name=pmid24532717>{{cite journal |last1=Gallagher |first1=Jennifer E. G. |last2=Zheng |first2=Wei |last3=Rong |first3=Xiaoqing |last4=Miranda |first4=Noraliz |last5=Lin |first5=Zhixiang |last6=Dunn |first6=Barbara |last7=Zhao |first7=Hongyu |last8=Snyder |first8=Michael P. |year=2014 |title=Divergence in a master variator generates distinct phenotypes and transcriptional responses |journal=Genes & Development |volume=28 |issue=4 |pages=409–21 |pmid=24532717 |pmc=3937518 |doi=10.1101/gad.228940.113}}</ref> In response to damage from 4NQO, cells attempt to repair and initiate a transcriptional response to detoxify the cell from 4NQO and its metabolites.<ref>{{cite journal |last1=Fry |first1=Rebecca C. |last2=Begley |first2=Thomas J. |last3=Samson |first3=Leona D. |year=2005 |title=Genome-Wide Responses to DNA-Damaging Agents |journal=Annual Review of Microbiology |volume=59 |pages=357–77 |pmid=16153173 |doi=10.1146/annurev.micro.59.031805.133658}}</ref> |
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==Technical== |
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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.<ref name=pmid16547075/> |
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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.<ref name=pmid24532717/> |
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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.<ref>{{cite journal |last1=Le Crom |first1=Stéphane |last2=Devaux |first2=Frédéric |last3=Marc |first3=Philippe |last4=Zhang |first4=Xiaoting |last5=Moye-Rowley |first5=W. Scott |last6=Jacq |first6=Claude |year=2002 |title=New Insights into the Pleiotropic Drug Resistance Network from Genome-Wide Characterization of the YRR1 Transcription Factor Regulation System|journal=Molecular and Cellular Biology|volume=22|issue=8|pages=2642–9 |pmc=133742 |pmid=11909958 |doi=10.1128/MCB.22.8.2642-2649.2002}}</ref> Yrr1 shifts cellular response in resistance to 4NQO and rates of respiration.<ref name=pmid24532717/> In a recent study in yeast, 4NQO was shown to affect chromatin remodelling, cell division and DNA damage repair pathways.<ref>Ogbede, J.U., Giaever, G. & Nislow, C. A genome-wide portrait of pervasive drug contaminants. Sci Rep 11, 12487 (2021). https://doi.org/10.1038/s41598-021-91792-1</ref> |
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==References== |
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{{Reflist}} |
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{{DEFAULTSORT:Nitroquinoline 1-oxide, 4-}} |
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