Page last updated: 2024-12-10

nitrobenzanthrone

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

3-nitrobenzanthrone: mutagenic environmental contaminant; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID2825690
CHEBI ID181932
SCHEMBL ID7168071
MeSH IDM0300997

Synonyms (20)

Synonym
CHEBI:181932
3-nitrobenzo[b]phenalen-7-one
7h-benz(de)anthracen-7-one, 3-nitro-
3-nitrobenzanthrone
ccris 9003
3-nitro-7h-benz(de)anthracen-7-one
nitrobenzanthrone
17117-34-9
SCHEMBL7168071
o4ojw7bc7w ,
unii-o4ojw7bc7w
QAJOWHGESRCVLY-UHFFFAOYSA-N
C20824
3-nitro-7h-benzo[d,e]anthracen-7-one
7h-benz[de]anthracen-7-one,3-nitro-
FT-0710181
3-nitro-7h-benzo[de]anthracen-7-one
DTXSID60881271
Q3598796
3-nitrobenzanthrone [iarc]

Research Excerpts

Overview

3-Nitrobenzanthrone (3-NBA) is a byproduct of diesel exhaust and is highly present in industrial and populated areas. It is a mutagen and suspected human carcinogen detected in diesel exhaust, airborne particulates, and urban soil.

ExcerptReferenceRelevance
"3-Nitrobenzanthrone (3-NBA) is a suspected human carcinogen present in diesel exhaust. "( Induction of the Antioxidant Response by the Transcription Factor NRF2 Increases Bioactivation of the Mutagenic Air Pollutant 3-Nitrobenzanthrone in Human Lung Cells.
de la Vega, L; Duan, L; Hayes, JD; Murray, JR; Penning, TM, 2019
)
1.44
"3-Nitrobenzanthrone (3-NBA) is a byproduct of diesel exhaust and is highly present in industrial and populated areas. "( Kinetic Investigation of Translesion Synthesis across a 3-Nitrobenzanthrone-Derived DNA Lesion Catalyzed by Human DNA Polymerase Kappa.
Phi, KK; Smith, MC; Suo, Z; Tokarsky, EJ, 2019
)
1.48
"3-Nitrobenzanthrone (3-NBA) is a highly mutagenic compound and possible human carcinogen found in diesel exhaust. "( TP53 and lacZ mutagenesis induced by 3-nitrobenzanthrone in Xpa-deficient human TP53 knock-in mouse embryo fibroblasts.
Arlt, VM; Kucab, JE; Luijten, M; Phillips, DH; Schmeiser, HH; van Steeg, H; Zwart, EP, 2016
)
1.42
"3-Nitrobenzanthrone (3-NBA) is a potent environmental mutagen and a potential human carcinogen present in diesel exhaust and airborne particulates. "( Mutagenic specificity of N-acetoxy-3-aminobenzanthrone, a major metabolically activated form of 3-nitrobenzanthrone, in shuttle vector plasmids propagated in human cells.
Kawanishi, M; Nishida, H; Takamura-Enya, T; Yagi, T, 2008
)
1.28
"3-Nitrobenzanthrone (3-NBA) is a mutagen and suspected human carcinogen detected in diesel exhaust, airborne particulate matter, and urban soil. "( Tissue-specific metabolic activation and mutagenicity of 3-nitrobenzanthrone in MutaMouse.
Chen, G; Douglas, GR; Gingerich, J; Soper, L; White, PA, 2008
)
1.31
"3-Nitrobenzanthrone (3-NBA) is a potent mutagen and suspected human carcinogen identified in diesel exhaust and urban air pollution."( Genotoxicity of 3-nitrobenzanthrone and 3-aminobenzanthrone in MutaMouse and lung epithelial cells derived from MutaMouse.
Arlt, VM; Douglas, GR; Gingerich, J; Phillips, DH; Schmeiser, HH; White, PA, 2008
)
1.24
"3-Nitrobenzanthrone (3-NBA) is a potent mutagen and a suspected human carcinogen present in particulate matter of diesel exhaust and ambient air pollution. "( The carcinogenic air pollutant 3-nitrobenzanthrone induces GC to TA transversion mutations in human p53 sequences.
Hollstein, MC; Krais, A; Schmeiser, HH; vom Brocke, J; Whibley, C, 2009
)
1.36
"3-Nitrobenzanthrone (3-NBA) is a mutagenic and carcinogenic environmental pollutant found in diesel exhaust and urban air pollution. "( 3-Nitrobenzanthrone and 3-aminobenzanthrone induce DNA damage and cell signalling in Hepa1c1c7 cells.
Arlt, VM; Holme, JA; Lagadic-Gossmann, D; Landvik, NE; Nagy, E; Phillips, DH; Refsnes, M; Schmeiser, HH; Solhaug, A; Tekpli, X, 2010
)
1.8
"3-Nitrobenzanthrone (3-NBA) is a potent mutagen and suspected human carcinogen identified in diesel exhaust. "( Theoretical investigations on the formation of nitrobenzanthrone-DNA adducts.
Arlt, VM; Phillips, DH; Reynisson, J, 2011
)
1.35
"3-Nitrobenzanthrone (3-NBA) is an extremely potent mutagen and suspect human carcinogen found in diesel exhaust. "( Carcinogenic 3-nitrobenzanthrone but not 2-nitrobenzanthrone is metabolised to an unusual mercapturic acid in rats.
Frantík, E; Hanzlíková, I; Himl, M; Linhart, I; Mráz, J; Silhánková, A, 2012
)
1.45
"3-Nitrobenzanthrone (3-NBA) is an extremely strong mutagen and carcinogen in rats inducing squamous cell carcinoma and adenocarcinoma. "( Development of a two-dimensional high-performance liquid chromatography system coupled with on-line reduction as a new efficient analytical method of 3-nitrobenzanthrone, a potential human carcinogen.
Hasei, T; Nakanishi, H; Toda, Y; Watanabe, T, 2012
)
1.3
"3-nitrobenzanthrone (3-NBA) is a potent mutagen and suspected human carcinogen identified in diesel exhaust and ambient air pollution. "( Activation of 3-nitrobenzanthrone and its metabolites by human acetyltransferases, sulfotransferases and cytochrome P450 expressed in Chinese hamster V79 cells.
Arlt, VM; Frank, H; Glatt, H; Muckel, E; Pabel, U; Phillips, DH; Schmeiser, HH; Seidel, A; Sorg, BL, 2003
)
1.39
"3-nitrobenzanthrone (3-NBA) is an extremely potent mutagen in the Salmonella reversion assay and a suspected human carcinogen identified in diesel exhaust and in ambient airborne particulate matter. "( DNA adducts and mutagenic specificity of the ubiquitous environmental pollutant 3-nitrobenzanthrone in Muta Mouse.
Arlt, VM; Hayashi, M; Honma, M; Phillips, DH; Schmeiser, HH; Suzuki, T; Zhan, L, 2004
)
1.27
"3-Nitrobenzanthrone (3-NBA) is a suspected human carcinogen found in diesel exhaust and ambient air pollution. "( 3-aminobenzanthrone, a human metabolite of the environmental pollutant 3-nitrobenzanthrone, forms DNA adducts after metabolic activation by human and rat liver microsomes: evidence for activation by cytochrome P450 1A1 and P450 1A2.
Arlt, VM; Hewer, A; Phillips, DH; Schmeiser, HH; Sorg, BL; Stiborova, M, 2004
)
1.28
"3-Nitrobenzanthrone (3-NBA) is an environmental pollutant and suspected human carcinogen found in emissions from diesel and gasoline engines and on the surface of ambient air particulate matter; human exposure to 3-NBA is likely to occur primarily via the respiratory tract. "( DNA adduct formation by the environmental contaminant 3-nitrobenzanthrone after intratracheal instillation in rats.
Arlt, VM; Bieler, CA; Cornelius, MG; Klein, R; Phillips, DH; Schmeiser, HH; Wiessler, M, 2005
)
1.3
"3-Nitrobenzanthrone (3-NBA) is a suspected human carcinogen found in diesel exhaust and ambient air pollution. "( Bioactivation of 3-aminobenzanthrone, a human metabolite of the environmental pollutant 3-nitrobenzanthrone: evidence for DNA adduct formation mediated by cytochrome P450 enzymes and peroxidases.
Arlt, VM; Henderson, CJ; Phillips, DH; Schmeiser, HH; Stiborova, M; Wolf, CR, 2006
)
1.28
"3-Nitrobenzanthrone (3-NBA) is a potent mutagen and potential human carcinogen identified in diesel exhaust and ambient air particulate matter. "( Synthesis, characterization, and 32p-postlabeling analysis of DNA adducts derived from the environmental contaminant 3-nitrobenzanthrone.
Arlt, VM; Bieler, CA; Hull, WE; Kliem, C; Mirza, A; Osborne, MR; Phillips, DH; Schmeiser, HH, 2005
)
1.26
"3-Nitrobenzanthrone (3-NBA) is a potent mutagen and possible human carcinogen present in diesel exhaust and airborne particulate matter. "( Assessment of 3-nitrobenzanthrone reductase activity in mammalian tissues by normal-phase HPLC with fluorescence detection.
Chen, G; Douglas, GR; Lambert, IB; White, PA, 2005
)
1.4
"3-Nitrobenzanthrone (3-NBA) is a potent mutagen and potential human carcinogen identified in diesel exhaust and ambient air particulate matter. "( Identification of three major DNA adducts formed by the carcinogenic air pollutant 3-nitrobenzanthrone in rat lung at the C8 and N2 position of guanine and at the N6 position of adenine.
Arlt, VM; Kanno, T; Kawanishi, M; Osborne, MR; Phillips, DH; Schmeiser, HH; Takamura-Enya, T; Yagi, T, 2006
)
1.28
"3-Nitrobenzanthrone (3-NBA) is an extremely potent mutagen in diesel exhaust. "( Carcinogenic 3-nitrobenzanthrone induces oxidative damage to isolated and cellular DNA.
Hisamatsu, Y; Kawanishi, S; Murata, M; Ohnishi, S; Takamura-Enya, T; Tezuka, T, 2006
)
1.41
"3-Nitrobenzanthrone (3-NBA) is a suspected human carcinogen identified in diesel exhaust and air pollution. "( Molecular mechanism of genotoxicity of the environmental pollutant 3-nitrobenzanthrone.
Arlt, VM; Frei, E; Henderson, CJ; Phillips, DH; Schmeiser, HH; Stiborová, M; Wolf, CR, 2005
)
1.28
"3-Nitrobenzanthrone (3-NBA) is an urban air pollutant and rat lung carcinogen that is among the most potent mutagens yet tested in the Salmonella reversion assay. "( DNA damage and acute toxicity caused by the urban air pollutant 3-nitrobenzanthrone in rats: characterization of DNA adducts in eight different tissues and organs with synthesized standards.
Adachi, S; Möller, L; Nagy, E; Takamura-Enya, T; Zeisig, M, 2006
)
1.29
"3-Nitrobenzanthrone is a powerful bacterial mutagen and carcinogen to mammals. "( Structural identification of DNA adducts derived from 3-nitrobenzanthrone, a potent carcinogen present in the atmosphere.
Hisamatsu, Y; Kawanishi, M; Takamura-Enya, T; Yagi, T, 2007
)
1.31
"3-Nitrobenzanthrone (3-NBA) is a carcinogen occurring in diesel exhaust and air pollution. "( The environmental pollutant and carcinogen 3-nitrobenzanthrone induces cytochrome P450 1A1 and NAD(P)H:quinone oxidoreductase in rat lung and kidney, thereby enhancing its own genotoxicity.
Arlt, VM; Dracínská, H; Frei, E; Hodek, P; Hudecek, J; Mizerovská, J; Phillips, DH; Schmeiser, HH; Stiborová, M, 2008
)
1.33
"3-Nitrobenzanthrone (NBA) is a powerful bacterial mutagen and a suspected human carcinogen present in diesel exhaust and airborne particulates [Enya, T., et al. "( Mutagenic specificity of a derivative of 3-nitrobenzanthrone in the supF shuttle vector plasmids.
Enya, T; Kawanishi, M; Matsui, S; Suzuki, H; Takebe, H; Yagi, T, 1998
)
1.28

Effects

2-Nitrobenzanthrone (2-NBA) has recently been detected in ambient air particulate matter. 3- nitrobenzenthrone has been isolated from diesel exhaust and airborne particles and identified as a potent direct-acting mutagen in vitro and genotoxic agent in vivo.

ExcerptReferenceRelevance
"2-Nitrobenzanthrone (2-NBA) has recently been detected in ambient air particulate matter. "( Mechanisms of the different DNA adduct forming potentials of the urban air pollutants 2-nitrobenzanthrone and carcinogenic 3-nitrobenzanthrone.
Arlt, VM; Dvorák, Z; Frei, E; Martínek, V; Phillips, DH; Schmeiser, HH; Simánek, V; Sístková, J; Stiborová, M; Svobodová, M; Ulrichová, J, 2010
)
1.3
"2-Nitrobenzanthrone (2-NBA) has recently been detected in ambient air particulate matter. "( Activation and detoxification metabolism of urban air pollutants 2-nitrobenzanthrone and carcinogenic 3-nitrobenzanthrone by rat and mouse hepatic microsomes.
Arlt, VM; Borek-Dohalska, L; Cechova, T; Frei, E; Moserova, M; Paca, J; Schmeiser, HH; Stiborova, M, 2012
)
1.34
"3-Nitrobenzanthrone (3-NBA) has been isolated from diesel exhaust and airborne particles and identified as a potent direct-acting mutagen in vitro and genotoxic agent in vivo. "( DNA adduct and tumor formations in rats after intratracheal administration of the urban air pollutant 3-nitrobenzanthrone.
Adachi, S; Hisamatsu, Y; Kawamura, K; Möller, L; Nagy, E; Sugeta, A; Zeisig, M, 2005
)
1.26
"2-Nitrobenzanthrone (2-NBA) has recently been detected in ambient air particulate matter. "( Mutagenicity and DNA adduct formation by the urban air pollutant 2-nitrobenzanthrone.
Arlt, VM; Gamboa da Costa, G; Glatt, H; Phillips, DH; Reynisson, J; Takamura-Enya, T, 2007
)
1.3

Toxicity

ExcerptReferenceRelevance
" The numerous toxic manifestations are discussed."( Nitroaromatic compounds: Environmental toxicity, carcinogenicity, mutagenicity, therapy and mechanism.
Kovacic, P; Somanathan, R, 2014
)
0.4

Dosage Studied

ExcerptRelevanceReference
" In this study, acid hydrolysate of globin from rats dosed intraperitoneally with 3-NBA was analysed by HPLC/MS to identify a novel type of cysteine adduct, 3-aminobenzanthron-2-ylcysteine (3-ABA-Cys), confirmed using a synthesised standard."( S-(3-Aminobenzanthron-2-yl)cysteine in the globin of rats as a novel type of adduct and possible biomarker of exposure to 3-nitrobenzanthrone, a potent environmental carcinogen.
Dušková, Š; Hanzlíková, I; Linhart, I; Mráz, J, 2017
)
0.66
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
phenanthrenesAny benzenoid aromatic compound that consists of a phenanthrene skeleton and its substituted derivatives thereof.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Research

Studies (86)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's3 (3.49)18.2507
2000's45 (52.33)29.6817
2010's34 (39.53)24.3611
2020's4 (4.65)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 21.63

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index21.63 (24.57)
Research Supply Index4.47 (2.92)
Research Growth Index5.36 (4.65)
Search Engine Demand Index18.60 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (21.63)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews5 (5.81%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other81 (94.19%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]