Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C17H12O6 |
| Molecular Weight | 312.2736 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]12OC=C[C@@]1([H])C3=C4OC(=O)C5=C(CCC5=O)C4=C(OC)C=C3O2
InChI
InChIKey=OQIQSTLJSLGHID-WNWIJWBNSA-N
InChI=1S/C17H12O6/c1-20-10-6-11-14(8-4-5-21-17(8)22-11)15-13(10)7-2-3-9(18)12(7)16(19)23-15/h4-6,8,17H,2-3H2,1H3/t8-,17+/m0/s1
| Molecular Formula | C17H12O6 |
| Molecular Weight | 312.2736 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Aflatoxin B1 is a very potent carcinogen produced by Aspergillus flavus and related fungi that grow on improperly stored food such as corn, rice, and peanuts. Dietary exposure to aflatoxin B1 is associated with an increased incidence of hepatocellular carcinoma, especially given co-infection with hepatitis B virus. Mechanism of carcinogenicity involves metabolic activation to aflatoxin B1-8,9 exo-epoxide by cytochrome p450 and formation of adducts with guanine DNA base.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Lack of expression of glutathione-S-transferase P, gamma-glutamyl transpeptidase, and alpha-fetoprotein messenger RNAs in liver tumors induced by peroxisome proliferators. | 1988 Sep 1 |
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| Effects of non-genotoxic hepatocarcinogens phenobarbital and nafenopin on phenotype and growth of different populations of altered foci in rat liver. | 1989 |
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| Catalytic activities of human liver cytochrome P-450 IIIA4 expressed in Saccharomyces cerevisiae. | 1990 Dec 25 |
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| Genetic analysis of aflatoxin B1 activation in rat hepatoma cells. | 1990 Jul |
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| Activation of P53 in HepG2 cells as surrogate to detect mutagens and promutagens in vitro. | 2010 Oct 5 |
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| New short term prediction method for chemical carcinogenicity by hepatic transcript profiling following 28-day toxicity tests in rats. | 2011 |
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| Human embryonic stem cell derived hepatocyte-like cells as a tool for in vitro hazard assessment of chemical carcinogenicity. | 2011 Dec |
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| Genomic profiling uncovers a molecular pattern for toxicological characterization of mutagens and promutagens in vitro. | 2011 Jul |
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| Aflatoxin B1-DNA adduct formation and mutagenicity in livers of neonatal male and female B6C3F1 mice. | 2011 Jul |
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| α4 is highly expressed in carcinogen-transformed human cells and primary human cancers. | 2011 Jun 30 |
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| Zebrafish (Danio rerio) embryos as a model for testing proteratogens. | 2011 Mar 15 |
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| Tricyclic compounds containing nonenolizable cyano enones. A novel class of highly potent anti-inflammatory and cytoprotective agents. | 2011 Mar 24 |
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| Aflatoxin B1--a potential endocrine disruptor--up-regulates CYP19A1 in JEG-3 cells. | 2011 May 10 |
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| Functional characterization of alpha-class glutathione s-transferases from the Turkey (meleagris gallopavo). | 2011 Nov |
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| Development and evaluation of a genomic signature for the prediction and mechanistic assessment of nongenotoxic hepatocarcinogens in the rat. | 2011 Nov |
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| 2'-Deoxyguanosine as a surrogate trapping agent for DNA reactive drug metabolites. | 2011 Nov 10 |
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| Characterization of primary human hepatocytes, HepG2 cells, and HepaRG cells at the mRNA level and CYP activity in response to inducers and their predictivity for the detection of human hepatotoxins. | 2012 Apr |
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| A single neonatal exposure to aflatoxin b1 induces prolonged genetic damage in two loci of mouse liver. | 2012 Aug |
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| Aflatoxins B(1), B(2) and G(1) modulate cytokine secretion and cell surface marker expression in J774A.1 murine macrophages. | 2012 Aug |
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| The ToxTracker assay: novel GFP reporter systems that provide mechanistic insight into the genotoxic properties of chemicals. | 2012 Jan |
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| Promotion of hepatocarcinogenesis by perfluoroalkyl acids in rainbow trout. | 2012 Jan |
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| Identification of early target genes of aflatoxin B1 in human hepatocytes, inter-individual variability and comparison with other genotoxic compounds. | 2012 Jan 15 |
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| Effect of aflatoxin B1 on nuclear receptors PXR, CAR, and AhR and their target cytochromes P450 mRNA expression in primary cultures of human hepatocytes. | 2012 Jan-Feb |
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| Development of a multiparametric cell-based protocol to screen and classify the hepatotoxicity potential of drugs. | 2012 May |
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| Testing an aflatoxin B1 gene signature in rat archival tissues. | 2012 May 21 |
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| Comparison of genotoxicant-modified transcriptomic responses in conventional and epigenetically stabilized primary rat hepatocytes with in vivo rat liver data. | 2012 Nov |
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| Cytochrome P450 2A13 mediates aflatoxin B1-induced cytotoxicity and apoptosis in human bronchial epithelial cells. | 2012 Oct 28 |
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| Comparison of hepatocarcinogen-induced gene expression profiles in conventional primary rat hepatocytes with in vivo rat liver. | 2012 Sep |
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| RNA-Seq profiling reveals novel hepatic gene expression pattern in aflatoxin B1 treated rats. | 2013 |
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| Alpha-class glutathione S-transferases in wild turkeys (Meleagris gallopavo): characterization and role in resistance to the carcinogenic mycotoxin aflatoxin B1. | 2013 |
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| The effects of aflatoxin B1 on transporters and steroid metabolizing enzymes in JEG-3 cells. | 2013 Apr 26 |
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| Detection of genotoxic and non-genotoxic carcinogens in Xpc(-/-)p53(+/-) mice. | 2013 Jan 15 |
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| HepG2 cells simultaneously expressing five P450 enzymes for the screening of hepatotoxicity: identification of bioactivable drugs and the potential mechanism of toxicity involved. | 2013 Jun |
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| Identification of novel liver-specific mRNAs in plasma for biomarkers of drug-induced liver injury and quantitative evaluation in rats treated with various hepatotoxic compounds. | 2013 Mar |
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| Integrated analysis of transcriptomics and metabonomics profiles in aflatoxin B1-induced hepatotoxicity in rat. | 2013 May |
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| Genomic models of short-term exposure accurately predict long-term chemical carcinogenicity and identify putative mechanisms of action. | 2014 |
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| Genome-wide miRNA-profiling of aflatoxin B1-induced hepatic injury using deep sequencing. | 2014 Apr 21 |
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| Hepatotoxic effects of mycotoxin combinations in mice. | 2014 Dec |
|
| Effect of selenium supplementation on aflatoxin B₁-induced histopathological lesions and apoptosis in bursa of Fabricius in broilers. | 2014 Dec |
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| Lophirones B and C extenuate AFB1-mediated oxidative onslaught on cellular proteins, lipids, and DNA through Nrf-2 expression. | 2014 Dec |
|
| The role of NAD(+)-dependent isocitrate dehydrogenase 3 subunit α in AFB1 induced liver lesion. | 2014 Jan 30 |
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| In vivo treatment with aflatoxin B1 increases DNA oxidation, base excision repair activity and 8-oxoguanine DNA glycosylase 1 levels in mouse lung. | 2014 Jul 3 |
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| Genetic or pharmacologic activation of Nrf2 signaling fails to protect against aflatoxin genotoxicity in hypersensitive GSTA3 knockout mice. | 2014 Jun |
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| Aflatoxin B1 disrupts the androgen biosynthetic pathway in rat Leydig cells. | 2014 Mar |
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| Up-regulation of nucleotide excision repair in mouse lung and liver following chronic exposure to aflatoxin B₁ and its dependence on p53 genotype. | 2014 Mar 1 |
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| Toxicity of aflatoxin B1 towards the vitamin D receptor (VDR). | 2015 Feb |
|
| Effects of aflatoxin B₁, fumonisin B₁ and their mixture on the aryl hydrocarbon receptor and cytochrome P450 1A induction. | 2015 Jan |
|
| Sulforaphane, a cancer chemopreventive agent, induces pathways associated with membrane biosynthesis in response to tissue damage by aflatoxin B1. | 2015 Jan 1 |
|
| Aflatoxin B1 augments the synthesis of corticotropin releasing hormone in JEG-3 placental cells. | 2015 Jul 25 |
|
| Population-based in vitro hazard and concentration-response assessment of chemicals: the 1000 genomes high-throughput screening study. | 2015 May |
Patents
Sample Use Guides
Aflatoxin B1 is ingested with contaminated food. Studies showed that aflatoxin B1 can also penetrate skin.
Route of Administration:
Other
Bronchial and colonic specimens were incubated with [3H]Aflatoxin B1 (AFB1) (0.5 uM). For identification of the AFB,-DNA adduct, the mucosae were pooled from 20 and 60 explants from the bronchus and the colon, respectively, homogenized in Tris-sodium dodecyl sulfate buffer, incubated with proteinase K for 2 hr, and extracted with water-saturated phenol. After centrifugation at 10,000 x g for 30 mm, DNA was isolated from the upper phase by precipitation with ice-cold ethanol and kept overnight at -20°C. DNA was redissolved in 0.1 M Tris-HCI buffer (pH 6.5), treated with RNase I at 37° for 1 hr, and extracted twice with chloroform/phenol (1/1). The DNA solution was kept -20° until identification of the adduct.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 20:19:29 GMT 2023
by
admin
on
Fri Dec 15 20:19:29 GMT 2023
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| Record UNII |
9N2N2Y55MH
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| Record Status |
Validated (UNII)
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| Record Version |
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C213
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