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A6636 Sigma

Aflatoxin B1 from Aspergillus flavus

from Aspergillus flavus

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Description

Warning

Possibly carcinogenic.

Application

Aflatoxin B1 is a carcinogenic compound that induces transversion of G to T at codon 249 of the p53 tumor suppressor gene. Aflatoxin B1 may be used as an internal standard when testing for aflatoxin contamination in food products.

Biochem/physiol Actions

Hepatocarcinogen. Food contaminant produced by Aspergillus flavus, a common soil fungus. Aflatoxin is biotransformed to genotoxic intermediates by P450 Phase I enzymes, mainly CYP3A4 via aflatoxin B1 3-hydroxylation. Detoxification depends on Phase II enzymes, such as Glutathione S-Transferase and AFB(1)-aldehyde reductase (AFAR).

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. A6636.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Price and Availability

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DISCOVER Bioactive Small Molecules

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Aflatoxin B<SUB>1</SUB> solution

2 μg/mL in acetonitrile, analytical standard

Aflatoxin G<SUB>1</SUB>

from Aspergillus flavus

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
UN 3462 6.1 / PGI
WGK Germany 
3
RTECS 
GY1925000

Protocols & Articles

Articles

Carcinogenesis and Epigenetics

Cancer research has revealed that the classical model of carcinogenesis, a three step process consisting of initiation, promotion, and progression, is not complete. The expansion of the carcinogenesi...
Vicki Caligur
BioFiles 2008, 3.5, 18.
Keywords: Acetylations, Adhesion, Alkylations, Apoptosis, Biofiles, Cancer, Carcinogens, Cell division, Cell proliferation, Cell signaling, DNA microarrays, Drug discovery, Environmental, Epigenetics, Events, Gene expression, Genetic, Hormones, Metabolism, Methylations, Microarray Analysis, Mutagens, PAGE, Recombination, Reductions, Sequences, Transcription, Type, transformation

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Peer-Reviewed Papers

References

Set your institution to view full text papers.

Using HTS-ELISA method to make anti-aflatoxin M1 monoclonal antibody Pei, S., et al. Wei Sheng Wu Xue Bao 50, 1406-11, (2010)

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Characterisation of aflatoxin and deoxynivalenol exposure among pregnant Egyptian women Piekkola, S., et al. Food Addit. Contam. Part A. Chem. Anal. Control. Expo. Risk Assess. 29, 962-71, (2012)

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Mechanism of action of dietary chemoprotective agents in rat liver: induction of phase I and II drug metabolizing enzymes and aflatoxin B1 metabolism. Manson MM, et al. Carcinogenesis 18, 1729-38, (1997)

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Aflatoxin B1 up-regulates insulin receptor substrate 2 and stimulates hepatoma cell migration. Ma Y, Kong Q, Hua H, et al. PLoS ONE 7(10), e47961, (2012)

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Development and application of salting-out assisted liquid/liquid extraction for multi-mycotoxin biomarkers analysis in pig urine with high performance liquid chromatography/tandem mass spectrometry. Song S, Ediage EN, Wu A, et al. J. Chromatogr. A 1292, 111-20, (2013)

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Biochemical and molecular aspects of mammalian susceptibility to aflatoxin B1 carcinogenicity. Massey TE, Stewart RK, Daniels JM, et al. Proc. Soc. Exp. Biol. Med. 208(3), 213-27, (1995)

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Bilirubin and related tetrapyrroles inhibit food-borne mutagenesis: a mechanism for antigenotoxic action against a model epoxide. Mölzer C, Huber H, Steyrer A, et al. J. Nat. Prod. 76(10), 1958-65, (2013)

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The molecular mechanism of aflatoxin B1-induced liver cancer: is mitotic recombination involved? Sengstag C Mol. Carcinog. 19(3), 147-52, (1997)

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Aflatoxin B1-induced DNA damage and its repair. Bedard LL and Massey TE Cancer Lett. 241(2), 174-83, (2006)

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Regulation of rat glutathione S-transferase A5 by cancer chemopreventive agents: mechanisms of inducible resistance to aflatoxin B1. Hayes JD, Pulford DJ, Ellis EM, et al. Chem. Biol. Interact. 111-112, 51-67, (1998)

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Sulforaphane, a cancer chemopreventive agent, induces pathways associated with membrane biosynthesis in response to tissue damage by aflatoxin B1. Techapiesancharoenkij N, Fiala JL, Navasumrit P, et al. Toxicol. Appl. Pharmacol. 282(1), 52-60, (2015)

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Survey of Aspergillus section Flavi and aflatoxin B(1) in brewer's grain used as pig feedstuff in Córdoba, Argentina. Asurmendi P, Barberis C, Dalcero A, et al. Mycotoxin Res. 29(1), 3-7, (2013)

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[Isolation and characterisation of an aflatoxin B1-degrading bacterium]. Li C, Li W, Yang W, et al. Wei Sheng Wu Xue Bao 52(9), 1129-36, (2012)

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[Study on the combined toxicity of aflatoxin B1 and deoxynivalenol]. Li B and Guo H Wei Sheng Yan Jiu 29(6), 393-5, (2000)

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Spectrophotometric determination of drugs with iodine. Karuna T, et al. J. Sci. Ind. Res. 65(10), 808, (2006)

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Synergistic interaction between aflatoxin B1 and hepatitis B virus in hepatocarcinogenesis. Kew MC Liver Int. 23(6), 405-9, (2003)

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Aflatoxin biosynthesis: current frontiers. Roze LV, Hong SY, and Linz JE Annu. Rev. Food Sci. Technol. 4, 293-311, (2013)

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Multi-component immunochromatographic assay for simultaneous detection of aflatoxin B1, ochratoxin A and zearalenone in agro-food. Li X, Li P, Zhang Q, et al. Biosens. Bioelectron. 49, 426-32, (2013)

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Genetic polymorphisms in DNA repair genes XRCC4 and XRCC5 and aflatoxin B1-related hepatocellular carcinoma. Long XD, Zhao D, Wang C, et al. Epidemiology 24(5), 671-81, (2013)

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Label-free homogeneous FRET immunoassay for the detection of mycotoxins that utilizes quenching of the intrinsic fluorescence of antibodies. Li T, Byun JY, Kim BB, et al. Biosens. Bioelectron. 42, 403-8, (2013)

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Activation and detoxication of aflatoxin B1. Guengerich FP, Johnson WW, Shimada T, et al. Mutat. Res. 402(1-2), 121-8, (1998)

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A simple and rapid optical biosensor for detection of aflatoxin B1 based on competitive dispersion of gold nanorods. Xu X, Liu X, Li Y, et al. Biosens. Bioelectron. 47, 361-7, (2013)

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Chemopreventive properties of chlorophylls towards aflatoxin B1: a review of the antimutagenicity and anticarcinogenicity data in rainbow trout. Dashwood R, Negishi T, Hayatsu H, et al. Mutat. Res. 399(2), 245-53, (1998)

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Polymorphisms in the coding region of X-ray repair complementing group 4 and aflatoxin B1-related hepatocellular carcinoma. Long XD, Yao JG, Zeng Z, et al. Hepatology 58(1), 171-81, (2013)

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Developing structure-activity relationships for the prediction of hepatotoxicity. Nigel Greene et al Chem. Res. Toxicol. 23, 1215-22, (2010)

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Aflatoxin B1 in poultry: toxicology, metabolism and prevention. Rawal S, Kim JE, and Coulombe R Res. Vet. Sci. 89(3), 325-31, (2010)

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Simultaneous determination of aflatoxin B(1) and ochratoxin A in licorice roots and fritillary bulbs by solid-phase extraction coupled with high-performance liquid chromatography-tandem mass spectrometry. Wang L, Wang Z, Gao W, et al. Food Chem. 138(2-3), 1048-54, (2013)

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Toxicity of increasing aflatoxin B1 concentrations from contaminated corn with or without clay adsorbent supplementation in ducklings. Wan XL, Yang ZB, Yang WR, et al. Poult. Sci. 92(5), 1244-53, (2013)

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In vitro and in vivo efficacy of a hydrated sodium calcium aluminosilicate to bind and reduce aflatoxin residues in tissues of broiler chicks fed aflatoxin B1. Neeff DV, Ledoux DR, Rottinghaus GE, et al. Poult. Sci. 92(1), 131-7, (2013)

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Ozonolysis efficiency and safety evaluation of aflatoxin B1 in peanuts. Diao E, Hou H, Chen B, et al. Food Chem. Toxicol. 55, 519-25, (2013)

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Integrated analysis of transcriptomics and metabonomics profiles in aflatoxin B1-induced hepatotoxicity in rat. Lu X, Hu B, Shao L, et al. Food Chem. Toxicol. 55, 444-55, (2013)

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Cytochrome P450 2A13 mediates the neoplastic transformation of human bronchial epithelial cells at a low concentration of aflatoxin B1. Zhang Z, Lu H, Huan F, et al. Int. J. Cancer 134(7), 1539-48, (2014)

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Interindividual variation in response to xenobiotic exposure established in precision-cut human liver slices. Jetten MJ, Claessen SM, Dejong CH, et al. Toxicology 323, 61-9, (2014)

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Assessment of the chemopreventive effect of casearin B, a clerodane diterpene extracted from Casearia sylvestris (Salicaceae). Prieto AM, dos Santos AG, Oliveira AP, et al. Food Chem. Toxicol. 53, 153-9, (2013)

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An outbreak of aflatoxin poisoning in dogs associated with aflatoxin B1-contaminated maize products. Wouters AT, Casagrande RA, Wouters F, et al. J. Vet. Diagn. Invest. 25(2), 282-7, (2013)

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A predictive ligand-based Bayesian model for human drug-induced liver injury. Sean Ekins et al Drug Metab. Dispos. 38, 2302-8, (2010)

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Kinetics of hydrolysis and reaction of aflatoxin B1 exo-8,9-epoxide and relevance to toxicity and detoxication. Guengerich FP and Johnson WW Drug Metab. Rev. 31(1), 141-58, (1999)

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Key roles of vitamins A, C, and E in aflatoxin B1-induced oxidative stress. Alpsoy L, Yalvac ME. Vitam. Horm. 86, 287-305, (2011)

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In vitro study on the effect of Saccharomyces cerevisiae strains on growth and mycotoxin production by Aspergillus carbonarius and Fusarium graminearum. Armando MR, Dogi CA, Poloni V, et al. Int. J. Food Microbiol. 161(3), 182-8, (2013)

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Growth, serum biochemistry, complement activity, and liver gene expression responses of Pekin ducklings to graded levels of cultured aflatoxin B1. Chen X, Horn N, Cotter PF, et al. Poult. Sci. 93(8), 2028-36, (2014)

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Development of a microwave-assisted-extraction-based method for the determination of aflatoxins B1, G1, B2, and G2 in grains and grain products. Chen S and Zhang H Anal. Bioanal. Chem 405(5), 1623-30, (2013)

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Simultaneous determination of bisphenol A, aflatoxin B1, ochratoxin A, and patulin in food matrices by liquid chromatography/mass spectrometry. Song W, Li C, and Moezzi B Rapid Commun. Mass Spectrom. 27(6), 671-80, (2013)

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Genetic organization and function of the aflatoxin B1 biosynthetic genes. Woloshuk CP and Prieto R FEMS Microbiol. Lett. 160(2), 169-76, (1998)

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Genome-wide miRNA-profiling of aflatoxin B1-induced hepatic injury using deep sequencing. Yang W, Lian J, Feng Y, et al. Toxicol. Lett. 226(2), 140-9, (2014)

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Application of the margin of exposure (MoE) approach to substances in food that are genotoxic and carcinogenic: example: aflatoxin B1 (AFB1). Benford D, Leblanc JC, and Setzer RW Food Chem. Toxicol. 48 Suppl 1, S34-41, (2010)

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Molecular basis of aflatoxin-induced mutagenesis-role of the aflatoxin B1-formamidopyrimidine adduct. Lin YC, Li L, Makarova AV, et al. Carcinogenesis 35(7), 1461-8, (2014)

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The effects of aflatoxin B1 on transporters and steroid metabolizing enzymes in JEG-3 cells. Huuskonen P, Myllynen P, Storvik M, et al. Toxicol. Lett. 218(3), 200-6, (2013)

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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. Guindon-Kezis KA, Mulder JE, and Massey TE Toxicology 321, 21-6, (2014)

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Mechanisms of aflatoxin B1 lung tumorigenesis. Massey TE, Smith GB, and Tam AS Exp. Lung Res. 26(8), 673-83, (2000)

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Etiological and molecular profile of hepatocellular cancer from India. Asim M, Sarma MP, and Kar P Int. J. Cancer 133(2), 437-45, (2013)

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The 1995 Pharmacological Society of Canada Merck Frosst Award. Cellular and molecular targets in pulmonary chemical carcinogenesis: studies with aflatoxin B1. Massey TE Can. J. Physiol. Pharmacol. 74(6), 621-8, (1996)

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Buckwheat achenes antioxidant profile modulates Aspergillus flavus growth and aflatoxin production. Chitarrini G, Nobili C, Pinzari F, et al. Int. J. Food Microbiol. 189, 1-10, (2014)

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Carry-over of aflatoxin B1 to aflatoxin M1 in high yielding Israeli cows in mid- and late-lactation. Britzi M, Friedman S, Miron J, et al. Toxins (Basel.) 5(1), 173-83, (2013)

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The hepatoprotective effect of sea buckthorn (Hippophae rhamnoides) berries on induced aflatoxin B1 poisoning in chickens 1. Solcan C, Gogu M, Floristean V, et al. Poult. Sci. 92(4), 966-74, (2013)

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Quantitative assessment of the effect of glutathione S-transferase genes GSTM1 and GSTT1 on hepatocellular carcinoma risk. Shen YH, Chen S, Peng YF, et al. Tumour Biol. 35(5), 4007-15, (2014)

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Hyperplasia, partial hepatectomy, and the carcinogenicity of aflatoxin B1. Roebuck BD J. Cell. Biochem. 91(2), 243-9, (2004)

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Comparative specificities of Calreticulin Transacetylase to O-acetyl, N-acetyl and S-acetyl derivative of 4-methylcoumarins and their inhibitory effect on AFB1-induced genotoxicity in vitro and in vivo. Kumar A, Ponnan P, Raj HG, et al. Food Chem. Toxicol. 52, 216-24, (2013)

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Removal of aflatoxin B(1) in edible plant oils by oscillating treatment with alkaline electrolysed water. Fan S, Zhang F, Liu S, et al. Food Chem. 141(3), 3118-23, (2013)

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Distribution of aflatoxigenic Aspergillus section Flavi in commercial poultry feed in Nigeria. Ezekiel CN, Atehnkeng J, Odebode AC, et al. Int. J. Food Microbiol. 189, 18-25, (2014)

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Trp266 determines the binding specificity of a porcine aflatoxin B₁ aldehyde reductase for aflatoxin B₁-dialdehyde. Wu J, Xu W, Zhang C, et al. Biochem. Pharmacol. 86(9), 1357-65, (2013)

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Cross-generational feeding of Bt (Bacillus thuringiensis)-maize to zebrafish (Danio rerio) showed no adverse effects on the parental or offspring generations. Sanden M, Ornsrud R, Sissener NH, et al. Br. J. Nutr. 110(12), 2222-33, (2013)

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The role of NAD(+)-dependent isocitrate dehydrogenase 3 subunit α in AFB1 induced liver lesion. Yang C, Fan J, Zhuang Z, et al. Toxicol. Lett. 224(3), 371-9, (2014)

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Efficiency of hydrated sodium calcium aluminosilicate to ameliorate the adverse effects of graded levels of aflatoxin B1 in broiler chicks. Chen X, Horn N, and Applegate TJ Poult. Sci. 93(8), 2037-47, (2014)

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Temporary modulation of responses to common vaccines and serum cation status in broilers during exposure to low doses of aflatoxin B1. Yunus AW and Böhm J Poult. Sci. 92(11), 2899-903, (2013)

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Lipid metabolism of commercial layers fed diets containing aflatoxin, fumonisin, and a binder. Siloto EV, Oliveira EF, Sartori JR, et al. Poult. Sci. 92(8), 2077-83, (2013)

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The effects of necrotic enteritis, aflatoxin B1, and virginiamycin on growth performance, necrotic enteritis lesion scores, and mortality in young broilers. Cravens RL, Goss GR, Chi F, et al. Poult. Sci. 92(8), 1997-2004, (2013)

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The natural product dihydrotanshinone I provides a prototype for uncharged inhibitors that bind specifically to the acetylcholinesterase peripheral site with nanomolar affinity. Beri V, Wildman SA, Shiomi K, et al. Biochemistry 52(42), 7486-99, (2013)

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Determination of aflatoxins B1, B2, G1, and G2 in olive oil, peanut oil, and sesame oil using immunoaffinity column cleanup, postcolumn derivatization, and liquid chromatography with fluorescence detection: first action 2013.05. Bao L, Liang C, Trucksess MW, et al. J. AOAC Int. 96(5), 1017-8, (2013)

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Mathematic modeling for optimum conditions on aflatoxin B₁degradation by the aerobic bacterium Rhodococcus erythropolis. Kong Q, Zhai C, Guan B, et al. Toxins (Basel.) 4(11), 1181-95, (2012)

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A novel mycotoxin purification system using magnetic nanoparticles for the recovery of aflatoxin B1 and zearalenone from feed. Kim HJ, Kim SH, Lee JK, et al. J. Vet. Sci. 13(4), 363-9, (2012)

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Immunofiltration assay for aflatoxin B1 based on the separation of pre-immune complexes. Saha D, Roy D, and Dhar TK J. Immunol. Methods 392(1-2), 24-8, (2013)

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Carcinogenic effects of aflatoxin B1 among wheat handlers. Saad-Hussein A, Taha MM, Beshir S, et al. Int. J. Occup. Environ. Health 20(3), 215-9, (2014)

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Aflatoxins B and g contamination and aflatoxigenic fungi in nutmeg. Okano K, Tomita T, Ohzu Y, et al. Shokuhin Eiseigaku Zasshi 53(5), 211-6, (2012)

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[Exposure to aflatoxin B1 in experimental animals and its public health significance]. Guzmán de Peña D Salud Publica. Mex. 49(3), 227-35, (2007)

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Regulation of glutathione S-transferases and aldehyde reductase by chemoprotectors: studies of mechanisms responsible for inducible resistance to aflatoxin B1. Hayes JD, McLeod R, Ellis EM, et al. IARC Sci. Publ. (139), 175-87, (1996)

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Activation of toxic chemicals by cytochrome P450 enzymes: regio- and stereoselective oxidation of aflatoxin B1. Guengerich FP, Ueng YF, Kim BR, et al. Adv. Exp. Med. Biol. 387, 7-15, (1996)

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p53 proteins and aflatoxin b1: the good, the bad, and the ugly. Liang TJ Hepatology 22(4 Pt 1), 1330-2, (1995)

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Merck 14,180

Beil. 19,V,10,566

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