Aflatoxin B1
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Basic Info
Common Name | Aflatoxin B1(F04874) |
2D Structure | |
Description | Aflatoxins are naturally occurring mycotoxins that are produced by many species of Aspergillus, a fungus, most notably Aspergillus flavus and Aspergillus parasiticus. At least 13 different types of aflatoxin are produced in nature. Aflatoxin B1 is considered the most toxic and is produced by both Aspergillus flavus and Aspergillus parasiticus. The native habitat of Aspergillus is in soil, decaying vegetation, hay, and grains undergoing microbiological deterioration and it invades all types of organic substrates whenever conditions are favorable for its growth. Favorable conditions include high moisture content (at least 7%) and high temperature. Aflatoxins B1 (AFB1) are contaminants of improperly stored foods; they are potent genotoxic and carcinogenic compounds, exerting their effects through damage to DNA. They can also induce mutations that increase oxidative damage. (A7847). Crops which are frequently affected by Aspergillus contamination include cereals (maize, sorghum, pearl millet, rice, wheat), oilseeds (peanut, soybean, sunflower, cotton), spices (chile peppers, black pepper, coriander, turmeric, ginger), and tree nuts (almond, pistachio, walnut, coconut, brazil nut). |
FRCD ID | F04874 |
CAS Number | 1162-65-8 |
PubChem CID | 14403 |
Formula | C17H12O6 |
IUPAC Name | None |
InChI Key | OQIQSTLJSLGHID-UHFFFAOYSA-N |
InChI | 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 |
Canonical SMILES | COC1=C2C3=C(C(=O)CC3)C(=O)OC2=C4C5C=COC5OC4=C1 |
Isomeric SMILES | COC1=C2C3=C(C(=O)CC3)C(=O)OC2=C4C5C=COC5OC4=C1 |
Synonyms | AFBI AFB1 Aflatoxin-B1 Cyclopenta[c]furo[3',2':4,5]furo[2,3-h][1]benzopyran-1,11-dione, 2,3,6a.alpha.,9a.alpha.-tetrahydro-4-methoxy- NSC529592 Aflaloxin B1 Cyclopenta[c]furo[3',2':4,5]furo[2,3-h][1]benzopyran-1,11-dione, 2,3,6a,9a-tetrahydro-4-methoxy-, (6aR-cis)- AC1L23RJ AC1Q6P7N SCHEMBL126479 |
Classifies | Fungal Toxin |
Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
Kingdom | Organic compounds |
Superclass | Phenylpropanoids and polyketides |
Class | Coumarins and derivatives |
Subclass | Furanocoumarins |
Intermediate Tree Nodes | Angular furanocoumarins - Aflatoxins |
Direct Parent | Difurocoumarocyclopentenones |
Alternative Parents | |
Molecular Framework | Aromatic heteropolycyclic compounds |
Substituents | Difurocoumarocyclopentenone - Benzopyran - 1-benzopyran - Coumaran - Anisole - Aryl alkyl ketone - Aryl ketone - Alkyl aryl ether - Pyranone - Pyran - Benzenoid - Heteroaromatic compound - Dihydrofuran - Lactone - Ketone - Ether - Acetal - Oxacycle - Organoheterocyclic compound - Organooxygen compound - Organic oxygen compound - Hydrocarbon derivative - Organic oxide - Aromatic heteropolycyclic compound |
Description | This compound belongs to the class of organic compounds known as difurocoumarocyclopentenones. These are polycyclic aromatic compounds containing a cyclopenten-2-one ring fused to the coumarin moiety of the difurocoumarin skeleton. |
Properties
Property Name | Property Value |
---|---|
Molecular Weight | 312.277 |
Hydrogen Bond Donor Count | 0 |
Hydrogen Bond Acceptor Count | 6 |
Rotatable Bond Count | 1 |
Complexity | 650 |
Monoisotopic Mass | 312.063 |
Exact Mass | 312.063 |
XLogP | 1.6 |
Formal Charge | 0 |
Heavy Atom Count | 23 |
Defined Atom Stereocenter Count | 0 |
Undefined Atom Stereocenter Count | 2 |
Defined Bond Stereocenter Count | 0 |
Undefined Bond Stereocenter Count | 0 |
Isotope Atom Count | 0 |
Covalently-Bonded Unit Count | 1 |
ADMET
Model | Result | Probability |
---|---|---|
Absorption | ||
Blood-Brain Barrier | BBB+ | 0.9264 |
Human Intestinal Absorption | HIA+ | 0.9846 |
Caco-2 Permeability | Caco2+ | 0.5377 |
P-glycoprotein Substrate | Substrate | 0.5200 |
P-glycoprotein Inhibitor | Inhibitor | 0.5594 |
Non-inhibitor | 0.5494 | |
Renal Organic Cation Transporter | Non-inhibitor | 0.7736 |
Distribution | ||
Subcellular localization | Mitochondria | 0.8353 |
Metabolism | ||
CYP450 2C9 Substrate | Non-substrate | 0.7461 |
CYP450 2D6 Substrate | Non-substrate | 0.8529 |
CYP450 3A4 Substrate | Non-substrate | 0.5578 |
CYP450 1A2 Inhibitor | Inhibitor | 0.8746 |
CYP450 2C9 Inhibitor | Inhibitor | 0.6650 |
CYP450 2D6 Inhibitor | Non-inhibitor | 0.5513 |
CYP450 2C19 Inhibitor | Inhibitor | 0.7727 |
CYP450 3A4 Inhibitor | Inhibitor | 0.5184 |
CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.6208 |
Excretion | ||
Toxicity | ||
Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.7855 |
Non-inhibitor | 0.9440 | |
AMES Toxicity | AMES toxic | 0.9737 |
Carcinogens | Non-carcinogens | 0.9673 |
Fish Toxicity | High FHMT | 0.9564 |
Tetrahymena Pyriformis Toxicity | High TPT | 0.9979 |
Honey Bee Toxicity | High HBT | 0.7512 |
Biodegradation | Not ready biodegradable | 0.6241 |
Acute Oral Toxicity | I | 0.8088 |
Carcinogenicity (Three-class) | Danger | 0.7481 |
Model | Value | Unit |
---|---|---|
Absorption | ||
Aqueous solubility | -3.7039 | LogS |
Caco-2 Permeability | 0.7714 | LogPapp, cm/s |
Distribution | ||
Metabolism | ||
Excretion | ||
Toxicity | ||
Rat Acute Toxicity | 3.5902 | LD50, mol/kg |
Fish Toxicity | -0.8170 | pLC50, mg/L |
Tetrahymena Pyriformis Toxicity | 1.4040 | pIGC50, ug/L |
References
Title | Journal | Date | Pubmed ID |
---|---|---|---|
Aflatoxin contamination in nuts marketed in Italy: preliminary results. | Ann Ig | 2018 Sep-Oct | 30062368 |
Simultaneous determination of trace Aflatoxin B<sub>1</sub> and Ochratoxin A by aptamer-based microchip capillary electrophoresis in food samples. | J Chromatogr A | 2018 Sep 28 | 30037541 |
Quantum dot nanobead-based multiplexed immunochromatographic assay for simultaneous detection of aflatoxin B<sub>1</sub> and zearalenone. | Anal Chim Acta | 2018 Sep 26 | 29801605 |
Maternal aflatoxin exposure during pregnancy and adverse birth outcomes in Uganda. | Matern Child Nutr | 2018 Sep 22 | 30242967 |
Contaminants in Grain-A Major Risk for Whole Grain Safety? | Nutrients | 2018 Sep 2 | 30200531 |
Graphene quantum dots-based nano-biointerface platform for food toxin detection. | Anal Bioanal Chem | 2018 Sep 14 | 30218125 |
In vitro model to assess the adsorption of oral veterinary drugs to mycotoxin binders in a feed- and aflatoxin B1-containing buffered matrix. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2018 Sep | 30016205 |
Co-occurrence of mycotoxins in commercial formula milk and cereal-based baby food on the Qatar market. | Food Addit Contam Part B Surveill | 2018 Sep | 29490584 |
Zearalenone reduction by commercial peroxidase enzyme and peroxidases from soybean bran and rice bran. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2018 Sep | 29889651 |
The production of yeast cell wall using an agroindustrial waste influences thewall thickness and is implicated on the aflatoxin B1 adsorption process. | Food Res Int | 2018 Sep | 30007690 |
Effects of gamma irradiation on aflatoxin B1 levels in soybean and on theproperties of soybean and soybean oil. | Appl Radiat Isot | 2018 Sep | 29852404 |
Mechanism and kinetics of degrading aflatoxin B<sub>1</sub> by salt tolerant Candida versatilis CGMCC 3790. | J Hazard Mater | 2018 Oct 5 | 30053743 |
Reduced graphene oxide and gold nanoparticle composite-based solid-phase extraction coupled with ultra-high-performance liquid chromatography-tandem mass spectrometry for the determination of 9 mycotoxins in milk. | Food Chem | 2018 Oct 30 | 29853368 |
Penicillium gravinicasei, a new species isolated from cave cheese in Apulia,Italy. | Int J Food Microbiol | 2018 Oct 3 | 29929177 |
Application of Stable Isotope Dilution and Liquid Chromatography Tandem Mass Spectrometry for Multi-Mycotoxin Analysis in Edible Oils. | J AOAC Int | 2018 Oct 10 | 30305203 |
Encapsulation of cinnamon essential oil in whey protein enhances the protective effect against single or combined sub-chronic toxicity of fumonisin B<sub>1</sub> and/or aflatoxin B<sub>1</sub> in rats. | Environ Sci Pollut Res Int | 2018 Oct | 30112645 |
Protective role of curcumin in ameliorating AFB<sub>1</sub>-induced apoptosis via mitochondrial pathway in liver cells. | Mol Biol Rep | 2018 Oct | 29974318 |
Sensitivity enhancement for mycotoxin determination by optical waveguide lightmode spectroscopy using gold nanoparticles of different size and origin. | Food Chem | 2018 Nov 30 | 29934142 |
Novel quartz crystal microbalance immunodetection of aflatoxin B<sub>1</sub> coupling cargo-encapsulated liposome with indicator-triggered displacement assay. | Anal Chim Acta | 2018 Nov 15 | 30119735 |
Assessing the combined toxicity of the natural toxins, aflatoxin B<sub>1</sub>, fumonisin B<sub>1</sub> and microcystin-LR by high content analysis. | Food Chem Toxicol | 2018 Nov | 30253246 |
Targets
- General Function:
- Glutathione transferase activity
- Specific Function:
- Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
- Gene Name:
- GSTA1
- Uniprot ID:
- P08263
- Molecular Weight:
- 25630.785 Da
References
- Sluis-Cremer N, Wallace L, Burke J, Stevens J, Dirr H: Aflatoxin B1 and sulphobromophthalein binding to the dimeric human glutathione S-transferase A1-1: a fluorescence spectroscopic analysis. Eur J Biochem. 1998 Oct 15;257(2):434-42. [9826190 ]
- General Function:
- Vitamin d3 25-hydroxylase activity
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide (PubMed:11159812). Catalyzes 4-beta-hydroxylation of cholesterol. May catalyze 25-hydroxylation of cholesterol in vitro (PubMed:21576599).
- Gene Name:
- CYP3A4
- Uniprot ID:
- P08684
- Molecular Weight:
- 57342.67 Da
- Mechanism of Action:
- In order to exert its toxic effects, aflatoxin B1 must first be activated to its epoxide, aflatoxin B1 2,3-oxide, by the cytochome P-450 enzymes CYP1A2 and CYP3A4.
References
- Eaton DL, Gallagher EP: Mechanisms of aflatoxin carcinogenesis. Annu Rev Pharmacol Toxicol. 1994;34:135-72. [8042848 ]
- General Function:
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function:
- Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related compounds.
- Gene Name:
- SLC22A11
- Uniprot ID:
- Q9NSA0
- Molecular Weight:
- 59970.945 Da
- Mechanism of Action:
- Mycotoxins are often able to enter the liver and kidney by human organic anion transporters (hOATs) and human organic cation transporters (hOCTs). They can also inhibit uptake of anions and cations by these transporters, interefering with the secretion of endogenous metabolites, drugs, and xenobiotics including themselves. This results in increased cellular accumulation of toxic compounds causing nephro- and hepatotoxicity.
References
- Tachampa K, Takeda M, Khamdang S, Noshiro-Kofuji R, Tsuda M, Jariyawat S, Fukutomi T, Sophasan S, Anzai N, Endou H: Interactions of organic anion transporters and organic cation transporters with mycotoxins. J Pharmacol Sci. 2008 Mar;106(3):435-43. Epub 2008 Mar 5. [18319568 ]
- General Function:
- Quaternary ammonium group transmembrane transporter activity
- Specific Function:
- Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creatinine, amantadine, memantine, acriflavine, 4-[4-(dimethylamino)-styryl]-N-methylpyridinium ASP, amiloride, metformin, N-1-methylnicotinamide (NMN), tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, cisplatin and oxaliplatin. Cisplatin may develop a nephrotoxic action. Transport of creatinine is inhibited by fluoroquinolones such as DX-619 and LVFX. This transporter is a major determinant of the anticancer activity of oxaliplatin and may contribute to antitumor specificity.
- Gene Name:
- SLC22A2
- Uniprot ID:
- O15244
- Molecular Weight:
- 62579.99 Da
- Mechanism of Action:
- Mycotoxins are often able to enter the liver and kidney by human organic anion transporters (hOATs) and human organic cation transporters (hOCTs). They can also inhibit uptake of anions and cations by these transporters, interefering with the secretion of endogenous metabolites, drugs, and xenobiotics including themselves. This results in increased cellular accumulation of toxic compounds causing nephro- and hepatotoxicity.
References
- Tachampa K, Takeda M, Khamdang S, Noshiro-Kofuji R, Tsuda M, Jariyawat S, Fukutomi T, Sophasan S, Anzai N, Endou H: Interactions of organic anion transporters and organic cation transporters with mycotoxins. J Pharmacol Sci. 2008 Mar;106(3):435-43. Epub 2008 Mar 5. [18319568 ]
- General Function:
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function:
- Mediates sodium-independent multispecific organic anion transport. Transport of prostaglandin E2, prostaglandin F2, tetracycline, bumetanide, estrone sulfate, glutarate, dehydroepiandrosterone sulfate, allopurinol, 5-fluorouracil, paclitaxel, L-ascorbic acid, salicylate, ethotrexate, and alpha-ketoglutarate.
- Gene Name:
- SLC22A7
- Uniprot ID:
- Q9Y694
- Molecular Weight:
- 60025.025 Da
- Mechanism of Action:
- Mycotoxins are often able to enter the liver and kidney by human organic anion transporters (hOATs) and human organic cation transporters (hOCTs). They can also inhibit uptake of anions and cations by these transporters, interefering with the secretion of endogenous metabolites, drugs, and xenobiotics including themselves. This results in increased cellular accumulation of toxic compounds causing nephro- and hepatotoxicity.
References
- Tachampa K, Takeda M, Khamdang S, Noshiro-Kofuji R, Tsuda M, Jariyawat S, Fukutomi T, Sophasan S, Anzai N, Endou H: Interactions of organic anion transporters and organic cation transporters with mycotoxins. J Pharmacol Sci. 2008 Mar;106(3):435-43. Epub 2008 Mar 5. [18319568 ]
- General Function:
- Superoxide dismutase copper chaperone activity
- Specific Function:
- May supply copper to copper-requiring proteins within the secretory pathway, when localized in the trans-Golgi network. Under conditions of elevated extracellular copper, it relocalized to the plasma membrane where it functions in the efflux of copper from cells.
- Gene Name:
- ATP7A
- Uniprot ID:
- Q04656
- Molecular Weight:
- 163372.275 Da
- Mechanism of Action:
- AFB1 inhibits activated Ca (2+)-ATPase by binding to an important site in the calmodulin-binding domain of the enzyme.
References
- Adebayo AO, Okunade GW, Olorunsogo OO: The anticalmodulin effect of aflatoxin B1 on purified erythrocyte Ca(2+)-ATPase. Biosci Rep. 1995 Aug;15(4):209-20. [8562872 ]
- General Function:
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
- Gene Name:
- CYP1A2
- Uniprot ID:
- P05177
- Molecular Weight:
- 58293.76 Da
- Mechanism of Action:
- In order to exert its toxic effects, aflatoxin B1 must first be activated to its epoxide, aflatoxin B1 2,3-oxide, by the cytochome P-450 enzymes CYP1A2 and CYP3A4.
References
- Eaton DL, Gallagher EP: Mechanisms of aflatoxin carcinogenesis. Annu Rev Pharmacol Toxicol. 1994;34:135-72. [8042848 ]
- General Function:
- Secondary active organic cation transmembrane transporter activity
- Specific Function:
- Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)-N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine, and metformin. The transport of organic cations is inhibited by a broad array of compounds like tetramethylammonium (TMA), cocaine, lidocaine, NMDA receptor antagonists, atropine, prazosin, cimetidine, TEA and NMN, guanidine, cimetidine, choline, procainamide, quinine, tetrabutylammonium, and tetrapentylammonium. Translocates organic cations in an electrogenic and pH-independent manner. Translocates organic cations across the plasma membrane in both directions. Transports the polyamines spermine and spermidine. Transports pramipexole across the basolateral membrane of the proximal tubular epithelial cells. The choline transport is activated by MMTS. Regulated by various intracellular signaling pathways including inhibition by protein kinase A activation, and endogenously activation by the calmodulin complex, the calmodulin-dependent kinase II and LCK tyrosine kinase.
- Gene Name:
- SLC22A1
- Uniprot ID:
- O15245
- Molecular Weight:
- 61153.345 Da
- Mechanism of Action:
- Mycotoxins are often able to enter the liver and kidney by human organic anion transporters (hOATs) and human organic cation transporters (hOCTs). They can also inhibit uptake of anions and cations by these transporters, interefering with the secretion of endogenous metabolites, drugs, and xenobiotics including themselves. This results in increased cellular accumulation of toxic compounds causing nephro- and hepatotoxicity.
References
- Tachampa K, Takeda M, Khamdang S, Noshiro-Kofuji R, Tsuda M, Jariyawat S, Fukutomi T, Sophasan S, Anzai N, Endou H: Interactions of organic anion transporters and organic cation transporters with mycotoxins. J Pharmacol Sci. 2008 Mar;106(3):435-43. Epub 2008 Mar 5. [18319568 ]
- General Function:
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function:
- Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS) (By similarity). Mediates the sodium-independent uptake of p-aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido-3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro-phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2-furanpropionate (CMPF), cidofovir, adefovir, 9-(2-phosphonylmethoxyethyl) guanine (PMEG), 9-(2-phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p-chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid (By similarity). PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate.
- Gene Name:
- SLC22A6
- Uniprot ID:
- Q4U2R8
- Molecular Weight:
- 61815.78 Da
- Mechanism of Action:
- Mycotoxins are often able to enter the liver and kidney by human organic anion transporters (hOATs) and human organic cation transporters (hOCTs). They can also inhibit uptake of anions and cations by these transporters, interefering with the secretion of endogenous metabolites, drugs, and xenobiotics including themselves. This results in increased cellular accumulation of toxic compounds causing nephro- and hepatotoxicity.
References
- Tachampa K, Takeda M, Khamdang S, Noshiro-Kofuji R, Tsuda M, Jariyawat S, Fukutomi T, Sophasan S, Anzai N, Endou H: Interactions of organic anion transporters and organic cation transporters with mycotoxins. J Pharmacol Sci. 2008 Mar;106(3):435-43. Epub 2008 Mar 5. [18319568 ]
- General Function:
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function:
- Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenadine. Transports benzylpenicillin (PCG), estrone-3-sulfate (E1S), cimetidine (CMD), 2,4-dichloro-phenoxyacetate (2,4-D), p-amino-hippurate (PAH), acyclovir (ACV) and ochratoxin (OTA).
- Gene Name:
- SLC22A8
- Uniprot ID:
- Q8TCC7
- Molecular Weight:
- 59855.585 Da
- Mechanism of Action:
- Mycotoxins are often able to enter the liver and kidney by human organic anion transporters (hOATs) and human organic cation transporters (hOCTs). They can also inhibit uptake of anions and cations by these transporters, interefering with the secretion of endogenous metabolites, drugs, and xenobiotics including themselves. This results in increased cellular accumulation of toxic compounds causing nephro- and hepatotoxicity.
References
- Tachampa K, Takeda M, Khamdang S, Noshiro-Kofuji R, Tsuda M, Jariyawat S, Fukutomi T, Sophasan S, Anzai N, Endou H: Interactions of organic anion transporters and organic cation transporters with mycotoxins. J Pharmacol Sci. 2008 Mar;106(3):435-43. Epub 2008 Mar 5. [18319568 ]