Aflatoxin M1
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| Category | Mycotoxins |
| Catalog number | BBF-00655 |
| CAS | 6795-23-9 |
| Molecular Weight | 328.27 |
| Molecular Formula | C17H12O7 |
| Purity | ≥95% |
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Description
It is produced by the strain of Aspergillus flavus, Asp. parasiticus. The compound of aflatoxin has the activity of anti-gram-positive bacteria, inhibits cell mitosis, has the effect of liver necrosis and carcinogenesis, and is a mycotoxin which contaminates food.
Specification
| Synonyms | AFLATOXIN M1; 4-Hydroxyaflatoxin B1; 3020O28I3; CCRIS 15; (6aR,9aR)-9a-hydroxy-4-methoxy-2,3,6a,9a-tetrahydrocyclopenta[c]furo[3',2':4,5]furo[2,3-h]chromene-1,11-dione; (6aR-cis)-2,3,6a,9a-tetrahydro-9a-hydroxy-4-methoxycyclopenta[c]furo[3',2':4,5]furo[2,3-h][1]benzopyran-1,11-dione; CHEBI:78576; Cyclopenta[c]furo[3',2':4,5]furo[2,3-h][1]benzopyran-1,11-dione,2,3,6a,9a-tetrahydro-9a-hydroxy-4-methoxy-,(6ar,9ar)- |
| Storage | 2-8 °C |
| IUPAC Name | (3R,7R)-3-hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaene-16,18-dione |
| Canonical SMILES | COC1=C2C3=C(C(=O)CC3)C(=O)OC2=C4C(=C1)OC5C4(C=CO5)O |
| InChI | InChI=1S/C17H12O7/c1-21-9-6-10-13(17(20)4-5-22-16(17)23-10)14-12(9)7-2-3-8(18)11(7)15(19)24-14/h4-6,16,20H,2-3H2,1H3/t16-,17-/m1/s1 |
| InChI Key | MJBWDEQAUQTVKK-IAGOWNOFSA-N |
| Source | 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. The toxin can also be found in the milk of animals which are fed contaminated feed. |
Properties
| Appearance | White to Yellow Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Boiling Point | 644.3 °C at 760 mmHg |
| Melting Point | 299 °C (dec.) |
| Density | 1.660 g/cm3 |
| Solubility | Soluble in Chloroform, Ethanol |
Toxicity
| Carcinogenicity | 2B, possibly carcinogenic to humans. |
| Mechanism Of Toxicity | Aflatoxins produce singlet oxygen upon their exposure to UV (365 nm) light. Singlet oxygen in turn activates them to mutagens and DNA binding species. Aflatoxin M1 is P450 activated to its epoxide. Aflatoxin metabolites can intercalate into DNA and alkylate the bases through their epoxide moiety, binding particularity to N7-guanine bases. In addition to randomly mutating DNA, this is thought to cause mutations in the p53 gene, an important gene in preventing cell cycle progression when there are DNA mutations, or signaling apoptosis. |
Reference Reading
1. Presence of Aflatoxin M1 in Commercial Milk in Paraguay
Andrea Alejandra Arrua, Francisco Paulo Ferreira, Cinthia Cazal, Danilo Fernández Rios, Juliana Moura-Mendes, Pablo David Arrúa, Horacio Daniel Lopez-Nicora, Cristhian Javier Grabowski J Food Prot . 2021 Dec 1;84(12):2128-2132. doi: 10.4315/JFP-21-196.
Abstract:The presence of aflatoxin M1 (AFM1) in milk is a public health concern because milk is a significant part of human diets worldwide. In economies where AFM1 monitoring is low or nonexistent, the possibility of AFM1 contamination might be increased. Our study was conducted to detect and quantify AFM1 in fluid milk and milk drinks of various brands, fat concentrations, packages, and heat treatments sold in the Metropolitan Area of Asunción, Paraguay. Eighty samples were collected from supermarkets in the Metropolitan Area of Asunción following a nonprobability sampling method. An enzyme-linked immunosorbent assay for AFM1 (25 to 500 ppt) was used to quantify the toxin, and results were analyzed with nonparametric methods. All samples were positive values for AFM1 (above the detection limit of 25 ng/kg); 85% of the samples had 30 to 50 ng/kg, and 15% had >500 ng/kg. No significant difference in AFM1 concentration was found based on fat concentration, heat treatment, or type of packaging of these milk products; however, significant differences were found between brands.
2. Aflatoxin B1 and M1: Biological Properties and Their Involvement in Cancer Development
Lorella Severino, Andrea Polo, Susan Costantini, Silvia Marchese, Andrea Ariano, Salvatore Velotto Toxins (Basel) . 2018 May 24;10(6):214. doi: 10.3390/toxins10060214.
Aflatoxins are fungal metabolites found in feeds and foods. When the ruminants eat feedstuffs containing Aflatoxin B1 (AFB1), this toxin is metabolized and Aflatoxin M1 (AFM1) is excreted in milk. International Agency for Research on Cancer (IARC) classified AFB1 and AFM1 as human carcinogens belonging to Group 1 and Group 2B, respectively, with the formation of DNA adducts. In the last years, some epidemiological studies were conducted on cancer patients aimed to evaluate the effects of AFB1 and AFM1 exposure on cancer cells in order to verify the correlation between toxin exposure and cancer cell proliferation and invasion. In this review, we summarize the activation pathways of AFB1 and AFM1 and the data already reported in literature about their correlation with cancer development and progression. Moreover, considering that few data are still reported about what genes/proteins/miRNAs can be used as damage markers due to AFB1 and AFM1 exposure, we performed a bioinformatic analysis based on interaction network and miRNA predictions to identify a panel of genes/proteins/miRNAs that can be used as targets in further studies for evaluating the effects of the damages induced by AFB1 and AFM1 and their capacity to induce cancer initiation.
3. Recent Advances in the Aptamer-Based Electrochemical Biosensors for Detecting Aflatoxin B1 and Its Pertinent Metabolite Aflatoxin M1
Somayeh Tajik, Soo Young Kim, Quyet Van Le, Ho Won Jang, Mohammadreza Shokouhimehr, Hadi Beitollahi, Zahra Dourandish, Kaiqiang Zhang Sensors (Basel) . 2020 Jun 8;20(11):3256. doi: 10.3390/s20113256.
The notable toxicological impacts of aflatoxin B1 (AFB1) and its main metabolite, aflatoxin M1 (AFM1), on human being health make the evaluation of food quality highly significant. Due to the toxicity of those metabolites-even very low content in foodstuffs-it is crucial to design a sensitive and reliable procedure for their detection. Electrochemical aptamer-based biosensors are considered the most encouraging option, based on multi-placed analysis, rapid response, high sensitivity and specificity. The present review specifically emphasizes the potential utilization of the electrochemical aptasensors for determining the AFM1 and AFB1 with different electrodes.
Spectrum
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
