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Merck

O1877

Sigma-Aldrich

Ochratoxin A

Ochratoxin A
1 of 1 reviewers received a sample product or took part in a promotion

from Petromyces albertensis, ≥98% (HPLC), powder, mycotoxin

Sinónimos:

N-[(3R)-(5-Chloro-8-hydroxy-3-methyl-1-oxo-7-isochromanyl)carbonyl]-L-phenylalanine

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About This Item

Fórmula empírica (notación de Hill):
C20H18ClNO6
Número de CAS:
Peso molecular:
403.81
Beilstein:
1301486
Número MDL:
Código UNSPSC:
12352200
ID de la sustancia en PubChem:
NACRES:
NA.77
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Nombre del producto

Ochratoxin A, from Petromyces albertensis, ≥98% (HPLC)

origen biológico

Petromyces albertensis

Nivel de calidad

Ensayo

≥98% (HPLC)

Formulario

powder

impurezas

Benzene, free

solubilidad

ethanol: soluble

Modo de acción

enzyme | inhibits
protein synthesis | interferes

temp. de almacenamiento

2-8°C

cadena SMILES

C[C@@H]1Cc2c(Cl)cc(c(O)c2C(=O)O1)C(=O)N[C@@H](Cc3ccccc3)C(O)=O

InChI

1S/C20H18ClNO6/c1-10-7-12-14(21)9-13(17(23)16(12)20(27)28-10)18(24)22-15(19(25)26)8-11-5-3-2-4-6-11/h2-6,9-10,15,23H,7-8H2,1H3,(H,22,24)(H,25,26)/t10-,15+/m1/s1

Clave InChI

RWQKHEORZBHNRI-BMIGLBTASA-N

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Categorías relacionadas

Aplicación

Ochratoxin A has been used as a mycotoxin:
  • to test its effect on metabolism and hypoxia in human embryonic kidney (HEK293) cells[1]
  • to test its cytotoxic effects in bovine mammary epithelial cells[2]
  • as a standard for gamma radiation studies with food products and in cytotoxic studies using Hep G2 cells[3]

Acciones bioquímicas o fisiológicas

Ochratoxin A (OTA), a renal toxin, is produced majorly by Aspergillus and Penicillium fungal species.[1] It is immunotoxic, teratogenic[2] myelotoxic, and mutagenic.[3] It effectively interrupts the intestinal barrier functions.[2] OTA displays a long elimination half-life[3] and stimulates the major inflammatory cytokines release.[2]
Ochratoxin A is a mycotoxin found in food that is nephrotoxic and carcinogenic in the kidney and induces differentiation in cloned renal cell lines. Increases endoplasmic reticulum ATP-dependent Ca2+ pump activity.

Nota de preparación

This product is also soluble in chloroform (9.80 - 10.20 mg/ml), methanol (10 mg/ml), ethanol (50 mM), and DMSO (100 mM).

Pictogramas

Skull and crossbonesHealth hazard

Palabra de señalización

Danger

Frases de peligro

Clasificaciones de peligro

Acute Tox. 2 Oral - Carc. 2

Código de clase de almacenamiento

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges


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Certificados de análisis (COA)

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Chong-Sun Khoi et al.
International journal of molecular sciences, 22(20) (2021-10-24)
Ochratoxin A (OTA), one of the major food-borne mycotoxins, impacts the health of humans and livestock by contaminating food and feed. However, the underlying mechanism of OTA nephrotoxicity remains unknown. This study demonstrated that OTA induced apoptosis through selective endoplasmic
Shanel Raghubeer et al.
Toxicology in vitro : an international journal published in association with BIBRA, 57, 211-216 (2019-03-17)
Cellular adaptation to hypoxia is controlled by hypoxia-inducible factor 1α (HIF1α), a transcription factor activated in response to oxygen tension, reactive oxygen species (ROS) and inflammation. Overexpression of HIF1α and HSP90 has been associated with cancer induction. Ochratoxin A (OTA)
H Schramek et al.
The Journal of pharmacology and experimental therapeutics, 283(3), 1460-1468 (1998-02-12)
The kidneys represent one of the main targets of ochratoxin A (OTA), a secondary fungal metabolite that is produced by certain species of Aspergillus and Penicillium. OTA has the ability to disturb Madin-Darby canine kidney (MDCK) cell pH homeostasis, leading
D Hoehler et al.
Biochimica et biophysica acta, 1357(2), 225-233 (1997-06-27)
Oxidative damage may be one of the manifestations of cellular damage in the toxicity of ochratoxin A (OA). OA; its three natural analogs, OB, OC and O alpha; and three synthetic analogs, the ethyl amide of OA (OE-OA), O-methylated OA
M Gekle et al.
Toxicology and applied pharmacology, 152(1), 282-291 (1998-10-17)
Ochratoxin A (OTA) is a ubiquitous fungal metabolite with predominant nephrotoxic action. OTA impairs postproximal renal electrolyte handling and increases the incidence of renal adenoma and carcinoma. Furthermore, it is supposed to be involved in the pathogenesis of different forms

Artículos

DNA damage and repair mechanism is vital for maintaining DNA integrity. Damage to cellular DNA is involved in mutagenesis, the development of cancer among others.

Questions

  1. Which solvents can be used for an OTA standard solution? PBS, alcoholic solvents (methanol or ethanol)?

    1 answer
    1. The analytical standard version of this compound, 34037, is a 10ug/mL solution in acetonitrile. This product is also soluble in chloroform (9.80 - 10.20 mg/ml), methanol (10 mg/ml), ethanol (50 mM), and DMSO (100 mM). The choice of solvent would be best determined by the researcher.

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Reviews

1 of 1 reviewers received a sample product or took part in a promotion

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