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O1877

Sigma-Aldrich

Ochratoxin A

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

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C20H18ClNO6
Numéro CAS:
303-47-9
Poids moléculaire :
403.81
Numéro Beilstein :
1301486
Numéro MDL:
MFCD00078079
Code UNSPSC :
12352200
ID de substance PubChem :
24897954
Nomenclature NACRES :
NA.77

product name

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

Source biologique

Petromyces albertensis

Niveau de qualité

300

Pureté

≥98% (HPLC)

Forme

powder

Impuretés

Benzene, free

Solubilité

ethanol: soluble

Mode d’action

enzyme | inhibits
protein synthesis | interferes

Température de stockage

2-8°C

Chaîne 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

Clé InChI

RWQKHEORZBHNRI-BMIGLBTASA-N

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Application

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

Actions biochimiques/physiologiques

Ochratoxin A (OTA), a renal toxin, is produced majorly by Aspergillus and Penicillium fungal species. It is immunotoxic, teratogenic myelotoxic, and mutagenic. It effectively interrupts the intestinal barrier functions. OTA displays a long elimination half-life and stimulates the major inflammatory cytokines release.
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.

Notes préparatoires

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

Pictogrammes

Skull and crossbonesHealth hazard
GHS06,GHS08

Mention d'avertissement

Danger

Mentions de danger

H300,H351

Classification des risques

Acute Tox. 2 Oral - Carc. 2

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

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

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Consulter la Bibliothèque de documents

C E Groves et al.
Journal of the American Society of Nephrology : JASN, 10(1), 13-20 (1999-01-16)
Primary cultures of rabbit renal proximal tubule cells grown under improved culture conditions were used to study the transepithelial transport of the nephrotoxic mycotoxin ochratoxin A. The basal-to-apical transepithelial flux, i.e., secretion, of this fluorescence organic acid was measured in
X Chong et al.
Biochemical pharmacology, 44(7), 1401-1409 (1992-10-06)
A disruption of calcium homeostasis, leading to a sustained increase in cytosolic calcium levels, has been associated with cytotoxicity in response to a variety of agents in different cell types. We have observed that administration of a single high dose
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)
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
G Dirheimer et al.
IARC scientific publications, 115(115), 171-186 (1991-01-01)
Ochratoxin A has a number of toxic effects in mammals, the most notable of which is nephrotoxicity. It is also immunosuppressive, teratogenic and carcinogenic. The biochemical and molecular aspects of its action were first studied in bacteria. The appearance of
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