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O1877

Sigma-Aldrich

Ochratoxin A

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

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C20H18ClNO6
CAS Number:
303-47-9
Molecular Weight:
403.81
Beilstein:
1301486
MDL number:
MFCD00078079
UNSPSC Code:
12352200
PubChem Substance ID:
24897954
NACRES:
NA.77

product name

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

biological source

Petromyces albertensis

Quality Level

300

Assay

≥98% (HPLC)

form

powder

impurities

Benzene, free

solubility

ethanol: soluble

Mode of action

enzyme | inhibits
protein synthesis | interferes

storage temp.

2-8°C

SMILES string

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

InChI key

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

Biochem/physiol Actions

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.

Preparation Note

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

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Statements

H300,H351

Hazard Classifications

Acute Tox. 2 Oral - Carc. 2

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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
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