Synonym
Ochratoxin C; HSDB 3439;
IUPAC/Chemical Name
ethyl ((R)-5-chloro-8-hydroxy-3-methyl-1-oxoisochromane-7-carbonyl)-L-phenylalaninate
InChi Key
BPZZWRPHVVDAPT-PXAZEXFGSA-N
InChi Code
InChI=1S/C22H22ClNO6/c1-3-29-21(27)17(10-13-7-5-4-6-8-13)24-20(26)15-11-16(23)14-9-12(2)30-22(28)18(14)19(15)25/h4-8,11-12,17,25H,3,9-10H2,1-2H3,(H,24,26)/t12-,17+/m1/s1
SMILES Code
O=C(OCC)[C@H](CC1=CC=CC=C1)NC(C2=CC(Cl)=C(C3=C2O)C[C@@H](C)OC3=O)=O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
Biological target:
Ochratoxin C is the ethyl ester analog of ochratoxin A, a mycotoxin produced by A. ochraceus, A. carbonarius, and P. verrucosum that is commonly found as a food contaminant.
In vitro activity:
Nanomolar concentrations of OTA lead to activation of a second member of the MAPK family, namely, c-jun amino-terminal-kinase (JNK) in MDCK-C7 cells but virtually not in MDCK-C11 cells, as determined by kinase assay and Western blot. Furthermore, OTA potentiated the effect of tumor necrosis factor-alpha on JNK activation. In parallel to its effects on JNK, nanomolar OTA induced apoptosis in MDCK-C7 cells but not in MDCK-C11 cells, as determined by DNA fragmentation, DNA ladder formation, and caspase activation.
Reference: J Pharmacol Exp Ther. 2000 Jun;293(3):837-44. https://pubmed.ncbi.nlm.nih.gov/10869383/
In vivo activity:
This study observed that administration of a single high dose or multiple lower doses of the carcinogenic nephrotoxin ochratoxin A (OTA) to rats resulted in an increase of the renal cortex endoplasmic reticulum ATP-dependent calcium pump activity. The increase was very rapid, being evident within 10 min of OTA administration and remained elevated for at least 6 hr thereafter.
Reference: Biochem Pharmacol. 1992 Oct 6;44(7):1401-9. https://pubmed.ncbi.nlm.nih.gov/1417961/
Preparing Stock Solutions
The following data is based on the
product
molecular weight
431.87
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Ou Y, Fu Q, Chen Y, Lin L, Wang J, Wu D, Wu Q, Xie J. Dietary Ochratoxin A Contamination Modulates Oxidative Stress, Inflammation Processes and Causes Fibrosis in in vitro and in vivo Lung Models. Front Biosci (Landmark Ed). 2023 Feb 2;28(2):22. doi: 10.31083/j.fbl2802022. PMID: 36866544.
2. Gekle M, Schwerdt G, Freudinger R, Mildenberger S, Wilflingseder D, Pollack V, Dander M, Schramek H. Ochratoxin A induces JNK activation and apoptosis in MDCK-C7 cells at nanomolar concentrations. J Pharmacol Exp Ther. 2000 Jun;293(3):837-44. PMID: 10869383.
3. Chong X, Rahimtula AD. Alterations in ATP-dependent calcium uptake by rat renal cortex microsomes following ochratoxin A administration in vivo or addition in vitro. Biochem Pharmacol. 1992 Oct 6;44(7):1401-9. doi: 10.1016/0006-2952(92)90542-q. PMID: 1417961.
4. Omar RF, Rahimtula AD, Bartsch H. Role of cytochrome P-450 in ochratoxin A-stimulated lipid peroxidation. J Biochem Toxicol. 1991 Fall;6(3):203-9. doi: 10.1002/jbt.2570060306. PMID: 1770504.
In vitro protocol:
1. Ou Y, Fu Q, Chen Y, Lin L, Wang J, Wu D, Wu Q, Xie J. Dietary Ochratoxin A Contamination Modulates Oxidative Stress, Inflammation Processes and Causes Fibrosis in in vitro and in vivo Lung Models. Front Biosci (Landmark Ed). 2023 Feb 2;28(2):22. doi: 10.31083/j.fbl2802022. PMID: 36866544.
2. Gekle M, Schwerdt G, Freudinger R, Mildenberger S, Wilflingseder D, Pollack V, Dander M, Schramek H. Ochratoxin A induces JNK activation and apoptosis in MDCK-C7 cells at nanomolar concentrations. J Pharmacol Exp Ther. 2000 Jun;293(3):837-44. PMID: 10869383.
In vivo protocol:
1. Chong X, Rahimtula AD. Alterations in ATP-dependent calcium uptake by rat renal cortex microsomes following ochratoxin A administration in vivo or addition in vitro. Biochem Pharmacol. 1992 Oct 6;44(7):1401-9. doi: 10.1016/0006-2952(92)90542-q. PMID: 1417961.
2. Omar RF, Rahimtula AD, Bartsch H. Role of cytochrome P-450 in ochratoxin A-stimulated lipid peroxidation. J Biochem Toxicol. 1991 Fall;6(3):203-9. doi: 10.1002/jbt.2570060306. PMID: 1770504.
1: Heussner AH, Bingle LE. Comparative Ochratoxin Toxicity: A Review of the Available Data. Toxins (Basel). 2015 Oct 22;7(10):4253-82. doi: 10.3390/toxins7104253. Review. PubMed PMID: 26506387; PubMed Central PMCID: PMC4626733.
2: Fuchs R, Hult K, Peraica M, Radić B, Plestina R. Conversion of ochratoxin C into ochratoxin A in vivo. Appl Environ Microbiol. 1984 Jul;48(1):41-2. PubMed PMID: 6476830; PubMed Central PMCID: PMC240300.
3: Remiro R, Ibáñez-Vea M, González-Peñas E, Lizarraga E. Validation of a liquid chromatography method for the simultaneous quantification of ochratoxin A and its analogues in red wines. J Chromatogr A. 2010 Dec 24;1217(52):8249-56. doi: 10.1016/j.chroma.2010.11.004. Epub 2010 Nov 9. PubMed PMID: 21111427.
4: Müller G, Burkert B, Möller U, Diller R, Rohrmann B, Rosner H, Köhler H. Ochratoxin A and some of its derivatives modulate radical formation of porcine blood monocytes and granulocytes. Toxicology. 2004 Jul 1;199(2-3):251-9. PubMed PMID: 15147798.
5: Zimmerli B, Dick R. Ochratoxin A in table wine and grape-juice: occurrence and risk assessment. Food Addit Contam. 1996 Aug-Sep;13(6):655-68. PubMed PMID: 8871123.
6: Roth A, Chakor K, Creppy EE, Kane A, Roschenthaler R, Dirheimer G. Evidence for an enterohepatic circulation of ochratoxin A in mice. Toxicology. 1988 Mar;48(3):293-308. PubMed PMID: 3344528.
7: Zhang Y, Wang L, Shen X, Wei X, Huang X, Liu Y, Sun X, Wang Z, Sun Y, Xu Z, Eremin SA, Lei H. Broad-Specificity Immunoassay for Simultaneous Detection of Ochratoxins A, B, and C in Millet and Maize. J Agric Food Chem. 2017 Jun 14;65(23):4830-4838. doi: 10.1021/acs.jafc.7b00770. Epub 2017 Jun 5. PubMed PMID: 28535353.
