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MedKoo Cat#: 555739 | Name: Ochratoxin-A
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Ochratoxin A (OTA) is a mycotoxin produced by several fungal species including Aspergillus ochraceus, A. carbonarius, A. niger and Penicillium verrucosum. OTA causes nephrotoxicity and renal tumors in a variety of animal species; however, human health effects are less well-characterized. Various studies have linked OTA exposure with the human diseases Balkan endemic nephropathy (BEN) and chronic interstitial nephropathy (CIN), as well as other renal diseases.

Chemical Structure

Ochratoxin-A
Ochratoxin-A
CAS#1448049-50-0

Theoretical Analysis

MedKoo Cat#: 555739

Name: Ochratoxin-A

CAS#: 1448049-50-0

Chemical Formula: C20H14D4ClNO6

Exact Mass: 407.1074

Molecular Weight: 407.84

Elemental Analysis: C, 58.90; H, 5.44; Cl, 8.69; N, 3.43; O, 23.54

Price and Availability

Size Price Availability Quantity
100mg USD 950.00 2 Weeks
200mg USD 1,650.00 2 Weeks
500mg USD 3,650.00 2 Weeks
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Synonym
Ochratoxin-A, EX-A1468; EX-A-1468; EX-A 1468; EXA1468; EXA-1468; EXA 1468;
IUPAC/Chemical Name
((R)-5-chloro-8-hydroxy-3-(methyl-d3)-1-oxoisochromane-7-carbonyl-3-d)-L-phenylalanine
InChi Key
RWQKHEORZBHNRI-ULNJQCCOSA-N
InChi Code
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/i1D3,10D
SMILES Code
O=C(O)[C@@H](NC(C1=C(O)C2=C(C(Cl)=C1)C[C@](C([2H])([2H])[2H])([2H])OC2=O)=O)CC3=CC=CC=C3
Appearance
Solid powder
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
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Ochratoxin A (OTA) is a mycotoxin.
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 407.84 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.

Recalculate based on batch purity %
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: Jia X, Wang Y, Cui J, Li Y, Wu W, Zhang X, Wang J. Ochratoxin A-induced DNA damage triggers G2 phase arrest via hMLH1-p53-p21 signaling pathway in human gastric epithelium immortalized cells in vitro. Toxicol Lett. 2024 Aug 6:S0378-4274(24)01075-0. doi: 10.1016/j.toxlet.2024.08.005. Epub ahead of print. PMID: 39117293. 2: Sánchez-Arroyo A, Plaza-Vinuesa L, de Las Rivas B, Mancheño JM, Muñoz R. Aspergillus niger Ochratoxinase Is a Highly Specific, Metal-Dependent Amidohydrolase Suitable for OTA Biodetoxification in Food and Feed. J Agric Food Chem. 2024 Aug 7. doi: 10.1021/acs.jafc.4c02944. Epub ahead of print. PMID: 39110482. 3: Choudhary KG, Sharffuddin C, Kumar A. Quantification using a HPLC-FLD-based Detector and Molecular Identifi-cation of Ochratoxin-A Producing Aspergillus Species Isolated from Stored Grain Samples. Recent Adv Food Nutr Agric. 2024 Jul 31. doi: 10.2174/012772574X302254240610094258. Epub ahead of print. PMID: 39092651. 4: Fiadey SE, Agyei-Amponsah J, Gryczka U, Otoo EA, Asamoah A, Ocloo FCK. Reduction in mycotoxin levels of African nutmeg (Monodora myristica) powder using a high-energy electron beam. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2024 Jul 31:1-7. doi: 10.1080/19440049.2024.2385039. Epub ahead of print. PMID: 39083482. 5: das Neves TT, Passamani FRF, de Souza Castro CR, Schwan RF, Batista LR, Silva CF. Saccharomyces cerevisiae CCMA 0159 showed a high capacity to inhibit OTA- producing Aspergillus species. Braz J Microbiol. 2024 Jul 31. doi: 10.1007/s42770-024-01460-5. Epub ahead of print. PMID: 39083222. 6: Toman J, Pickova D, Rejman L, Ostry V, Malir F. Investigation of ochratoxin A in air-dry-cured hams. Meat Sci. 2024 Jul 14;217:109605. doi: 10.1016/j.meatsci.2024.109605. Epub ahead of print. PMID: 39068743. 7: Oluwakayode A, Sulyok M, Krska R, Medina A. The effect of the interactions of water activity, and temperature on OTA, OTB, and OTα produced by Penicillium verrucosum in a mini silo of natural and inoculated wheat using CO2 production as fungal activity sentinel. Food Chem. 2024 Jul 23;460(Pt 2):140590. doi: 10.1016/j.foodchem.2024.140590. Epub ahead of print. PMID: 39067424. 8: Xu Y, Jia X, Yang S, Cao M, He B, Ren W, Suo Z. Simultaneous Determination of Aflatoxin B1 and Ochratoxin A in Cereals by a Novel Electrochemical Aptasensor Using Metal-Organic Framework as Signal Carrier. Foods. 2024 Jul 10;13(14):2177. doi: 10.3390/foods13142177. PMID: 39063260; PMCID: PMC11276064. 9: Yoon JW, Kim MO, Shin S, Kwon WS, Kim SH, Kwon YJ, Lee SI. Spirobenzofuran Mitigates Ochratoxin A-Mediated Intestinal Adverse Effects in Pigs through Regulation of Beta Defensin 1. Toxics. 2024 Jul 3;12(7):487. doi: 10.3390/toxics12070487. PMID: 39058139; PMCID: PMC11281199. 10: Liao C, Xu F, Yu Z, Ding K, Jia Y. The Novel Role of the NLRP3 Inflammasome in Mycotoxin-Induced Toxicological Mechanisms. Vet Sci. 2024 Jun 28;11(7):291. doi: 10.3390/vetsci11070291. PMID: 39057975; PMCID: PMC11281663. 11: Zhou Y, Lu W, Huang K, Gan F. Ferroptosis is involved in quercetin-mediated alleviation of Ochratoxin A-induced kidney damage. Food Chem Toxicol. 2024 Jul 23:114877. doi: 10.1016/j.fct.2024.114877. Epub ahead of print. PMID: 39053875. 12: Mangiapelo L, Frangiamone M, Vila-Donat P, Paşca D, Ianni F, Cossignani L, Manyes L. Grape pomace as a novel functional ingredient: Mitigating ochratoxin A bioaccessibility and unraveling cytoprotective mechanisms in vitro. Curr Res Food Sci. 2024 Jun 25;9:100800. doi: 10.1016/j.crfs.2024.100800. PMID: 39040226; PMCID: PMC11261260. 13: Yulia E, Martin PN. Development of a rapid method for determination of Ochratoxin A in grape mash and wine. Mycotoxin Res. 2024 Jul 21. doi: 10.1007/s12550-024-00543-4. Epub ahead of print. PMID: 39033481. 14: Tang Y, Ma P, Khan IM, Cao W, Zhang Y, Wang Z. Lateral flow assay for simultaneous detection of multiple mycotoxins using nanozyme to amplify signals. Food Chem. 2024 Jul 14;460(Pt 1):140398. doi: 10.1016/j.foodchem.2024.140398. Epub ahead of print. PMID: 39032299. 15: Xie X, He Z, Sun Z, Zhang S, Cao H, Hammock BD, Liu X. Shark anti-idiotypic variable new antigen receptor specific for an alpaca nanobody: Exploration of a nontoxic substitute to ochratoxin A in immunoassay. J Hazard Mater. 2024 Jul 19;477:135264. doi: 10.1016/j.jhazmat.2024.135264. Epub ahead of print. PMID: 39032175. 16: Wang J, Xie Y, Wu T, Chen Y, Jiang M, Li X, Ye Y, Zhou E, Yang Z. Phytic acid alleviates ochratoxin A-induced renal damage in chicks by modulating ferroptosis and the structure of the intestinal microbiota. Poult Sci. 2024 Jun 26;103(9):104027. doi: 10.1016/j.psj.2024.104027. Epub ahead of print. PMID: 39024690. 17: Rodríguez-Cañás I, González-Jartín JM, Alvariño R, Alfonso A, Vieytes MR, Botana LM. Identification of mycotoxins in yogurt samples using an optimized QuEChERS extraction and UHPLC-MS/MS detection. Mycotoxin Res. 2024 Jul 17. doi: 10.1007/s12550-024-00547-0. Epub ahead of print. PMID: 39017819. 18: Feng X, Ding L, Hao N, Wang K. A Piezoelectric Nanogenerator-Driven Dual- Mode Platform for Visualization and Impedance Sensing. Anal Chem. 2024 Jul 16. doi: 10.1021/acs.analchem.4c02495. Epub ahead of print. PMID: 39014979. 19: Burgon VH, da Silva ARP, Milani RF, Taniwaki MH, Iamanaka BT, Morgano MA. Occurrence of ochratoxin A in cocoa beans and bean-to-bar chocolates. Braz J Microbiol. 2024 Jul 15. doi: 10.1007/s42770-024-01451-6. Epub ahead of print. PMID: 39009936. 20: Ahmad MS, Alanazi YA, Alrohaimi Y, Shaik RA, Alrashidi S, Al-Ghasham YA, Alkhalifah YS, Ahmad RK. Occurrence, evaluation, and human health risk assessment of ochratoxin a in infant formula and cereal-based baby food: a global literature systematic review. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2024 Jul 15:1-16. doi: 10.1080/19440049.2024.2376157. Epub ahead of print. PMID: 39008630.

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