Ochratoxin B | CAS#4825-86-9 | vasoconstrictor mycotoxin

MedKoo Cat#: 597765 | Name: Ochratoxin B

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Description:

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

Ochratoxin B is a potential vasoconstrictor mycotoxin with the presence of calcium-channel antagonist.

Chemical Structure

Ochratoxin B

CAS#4825-86-9

Theoretical Analysis

MedKoo Cat#: 597765

Name: Ochratoxin B

CAS#: 4825-86-9

Chemical Formula: C20H19NO6

Exact Mass: 369.1212

Molecular Weight: 369.37

Elemental Analysis: C, 65.03; H, 5.19; N, 3.79; O, 25.99

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 330.00
5mg	USD 740.00

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Synonym

Ochratoxin B; CCRIS 5094; HSDB 3438;

IUPAC/Chemical Name

(8-hydroxy-3-methyl-1-oxoisochromane-7-carbonyl)-L-phenylalanine

InChi Key

DAEYIVCTQUFNTM-MHTVFEQDSA-N

InChi Code

InChI=1S/C20H19NO6/c1-11-9-13-7-8-14(17(22)16(13)20(26)27-11)18(23)21-15(19(24)25)10-12-5-3-2-4-6-12/h2-8,11,15,22H,9-10H2,1H3,(H,21,23)(H,24,25)/t11?,15-/m0/s1

SMILES Code

O=C(O)[C@H](CC1=CC=CC=C1)NC(C2=C(O)C3=C(C=C2)CC(C)OC3=O)=O

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

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Ochratoxin B, a secondary metabolite of Aspergillus ochraceus, is the nonchlorinated analogue of the mycotoxin Ochratoxin A.

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/

	Solvent	mg/mL	mM
Solubility
	DMF	10.0	27.07
	DMSO	15.0	40.61
	Ethanol	50.0	135.36
	Ethanol:PBS (pH 7.2) (1:1)	0.5	1.35

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 369.37 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:

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: Chatopadhyay P, Tariang B, Agnihotri A, Veer V. Synergism of ochratoxin B and calcium-channel antagonist verapamil caused mitochondrial dysfunction. Toxicol Mech Methods. 2014 Sep;24(6):428-32. doi: 10.3109/15376516.2014.936543. Epub 2014 Aug 4. PubMed PMID: 24968897. 2: Di Stefano V, Avellone G, Pitonzo R, Capocchiano VG, Mazza A, Cicero N, Dugo G. Natural co-occurrence of ochratoxin A, ochratoxin B and aflatoxins in Sicilian red wines. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2015;32(8):1343-51. doi: 10.1080/19440049.2015.1055521. Epub 2015 Jul 9. PubMed PMID: 26133228. 3: Schmidt-Heydt M, Cramer B, Graf I, Lerch S, Humpf HU, Geisen R. Wavelength-dependent degradation of ochratoxin and citrinin by light in vitro and in vivo and its implications on Penicillium. Toxins (Basel). 2012 Dec 14;4(12):1535-51. doi: 10.3390/toxins4121535. PubMed PMID: 23242320; PubMed Central PMCID: PMC3528261. 4: Lates V, Yang C, Popescu IC, Marty JL. Displacement immunoassay for the detection of ochratoxin A using ochratoxin B modified glass beads. Anal Bioanal Chem. 2012 Mar;402(9):2861-70. doi: 10.1007/s00216-012-5721-4. Epub 2012 Feb 14. PubMed PMID: 22331050. 5: Breitholtz-Emanuelsson A, Fuchs R, Hult K, Appelgren LE. Synthesis of 14C-ochratoxin A and 14C-ochratoxin B and a comparative study of their distribution in rats using whole body autoradiography. Pharmacol Toxicol. 1992 Apr;70(4):255-61. PubMed PMID: 1608909. 6: Størmer FC, Kolsaker P, Holm H, Rogstad S, Elling F. Metabolism of ochratoxin B and its possible effects upon the metabolism and toxicity of ochratoxin A in rats. Appl Environ Microbiol. 1985 May;49(5):1108-12. PubMed PMID: 4004232; PubMed Central PMCID: PMC238514. 7: Sanzani SM, Reverberi M, Fanelli C, Ippolito A. Detection of ochratoxin A using molecular beacons and real-time PCR thermal cycler. Toxins (Basel). 2015 Mar 9;7(3):812-20. doi: 10.3390/toxins7030812. PubMed PMID: 25760080; PubMed Central PMCID: PMC4379526. 8: 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. 9: Nguyen HDT, McMullin DR, Ponomareva E, Riley R, Pomraning KR, Baker SE, Seifert KA. Ochratoxin A production by Penicillium thymicola. Fungal Biol. 2016 Aug;120(8):1041-1049. doi: 10.1016/j.funbio.2016.04.002. Epub 2016 Apr 12. PubMed PMID: 27521635. 10: Heussner AH, Ausländer S, Dietrich DR. Development and characterization of a monoclonal antibody against Ochratoxin B and its application in ELISA. Toxins (Basel). 2010 Jun;2(6):1582-94. doi: 10.3390/toxins2061582. Epub 2010 Jun 21. PubMed PMID: 22069651; PubMed Central PMCID: PMC3153249. 11: Han Z, Zheng Y, Luan L, Ren Y, Wu Y. Analysis of ochratoxin A and ochratoxin B in traditional Chinese medicines by ultra-high-performance liquid chromatography-tandem mass spectrometry using [(13)C(20)]-ochratoxin A as an internal standard. J Chromatogr A. 2010 Jun 25;1217(26):4365-74. doi: 10.1016/j.chroma.2010.04.052. Epub 2010 Apr 28. PubMed PMID: 20483416. 12: Chrouda A, Sbartai A, Baraket A, Renaud L, Maaref A, Jaffrezic-Renault N. An aptasensor for ochratoxin A based on grafting of polyethylene glycol on a boron-doped diamond microcell. Anal Biochem. 2015 Nov 1;488:36-44. doi: 10.1016/j.ab.2015.07.012. Epub 2015 Aug 7. PubMed PMID: 26255699. 13: Sharma A, Hayat A, Mishra RK, Catanante G, Bhand S, Marty JL. Titanium Dioxide Nanoparticles (TiO₂) Quenching Based Aptasensing Platform: Application to Ochratoxin A Detection. Toxins (Basel). 2015 Sep 22;7(9):3771-84. doi: 10.3390/toxins7093771. PubMed PMID: 26402704; PubMed Central PMCID: PMC4591649. 14: Uchigashima M, Yamaguchi Murakami Y, Narita H, Nakajima M, Miyake S. Development of an immuno-affinity column for ochratoxin analysis using an organic solvent-tolerant monoclonal antibody. Methods. 2012 Feb;56(2):180-5. doi: 10.1016/j.ymeth.2011.09.006. Epub 2011 Sep 16. PubMed PMID: 21945577. 15: Zhang X, Li J, Cheng Z, Zhou Z, Ma L. High-performance liquid chromatography-tandem mass spectrometry method for simultaneous detection of ochratoxin A and relative metabolites in Aspergillus species and dried vine fruits. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2016 Aug;33(8):1355-66. doi: 10.1080/19440049.2016.1209691. Epub 2016 Jul 21. PubMed PMID: 27442910. 16: Breitholtz Emanuelsson A, Fuchs R, Hult K, Appelgren LE. Distribution of 14C-ochratoxin A and 14C-ochratoxin B in rats: a comparison based on whole-body autoradiography. IARC Sci Publ. 1991;(115):201-3. PubMed PMID: 1820334. 17: Knasmüller S, Cavin C, Chakraborty A, Darroudi F, Majer BJ, Huber WW, Ehrlich VA. Structurally related mycotoxins ochratoxin A, ochratoxin B, and citrinin differ in their genotoxic activities and in their mode of action in human-derived liver (HepG2) cells: implications for risk assessment. Nutr Cancer. 2004;50(2):190-7. PubMed PMID: 15623466. 18: Heussner AH, Moeller I, Day BW, Dietrich DR, O'Brien E. Production and characterization of monoclonal antibodies against ochratoxin B. Food Chem Toxicol. 2007 May;45(5):827-33. Epub 2006 Nov 7. PubMed PMID: 17161512. 19: Mally A, Keim-Heusler H, Amberg A, Kurz M, Zepnik H, Mantle P, Völkel W, Hard GC, Dekant W. Biotransformation and nephrotoxicity of ochratoxin B in rats. Toxicol Appl Pharmacol. 2005 Aug 1;206(1):43-53. Epub 2005 Jan 7. PubMed PMID: 15963343. 20: 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.