Okadaic Acid

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

MedKoo CAT#: 561543

CAS#: 78111-17-8

Description: Okadaic Acid is a toxin produced by several species of dinoflagellates, and is known to accumulate in both marine sponges and shellfish. Okadaic Acid and its relatives are protein phosphatase inhibitors, specifically targeting protein phosphatase 1 (PP1) and protein phosphatase 2A (PP2A).


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Okadaic Acid is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 561543
Name: Okadaic Acid
CAS#: 78111-17-8
Chemical Formula: C44H68O13
Exact Mass: 804.466
Molecular Weight: 805.01
Elemental Analysis: C, 65.65; H, 8.51; O, 25.84


Synonym: Okadaic Acid;

IUPAC/Chemical Name: (R)-2-hydroxy-3-((2S,5R,6R,8S)-5-hydroxy-8-((R,E)-4-((2R,4a'R,5R,6'S,8'R,8a'S)-8'-hydroxy-6'-((1S,3S)-1-hydroxy-3-((2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-7'-methyleneoctahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-5-yl)but-3-en-2-yl)-10-methyl-1,7-dioxaspiro[5.5]undec-10-en-2-yl)-2-methylpropanoic acid

InChi Key: QNDVLZJODHBUFM-WFXQOWMNSA-N

InChi Code: InChI=1S/C44H68O13/c1-25-21-34(55-44(23-25)35(46)12-11-31(54-44)24-41(6,50)40(48)49)26(2)9-10-30-14-18-43(53-30)19-15-33-39(57-43)36(47)29(5)38(52-33)32(45)22-28(4)37-27(3)13-17-42(56-37)16-7-8-20-51-42/h9-10,23,26-28,30-39,45-47,50H,5,7-8,11-22,24H2,1-4,6H3,(H,48,49)/b10-9+/t26-,27-,28+,30+,31+,32+,33-,34+,35-,36-,37+,38+,39-,41-,42+,43-,44-/m1/s1

SMILES Code: OC([C@](C)(O)C[C@]1([H])CC[C@@H](O)[C@@]2(O[C@@]([C@H](C)/C=C/[C@]3([H])O[C@]4(CC[C@](O[C@@]([C@@H](O)C[C@H](C)[C@@]5([H])O[C@@]6(CCCCO6)CC[C@H]5C)([H])C([C@H]7O)=C)([H])[C@@]7([H])O4)CC3)([H])CC(C)=C2)O1)=O


Technical Data

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:
>2 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).

Harmonized System Code:
293490


References

1: Fujiki H, Sueoka E, Rawangkan A, Suganuma M. Human cancer stem cells are a target for cancer prevention using (-)-epigallocatechin gallate. J Cancer Res Clin Oncol. 2017 Sep 23. doi: 10.1007/s00432-017-2515-2. [Epub ahead of print] Review. PubMed PMID: 28942499.

2: Suzuki T. Regulatory Levels, Monitoring System of Shellfish Toxins and Instrumental Analyses. Shokuhin Eiseigaku Zasshi. 2016;57(5):117-131. Review. Japanese. PubMed PMID: 27784862.

3: Lee TC, Fong FL, Ho KC, Lee FW. The Mechanism of Diarrhetic Shellfish Poisoning Toxin Production in Prorocentrum spp.: Physiological and Molecular Perspectives. Toxins (Basel). 2016 Sep 22;8(10). pii: E272. doi: 10.3390/toxins8100272. Review. PubMed PMID: 27669302; PubMed Central PMCID: PMC5086633.

4: Wakimoto T, Egami Y, Abe I. Calyculin: Nature's way of making the sponge-derived cytotoxin. Nat Prod Rep. 2016 Jun 2;33(6):751-60. doi: 10.1039/c5np00123d. Review. PubMed PMID: 26923942.

5: Rasmussen SA, Andersen AJ, Andersen NG, Nielsen KF, Hansen PJ, Larsen TO. Chemical Diversity, Origin, and Analysis of Phycotoxins. J Nat Prod. 2016 Mar 25;79(3):662-73. doi: 10.1021/acs.jnatprod.5b01066. Epub 2016 Feb 22. Review. PubMed PMID: 26901085.

6: Kleppe R, Herfindal L, Døskeland SO. Cell Death Inducing Microbial Protein Phosphatase Inhibitors--Mechanisms of Action. Mar Drugs. 2015 Oct 22;13(10):6505-20. doi: 10.3390/md13106505. Review. PubMed PMID: 26506362; PubMed Central PMCID: PMC4626703.

7: Zimmer ER, Leuzy A, Souza DO, Portela LV. Inhibition of Protein Phosphatase 2A: Focus on the Glutamatergic System. Mol Neurobiol. 2016 Aug;53(6):3753-3755. doi: 10.1007/s12035-015-9321-0. Epub 2015 Jul 4. Review. PubMed PMID: 26141124.

8: Nazem A, Sankowski R, Bacher M, Al-Abed Y. Rodent models of neuroinflammation for Alzheimer's disease. J Neuroinflammation. 2015 Apr 17;12:74. doi: 10.1186/s12974-015-0291-y. Review. PubMed PMID: 25890375; PubMed Central PMCID: PMC4404276.

9: Romero A, Egea J, González-Muñoz GC, Martín de Saavedra MD, del Barrio L, Rodríguez-Franco MI, Conde S, López MG, Villarroya M, de los Ríos C. ITH12410/SC058: a new neuroprotective compound with potential in the treatment of Alzheimer's disease. ACS Chem Neurosci. 2014 Sep 17;5(9):770-5. doi: 10.1021/cn500131t. Epub 2014 Jul 15. Review. PubMed PMID: 25008046.

10: Kamat PK, Rai S, Swarnkar S, Shukla R, Nath C. Molecular and cellular mechanism of okadaic acid (OKA)-induced neurotoxicity: a novel tool for Alzheimer's disease therapeutic application. Mol Neurobiol. 2014 Dec;50(3):852-65. doi: 10.1007/s12035-014-8699-4. Epub 2014 Apr 8. Review. PubMed PMID: 24710687.

11: Reguera B, Riobó P, Rodríguez F, Díaz PA, Pizarro G, Paz B, Franco JM, Blanco J. Dinophysis toxins: causative organisms, distribution and fate in shellfish. Mar Drugs. 2014 Jan 20;12(1):394-461. doi: 10.3390/md12010394. Review. PubMed PMID: 24447996; PubMed Central PMCID: PMC3917280.

12: Valdiglesias V, Prego-Faraldo MV, Pásaro E, Méndez J, Laffon B. Okadaic acid: more than a diarrheic toxin. Mar Drugs. 2013 Oct 31;11(11):4328-49. doi: 10.3390/md11114328. Review. PubMed PMID: 24184795; PubMed Central PMCID: PMC3853731.

13: Heijman J, Dewenter M, El-Armouche A, Dobrev D. Function and regulation of serine/threonine phosphatases in the healthy and diseased heart. J Mol Cell Cardiol. 2013 Nov;64:90-8. doi: 10.1016/j.yjmcc.2013.09.006. Epub 2013 Sep 16. Review. PubMed PMID: 24051368.

14: de Jesus Raposo MF, de Morais RM, de Morais AM. Health applications of bioactive compounds from marine microalgae. Life Sci. 2013 Oct 10;93(15):479-86. doi: 10.1016/j.lfs.2013.08.002. Epub 2013 Aug 28. Review. PubMed PMID: 23994664.

15: Prego-Faraldo MV, Valdiglesias V, Méndez J, Eirín-López JM. Okadaic acid meet and greet: an insight into detection methods, response strategies and genotoxic effects in marine invertebrates. Mar Drugs. 2013 Aug 9;11(8):2829-45. doi: 10.3390/md11082829. Review. PubMed PMID: 23939476; PubMed Central PMCID: PMC3766868.

16: Fujiki H, Sueoka E, Suganuma M. Tumor promoters: from chemicals to inflammatory proteins. J Cancer Res Clin Oncol. 2013 Oct;139(10):1603-14. doi: 10.1007/s00432-013-1455-8. Epub 2013 Jun 12. Review. PubMed PMID: 23756937.

17: Medina M, Avila J, Villanueva N. Use of okadaic acid to identify relevant phosphoepitopes in pathology: a focus on neurodegeneration. Mar Drugs. 2013 May 21;11(5):1656-68. doi: 10.3390/md11051656. Review. PubMed PMID: 23697949; PubMed Central PMCID: PMC3707166.

18: Sassolas A, Hayat A, Catanante G, Marty JL. Detection of the marine toxin okadaic acid: assessing seafood safety. Talanta. 2013 Feb 15;105:306-16. doi: 10.1016/j.talanta.2012.10.049. Epub 2012 Nov 6. Review. PubMed PMID: 23598023.

19: Hata Y, Timalsina S, Maimaiti S. Okadaic Acid: a tool to study the hippo pathway. Mar Drugs. 2013 Mar 14;11(3):896-902. doi: 10.3390/md11030896. Review. PubMed PMID: 23493077; PubMed Central PMCID: PMC3705378.

20: Munday R. Is protein phosphatase inhibition responsible for the toxic effects of okadaic Acid in animals? Toxins (Basel). 2013 Feb 4;5(2):267-85. doi: 10.3390/toxins5020267. Review. PubMed PMID: 23381142; PubMed Central PMCID: PMC3640535.