Synonym
CPA; Cyclopiazonic Acid; NSC 117181; NSC117181; NSC-117181;
IUPAC/Chemical Name
(6aR,11aS,11bR)-10-acetyl-11-hydroxy-7,7-dimethyl-2,6,6a,7,11a,11b-hexahydro-9H-pyrrolo[1',2':2,3]isoindolo[4,5,6-cd]indol-9-one
InChi Key
SZINUGQCTHLQAZ-DQYPLSBCSA-N
InChi Code
InChI=1S/C20H20N2O3/c1-9(23)14-18(24)17-16-11-8-21-13-6-4-5-10(15(11)13)7-12(16)20(2,3)22(17)19(14)25/h4-6,8,12,16-17,21,24H,7H2,1-3H3/t12-,16+,17+/m1/s1
SMILES Code
OC([C@@H](N1C2(C)C)[C@H]([C@H]2C3)C4=CNC5=CC=CC3=C54)=C(C(C)=O)C1=O
Purity
>95% (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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
336.39
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 |
1: Chalivendra SC, DeRobertis C, Chang PK, Damann KE. Cyclopiazonic Acid Is a Pathogenicity Factor for Aspergillus flavus and a Promising Target for Screening Germplasm for Ear Rot Resistance. Mol Plant Microbe Interact. 2017 May;30(5):361-373. doi: 10.1094/MPMI-02-17-0026-R. Epub 2017 Apr 24. PubMed PMID: 28447887.
2: Maragos CM, Sieve KK, Bobell J. Detection of cyclopiazonic acid (CPA) in maize by immunoassay. Mycotoxin Res. 2017 May;33(2):157-165. doi: 10.1007/s12550-017-0275-0. Epub 2017 Apr 5. PubMed PMID: 28378232.
3: Uka V, Moore GG, Arroyo-Manzanares N, Nebija D, De Saeger S, Diana Di Mavungu J. Unravelling the Diversity of the Cyclopiazonic Acid Family of Mycotoxins in Aspergillus flavus by UHPLC Triple-TOF HRMS. Toxins (Basel). 2017 Jan 13;9(1). pii: E35. doi: 10.3390/toxins9010035. PubMed PMID: 28098779; PubMed Central PMCID: PMC5308267.
4: Ansari P, Häubl G. Determination of cyclopiazonic acid in white mould cheese by liquid chromatography-tandem mass spectrometry (HPLC-MS/MS) using a novel internal standard. Food Chem. 2016 Nov 15;211:978-82. doi: 10.1016/j.foodchem.2016.05.063. Epub 2016 May 11. PubMed PMID: 27283720.
5: Cui R, Wang Y, Wang L, Li G, Lan K, Altmeyer R, Zou G. Cyclopiazonic acid, an inhibitor of calcium-dependent ATPases with antiviral activity against human respiratory syncytial virus. Antiviral Res. 2016 Aug;132:38-45. doi: 10.1016/j.antiviral.2016.05.010. Epub 2016 May 17. PubMed PMID: 27210812.
6: Selli C, Tosun M. Effects of cyclopiazonic acid and dexamethasone on serotonin-induced calcium responses in vascular smooth muscle cells. J Physiol Biochem. 2016 Jun;72(2):245-53. doi: 10.1007/s13105-016-0474-8. Epub 2016 Mar 4. PubMed PMID: 26944908; PubMed Central PMCID: PMC4873523.
7: Tokuoka M, Kikuchi T, Shinohara Y, Koyama A, Iio S, Kubota T, Kobayashi J, Koyama Y, Totsuka A, Shindo H, Sato K. Cyclopiazonic acid biosynthesis gene cluster gene cpaM is required for speradine A biosynthesis. Biosci Biotechnol Biochem. 2015;79(12):2081-5. doi: 10.1080/09168451.2015.1065167. Epub 2015 Jul 24. Erratum in: Biosci Biotechnol Biochem. 2015;80(1):214. PubMed PMID: 26207447.
8: Hymery N, Masson F, Barbier G, Coton E. Cytotoxicity and immunotoxicity of cyclopiazonic acid on human cells. Toxicol In Vitro. 2014 Aug;28(5):940-7. doi: 10.1016/j.tiv.2014.04.003. Epub 2014 Apr 18. PubMed PMID: 24747294.
9: Selli C, Erac Y, Tosun M. Cyclopiazonic acid alters serotonin-induced responses in rat thoracic aorta. Vascul Pharmacol. 2014 May-Jun;61(2-3):43-8. doi: 10.1016/j.vph.2014.03.008. Epub 2014 Apr 2. PubMed PMID: 24704610.
10: Kotšubei A, Gorgel M, Morth JP, Nissen P, Andersen JL. Probing determinants of cyclopiazonic acid sensitivity of bacterial Ca2+-ATPases. FEBS J. 2013 Nov;280(21):5441-9. doi: 10.1111/febs.12310. Epub 2013 May 28. PubMed PMID: 23621633.
