Piericidin A


Catalog No. Size PriceQuantity
M12140-2 2mg solid $990
M12140-10 10mg solid $3,960

Description

Piericidin A (AR-054) is a natural mitochondrial NADH-ubiquinone oxidoreductase (complex I) inhibitor. Piericidin A is a potent neurotoxin and inhibits mitochondrial respiration by disrupting the electron transport system through its action on NADH-ubiquinone reductase. Piericidin A is also a potential quorum-sensing inhibitor that suppresses the expression of the virulence genes of Erwinia carotovora subsp. atroseptica (Eca). Piericidin A is an ADC cytotoxin and has anti-bacterial, anticancer, insecticidal activity.

Product information

CAS Number: 2738-64-9

Molecular Weight: 415.57

Formula: C25H37NO4

Synonym:

AR-054

Chemical Name: 2-[(2E, 5E, 7E, 9R, 10R, 11E)-10-hydroxy-3, 7, 9, 11-tetramethyltrideca-2, 5, 7, 11-tetraen-1-yl]-5, 6-dimethoxy-3-methylpyridin-4-ol

Smiles: C[C@H](/C=C(\C)/C=C/C/C(/C)=C/CC1=NC(OC)=C(OC)C(O)=C1C)[C@@H](O)/C(/C)=C/C

InChiKey: BBLGCDSLCDDALX-LKGBESRRSA-N

InChi: InChI=1S/C25H37NO4/c1-9-18(4)22(27)19(5)15-17(3)12-10-11-16(2)13-14-21-20(6)23(28)24(29-7)25(26-21)30-8/h9-10,12-13,15,19,22,27H,11,14H2,1-8H3,(H,26,28)/b12-10+,16-13+,17-15+,18-9+/t19-,22+/m1/s1

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: Soluble in DMSO

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥360 days if stored properly.

Stock Solution Storage: 0 - 4 oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

In a cell free assay, the potency of Piericidin A to inhibit mitochondrial complex I is ∼2 fold smaller than the one of annonacin. In cultured neurons, Piericidin A potently induces the redistribution of phosphorylated tau from the dendrites into the cell soma and induces cell death. The viability of Tn5B1-4 cells is inhibited by Piericidin A in a time- and concentration-dependent manner with IC50 value of 0.061 μM, whilst Piericidin A shows slight inhibitory effect on the viability of HepG2 and Hek293 cells with IC50 value of 233.97 μM and 228.96 μM, respectively. Piericidin A induces apoptosis of Tn5B1-4 cells coincides with a decrease in the mitochondrial membrane potential.

In Vivo:

Piericidin A (0.5 mg/kg/d; for 28 days via osmotic minipumps) significantly increases the number of phospho-tau immunoreactive cells in the cerebral cortex in P301S+/+ mice. Piericidin A leads to increased levels of pathologically phosphorylated tau only in P301S+/+ mice. The synaptic density is reduced by Piericidin A treatment in P301S+/+ mice. Exposure to Piericidin A aggravates the course of genetically determined tau pathology.

References:

  1. Matthias Höllerhage, et al. Piericidin A Aggravates Tau Pathology in P301S Transgenic Mice. PLoS One. 2014 Dec 1;9(12):e113557.
  2. Ji Eun Kang, et al. Efficacies of Quorum Sensing Inhibitors, Piericidin A and Glucopiericidin A, Produced by Streptomyces Xanthocidicus KPP01532 for the Control of Potato Soft Rot Caused by Erwinia Carotovora Subsp. Atroseptica. Microbiol Res. 2016 Mar;184:32-41.
  3. Solange Muhayimana, et al. Cytotoxic Selectivity and Apoptosis Induction of Piericidin A Contributes Potentially to Its Insecticidal Effect Against Mythimna Separata (Lepidoptera: Noctuidae) Larvae. Pestic Biochem Physiol. 2019 Jun;157:19-25.

Products are for research use only. Not for human use.

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