Piericidin A - CAS 2738-64-9

Piericidin A - CAS 2738-64-9 Catalog number: BADC-00832

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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.

General Information

Category
ADCs Cytotoxin
Product Name
Piericidin A
CAS
2738-64-9
Catalog Number
BADC-00832
Molecular Formula
C25H37NO4
Molecular Weight
415.57 g/mol

Chemical Structure

  • Piericidin A
Purity
>95.0%
Appearance
Yellow solid
Synonyms
Shaoguanmycin B
Solubility
10 mM in DMSO
Storage
Store at -20 °C, keep in dry and avoid sunlight.
Shelf Life
0-4℃ for short term (days to weeks), or -20℃ for long term (months).
Shipping
Room temperature, or blue ice upon request.
Boiling Point
614.9±55.0°C (Predicted)
Melting Point
220-225°C
Density
1.044±0.06 g/cm3 (Predicted)
Canonical SMILES
CC=C(C)C(C(C)C=C(C)C=CCC(=CCC1=C(C(=O)C(=C(N1)OC)OC)C)C)O
InChI Key
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
Source
Streptomyces sp.
BiologicalActivity
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[1][2][2] . 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[1] . 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 μ M, respectively. Piericidin A induces apoptosis of Tn5B1-4 cells coincides with a decrease in the mitochondrial membrane potential[3] . 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[1]

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Historical Records: N-Succinimidyl 3-(Bromoacetamido)propionate | Ac-S-PEG8-NHS | APN-PEG4-tetrazine | (S)-2-(N-Methyl-3-(Methyldisulfanyl)propanamido)propanoic Acid | Propargyl-PEG9-bromide | NH2-PEG4-CH2CH2COOH | Mal-PEG-NHS | Bis-PEG9-acid | Dolastatin 15 | Propargyl-PEG4-Br | Piericidin A
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