CAS 2738-64-9|Piericidin A1
Introduction：Basic information about CAS 2738-64-9|Piericidin A1, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | Piericidin A1 | ||
|---|---|---|---|
| CAS Number | 2738-64-9 | Molecular Weight | 415.566 |
| Density | 1.1±0.1 g/cm3 | Boiling Point | 591.7±50.0 °C at 760 mmHg |
| Molecular Formula | C25H37NO4 | Melting Point | / |
| MSDS | ChineseUSA | Flash Point | 311.6±30.1 °C |
Names
| Name | Piericidin A |
|---|---|
| Synonym | More Synonyms |
Piericidin A1 BiologicalActivity
| 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[1][2][2]. |
|---|---|
| Related Catalog | Research Areas >>CancerResearch Areas >>InfectionSignaling Pathways >>Antibody-drug Conjugate >>ADC CytotoxinResearch Areas >>Neurological DiseaseSignaling Pathways >>Anti-infection >>Bacterial |
| 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 μM, 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]. |
| 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. |
Chemical & Physical Properties
| Density | 1.1±0.1 g/cm3 |
|---|---|
| Boiling Point | 591.7±50.0 °C at 760 mmHg |
| Molecular Formula | C25H37NO4 |
| Molecular Weight | 415.566 |
| Flash Point | 311.6±30.1 °C |
| Exact Mass | 415.272247 |
| PSA | 71.81000 |
| LogP | 4.26 |
| Vapour Pressure | 0.0±3.8 mmHg at 25°C |
| Index of Refraction | 1.534 |
| InChIKey | BBLGCDSLCDDALX-LKGBESRRSA-N |
| SMILES | CC=C(C)C(O)C(C)C=C(C)C=CCC(C)=CCc1[nH]c(OC)c(OC)c(=O)c1C |
| Storage condition | 2-8°C |
Toxicological Information
CHEMICAL IDENTIFICATION |
ACUTE TOXICITY DATA - TYPE OF TEST :
- LDLo - Lowest published lethal dose
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 360 ug/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- ABCHA6 Agricultural and Biological Chemistry. (Maruzen Co. Ltd., POB 5050, Tokyo International, Tokyo 100-31, Japan) V.25- 1961- Volume(issue)/page/year: 34,1101,1970
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 3170 ug/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- ABCHA6 Agricultural and Biological Chemistry. (Maruzen Co. Ltd., POB 5050, Tokyo International, Tokyo 100-31, Japan) V.25- 1961- Volume(issue)/page/year: 32,1115,1968
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Administration onto the skin
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 2520 ug/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- ABCHA6 Agricultural and Biological Chemistry. (Maruzen Co. Ltd., POB 5050, Tokyo International, Tokyo 100-31, Japan) V.25- 1961- Volume(issue)/page/year: 32,1115,1968
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 870 ug/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- ABCHA6 Agricultural and Biological Chemistry. (Maruzen Co. Ltd., POB 5050, Tokyo International, Tokyo 100-31, Japan) V.25- 1961- Volume(issue)/page/year: 27,576,1963
- TYPE OF TEST :
- LDLo - Lowest published lethal dose
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 1 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- JANTAJ Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo, 141, Japan) V.2-5, 1948-52; V.21- 1968- Volume(issue)/page/year: 40,149,1987
Safety Information
| Personal Protective Equipment | Eyeshields;Faceshields;full-face respirator (US);Gloves;multi-purpose combination respirator cartridge (US);type ABEK (EN14387) respirator filter |
|---|---|
| Hazard Codes | T+ |
| Risk Phrases | 26/27/28-20/21/22 |
| Safety Phrases | 28-36/37-45 |
| RIDADR | UN 3382 6.1/PG 1 |
Articles23
More Articles| Isolation and characterizations of quinone analogue-resistant mutants of bo-type ubiquinol oxidase from Escherichia coli. Biochemistry 37(37) , 12744-52, (1998) Cytochrome bo is a member of the heme-copper terminal oxidase superfamily and serves as a four-subunit ubiquinol oxidase in the aerobic respiratory chain of Escherichia coli. To probe the location and... | |
| Etoposide-resistant HT-29 human colon carcinoma cells during glucose deprivation are sensitive to piericidin A, a GRP78 down-regulator. J. Cell Physiol. 215(1) , 243-50, (2008) Glucose deprivation, a pathophysiological cell condition, causes up-regulation of GRP78 and induction of etoposide resistance in human cancer cells. The induction of drug resistance can be partly expl... | |
| Genetic evidence for the existence of two quinone related inhibitor binding sites in NADH-CoQ reductase. Biochim. Biophys. Acta 1319(1) , 1-4, (1997) Using the NADH-CoQ reductase of Rhodobacter capsulatus as a model for the mitochondrial Complex I, we have for the first time isolated bacterial mutants resistant to piericidin-A, a classical inhibito... |
Synonyms
| Piericidin A1 |
| 2-[(2E,5E,7E,9R,10R,11E)-10-Hydroxy-3,7,9,11-tetramethyl-2,5,7,11-tridecatetraen-1-yl]-5,6-dimethoxy-3-methyl-4(1H)-pyridinone |
| 4(1H)-Pyridinone, 2-[(2E,5E,7E,9R,10R,11E)-10-hydroxy-3,7,9,11-tetramethyl-2,5,7,11-tridecatetraen-1-yl]-5,6-dimethoxy-3-methyl- |
| 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 |
| piericidin a |
