Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C25H37NO4 |
Molecular Weight | 415.5656 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 4 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=C(OC)C(O)=C(C)C(C\C=C(/C)C\C=C\C(C)=C\[C@@H](C)[C@@H](O)C(\C)=C\C)=N1
InChI
InChIKey=BBLGCDSLCDDALX-LKGBESRRSA-N
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
Piericidin A (also named piericidin A1 in some references) was reported as a new insecticidal metabolite, produced by cultures of the soil-derived actinomycete Streptomyces mobaraensis. Piericidin A resembles coenzyme Q in its overall structure containing a pyridine ring with two adjacent methoxy groups. The most widely recognized biological target of Piericidin A is the mitochondrial electron transport chain protein NADH-ubiquinone reductase (Complex I). Respiratory inhibition by piericidin A can be reversed by the addition of vitamin-K3 (menadione) to the inhibited respiratory chain in mammalian mitochondria. Piericidin A increases ROS production. Piericidin A showed significant cytotoxic activities against several tumor cells, such as mouse leukemia cell line, human colon carcinoma cells and was selectively cytotoxic toward human multiple myeloma cells. Moreover, it was identified as a highly selective antitumor agent with greater selectivity and potency than the comparison standard mitomycin C. Piericidin A aggravates the course of genetically determined tau pathology.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: GRP78 upregulation Sources: https://www.ncbi.nlm.nih.gov/pubmed/17941090 |
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Target ID: NADH-ubiquinone reductase (Complex I) |
0.6 nM [Ki] | ||
Target ID: GO:1903409 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4290528 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Piericidin A: a new inhibitor of mitochondrial electron transport. | 1966 Nov 22 |
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Characteristics of the binding of rotenone in the respiratory chain and the inhibition sites of amytal and piericidin A. | 1967 Sep |
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Studies on the respiratory chain-linked reduced nicotinamide adenine dinucleotide dehydrogenase. 13. Binding sites of rotenone, piericidin A, and amytal in the respiratory chain. | 1968 Feb 25 |
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Total synthesis of piericidin A1 and B1 and key analogues. | 2006 Sep 13 |
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Etoposide-resistant HT-29 human colon carcinoma cells during glucose deprivation are sensitive to piericidin A, a GRP78 down-regulator. | 2008 Apr |
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Piericidin A aggravates Tau pathology in P301S transgenic mice. | 2014 |
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The unique chemistry and biology of the piericidins. | 2016 Aug |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25437199
Curator's Comment: toxicity investigation
Mice: 0.5 mg/kg/d for a period of 28 days
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17941090
Piericidin A suppressed the accumulation of GRP78 protein and was also highly toxic to etoposide-resistant HT-29 cells, with IC50 values for colony formation of 6.4 and 7.7 nM under 2-deoxyglucose supplemented and glucose-deprived conditions, respectively.
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6437838
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PIERICIDIN A
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2738-64-9
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138511
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DTXSID80880044
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8VT513UJ9R
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SUBSTANCE RECORD