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MedKoo Cat#: 564036 | Name: Piericidin A
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Piericidin A is an irreversible inhibitor of mitochondrial complex I that strongly associates with ubiquinone binding sites in both mitochondrial and bacterial forms of the enzyme. Piericidin A induces transcription of the p53-responsive SESN2 gene which plays an important role in the stress response and homeostatic regulation.

Chemical Structure

Piericidin A
Piericidin A
CAS#2738-64-9

Theoretical Analysis

MedKoo Cat#: 564036

Name: Piericidin A

CAS#: 2738-64-9

Chemical Formula: C25H37NO4

Exact Mass: 415.2723

Molecular Weight: 415.57

Elemental Analysis: C, 72.26; H, 8.97; N, 3.37; O, 15.40

Price and Availability

Size Price Availability Quantity
1mg USD 305.00
5mg USD 790.00
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Synonym
Shaoguanmycin B; Shaoguanmycin-B; ShaoguanmycinB; AR 054; AR054; AR-054; Piericidin A; Piericidin-A; PiericidinA
IUPAC/Chemical Name
2-[(2E,5E,7E,9R,10R,11E)-10-Hydroxy-3,7,9,11-tetramethyltrideca-2,5,7,11-tetraenyl]-5,6-dimethoxy-3-methyl-1H-pyridin-4-one
InChi Key
BBLGCDSLCDDALX-LKGBESRRSA-N
InChi Code
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
SMILES Code
O=C1C(C)=C(C/C=C(C)/C/C=C/C(C)=C/[C@@H](C)[C@@H](O)/C(C)=C/C)NC(OC)=C1OC
Appearance
Solid powder
Purity
>98% (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
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Piericidin A (AR-054) is a natural mitochondrial NADH-ubiquinone oxidoreductase (complex I) inhibitor.
In vitro activity:
This study demonstrates that the viability of Tn5B1-4 cells is inhibited by PIA (piericidin A) in a time- and concentration-dependent manner with IC50 value of 0.061 μM, whilst PIA shows slight inhibitory effect on the viability of HepG2 and Hek293 cells with IC50 value of 233.97 and 228.96 μM, respectively. The inhibitory effect of PIA on the proliferation of Tn5B1-4 cells is significant and persistent, causing a series of morphological changes including cell shrinkage, condensed and fragmented nuclei. Intracellular biochemical assays show that PIA induces apoptosis of Tn5B1-4 cells coincides with a decrease in the mitochondrial membrane potential. Reference: Pestic Biochem Physiol. 2019 Jun;157:19-25. https://pubmed.ncbi.nlm.nih.gov/31153468/
In vivo activity:
Piericidin A significantly increased the number of phospho-tau immunoreactive cells in the cerebral cortex in P301S+/+ mice, but only to a variable and mild extent in wild-type mice. Furthermore, piericidin A led to increased levels of pathologically phosphorylated tau only in P301S+/+ mice. While this study observed no apparent cell loss in the frontal cortex, the synaptic density was reduced by piericidin A treatment in P301S+/+ mice. Reference: PLoS One. 2014 Dec 1;9(12):e113557. https://pubmed.ncbi.nlm.nih.gov/25437199/
Solvent mg/mL mM comments
Solubility
DMSO 10.0 24.06
Ethanol 5.0 12.03
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 415.57 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.

Recalculate based on batch purity %
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
Formulation protocol:
1. Muhayimana S, Zhang X, Xu J, Xiong H, Luan S, Zhu Q, Huang Q. 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. doi: 10.1016/j.pestbp.2019.03.002. Epub 2019 Mar 5. PMID: 31153468. 2. Andrés MT, Fierro JF. Antimicrobial mechanism of action of transferrins: selective inhibition of H+-ATPase. Antimicrob Agents Chemother. 2010 Oct;54(10):4335-42. doi: 10.1128/AAC.01620-09. Epub 2010 Jul 12. PMID: 20625147; PMCID: PMC2944611. 3. Schleifer G, Marutani E, Ferrari M, Sharma R, Skinner O, Goldberger O, Grange RMH, Peneyra K, Malhotra R, Wepler M, Ichinose F, Bloch DB, Mootha VK, Zapol WM. Impaired hypoxic pulmonary vasoconstriction in a mouse model of Leigh syndrome. Am J Physiol Lung Cell Mol Physiol. 2019 Feb 1;316(2):L391-L399. doi: 10.1152/ajplung.00419.2018. Epub 2018 Dec 6. PMID: 30520688; PMCID: PMC6397345. 4. Höllerhage M, Deck R, De Andrade A, Respondek G, Xu H, Rösler TW, Salama M, Carlsson T, Yamada ES, Gad El Hak SA, Goedert M, Oertel WH, Höglinger GU. Piericidin A aggravates Tau pathology in P301S transgenic mice. PLoS One. 2014 Dec 1;9(12):e113557. doi: 10.1371/journal.pone.0113557. Erratum in: PLoS One. 2015;10(3):e0122907. PMID: 25437199; PMCID: PMC4249965.
In vitro protocol:
1. Muhayimana S, Zhang X, Xu J, Xiong H, Luan S, Zhu Q, Huang Q. 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. doi: 10.1016/j.pestbp.2019.03.002. Epub 2019 Mar 5. PMID: 31153468. 2. Andrés MT, Fierro JF. Antimicrobial mechanism of action of transferrins: selective inhibition of H+-ATPase. Antimicrob Agents Chemother. 2010 Oct;54(10):4335-42. doi: 10.1128/AAC.01620-09. Epub 2010 Jul 12. PMID: 20625147; PMCID: PMC2944611.
In vivo protocol:
1. Schleifer G, Marutani E, Ferrari M, Sharma R, Skinner O, Goldberger O, Grange RMH, Peneyra K, Malhotra R, Wepler M, Ichinose F, Bloch DB, Mootha VK, Zapol WM. Impaired hypoxic pulmonary vasoconstriction in a mouse model of Leigh syndrome. Am J Physiol Lung Cell Mol Physiol. 2019 Feb 1;316(2):L391-L399. doi: 10.1152/ajplung.00419.2018. Epub 2018 Dec 6. PMID: 30520688; PMCID: PMC6397345. 2. Höllerhage M, Deck R, De Andrade A, Respondek G, Xu H, Rösler TW, Salama M, Carlsson T, Yamada ES, Gad El Hak SA, Goedert M, Oertel WH, Höglinger GU. Piericidin A aggravates Tau pathology in P301S transgenic mice. PLoS One. 2014 Dec 1;9(12):e113557. doi: 10.1371/journal.pone.0113557. Erratum in: PLoS One. 2015;10(3):e0122907. PMID: 25437199; PMCID: PMC4249965.
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The immunotoxicity of ten insecticides against insect hemocyte cells in vitro. In Vitro Cell Dev Biol Anim. 2022 Dec;58(10):912-921. doi: 10.1007/s11626-022-00738-y. Epub 2022 Nov 28. PMID: 36443536. 5: Schiller J, Zickermann V. Binding of Natural Inhibitors to Respiratory Complex I. Pharmaceuticals (Basel). 2022 Aug 31;15(9):1088. doi: 10.3390/ph15091088. PMID: 36145309; PMCID: PMC9503403. 6: de Haan LR, Reiniers MJ, Reeskamp LF, Belkouz A, Ao L, Cheng S, Ding B, van Golen RF, Heger M. Experimental Conditions That Influence the Utility of 2'7'-Dichlorodihydrofluorescein Diacetate (DCFH2-DA) as a Fluorogenic Biosensor for Mitochondrial Redox Status. Antioxidants (Basel). 2022 Jul 22;11(8):1424. doi: 10.3390/antiox11081424. PMID: 35892626; PMCID: PMC9329753. 7: LaMoia TE, Butrico GM, Kalpage HA, Goedeke L, Hubbard BT, Vatner DF, Gaspar RC, Zhang XM, Cline GW, Nakahara K, Woo S, Shimada A, Hüttemann M, Shulman GI. Metformin, phenformin, and galegine inhibit complex IV activity and reduce glycerol-derived gluconeogenesis. Proc Natl Acad Sci U S A. 2022 Mar 8;119(10):e2122287119. doi: 10.1073/pnas.2122287119. Epub 2022 Mar 1. PMID: 35238637; PMCID: PMC8916010. 8: Li K, Chen S, Pang X, Cai J, Zhang X, Liu Y, Zhu Y, Zhou X. Natural products from mangrove sediments-derived microbes: Structural diversity, bioactivities, biosynthesis, and total synthesis. Eur J Med Chem. 2022 Feb 15;230:114117. doi: 10.1016/j.ejmech.2022.114117. Epub 2022 Jan 12. PMID: 35063731. 9: Liang Z, Chen Y, Gu T, She J, Dai F, Jiang H, Zhan Z, Li K, Liu Y, Zhou X, Tang L. LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High- Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice. J Med Chem. 2021 Jul 22;64(14):9943-9959. doi: 10.1021/acs.jmedchem.1c00175. Epub 2021 Jul 12. PMID: 34251816. 10: Nuber F, Mérono L, Oppermann S, Schimpf J, Wohlwend D, Friedrich T. A Quinol Anion as Catalytic Intermediate Coupling Proton Translocation With Electron Transfer in E. coli Respiratory Complex I. Front Chem. 2021 May 7;9:672969. doi: 10.3389/fchem.2021.672969. PMID: 34026733; PMCID: PMC8138167. 11: Bridges HR, Fedor JG, Blaza JN, Di Luca A, Jussupow A, Jarman OD, Wright JJ, Agip AA, Gamiz-Hernandez AP, Roessler MM, Kaila VRI, Hirst J. Structure of inhibitor-bound mammalian complex I. Nat Commun. 2020 Oct 16;11(1):5261. doi: 10.1038/s41467-020-18950-3. PMID: 33067417; PMCID: PMC7567858. 12: Sako K, Futamura Y, Shimizu T, Matsui A, Hirano H, Kondoh Y, Muroi M, Aono H, Tanaka M, Honda K, Shimizu K, Kawatani M, Nakano T, Osada H, Noguchi K, Seki M. Inhibition of mitochondrial complex I by the novel compound FSL0260 enhances high salinity-stress tolerance in Arabidopsis thaliana. Sci Rep. 2020 May 26;10(1):8691. doi: 10.1038/s41598-020-65614-9. PMID: 32457324; PMCID: PMC7250896. 13: Manenda MS, Picard MÈ, Zhang L, Cyr N, Zhu X, Barma J, Pascal JM, Couture M, Zhang C, Shi R. Structural analyses of the Group A flavin-dependent monooxygenase PieE reveal a sliding FAD cofactor conformation bridging OUT and IN conformations. J Biol Chem. 2020 Apr 3;295(14):4709-4722. doi: 10.1074/jbc.RA119.011212. Epub 2020 Feb 28. PMID: 32111738; PMCID: PMC7136001. 14: Wong HS, Monternier PA, Brand MD. S1QELs suppress mitochondrial superoxide/hydrogen peroxide production from site IQ without inhibiting reverse electron flow through Complex I. Free Radic Biol Med. 2019 Nov 1;143:545-559. doi: 10.1016/j.freeradbiomed.2019.09.006. Epub 2019 Sep 10. PMID: 31518685. 15: Li K, Liang Z, Chen W, Luo X, Fang W, Liao S, Lin X, Yang B, Wang J, Tang L, Liu Y, Zhou X. Iakyricidins A-D, Antiproliferative Piericidin Analogues Bearing a Carbonyl Group or Cyclic Skeleton from Streptomyces iakyrus SCSIO NS104. J Org Chem. 2019 Oct 4;84(19):12626-12631. doi: 10.1021/acs.joc.9b01270. Epub 2019 Aug 7. PMID: 31347367. 16: Zhou X, Liang Z, Li K, Fang W, Tian Y, Luo X, Chen Y, Zhan Z, Zhang T, Liao S, Liu S, Liu Y, Fenical W, Tang L. Exploring the Natural Piericidins as Anti- Renal Cell Carcinoma Agents Targeting Peroxiredoxin 1. J Med Chem. 2019 Aug 8;62(15):7058-7069. doi: 10.1021/acs.jmedchem.9b00598. Epub 2019 Jul 25. PMID: 31298537. 17: Muhayimana S, Zhang X, Xu J, Xiong H, Luan S, Zhu Q, Huang Q. 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. doi: 10.1016/j.pestbp.2019.03.002. Epub 2019 Mar 5. PMID: 31153468. 18: Schleifer G, Marutani E, Ferrari M, Sharma R, Skinner O, Goldberger O, Grange RMH, Peneyra K, Malhotra R, Wepler M, Ichinose F, Bloch DB, Mootha VK, Zapol WM. Impaired hypoxic pulmonary vasoconstriction in a mouse model of Leigh syndrome. Am J Physiol Lung Cell Mol Physiol. 2019 Feb 1;316(2):L391-L399. doi: 10.1152/ajplung.00419.2018. Epub 2018 Dec 6. PMID: 30520688; PMCID: PMC6397345. 19: Imoto M. Chemistry and biology for the small molecules targeting characteristics of cancer cells. Biosci Biotechnol Biochem. 2018 Sep 24:1-10. doi: 10.1080/09168451.2018.1518704. Epub ahead of print. PMID: 30247093. 20: Nichols BA, Oswald NW, McMillan EA, McGlynn K, Yan J, Kim MS, Saha J, Mallipeddi PL, LaDuke SA, Villalobos PA, Rodriguez-Canales J, Wistuba II, Posner BA, Davis AJ, Minna JD, MacMillan JB, Whitehurst AW. HORMAD1 Is a Negative Prognostic Indicator in Lung Adenocarcinoma and Specifies Resistance to Oxidative and Genotoxic Stress. Cancer Res. 2018 Nov 1;78(21):6196-6208. doi: 10.1158/0008-5472.CAN-18-1377. Epub 2018 Sep 5. PMID: 30185546; PMCID: PMC6440700.