Oligomycin A
Product Code: AG-CN2-0517
Product Group: Natural Products and Extracts
Supplier: AdipoGen Life Sciences
| Code | Size | Price |
|---|
| AG-CN2-0517-M001 | 1 mg | £55.00 |
Quantity:
| AG-CN2-0517-M005 | 5 mg | £120.00 |
Quantity:
| AG-CN2-0517-M010 | 10 mg | £210.00 |
Quantity:
Prices exclude any Taxes / VAT
Overview
Regulatory Status: RUO
Target Species: Universal
Shipping:
AMBIENT
Storage:
-20°C
Documents
Further Information
Alternate Names/Synonyms:
MCH 32
Appearance:
White to off-white solid.
CAS:
579-13-5
EClass:
32160000
Form (Short):
liquid
Handling Advice:
Keep cool and dry.Protect from light.
InChi:
InChI=1S/C45H74O11/c1-12-34-17-15-13-14-16-27(4)42(51)44(11,53)43(52)32(9)40(50)31(8)39(49)30(7)38(48)26(3)18-21-37(47)54-41-29(6)35(20-19-34)55-45(33(41)10)23-22-25(2)36(56-45)24-28(5)46/h13-15,17-18,21,25-36,38,40-42,46,48,50-51,53H,12,16,19-20,22-24H2,1-11H3/b14-13+,17-15+,21-18+/t25-,26-,27+,28+,29+,30-,31-,32-,33-,34-,35-,36-,38+,40+,41+,42-,44+,45-/m0/s1
InChiKey:
MNULEGDCPYONBU-AWJDAWNUSA-N
Long Description:
Chemical. CAS: 579-13-5. Formula: C45H74O11. MW: 791.1. Synthetic. Originally isolated from Streptomyces diastatochromogenes. Potent mitochondrial ATP synthase (ATPases (F1F0)) inhibitor, consequently leading to inhibition of oxidative phosphorylation (OXPHOS). Useful agent for immunometabolism research. Inhibits ATP synthase by blocking its proton channel (F0 subunit), which is necessary for oxidative phosphorylation of ADP to ATP (energy production), significantly reducing electron flow through the electron transport chain. Anticancer agent. Shown to induce apoptosis/necroptosis in a variety of cell types, as well as autophagy. Shown to activate AMPK. Broad antifungal, antibiotic and nematocidal agent.
MDL:
MFCD00065705
Molecular Formula:
C45H74O11
Molecular Weight:
791.1
Package Type:
Vial
Product Description:
Potent mitochondrial ATP synthase (ATPases (F0F1)) inhibitor, consequently leading to inhibition of oxidative phosphorylation (OXPHOS). Useful agent for immunometabolism research. Inhibits ATP synthase by blocking its proton channel (F0 subunit), which is necessary for oxidative phosphorylation of ADP to ATP (energy production), significantly reducing electron flow through the electron transport chain. Anticancer agent. Shown to induce apoptosis/necroptosis in a variety of cell types, as well as autophagy. Shown to activate AMPK. Broad antifungal, antibiotic and nematocidal agent.
Purity:
>95%
SMILES:
C[C@H]1CC[C@@]2([C@@H](C)[C@H](OC(/C=C/[C@H](C)[C@@H](O)[C@H](C)C([C@H](C)[C@@H](O)[C@@H]3C)=O)=O)[C@H](C)[C@H](CC[C@@H](CC)/C=C/C=C/C[C@@H](C)[C@H](O)[C@@](C)(O)C3=O)O2)O[C@H]1C[C@H](O)C
Solubility Chemicals:
Soluble in DMSO (20mg/ml), ethanol (20mg/ml) or DMF (20mg/ml).
Source / Host:
Originally isolated from Streptomyces diastatochromogenes.
Transportation:
Non-hazardous
UNSPSC Category:
Natural Products/Extracts
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 2 years after receipt when stored at -20°C.
References
Oligomycin, a new antifungal antibiotic: R.M. Smith, et al.; Antibiot. Chemother. 4, 962 (1954) | The use of oligomycin as an inhibitor of oxidative phosphorylation: F. Huijing & E.C. Slater; J. Biochem. 49, 493 (1961) | Inhibitors of the ATP synthethase system: P.E. Linnett & R.B. Beechey; Methods Enzymol. 55, 472 (1979) | Apoptolidin, a selective cytotoxic agent, is an inhibitor of F0F1-ATPase: A.R. Salomon, et al.; Chem. Biol. 8, 71 (2001) | Oligomycin, inhibitor of the F0 part of H+-ATP-synthase, suppresses the TNF-induced apoptosis: L.A. Shchepina, et al.; Oncogene 21, 8149 (2002) | Activation of AMP-Activated Protein Kinase Leads to the Phosphorylation of Elongation Factor 2 and an Inhibition of Protein Synthesis: S. Horman, et al.; Curr. Biol. 12, 1419 (2002) | Down-regulation of mitochondrial F1F0-ATP synthase in human colon cancer cells with induced 5-fluorouracil resistance: Y.K. Shin, et al.; Cancer Res. 65, 3162 (2005) | Oligomycin A induces autophagy in the IPLB-LdFB insect cell line: G. Tettamanti, et al.; Cell Tissue Res. 326, 179 (2006) | Age-dependent cell death and the role of ATP in hydrogen peroxide-induced apoptosis and necrosis: N. Miyoshi, et al.; PNAS 103, 1727 (2006) | A new strain of Streptomyces avermitilis produces high yield of oligomycin A with potent anti-tumor activity on human cancer cell lines in vitro: X. Lin, et al.; Appl. Microbiol. Biotechnol. 81, 839 (2009) | Mitochondrial proton and electron leaks: M. Jastroch, et al.; Essays Biochem. 47, 53 (2010) | Mitochondria as new therapeutic targets for eradicating cancer stem cells: Quantitative proteomics and functional validation via MCT1/2 inhibition: R. Lamb, et al.; Oncotarget 5, 11029 (2014) | A guide to immunometabolism for immunologists: L.A. O'Neill, et al.; Nat. Rev. Immunol. 16, 553 (2016) (Review) | The phenotype of peritoneal mouse macrophages depends on the mitochondria and ATP/ADP homeostasis: W. Chen, et al.; Cell Immunol. 324, 1 (2018) | Role of mitochondrial function in the invasiveness of human colon cancer cells: C.S. Lin, et al.; Oncol. Rep. 39, 316 (2018)
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