Oligomycin A

Specifications / Handling

More Information
Product Details
Synonyms	MCH 32
Product Type	Chemical
Properties
Formula	C₄₅H₇₄O₁₁
MW	791.1
CAS	579-13-5
RTECS	RK3328000
Source/Host Chemicals	Originally isolated from Streptomyces diastatochromogenes.
Purity Chemicals	≥95%
Appearance	White to off-white solid.
Solubility	Soluble in DMSO (20mg/ml), ethanol (20mg/ml) or DMF (20mg/ml).
InChi Key	MNULEGDCPYONBU-AWJDAWNUSA-N
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
Shipping and Handling
Shipping	AMBIENT
Short Term Storage	+4°C
Long Term Storage	-20°C
Handling Advice	Keep cool and dry. Protect from light.
Use/Stability	Stable for at least 2 years after receipt when stored at -20°C.
Documents
MSDS	Download PDF
Product Specification Sheet
Datasheet	Download PDF

Product-specific References

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.

Product 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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