Oligomycin A (CAS: 579-13-5)

C₄₅H₇₄O₁₁

• 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.

1. Oligomycin, a new antifungal antibiotic: R.M. Smith, et al.; Antibiot. Chemother. 4, 962 (1954)
2. The use of oligomycin as an inhibitor of oxidative phosphorylation: F. Huijing & E.C. Slater; J. Biochem. 49, 493 (1961)
3. Inhibitors of the ATP synthethase system: P.E. Linnett & R.B. Beechey; Methods Enzymol. 55, 472 (1979)
4. Apoptolidin, a selective cytotoxic agent, is an inhibitor of F0F1-ATPase: A.R. Salomon, et al.; Chem. Biol. 8, 71 (2001)
5. Oligomycin, inhibitor of the F0 part of H+-ATP-synthase, suppresses the TNF-induced apoptosis: L.A. Shchepina, et al.; Oncogene 21, 8149 (2002)
6. 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)
7. 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)
8. Oligomycin A induces autophagy in the IPLB-LdFB insect cell line: G. Tettamanti, et al.; Cell Tissue Res. 326, 179 (2006)
9. Age-dependent cell death and the role of ATP in hydrogen peroxide-induced apoptosis and necrosis: N. Miyoshi, et al.; PNAS 103, 1727 (2006)
10. 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)
11. Mitochondrial proton and electron leaks: M. Jastroch, et al.; Essays Biochem. 47, 53 (2010)
12. 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)
13. A guide to immunometabolism for immunologists: L.A. O'Neill, et al.; Nat. Rev. Immunol. 16, 553 (2016) (Review)
14. The phenotype of peritoneal mouse macrophages depends on the mitochondria and ATP/ADP homeostasis: W. Chen, et al.; Cell Immunol. 324, 1 (2018)
15. Role of mitochondrial function in the invasiveness of human colon cancer cells: C.S. Lin, et al.; Oncol. Rep. 39, 316 (2018)