# Oligomycin

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**Oligomycins** are [macrolides](/source/Macrolide) created by *[Streptomyces](/source/Streptomyces)* that are strong antibacterial agents but are often [poisonous](/source/Poisonous) to other organisms, including humans.

## Function

Oligomycins have use as [antibiotics](/source/Antibiotics). However, in humans, they have limited or no clinical use due to their toxic effects on [mitochondria](/source/Mitochondrion) and [ATP synthase](/source/ATP_synthase).[1]

Oligomycin A is an [inhibitor](/source/Enzyme_inhibitor) of ATP synthase.[1] In oxidative phosphorylation research, it is used to prevent stage 3 (phosphorylating) respiration. Oligomycin A inhibits ATP synthase by blocking its proton channel (FO subunit), which is necessary for [oxidative phosphorylation](/source/Oxidative_phosphorylation) of [ADP](/source/Adenosine_diphosphate) to [ATP](/source/Adenosine_triphosphate) (energy production). The inhibition of ATP synthesis by oligomycin A will significantly reduce electron flow through the [electron transport chain](/source/Electron_transport_chain); however, electron flow is not stopped completely due to a process known as *proton leak* or *[mitochondrial uncoupling](/source/Mitochondrial_uncoupling)*.[2] This process is due to [facilitated diffusion](/source/Facilitated_diffusion) of protons into the [mitochondrial matrix](/source/Mitochondrial_matrix) through an [uncoupling protein](/source/Uncoupling_protein) such as [thermogenin](/source/Thermogenin), or [UCP1](/source/UCP1).

Administering oligomycin to rats can result in very high levels of lactate accumulating in the blood and urine.[3]

Oligomycins[4] R1 R2 R3 R4 R5 Oligomycin A CH3 H OH H,H CH3 Oligomycin B CH3 H OH O CH3 Oligomycin C CH3 H H H,H CH3 Oligomycin D (Rutamycin A) H H OH H,H CH3 Oligomycin E CH3 OH OH O CH3 Oligomycin F CH3 H OH H,H CH2CH3 Rutamycin B H H H H,H CH3 44-Homooligomycin A CH2CH3 H OH H,H CH3 44-Homooligomycin B CH2CH3 H OH O CH3

## References

1. Mackieh R, Al-Bakkar N, Kfoury M, Roufayel R, Sabatier JM, Fajloun Z (March 2023). "Inhibitors of ATP Synthase as New Antibacterial Candidates". *Antibiotics*. **12** (4): 650. [doi:10.3390/antibiotics12040650](https://doi.org/10.3390/antibiotics12040650). [PMC 10135114](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10135114). [PMID 37107012](https://pubmed.ncbi.nlm.nih.gov/37107012)

1. Jastroch M, Divakaruni AS, Mookerjee S, Treberg JR, Brand MD (2010). "Mitochondrial proton and electron leaks". *Essays in Biochemistry*. **47** (1): 53–67. [doi:10.1042/bse0470053](https://doi.org/10.1042/bse0470053). [PMC 3122475](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3122475). [PMID 20533900](https://pubmed.ncbi.nlm.nih.gov/20533900)

1. Kramar R, Hohenegger M, Srour AN, Khanakah G (December 1984). "Oligomycin toxicity in intact rats". *Agents and Actions*. **15** (5–6): 660–663. [doi:10.1007/BF01966788](https://doi.org/10.1007/BF01966788). [PMID 6532186](https://pubmed.ncbi.nlm.nih.gov/6532186). [S2CID 7837164](https://api.semanticscholar.org/CorpusID:7837164)

1. Nakata M, Ishiyama T, Akamatsu S, Hirose Y, Maruoka H, Suzuki R, Tatsuta K (1995). "Synthetic studies on oligomycins. Synthesis of the oligomycin B spiroketal and polypropionate portions". *Bulletin of the Chemical Society of Japan*. **68** (3): 967–89. [doi:10.1246/bcsj.68.967](https://doi.org/10.1246/bcsj.68.967)

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