Oligomycin B

Oligomycin B is a minor analog of a class of macrocyclic lactones isolated from selected strains of Streptomyces spp. It is a non-selective inhibitor of mitochondrial F1F0 ATP synthase in eukaryotes. Oligomycins exhibit apoptotic cytotoxicity and mitochondrial toxicity. It can induce apoptosis in a variety of cell types. It is practically free of homologs. Oligomycin B has the base structure of Oligomycin A but the spirocyclic ring with the 2-hydroxypropyl has been substituted by an oxo group.
Oligomycin is a macrolide antibiotic complex from Streptomyces. It is an inhibitor of mitochondrial F1F0 ATP synthase. The Oligomycin complex was first reported in 1954, from a strain of Streptomyces diastatochromogenes from soil highly active against fungi. The Oligomycin class includes the analogs/isomers A through G. Different isomers are highly specific for the disruption of mitochondrial metabolism. Oligomycin can be used to study the mechanistic aspects of ATP formation in tumor cell biology and apoptosis.
Oligomycin B is soluble in ethanol, methanol, DMSO and DMF. Practically insoluble in water.

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Background

Oligomycin inhibits phosphoryl group transfer in mitochondrial membrane-bound ATP synthase (F1F0 ATPase), blocking proton translocation and leading to hyperpolarization of inner mitochondrial membrane. The result is that mitochondrial ATP is not synthesized, as this enzyme is responsible for ATP production in mammals via a rotary catalytic mechanism.
After more than 50 years of studies on the binding site of Oligomycin, a team at the Rosalind Franklin University (North Chicago, IL) discovered that it binds to the subunit-c of the F0 portion of the ATP synthase. The residues involved in the binding site are conserved from yeast to humans (Symersky et al, 2012).