Oligomycin A

Oligomycin A, also known as MCH 32, is an inhibitor of ATP synthase. Oligomycin A inhibits ATP synthase by blocking its proton channel (Fo subunit), which is necessary for oxidative phosphorylation of ADP to ATP (energy production). The inhibition of ATP synthesis by oligomycin A will significantly reduce electron flow through the electron transport chain; however, electron flow is not stopped completely due to a process known as proton leak or mitochondrial uncoupling. This process is due to facilitated diffusion of protons into the mitochondrial matrix through an uncoupling protein such as thermogenin, or UCP1.

Product information

CAS Number: 579-13-5

Molecular Weight: 789.05

Formula: C45H72O11

Synonym:

MCH 32

MCH-32

MCH32

Chemical Name: (1S, 2'R, 4E, 5'R, 6R, 6'S, 7S, 8R, 10S, 11S, 12R, 14S, 15R, 16S, 18E, 20E, 22S, 25R, 28R, 29S)-22-ethyl-3', 4', 5', 6'-tetrahydro-7, 11, 14, 15-tetrahydroxy-6'-[(1Z)-2-hydroxy-1-propen-1-yl]-5', 6, 8, 10, 12, 14, 16, 28, 29-nonamethyl-spiro[2, 26-dioxabicyclo[23.3.1]nonacosa-4, 18, 20-triene-27, 2'-[2H]pyran]-3, 9, 13-trione

Smiles: C[C@]1(O)[C@H](O)[C@@H](C)CC=CC=C[C@H](CC[C@H]2O[C@@]3(CC[C@@H](C)[C@@H](/C=C(/C)\O)O3)[C@H](C)[C@@H](OC(=O)C=C[C@@H](C)[C@H](O)[C@@H](C)C(=O)[C@@H](C)[C@H](O)[C@@H](C)C1=O)[C@H]2C)CC |t:8,10,35|

InChiKey: STEWZSZUSBALCS-WFFJUDJESA-N

InChi: InChI=1S/C45H72O11/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/h13-15,17-18,21,24-27,29-36,38,40-42,46,48,50-51,53H,12,16,19-20,22-23H2,1-11H3/b14-13-,17-15-,21-18-,28-24-/t25-,26-,27+,29+,30-,31-,32-,33-,34-,35-,36-,38+,40+,41+,42-,44+,45-/m1/s1

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: DMSO: 10 mg/mL(12.64 mM). Water: Insoluble.

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

Oligomycin A is an inhibitor of ATP synthase, inhibits oxidative phosphorylation and all the ATP-dependent processes occurring on the coupling membrane of mitochondria.Oligomycin A inhibits ATP synthase by blocking its proton channel (Fo subunit), which is necessary for oxidative phosphorylation of ADP to ATP. The inhibition of ATP synthesis by oligomycin A will significantly reduce electron flow through the electron transport chain; however, electron flow is not stopped completely due to a process known as proton leak or mitochondrial uncoupling. In a group of cancer cells, Oligomycin at 100 ng/ml completely inhibits oxidative phosphorylation activity in 1 h and induces various levels of glycolysis gains by 6 h. Oligomycin, inhibitor of the F0 part of H+-ATP-synthase, suppresses the TNF-induced apoptosis. Oligomycin inhibits mitochondrial respiration in melanoma, sensitizes melanoma cells to therapy, blocks the emergence of the slow-cycling, long-term tumor-maintaining melanoma cells.

References:

1. Shchepina LA, et al. Oncogene, 2002, 21(53):8149-8157.
2. Hao W, et al. J Biol Chem, 2010, 285(17), 12647-12654.
3. Jastroch M, et al. Essays Biochem. 2010;47:53-67.

Products are for research use only. Not for human use.