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Purity: ≥98%
Oligomycin A (also known as MCH 32) is a naturally occuring macrolide produced by Streptomyces. It is a potent inhibitor of ATP synthase, which blocks oxidative phosphorylation and all the ATP-dependent processes occurring on the coupling membrane of mitochondria. Oligomycin A inhibits mitochondrial F0F1-ATPase with a Ki of 1 μM and shows anti-fungal activity. Oligomycin A blocks proton channel of ATP synthase, which is necessary for transforming ADP to ATP by oxidative phosphorylation, accomplishing the inhibition of ATP synthase.
| Targets |
F0F1-ATPase （Ki = 1 μM）
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| ln Vitro |
Oligomycin A inhibits the mitochondrial F0F1-ATPase with a Ki of 1 μM. Oligomycin A is cytotoxic to the NCI-60 cell line, with a GI50 of 10 nM. Oligomycin A inhibits Triton X-100 solubilized ATPase with a Ki of 0.1 μM. In addition, Oligomycin A exhibits antifungal properties [1]. Oligomycin A (2.4 μM) prevents sperm from achieving viable in vitro capacitation (IVC) and inhibits progesterone-induced in vitro acrosome exocytosis (IVAE), resulting in peak O2 depletion and ATP levels [2].
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| ln Vivo |
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| Cell Assay |
Incubation of boar spermatozoa in a capacitation medium with oligomycin A, a specific inhibitor of the F0 component of the mitochondrial ATP synthase, induced an immediate and almost complete immobilisation of cells. Oligomycin A also inhibited the ability of spermatozoa to achieve feasible in vitro capacitation (IVC), as measured through IVC-compatible changes in motility patterns, tyrosine phosphorylation levels of the acrosomal p32 protein, membrane fluidity and the ability of spermatozoa to achieve subsequent, progesterone-induced in vitro acrosome exocytosis (IVAE). Both inhibitory effects were caused without changes in the rhythm of O2 consumption, intracellular ATP levels or mitochondrial membrane potential (MMP). IVAE was accompanied by a fast and intense peak in O2 consumption and ATP levels in control spermatozoa. Oligomycin A also inhibited progesterone-induced IVAE as well as the concomitant peaks of O2 consumption and ATP levels. The effect of oligomycin on IVAE was also accompanied by concomitant alterations in the IVAE-induced changes on intracellular Ca(2+) levels and MMP. Our results suggest that the oligomycin A-sensitive mitochondrial ATP-synthase activity is instrumental in the achievement of an adequate boar sperm motion pattern, IVC and IVAE. However, this effect seems not to be linked to changes in the overall maintenance of adequate energy levels in stages other than IVAE.[2]
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| Toxicity/Toxicokinetics |
mouse LD50 intraperitoneal 1500 ug/kg
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| References |
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| Additional Infomation |
Oligomycin A is an oligomycin with formula C45H74011. An inhibitor of mitochondrial F1FO ATP synthase that induces apoptosis in a variety of cell types and exhibits antifungal, antitumour, and nematicidal activities, but its clinical application has been limited by poor solubility in water and other biocompatible solvents. It has a role as an EC 3.6.3.14 (H(+)-transporting two-sector ATPase) inhibitor, an antineoplastic agent and a nematicide. It is a diketone, a pentol, an antibiotic antifungal agent and an oligomycin.
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| Molecular Formula |
C45H74O11
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| Molecular Weight |
791.06
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| Exact Mass |
790.523
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| Elemental Analysis |
C, 68.50; H, 9.20; O, 22.30
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| CAS # |
579-13-5
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| Related CAS # |
Oligomycin;1404-19-9;Oligomycin D;1404-59-7;Oligomycin C;11052-72-5;Oligomycin B;11050-94-5
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| PubChem CID |
52947716
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| Appearance |
White to off-white solid powder
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| Density |
1.1±0.1 g/cm3
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| Boiling Point |
886.3±65.0 °C at 760 mmHg
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| Melting Point |
150-151ºC
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| Flash Point |
252.0±27.8 °C
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| Vapour Pressure |
0.0±0.6 mmHg at 25°C
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| Index of Refraction |
1.543
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| LogP |
6.17
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| Hydrogen Bond Donor Count |
5
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| Hydrogen Bond Acceptor Count |
11
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
56
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| Complexity |
1390
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| Defined Atom Stereocenter Count |
18
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| SMILES |
CC[C@@H]\1CC[C@H]2[C@H]([C@H]([C@@H]([C@]3(O2)CC[C@@H]([C@@H](O3)C[C@@H](C)O)C)C)OC(=O)/C=C/[C@@H]([C@H]([C@@H](C(=O)[C@@H]([C@H]([C@@H](C(=O)[C@]([C@H]([C@@H](C/C=C/C=C1)C)O)(C)O)C)O)C)C)O)C)C
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| InChi Key |
STEWZSZUSBALCS-HQBODTQXSA-N
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| InChi Code |
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
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| Chemical Name |
(1S,2R,4E,5R,6R,6S,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
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| Synonyms |
05HQS4AI99; 579-13-5; Oligomycin A; EINECS 209-437-3; UNII-05HQS4AI99; BRN 5702132; RP-32705; MCH-32;
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (3.16 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: 2.5 mg/mL (3.16 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (3.16 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. Solubility in Formulation 4: ≥ 2.5 mg/mL (3.16 mM) (saturation unknown) in 10% EtOH + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear EtOH stock solution to 400 μL of PEG300 and mix evenly; then add 50 μL of Tween-80 to the above solution and mix evenly; then add 450 μL of normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 5: ≥ 2.5 mg/mL (3.16 mM) (saturation unknown) in 10% EtOH + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear EtOH stock solution to 900 μL of corn oil and mix evenly. Solubility in Formulation 6: 30% PEG400+0.5% Tween80+5% Propylene glycol :15 mg/mL |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.2641 mL | 6.3206 mL | 12.6413 mL | |
| 5 mM | 0.2528 mL | 1.2641 mL | 2.5283 mL | |
| 10 mM | 0.1264 mL | 0.6321 mL | 1.2641 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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