Oligomycin A (MCH-32)

Cat No.:V0064 Purity: ≥98%

COA Product Data Instructions for use SDS

Oligomycin A (also known as MCH 32)is a naturally occuring macrolide produced by Streptomyces.

Oligomycin A (MCH-32) Chemical Structure CAS No.: 579-13-5
Product category: ATP Synthase

This product is for research use only, not for human use. We do not sell to patients.

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Cell 2020,183:1202-1218.e25.

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Nature 2021,597(7874):119-125.

Cell 2020,183:1202-1218.e25.

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Purity & Quality Control Documentation

Current batch：

Purity: ≥98%

COA

MSDS

Instructions

Product Description
Bioactivity & Protocols
Physicochemical Properties
Solubility Data
Calculators
Biological Data

Product Description

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.

Biological Activity I Assay Protocols (From Reference)

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].

ln Vivo

N/A

Animal Protocol

N/A

References

[1]. Salomon AR, et al. Apoptolidin, a selective cytotoxic agent, is an inhibitor of F0F1-ATPase. Chem Biol. 2001 Jan;8(1):71-80.
[2]. Ramió-Lluch L, et al. Oligomycin A-induced inhibition of mitochondrial ATP-synthase activity suppresses boar sperm motility and in vitro capacitation achievement without modifying overall sperm energy levels. Reprod Fertil Dev. 2014;26(6):883-97

These protocols are for reference only. InvivoChem does not independently validate these methods.

Physicochemical Properties

Molecular Formula	C45H74O11
Molecular Weight	791.06
CAS #	579-13-5
Related CAS #	Oligomycin;1404-19-9;Oligomycin D;1404-59-7;Oligomycin C;11052-72-5;Oligomycin B;11050-94-5
SMILES	O1[C@@]2([H])C([H])([H])C([H])([H])[C@]([H])(C([H])=C([H])C([H])=C([H])C([H])([H])[C@@]([H])(C([H])([H])[H])[C@@]([H])([C@](C([H])([H])[H])(C([C@@]([H])(C([H])([H])[H])[C@@]([H])([C@@]([H])(C([H])([H])[H])C([C@@]([H])(C([H])([H])[H])[C@@]([H])([C@@]([H])(C([H])([H])[H])C([H])=C([H])C(=O)O[C@]([H])(C2([H])C([H])([H])[H])[C@]([H])(C([H])([H])[H])[C@]21C([H])([H])C([H])([H])[C@]([H])(C([H])([H])[H])[C@]([H])(C([H])([H])[C@@]([H])(C([H])([H])[H])O[H])O2)O[H])=O)O[H])=O)O[H])O[H])C([H])([H])C([H])([H])[H] \|c:66,t:12,16\|
InChi Key	STEWZSZUSBALCS-HQBODTQXSA-N
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
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
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)

Solubility Data

Solubility (In Vitro)

DMSO: 10 mg/mL (12.6 mM)

Water:<1 mg/mL

Ethanol:<1 mg/mL

Solubility (In Vivo)

30% PEG400+0.5% Tween80+5%Propylene glycol:15 mg/mL

(Please use freshly prepared in vivo formulations for optimal results.)

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.

Calculator

Mass

Concentration

Volume

Molecular Weight*

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Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

Calculate the Mass of a compound required to prepare a solution of known volume and concentration
Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume

See Example

An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?

Enter 350.26 in the Molecular Weight (MW) box
Enter 10 in the Concentration box and choose the correct unit (mM)
Enter 5 in the Volume box and choose the correct unit (mL)
Click the “Calculate” button
The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Concentration (Start)

Volume (Start)

Concentration (End)

Volume (End)

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Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:

Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
Enter 25 into the Concentration (End) box and select the correct unit (mM)
Enter 25 into the Volume (End) box and choose the correct unit (mL)
Click the “Calculate” button
The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box

Molecular formula

Total molecular weight

g/mol

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Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4 c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:

To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.

Definitions of molecular mass, molecular weight, molar mass and molar weight:

Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.

Volume (to add to vial)

Mass (in vial)

Desired Reconstitution Concentration

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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
Click the “Calculate” button
The answer appears in the Volume (to add to vial) box

In vivo Formulation Calculator (Clear solution)

Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)

Dosage mg/kg

Average weight of animals g

Dosing volume per animal μL

Number of animals

Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)

% DMSO

% Tween 80

% ddH₂O

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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.

Note： (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.

Biological Data

Oligomycin at 100 ng/ml inhibits OXPHOS activity and stimulates various glycolysis gains in cancer cells. J Biol Chem. 2010 Apr 23;285(17):12647-54.
Oligomycin treatment on cellular ATP levels. J Biol Chem. 2010 Apr 23;285(17):12647-54.
Compare oligomycin- and hypoxia-induced glycolysis shift. A, H1299 cells were treated with 100 ng/ml oligomycin (OM-100) and 0.2% hypoxia for 24 h. J Biol Chem. 2010 Apr 23;285(17):12647-54.