OLIGOMYCIN Chemical Properties

Melting point:

84-100 °C

Density 

1.143 g/cm³

storage temp. 

−20°C

solubility 

Soluble in DMSO (up to 300 mg/ml) or in Ethanol (up to 200 mg/ml)

form 

White solid

color 

White

Water Solubility 

Sparingly soluble in water. Soluble in DMSO (20mg/ml) and ethanol (30mg/ml) /n

BRN 

7615308

Stability:

Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.

Safety Information

Hazard Codes 

Xn,T

Risk Statements 

22

Safety Statements 

24/25

RIDADR 

2811

WGK Germany 

3

RTECS 

RK3325000

F 

3-10

HazardClass 

6.1(b)

PackingGroup 

III

HS Code 

29419090

MSDS

• Language:English Provider:ACROS

OLIGOMYCIN Usage And Synthesis

Description

Oligomycin (1404-19-9) inhibits mitochondrial F1F0?ATP synthase.1?A useful tool for decreasing cellular ATP levels.2?Induces autophagy.3?Stimulates lysosome acidification.4?Oligomycin protects against ischemic kidney in male rats.5

Chemical Properties

White to pale yellow powder

Uses

Oligomycin is a specific inhibitor of the mitochondrial ATP-synthase.

General Description

A mixture of A, B, and C isomers. A macrolide antibiotic that inhibits membrane-bound mitochondrial ATP synthase, preventing phosphoryl group transfer. Induces apoptosis in cultured human lymphoblastoid and other mammalian cells.

Biochem/physiol Actions

Product does not compete with ATP.

in vitro

in a549, h1299, h1975, h520, 786-0, h838, and u87mg cancer cell lines, 100 ng/ml oligomycin could completely inhibit oxphos phosphorylation activity and stimulate various levels of glycolysis gains [1]. besides, 5 μg/ml oligomycin could inhibit the f0 part of h+-atp-synthase, and strongly suppress cytochrome c release and apoptosis in hela cells induced by tnf [2]. furthermore, oligomycin could inhibit mitochondrial respiration, and sensitize melanoma cells to cisplatin treatment to inhibit cell invasion [3].

Enzyme inhibitor

These macrolide antibiotics from Streptomyces diastatochromogenes have three major members: Oligomycin A (FW = 791.08 g/mol; CAS 14104-19- 9), Oligomycin B (FW = 805.06 g/mol; CAS 11050-94-5), and Oligomycin C (FW = 775.08 g/mol; CAS 11052-72-5). Others include Oligomycin D (also known as rutamycin; FW = 777.05 g/mol; CAS 1404-59-7), Rutamycin B (isolated from Streptomyces aureofaciens (See also Rutamycin)), and Oligomycin E (FW = 822.07 g/mol; CAS 110231-34-0; isolated from Streptomyces sp. MCI-2225). Primary Mode of Inhibitory Action: The oligomycins inhibit the ATP synthesis activity of the mitochondrial FoF1 ATP synthase, defining the “o” (not 0) in the first subscript. The ATPase activity of the isolated F1 complex is unaffected by oligomycins, unlike the Fo portion. Oligomycin-sensitivity conferring ptrotein (OSCP) interacts with other components in the ATP synthase complex and facilitates oligomycin’s binding to the Fo unit. The Fo complex is, in fact, an integral membrane protein that functions as a proton channel. Other Actions: Oligomycins also inhibit Na+/K+-exchanging ATPases that transport sodium ions from the inside to the outside of animal cells while translocating potassium ions in the reverse direction with the concomitant hydrolysis of ATP. Oligomycin inhibits Na+ translocation in vivo (i.e., the enzyme activity is inhibited by stabilizing the Na+ occlusion but not the K+ occlusion). Other Properties: The oligomycins are slightly soluble in water (e.g., oligomycin A has a solubility of 2 μg per 100 mL at 25°C) and are considerable more soluble in water-miscible solvents such as ethanol, acetone, and glacial acetic acid. Target(s): aldehyde oxidase; ammonia kinase; apyrase, membrane-bound; ATP synthase, or FoF1 ATP synthase; calcidiol 1-monooxygenase; copper-exporting ATPase, partially inhibited; endopeptidase La, weakly inhibited; H+-transporting ATPase, lysosomal; Na+/K+-exchanging ATPase (24- 32); nucleoside triphosphatase; photophosphorylation in Rhodospirillum rubrum; xenobiotic-transporting ATPases.

target

atp synthase

References

1) Antoniel?et al. (2014),?The oligomycin-sensitivity conferring protein of mitochondrial ATP synthase: emerging new roles in mitochondrial pathophysiology;? J. Mol. Sci.,?15?7513 2) Ng et al. (2014),?Essential role of TID1 in maintaining mitochondrial membrane potential homogeneity and mitochondrial DNA integrity;? Mol. Cell Biol.,?34?1427 3) Tettamonti?et al. (2006),?Oligomycin A induces autophagy in the IPLB-LdFB insect cell line;? Cell Tissue Res.,?326?179 4) van Dyke?et al. (1993),?Acidification of rat liver lysosomes:quantification and comparison with endosomes;? Am. J. Physiol.,?265?C901 5) Tanaka?et al. (2013),?Oligomycin, an F1Fo-ATPase inhibitor, protects against ischemic acute kidney injury in male but not in female rats;? J. Pharmacol. Sci.,?123?227

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