1404-19-9 Usage
Description
Oligomycin is a macrolide antibiotic that consists of a mixture of A, B, and C isomers. It is a specific inhibitor of the mitochondrial ATP-synthase, which plays a crucial role in cellular energy production. Oligomycin inhibits membrane-bound mitochondrial ATP synthase, preventing the transfer of phosphoryl groups. This action leads to a decrease in cellular ATP levels, induction of autophagy, stimulation of lysosome acidification, and protection against ischemic kidney injury in male rats. It is a white to pale yellow powder in appearance.
Uses
1. Used in Pharmaceutical Industry:
Oligomycin is used as a specific inhibitor for mitochondrial ATP-synthase for research purposes. It helps in understanding the role of ATP synthase in cellular energy production and its potential as a target for therapeutic intervention.
2. Used in Cellular Research:
Oligomycin is used as a tool to decrease cellular ATP levels, which can be useful in studying the effects of reduced ATP on cellular processes and metabolism.
3. Used in Autophagy Studies:
Oligomycin is used to induce autophagy, a cellular process that involves the degradation and recycling of cellular components. This application is valuable for understanding the role of autophagy in various diseases and conditions.
4. Used in Lysosome Function Research:
Oligomycin is used to stimulate lysosome acidification, which can help researchers study the function and regulation of lysosomes in cellular processes.
5. Used in Kidney Protection Studies:
Oligomycin is used in research to protect against ischemic kidney injury in male rats, which can provide insights into potential therapeutic applications for kidney diseases and conditions.
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
Check Digit Verification of cas no
The CAS Registry Mumber 1404-19-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,4,0 and 4 respectively; the second part has 2 digits, 1 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 1404-19:
(6*1)+(5*4)+(4*0)+(3*4)+(2*1)+(1*9)=49
49 % 10 = 9
So 1404-19-9 is a valid CAS Registry Number.
InChI:InChI=1/C45H74O11/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/h13-15,17-18,21,25-36,38,40-42,46,48,50-51,53H,12,16,19-20,22-24H2,1-11H3/b14-13+,17-15-,21-18+
