OLIGOMYCIN

OLIGOMYCIN Basic information
Product Name:OLIGOMYCIN
Synonyms:OLIGOMYCIN FROM STREPTOMYCES*DIASTATOCHR OMOGENE;OLIGOMYCIN, MIXTURE OF THE COMPONENTS A, B AND C;OLIGOMYCIN, MIXTURE OF A, B AND C;OligomycinABCcomplex;oligomycin from streptomyces diastatochromogenes;Nystatin dehydrate;OLIGOMYCIN, MIXTURE OF A, B AND C, FROM STREPTOMYCES DIASTATOCHROMOGENES;diastatochromogenes
CAS:1404-19-9
MF:C135H220O33
MW:2371.1715
EINECS:215-767-9
Product Categories:MacrolidesNitric Oxide and Cell Stress;Mitochondrial InhibitorsMore...Close...;Antibiotics;Antibiotics A to;Antibiotics by Application;Antibiotics N-SAntibiotics;AntifungalAntibiotics;Antineoplastic and Immunosuppressive AntibioticsAntibiotics;Cell Stress;Chemical Structure Class;Inhibits an EnzymeAntibiotics;Mechanism of Action;Spectrum of Activity;antibiotic
Mol File:1404-19-9.mol
OLIGOMYCIN Structure
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
3-10
HazardClass 6.1(b)
PackingGroup III
HS Code 29419090
MSDS Information
ProviderLanguage
ACROS English
OLIGOMYCIN Usage And Synthesis
DescriptionOligomycin (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 PropertiesWhite to pale yellow powder
UsesOligomycin is a specific inhibitor of the mitochondrial ATP-synthase.
General DescriptionA 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 ActionsProduct does not compete with ATP.
in vitroin 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 inhibitorThese 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.
targetatp synthase
References1) 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
OLIGOMYCIN Preparation Products And Raw materials
oligomycin sensitivity-conferring protein METHYL ISOCYANOACETATE OLIGOMYCIN COMPLEX,OLIGOMYCIN A, STREPTOMYCES DIASTATOCHROMOGENES,OLIGOMYCIN, STREPTOMYCES DIASTATOCHROMOGENES,OLIGOMYCIN A N-BUTYLISOCYANIDE oligomycin G oligomycin E Tris(2,4-pentanedionato)chroMiuM(III) DICHLORO(ETHYLENEDIAMINE)PLATINUM(II) SALCOMINE OLIGOMYCIN C,OLIGOMYCIN C, STREPTOMYCES DIASTATOCHROMOGENES,Oligomycin A, 12-deoxy- 2,4-PENTANEDIONE, SILVER DERIVATIVE Tosylmethyl isocyanide COBALT(II) ACETYLACETONATE Oligomycin A, 28-oxo- ,Oligomycin B fromStreptomyces diastatochromogenes,OLIGOMYCIN B,OLIGOMYCIN B, STREPTOMYCES DIASTATOCHROMOGENES Cupric acetylacetonate Ethyl isocyanoacetate Ferric acetylacetonate COBALT ETHYLENE DIAMINE CHLORIDE

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