O4876

Oligomycin

Name: Oligomycin
Brand: SIGMA

from Streptomyces diastatochromogenes, ≥90% total oligomycins basis (HPLC), powder, antibiotic

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About This Item

CAS Number:

1404-19-9

UNSPSC Code:

12352200

PubChem Substance ID:

24898006

NACRES:

NA.77

Beilstein/REAXYS Number:

7615308

MDL number:

MFCD01779388

Product Name

Oligomycin from Streptomyces diastatochromogenes, ≥90% total oligomycins basis (HPLC)

InChI

1S/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+

InChI key

MNULEGDCPYONBU-ZUSSGZTJSA-N

assay

≥90% total oligomycins basis (HPLC)

form

powder

antibiotic activity spectrum

fungi

mode of action

enzyme | inhibits

storage temp.

−20°C

Quality Level

200

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Related Categories

Antibiotics

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

Biochemicals

Cell Culture Supplements & Reagents

Application

Oligomycin from Streptomyces diastatochromogenes is used:

in the inhibition of mitochondrial ATP production Leigh syndrome (LS) cells.
in ATP-linked respiration and maximal capacity respiration assay in astrocytes.
in measurement of oxygen consumption rate (OCR) and extracellular acidification rates in breast cancer cell lines.

Biochem/physiol Actions

Oligomycin belongs to the macrolide group of antibiotics. It inhibits mitochondrial ATP-synthase enzyme and phosphoryl group transfer. Oligomycin interacts with ATP synthase subunit-c in the Fo portion and impairs proton transport.

General description

Chemical structure: macrolide

Other Notes

2024 CiteAb Award Winner for Supplier Succeeding in Parkinson′s Research

A mixture of oligomycins A, B, and C.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Oligomycin, inhibitor of the F 0 part of H+-ATP-synthase, suppresses the TNF-induced apoptosis

Shchepina LA, et al.

Oncogene, 21(53), 8149-8149 (2002)

Drug screening identifies Sigma-1-Receptor as a target for the therapy of VWM leukodystrophy

Atzmon A, et al.

Frontiers in Molecular Neuroscience, 11 (2018)

Identification of ataxia-associated mtDNA mutations (m.4052T>C and m.9035T>C) and evaluation of their pathogenicity in transmitochondrial cybrids.

Marianna Sikorska et al.

Muscle & nerve, 40(3), 381-394 (2009-07-25)

The potential pathogenicity of two homoplasmic mtDNA point mutations, 9035T>C and 4452T>C, found in a family afflicted with maternally transmitted cognitive developmental delay, learning disability, and progressive ataxia was evaluated using transmitochondrial cybrids. We confirmed that the 4452T>C transition in

Oligomycin frames a common drug-binding site in the ATP synthase

Symersky J, et al.

Proceedings of the National Academy of Sciences of the USA, 109(35), 13961-13965 (2012)

Synthesis and cytotoxicity of oligomycin A derivatives modified in the side chain

Lysenkova LN, et al.

Bioorganic & Medicinal Chemistry, 21(11), 2918-2924 (2013)

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