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O4876

Sigma-Aldrich

Oligomycin

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

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About This Item

CAS Number:
1404-19-9
Beilstein:
7615308
MDL number:
MFCD01779388
UNSPSC Code:
12352200
PubChem Substance ID:
24898006
NACRES:
NA.77

product name

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

Assay

≥90% total oligomycins basis (HPLC)

form

powder

antibiotic activity spectrum

fungi

Mode of action

enzyme | inhibits

storage temp.

−20°C

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

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General description

Chemical structure: macrolide

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.

Other Notes

A mixture of oligomycins A, B, and C.
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Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
Synthesis and cytotoxicity of oligomycin A derivatives modified in the side chain
Lysenkova LN, et al.
Bioorganic & Medicinal Chemistry, 21(11), 2918-2924 (2013)
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)
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)
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