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Sigma-Aldrich

Oligomycin

≥90% (mixture of A, B, and C isomers, HPLC), powder, Antibiotic, Calbiochem

Synonym(s):

Oligomycin

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About This Item

Empirical Formula (Hill Notation):
C45H74O11
CAS Number:
1404-19-9
Molecular Weight:
791.06
MDL number:
MFCD01779388
UNSPSC Code:
12352200
NACRES:
NA.77

product name

Oligomycin, A mixture of A, B, and C isomers.

Quality Level

100

Assay

≥90% (mixture of A, B, and C isomers, HPLC)

form

powder

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze

color

white

shipped in

ambient

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

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

Cell permeable: no
Primary Target
Membrane-bound mitochondrial ATPase (F1)
Product does not compete with ATP.
Reversible: no

Warning

Toxicity: Irritant (B)

Reconstitution

Following reconstitution, aliquot and freeze (-20°C. Stock solutions are stable for up to 2 months at -20°C.

Other Notes

Wolvetang, E.J., et al. 1994. FEBS Lett.339, 40.
Amoroso, S., et al. 1993. J. Pharmacol. Exp. Ther.264, 515.
Brustovetsky, N.N., et al. 1993. FEBS Lett.315, 233.
Nagamune, H., et al. 1993. Biochim. Biophys. Acta1141, 231.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Birte Plitzko et al.
Bio-protocol, 8(10), e2850-e2850 (2018-05-20)
Mammalian cells generate ATP by mitochondrial (oxidative phosphorylation) and non-mitochondrial (glycolysis) metabolism. Cancer cells are known to reprogram their metabolism using different strategies to meet energetic and anabolic needs ( Koppenol et al., 2011 ; Zheng, 2012). Additionally, each cancer
Shuo Wan et al.
Frontiers in immunology, 12, 685984-685984 (2021-08-10)
Angiostrongylus cantonensis (AC), which parasitizes in the brain of the non-permissive host, such as mouse and human, is an etiologic agent of eosinophilic meningitis. Excretory-secretory (ES) products play an important role in the interaction between parasites and hosts' immune responses.
Thomas A Ryan et al.
The EMBO journal, 39(11), e102539-e102539 (2020-04-21)
Multiple mitochondrial quality control pathways exist to maintain the health of mitochondria and ensure cell homeostasis. Here, we investigate the role of the endosomal adaptor Tollip during the mitochondrial stress response and identify its interaction and colocalisation with the Parkinson's
Shirong Yang et al.
Cancer communications (London, England), 41(8), 695-714 (2021-06-24)
Mitochondria are key regulators in cell proliferation and apoptosis. Alterations in mitochondrial function are closely associated with inflammation and tumorigenesis. This study aimed to investigate whether mitochondrial transcription factor A (TFAM), a key regulator of mitochondrial DNA transcription and replication
Pengcheng Zhang et al.
iScience, 25(1), 103709-103709 (2022-01-25)
SIRT1 is a metabolic sensor regulating energy homeostasis. The present study revealed that mice with selective overexpression of human SIRT1 in adipose tissue (Adipo-SIRT1) were protected from high-fat diet (HFD)-induced metabolic abnormalities. Adipose SIRT1 was enriched at mitochondria-ER contacts (MERCs)
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