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A8674

Sigma-Aldrich

Antimycin A from Streptomyces sp.

Synonym(s):

Antipiricullin

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About This Item

CAS Number:
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

form

powder

Quality Level

antibiotic activity spectrum

fungi

mode of action

enzyme | inhibits

storage temp.

−20°C

SMILES string

[H]C(=O)Nc1cccc(C(=O)N[C@H]2[C@@H](C)OC(=O)C(CCCCCC)[C@@H](OC(=O)CC(C)C)[C@H](C)OC2=O)c1O

InChI

1S/C28H40N2O9/c1-6-7-8-9-11-20-25(39-22(32)14-16(2)3)18(5)38-28(36)23(17(4)37-27(20)35)30-26(34)19-12-10-13-21(24(19)33)29-15-31/h10,12-13,15-18,20,23,25,33H,6-9,11,14H2,1-5H3,(H,29,31)(H,30,34)/t17-,18+,20?,23+,25+/m1/s1

InChI key

UIFFUZWRFRDZJC-RBVQMQRASA-N

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General description

Antimycin is an antibiotic produced by Streptomyces species. It inhibits mitochondrial electron transport chain complex III and favors reactive oxygen species (ROS) production, impairing mitochondrial depolarization. It inhibits nitric oxide-mediated apoptosis and modulatescytochrome C release. It suppresses tumorigenesis in lung cancer cells and could be a potential therapeutic agent.Antimycin A serves as a positive control for superoxide generation.
Chemical structure: peptide

Application

Antimycin A from Streptomyces sp. has been used:
  • as a respiratory chain inhibitor in neuronal cultures
  • in organello ATP production assay in Trypanosoma brucei cells
  • in respiration assay for papillary thyroid carcinoma (PTC) cell lines
Antimycin A has been used to study the specific sites of reactive oxygen species production in mitochondria isolated from skeletal muscle of chronic obstructive pulmonary disease patients, and its relationship with local oxidative stress induced by exercise

Biochem/physiol Actions

Inhibitor of electron transfer at complex III. Induces apoptosis.

Quality

A mixture of antimycins.

pictograms

Skull and crossbonesEnvironment

signalword

Danger

hcodes

Hazard Classifications

Acute Tox. 2 Oral - Aquatic Acute 1

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges


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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Autophagic clearance of mitochondria in the kidney copes with metabolic acidosis
Namba T, et al.
Journal of the American Society of Nephrology, 25(10), 2254-2266 (2014)
A phylogenetic and evolutionary analysis of antimycin biosynthesis
Joynt R and Seipke RF
Microbiology, 164(1), 28-39 (2017)
Oligomycin and antimycin A prevent nitric oxide-induced apoptosis by blocking cytochrome C leakage
Dairaku N, et al.
The Journal of Laboratory and Clinical Medicine, 143(3), 143-151 (2004)
Veronica Lindström et al.
Molecular and cellular neurosciences, 82, 143-156 (2017-04-30)
The presence of Lewy bodies, mainly consisting of aggregated α-synuclein, is a pathological hallmark of Parkinson's disease (PD) and dementia with Lewy bodies (DLB). The α-synuclein inclusions are predominantly found in neurons, but also appear frequently in astrocytes. However, the
ATP production in isolated mitochondria of procyclic Trypanosoma brucei
Mitochondria, 379-387 (2007)

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