Skip to Content
MilliporeSigma
All Photos(4)

Key Documents

A8674

Sigma-Aldrich

Antimycin A from Streptomyces sp.

Synonym(s):

Antipiricullin

Sign Into View Organizational & Contract Pricing


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

Looking for similar products? Visit Product Comparison Guide

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

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

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)
A preclinical evaluation of antimycin a as a potential antilung cancer stem cell agent
Yeh CT, et al.
Evidence-Based Complementary and Alternative Medicine : ECAM, 2013(3), 143-151 (2013)
Mitochondrial modulation-induced activation of vagal sensory neuronal subsets by antimycin A, but not CCCP or rotenone, correlates with mitochondrial superoxide production
Stanford KR and Taylor-Clark TE
PLoS ONE, 13(5), e0197106-e0197106 (2018)
ATP production in isolated mitochondria of procyclic Trypanosoma brucei
Mitochondria, 379-387 (2007)

Related Content

DISCOVER Bioactive Small Molecules for Nitric Oxide & Cell Stress Research

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service