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A8674

Sigma-Aldrich

Antimycin A from Streptomyces sp.

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

Quality Level

Mode of action

enzyme | inhibits

antibiotic activity spectrum

fungi

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 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.
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

Packaging

25, 50, 100 mg in glass bottle

Biochem/physiol Actions

Inhibitor of electron transfer at complex III. Induces apoptosis.

Quality

A mixture of antimycins.

Pictograms

Skull and crossbonesEnvironment

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 2 Oral - Aquatic Acute 1

Storage Class Code

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

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. What is the molecular weight of Antimycin A, Product A8674?

    The product is a mixture of antimycins, each with a unique molecular weight. The approximate molecular weights (g/mole) for the components are A1: 548.6; A2: 534.6; A3: 520.6; A4:506.6.  The percentages of each component are lot specific and are determined by HPLC.  This information can be found on the Certificate of Analysis.  We averaged the molecular weights for four lots and obtained an approximate molecular weight of 532 g/mole.

  4. What is Antimycin A, Product A8674, soluble in?

    Antimycin A is soluble in DMSO at 2 mg/mL and in 95% ethanol at 50 mg/mL. It is also freely soluble in ether, acetone, and chloroform. It is insoluble in water.

  5. Can solutions of Antimycin A, Product A8674, be stored?

    It has been reported that in a 95% alcoholic solution, Antimycin A is stable for four months at 4 °C.

  6. What is the working concentration for Antimycin A, Product A8674?

    A concentration of 2 micrograms/ml (1000 fold dilution from a DMSO stock solutions) was reportedly used on endothelial cells per Wilkinson, J.A., and Jacob, R., Agonist-induced calcium and oxidative stress responses in endothelial cells. Biochem. Soc. Trans., 31, 960-962 (2003).

  7. What is the shipping and storage temperature for Product A8674, Antimycin A from Streptomyces?

    Antimycin A is stable at ambient temperature for up to 2 weeks and is shipped at ambient temperatures to reduce shipping costs to the customer. Once received, it should be stored in the freezer at -20°C.

  8. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  9. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  10. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

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)
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)
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 phylogenetic and evolutionary analysis of antimycin biosynthesis
Joynt R and Seipke RF
Microbiology, 164(1), 28-39 (2017)

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