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Merck

A8674

Antimycin A

from Streptomyces sp., mitochondrial electron transport chain complex III inhibitor, powder

Sinónimos:

Antipiricullin

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25 MG

MXP 2,232.00

50 MG

MXP 4,078.00

100 MG

MXP 7,081.00

MXP 2,232.00


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

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Nombre del producto

Antimycin A from Streptomyces sp.,

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 key

UIFFUZWRFRDZJC-RBVQMQRASA-N

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

form

powder

antibiotic activity spectrum

fungi

mode of action

enzyme | inhibits

storage temp.

−20°C

Quality Level

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Este artículo
A3835H6649A4888
form

powder

form

powder

form

powder

form

powder

Quality Level

300

Quality Level

200

Quality Level

200

Quality Level

300

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

2-8°C

antibiotic activity spectrum

fungi

antibiotic activity spectrum

fungi

antibiotic activity spectrum

viruses

antibiotic activity spectrum

fungi, yeast

mode of action

enzyme | inhibits

mode of action

enzyme | inhibits

mode of action

enzyme | inhibits

mode of action

cell membrane | interferes

Analysis Note

A mixture of antimycins.

Application

Antimycin A from Streptomyces sp. has been used:
  • as a respiratory chain inhibitor in neuronal cultures[1][2]
  • in organello ATP production assay in Trypanosoma brucei cells[3]
  • in respiration assay for papillary thyroid carcinoma (PTC) cell lines[4]
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.

General description

Antimycin is an antibiotic[5] produced by Streptomyces species. [6] It inhibits mitochondrial electron transport chain complex III and favors reactive oxygen species (ROS) production, impairing mitochondrial depolarization.[7] It inhibits nitric oxide-mediated apoptosis and modulatescytochrome C release.[8] It suppresses tumorigenesis in lung cancer cells and could be a potential therapeutic agent.[9]Antimycin A serves as a positive control for superoxide generation.
Chemical structure: peptide

pictograms

Skull and crossbonesEnvironment

signalword

Danger

hcodes

Hazard Classifications

Acute Tox. 2 Oral - Aquatic Acute 1

Clase de almacenamiento

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

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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


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Certificados de análisis (COA)

Lot/Batch Number

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Encuentre la documentación para los productos que ha comprado recientemente en la Biblioteca de documentos.

Visite la Librería de documentos

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)
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
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)

Artículos

DISCOVER Bioactive Small Molecules for Nitric Oxide & Cell Stress Research

Questions

1–10 of 10 Questions  
  1. What is MW of Antimycin A from Streptomyces sp. (A8674)?

    1 answer
    1. The product is a mixture of antimycin forms, each with a unique molecular weight. The approximate molecular weights of each form are as follows:
      Antimycin A1 - 548.6 g/mol
      Antimycin A2 - 534.6 g/mol
      Antimycin A3 - 520.6 g/mol
      Antimycin A4 - 506.6 g/mol
      The percentage of each form is lot specific and are determined by HPLC. This information is reported in the Certificate of Analysis. A review of recent lots indicates an approximate average molecular weight of 532 g/mole.

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  2. How long we can keep antimycin a solution in dmso and at what temperature its storage is preferable.

    1 answer
    1. This product is tested for solubility in ethanol at 50 mg/mL. Stock solutions prepared in ethanol are stable when stored in aliquots at –20 °C. The solution stability in DMSO has not been determined but is expected to be comparable to ethanol. While a time frame has not been established, stock solutions are quite stable. A general range of 1-3 months is suggested.

      Helpful?

  3. Hello,I bought your company's product but I don't have a instruction book.So I wonder the solubility of this reagent in different solvents.

    1 answer
    1. This product is tested for solubility in ethanol at 49 - 51 mg/mL. The rate varies slightly from lot to lot and is reported on the batch-specific Certificate of Analysis. Other published solvents include ether, acetone, chloroform, and other alcohols. Rates of each are not published. A Certificate may be downloaded in the DOCUMENTATION section, under 'Certificate of Analysis':
      https://www.sigmaaldrich.com/product/sigma/a8674#product-documentation

      Helpful?

  4. I have already known that Antimycin A is stable in a 95% alcoholic solution for four months at 4 °C.But how can I keep it as long as possible?

    1 answer
    1. Unfortunately, the stability of this product in solution is not determined.

      Helpful?

  5. Is this product light sensitive?

    1 answer
    1. According to the SDS and a publication in the Journal of the American Chemical Society (JACS, 71, 2436, 1949), this compound, in alcoholic solutions, appears
      to be stable nearly indefinitely under ordinary laboratory conditions. No particular sensitivity to light or to atmospheric oxygen has been noted. Please see the link below to review the information listed in the SDS, section 7.2:
      https://www.sigmaaldrich.com/US/en/sds/sigma/a8674

      Helpful?

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

    1 answer
    1. 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.

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

    1 answer
    1. 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.

      Helpful?

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

    1 answer
    1. 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.

      Helpful?

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

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

      Helpful?

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

    1 answer
    1. 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).

      Helpful?

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