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A8674

Sigma-Aldrich

Antimycin A from Streptomyces sp.

CAS Number:
MDL number:
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 produced by Streptomyces species. [96] It inhibits mitochondrial electron transport chain complex III and favors reactive oxygen species (ROS) production, impairing mitochondrial depolarization.[97] It inhibits nitric oxide-mediated apoptosis and modulatescytochrome C release.[98] It suppresses tumorigenesis in lung cancer cells and could be a potential therapeutic agent.[99]
Chemical structure: peptide

Application

Antimycin A from Streptomyces sp. has been used:
  • as a respiratory chain inhibitor in neuronal cultures
[79][10]
  • in organello ATP production assay in Trypanosoma brucei cells
  • [01]
  • in respiration assay for papillary thyroid carcinoma (PTC) cell lines
  • [02]
    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

    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

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    Certificate of Origin

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