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Key Documents

A8674

Sigma-Aldrich

Antimycin A from Streptomyces sp.

Sinônimo(s):

Antipiricullin

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About This Item

Número CAS:
Número MDL:
Código UNSPSC:
12352200
ID de substância PubChem:
NACRES:
NA.77

forma

powder

Nível de qualidade

espectro de atividade do antibiótico

fungi

Modo de ação

enzyme | inhibits

temperatura de armazenamento

−20°C

cadeia de caracteres SMILES

[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

chave InChI

UIFFUZWRFRDZJC-RBVQMQRASA-N

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Descrição geral

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

Aplicação

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

Ações bioquímicas/fisiológicas

Inhibitor of electron transfer at complex III. Induces apoptosis.

Qualidade

A mixture of antimycins.

Pictogramas

Skull and crossbonesEnvironment

Palavra indicadora

Danger

Frases de perigo

Classificações de perigo

Acute Tox. 2 Oral - Aquatic Acute 1

Código de classe de armazenamento

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

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

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


Certificados de análise (COA)

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Decylubiquinone ≥97% (HPLC)

Sigma-Aldrich

D7911

Decylubiquinone

BAM15 ≥98% (HPLC)

Sigma-Aldrich

SML1760

BAM15

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)

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