ANTIMYCIN A Chemical Properties

Melting point:

141-142℃

Boiling point:

598.78°C (rough estimate)

Density 

1.6009 (rough estimate)

refractive index 

1.5800 (estimate)

storage temp. 

2-8°C

solubility 

Ethanol: soluble

form 

White to faint yellow powder.

Water Solubility 

Soluble in 100% ethanol. Insoluble in water.

Sensitive 

Light Sensitive

Stability:

Light Sensitive

InChIKey

UIFFUZWRFRDZJC-RBVQMQRASA-N

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

EPA Substance Registry System

Antimycin A (1397-94-0)

Safety Information

Hazard Codes 

T,N

Risk Statements 

25-50

Safety Statements 

26-36/37/39-45-61

RIDADR 

UN 3462 6.1/PG 2

WGK Germany 

3

RTECS 

CD0350000

F 

18

HazardClass 

6.1(a)

PackingGroup 

II

HS Code 

2941900000

Storage Class

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

Hazard Classifications

Acute Tox. 2 Oral
Aquatic Acute 1

Hazardous Substances Data

1397-94-0(Hazardous Substances Data)

Toxicity

LDLo orl-rat: 30 mg/kg 85ERAY 2,1078,78

MSDS

• Language:English Provider:SigmaAldrich

ANTIMYCIN A Usage And Synthesis

Description

Antimycin (A3 C26H36N2O9) and (AntimycinA1) C28H40N2O9 are crystalline solids. Molecularweight= 512.8 (A); 520.64 (A3-); 506.6 (A4-); Freezing/Melting point= 170°175℃; 149°150℃ (A1); 174°175℃(A3). They are complex 9-membered (2 oxygens and 7 carbons) ring derivatives with complex side chains. HazardIdentification (based on NFPA-704 M Rating System):Health 3, Flammability 0, Reactivity 0. Practically insolublein water.

Chemical Properties

Antimycin (A3C26H36N2O9) and (Antimycin A1) C28H40N2O9 are crystalline solids.

Uses

antifungal, antiviral, interferes in cytochrome oxidation

Uses

Antimycin A is a complex of related macrocyclic lactones, predominantly A1 to A4, isolated from several species of Streptomyces, first reported in the early 1950s for potent antifungal activity. There are over 20 known analogues in the antimycin A class, mostly involving variation of the fatty acid ester chain length or adjacent alkyl starting unit. Antimycin A binds to cytochrome C reductase at the Qi site, inhibiting the oxidation of ubiquinol to ubiquinone. Antimycin A is widely used as a bioprobe of respiration and other applications with over 5,000 literature citations.

Uses

Antimycin A is 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.

Definition

ChEBI: Antimycin A is a nine-membered bis-lactone having methyl substituents at the 2- and 6-positions, an n-hexyl substituent at the 8-position, an acyloxy substituent at the 7-position and an aroylamido substituent at the 3-position. It is produced by Streptomyces bacteria and has found commercial use as a fish poison. It has a role as a piscicide, a mitochondrial respiratory-chain inhibitor and an antifungal agent. It is a macrodiolide, a member of formamides, a member of benzamides and a member of phenols.

General Description

Solid. Specific uses for ANTIMYCIN A were not found. ANTIMYCIN A1,and ANTIMYCIN A3 are reported as antibiotics produced by Streptomyces for use as a fungicide and possibly as an insecticide and miticide. Registered only as a pesticide in the U.S.

Fire Hazard

When heated to decomposition, ANTIMYCIN A emits toxic fumes of oxides of nitrogen.

Agricultural Uses

Fungicide, Piscicide: A U.S. EPA restricted Use Pesticide (RUP). May also be used as an insecticide.

Trade name

FINTROL®; VIROSIN®

Safety Profile

Poison by ingestion,intraperitoneal, subcutaneous, and intravenous routes.When heated to decomposition it emits toxic fumes ofNOx.

Potential Exposure

Specific uses for antimycin A were not found, however, antimycin A1, and antimycin A3 are reported to be antibiotic substances produced by streptomyces for use as a fungicide, possible insecticide and miticide. Registered as a pesticide in the U.S.

First aid

f this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seekmedical attention immediately. If this chemical contactsthe skin, remove contaminated clothing and wash immedi ately with soap and water. Seek medical attention258 Antimycin Aimmediately. If this chemical has been inhaled, removefrom exposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing hasstopped and CPR if heart action has stopped. Transferpromptly to a medical facility. When this chemical hasbeen swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit.

storage

Color Code—Blue: Health Hazard/Poison: Store ina secure poison location. Prior to working with this chemicalyou should be trained on its proper handling and storage.

Shipping

UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.

Background

Antimycin A is an inhibitor of electron transport from cytochrome b to cytochrome complex III. Binding of Antimycin A to cytochrome c reductase inhibits the oxidation of ubiquinol, disrupts the Q-cycle of enzyme turnover, and halts cellular respiration. Consequently, this small, non-peptide ligand inhibitor has been used for decades to characterize the mitochondrial respiratory chain. Antimycin A has long been used as a piscicide in commercial fish farms, and possesses strong antifungal, insecticidal, and nematocidal activities. Treatment of HeLa cells with Antimycin A results in the loss of mitochondrial membrane potential and inhibition of cell growth through apoptosis. Antimycin A strongly generates reactive oxygen species and induces glutathione depletion in these cells. Antimycin A binds and inhibits Bcl2/Bcl-xL-related anti-apoptotic proteins, which are commonly over-produced by cancer cells.

References

[1] Cramer, W.A. et al. (2011) Biochim Biophys Acta 1807, 788-802.
[2] Labs, M. et al. (2016) Photosynth Res 129, 231-8.
[3] Lennon, R.E. (1973) Adv Appl Microbiol 16, 55-96.
[4] Park, W.H. et al. (2007) J Cell Biochem 102, 98-109.
[5] Tzung, S.P. et al. (2001) Nat Cell Biol 3, 183-91.
[6] Kim, K.M. et al. (2001) Biochemistry 40, 4911-22.

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