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enniatin B1

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enniatin B1 Basic information

Product Name:
enniatin B1
Synonyms:
  • enniatin B1
  • 2-(N-Methyl-L-isoleucine)enniatin B
  • 3-Butan-2-yl-4,10,16-trimethyl-6,9,12,15,18-penta(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone
  • Cyclo[(2R)-2-hydroxy-3-methylbutanoyl-N-methyl-L-isoleucyl-(2R)-2-hydroxy-3-methylbutanoyl-N-methyl-L-valyl-(2R)-2-hydroxy-3-methylbutanoyl-N-methyl-L-valyl]
CAS:
19914-20-6
MF:
C34H59N3O9
MW:
653.85
Product Categories:
  • Antibiotic
Mol File:
19914-20-6.mol
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enniatin B1 Chemical Properties

Melting point:
178.5 °C
Boiling point:
833.8±65.0 °C(Predicted)
Density 
1.031±0.06 g/cm3(Predicted)
storage temp. 
-20°C
solubility 
DMSO: soluble10mg/mL
form 
White to off-white crystalline solid.
pka
-1.45±0.70(Predicted)
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Safety Information

Hazard Codes 
T
Risk Statements 
23/24/25
Safety Statements 
45
RIDADR 
2811
WGK Germany 
3
HazardClass 
6.1(a)
PackingGroup 
I
HS Code 
2941900000
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enniatin B1 Usage And Synthesis

Uses

Enniatins are a family of depsipeptide ionophores, produced several Fusarium species. More recently, the effects of the enniatins on acyl-CoA cholesterol transferase, transporters and the selectivity of their antitumour action have received more focus. Enniatin B1 is one of four major analogues of the enniatin complex and has not previously been available for investigation.

Uses

Enniatins are a family of depsipeptide ionophores produced by several Fusarium species. Recently, the effects of the enniatins on acyl-CoA cholesterol transferase, transporters and the selectivity of their antitumor action have received more focus. Enniatin B1 is one of four major analogues of the enniatin complex.

Uses

Enniatins are cyclohexadepsipeptides commonly isolated from fungi and are known to have antibiotic properties. Many act as ionophores, forming pores in cellular membranes to allow selective ion transport. Enniatin B1 is one of four major analogs of the enniatin complex . It has been shown to induce apoptosis in several cancer lines (EC50s ≤ 10 μM) and to decrease the activation of the cell proliferation kinase, ERK (p44/p42). Enniatin B1 also inhibits the multi-drug resistance transporter Pdr5p from S. cerevisiae and has been used to examine drug resistance mechanisms.

Biochem/physiol Actions

Enniatins are a group of cyclohexadepsipeptide mycotoxins produced by Gnomonia errabuda and several Fusaria species, with phytotoxic, antibiotic, and insecticidal activities. Enniatins function as ionophors by their incorporation into the cellular membrane to form dimeric structures that transport monovalent ions across the membrane (especially the mitochondrial membranes) affecting oxidative phosphorylation uncoupling. It has been demonstrated that enniatins have a cytotoxic effect on human cancer cells. Furthermore, incubation of H4IIE hepatoma cells with enniatins strongly diminished phosphorylation of the ERK (p44/p42). Enniatins B and B1 inhibit the multi-drug resistance transporter Pdr5p from Saccharomyces cerevisiae, indicating their beneficial potential in cases of drug resistant patients.

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