A natural inhibitor of Pdr5p in yeast
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Enniatin B

Item No. 15382

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
cyclo[(2R)-2-hydroxy-3-methylbutanoyl-N-methyl-L-valyl-(2R)-2-hydroxy-3-methylbutanoyl-N-methyl-L-valyl-(2R)-2-hydroxy-3-methylbutanoyl-N-methyl-L-valyl
CAS Number
917-13-5
Synonyms
  • Antibiotic 86/88
Molecular Formula
C33H57N3O9
Formula Weight
639.8
Purity
≥95%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMF: SolubleDMSO: SolubleEthanol: SolubleMethanol: Soluble
SMILES
O=C(O[C@H](C(C)C)C(N([C@H](C(O[C@@H](C(N([C@H](C(O[C@@H]1C(C)C)=O)C(C)C)C)=O)C(C)C)=O)C(C)C)C)=O)[C@H](C(C)C)N(C)C1=O
InChi Code
InChI=1S/C33H57N3O9/c1-16(2)22-31(40)43-26(20(9)10)29(38)35(14)24(18(5)6)33(42)45-27(21(11)12)30(39)36(15)23(17(3)4)32(41)44-25(19(7)8)28(37)34(22)13/h16-27H,1-15H3/t22-,23-,24-,25+,26+,27+/m0/s1
InChi Key
MIZMDSVSLSIMSC-VYLWARHZSA-N
Origin
Fungi/Fusarium sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    Enniatin B is a relatively poor ionophore with some capacity to facilitate import of K+ and Na+ across membranes.1 It inhibits the pleiotropic drug resistance protein 5 (Pdr5p) in yeast.2 Through this mechanism enniatin B, at concentrations as low as 0.8 μM, augments the ability of cerulenin (Item No. 10005647) or cycloheximide (Item No. 14126) to impair cell proliferation in cells overexpressing Pdr5p, an effect that is not observed in cells lacking Pdr5p.2 Like other enniatins, enniatin B inhibits acyl-CoA: cholesterol acyltransferase (IC50 = 113 μM), blocking cholesteryl ester formation.3 Enniatin B (1 μM) also increases caspase activity and induces apoptosis in H4IIE hepatoma cells and, when mixed with other enniatins, alters p53 signaling in human cancer cells.4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kamyar, M.R., Rawnduzi, P., Studenik, C.R., et al. Investigation of the electrophysiological properties of enniatins. Arch. Biochem. Biophys. 429(2), 215-223 (2004).

    2. Hiraga, K., Yamamoto, S., Fukuda, H., et al. Enniatin has a new function as an inhibitor of Pdr5p, one of the ABC transporters in Saccharomyces cerevisiae. Biochem. Bioph. Res. Commun. 328(4), 1119-1125 (2005).

    3. Tomoda, H., Huang, X.H., Cao, J., et al. Inhibition of acyl-CoA: Cholesterol acyltransferase activity by cyclodepsipeptide antibiotics. J. Antibiot. (Tokyo) 45(10), 1626-1632 (1992).

    4. Wätjen, W., Debbab, A., Hohlfeld, A., et al. Enniatins A1, B and B1 from an endophytic strain of Fusarium tricinctum induce apoptotic cell death in H4IIE hepatoma cells accompanied by inhibition of ERK phosphorylation. Mol. Nutr. Food Res. 53(4), 431-440 (2009).

    5. Dornetshuber, R., Heffeter, P., Kamyar, M.R., et al. Enniatin exerts p53-dependent cytostatic and p53-independent cytotoxic activities against human cancer cells. Chem. Res. Toxicol. 20(3), 465-473 (2007).