Enniatin B

Enniatins are cyclichexadepsipeptides commonly isolated from fungi. Many act as ionophores, forming pores in cellular membranes to allow selective ion transport. Enniatin B is a relatively poor ionophore with some capacity to facilitate import of K+ and Na+ across membranes. It inhibits the pleiotropic drug resistance protein 5 (Pdr5p) in yeast. Through this mechanism enniatin B, at concentrations as low as 0.8 µM, augments the ability of cerulenin (Cay-10005647) or cycloheximide (Cay-14126) to impair cell proliferation in cells overexpressing Pdr5p, an effect that is not observed in cells lacking Pdr5p. Like other enniatins, enniatin B inhibits acyl-CoA: cholesterol acyltransferase (IC50 = 113 µM), blocking cholesteryl ester formation. 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.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: (Request formulation change), A powder. Solubility: DMF: Soluble, DMSO: Soluble, Ethanol: Soluble, Methanol: 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..