A polyether ionophore antibiotic
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Dianemycin

Item No. 21679

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2S,4R,6E,8S)-8-[(2S,2′R,4′S,5R,5′S,7R,7′R,8R,9S,9′S,10′R)-9-hydroxy-2,4′,8,10′-tetramethyl-2′-[(2S,3S,5R,6R)-tetrahydro-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyl-2H-pyran-2-yl]-9′-[[(2S,5S,6R)-tetrahydro-5-methoxy-6-methyl-2H-pyran-2-yl]oxy][2,7′-bi-1,6-dioxaspiro[4.5]dec]-7-yl]-2,4,6-trimethyl-5-oxo-6-nonenoic acid
CAS Number
35865-33-9
Synonyms
  • Nanchangmycin (free acid)
Molecular Formula
C47H78O14
Formula Weight
867.1
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mLDMSO: 25 mg/mLEthanol: 25 mg/mL
λmax
232 nm
SMILES
C/C(C([C@H](C)C[C@H](C)C(O)=O)=O)=C\[C@H](C)[C@@]1([H])O[C@@]2(CC[C@]([C@]3([H])O[C@@]4([C@@H](C)C[C@@]([C@]5([H])[C@@H](C)C[C@@H](C)[C@@](CO)(O)O5)([H])O4)[C@H](C)[C@@H](O[C@@]6([H])O[C@@H](C)[C@H](OC)CC6)C3)(C)O2)C[C@H](O)[C@H]1C
InChi Code
InChI=1S/C47H78O14/c1-24(40(50)25(2)18-28(5)43(51)52)17-26(3)41-31(8)34(49)22-45(59-41)16-15-44(11,61-45)38-21-36(56-39-14-13-35(54-12)33(10)55-39)32(9)47(58-38)30(7)20-37(57-47)42-27(4)19-29(6)46(53,23-48)60-42/h17,25-39,41-42,48-49,53H,13-16,18-23H2,1-12H3,(H,51,52)/b24-17+/t25-,26+,27+,28+,29-,30+,31-,32-,33+,34+,35-,36+,37-,38-,39-,41-,42+,44+,45-,46+,47+/m1/s1
InChi Key
FELYAZAWTURXNF-NNRRCCSUSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Dianemycin is a polyether ionophore antibiotic produced by S. nanchangensis NS3226 that has insecticidal and in vitro antibacterial properties.1,2 Dianemycin exhibits antiviral properties against Zika virus (ZIKV) by blocking viral entry in vitro in a spectrum of cell types, including U2OS, human microvascular endothelial cells, and placental Jeg3 cells (IC50s = 100, 400, and 970 nM, respectively).3 Dianemycin also blocks ZIKV entry into primary cells, including extravillous trophoblasts, human primary uterine microvascular endothelial cells, human umbilical vein endothelial cells, and murine primary midbrain neuron-glia cultures.3 Efficacy of dianemycin extends to other viruses where it blocks entry into U2OS cells by West Nile, dengue, Sindbis, and chikungunya viruses.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Sun, Y., Zhou, X., Dong, H., et al. A complete gene cluster from Streptomyces nanchangensis NS3226 encoding biosynthesis of the polyether ionophore nanchangmycin. Chem. Biol. 10(5), 431-441 (2003).

    2. Liu, T., Lin, X., Zhou, X., et al. Mechanism of thioesterase-catalyzed chain release in the biosynthesis of the polyether antibiotic nanchangmycin. Chem. Biol. 15(5), 449-458 (2008).

    3. Rausch, K., Hackett, B., Weinbren, N.R., S., et al. Screening bioactives reveals nanchangmycin as a broad spectrum antiviral active against Zika virus. Cell Rep. 18(3), 804-815 (2017).