A macrodiolide antibiotic
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Elaiophylin

Item No. 15583

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
CAS Number
37318-06-2
Synonyms
  • Azalomycin-B
  • Gopalamicin
  • Salbomycin
Molecular Formula
C54H88O18
Formula Weight
1025.3
Purity
≥95%
Formulation (Request formulation change)
A neat solid
Solubility(Learn about Variance in Solubility)
DMSO: 20 mg/mlEthanol: 1 mg/ml (sonication)
λmax
253 nm
SMILES
CC[C@H]1[C@@H](C[C@@]([C@@H](C)[C@H](O)[C@@H]([C@](OC(/C=C/C=C/[C@H](C)[C@]([C@@H](C)[C@@H](O)[C@@H]([C@@](C[C@H]2O[C@@](O[C@@H](C)[C@H]3O)([H])C[C@@H]3O)(O[C@H](C)[C@H]2CC)O)C)([H])O4)=O)([H])[C@H](/C=C/C=C/C4=O)C)C)(O)O[C@@H]1C)O[C@@](O[C@@H](C)[C@H]5O)([H])C[C@@H]5O
InChi Code
InChI=1S/C54H88O18/c1-13-37-33(9)71-53(63,25-41(37)67-45-23-39(55)49(61)35(11)65-45)31(7)47(59)29(5)51-27(3)19-15-17-22-44(58)70-52(28(4)20-16-18-21-43(57)69-51)30(6)48(60)32(8)54(64)26-42(38(14-2)34(10)72-54)68-46-24-40(56)50(62)36(12)66-46/h15-22,27-42,45-52,55-56,59-64H,13-14,23-26H2,1-12H3/b19-15+,20-16+,21-18+,22-17+/t27-,28-,29-,30-,31-,32-,33+,34+,35-,36-,37+,38+,39-,40-,41+,42+,45-,46-,47+,48+,49+,50+,51-,52-,53+,54+/m0/s1
InChi Key
OSERMIPXNLXAPD-MJMYBOKFSA-N
Origin
Bacterium/Streptomyces hygroscopicus
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

    Elaiophylin is a macrodiolide antibiotic that can be isolated from various strains of Streptomyces.1,2 It displays in vitro anti-protozoal activity against both Plasmodium and Trypanosoma (IC50s = 370 and 460 ng/ml, respectively) and cytotoxicity against human fetal lung fibroblast MRC-5 cells (IC50 = 870 ng/ml).3 Elaiophylin alone has no activity against Candida, although it enhances the anti-fungal activity of rapamycin (Item No. 13346).2 Elaiophylin also forms stable, long-lasting ion channels in bilayer membranes that are selective for cations.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Fiedler, H.P., Wörner, W., Zähner, H., et al. Metabolic products of microorganisms. 200 Isolation and characterization of niphithricins A, B, and elaiophylin, antibiotics produced by Streptomyces violaceoniger. J. Antibiot. (Tokyo) 34(9), 1107-1118 (1981).

    2. Fang, A., Wong, G.K., and Demain, A.L. Enhancement of the antifungal activity of rapamycin by the coproduced elaiophylin and nigericin. J. Antibiot. (Tokyo) 53(2), 158-162 (2000).

    3. Otoguro, K., Iwatsuki, M., Ishiyama, A., et al. In vitro and in vivo antiprotozoal activities of bispolides and their derivatives. J. Antibiot. (Tokyo) 63(5), 275-277 (2010).

    4. Grigoriev, P.A., Schlegel, R., and Gräfe, U. Cation selective ion channels formed by macrodiolide antibiotic elaiophylin in lipid bilayer membranes. Bioelectrochemistry 54(1), 11-15 (2001).