Lagosin

- Overview
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    Background
    
    Lagosin, a polyene macrolide antibiotic, has first been extracted from an isolate of a Streptomyces species present in a sample of soil collected in Lagos, Nigeria [1]. It has been reported that the three polyene macrolide antibiotics, fungichromin, lagosin, and cogomycin, showed some stereochemical differences at one or more centers [1].
    Lagosin was the most polar member of the filipin family of fungicides with broad spectrum antifungal and antitumor activity, acting via interaction with cell membrane sterols. The antibiotic lagosin, which appeared to be identical to, or a stereoisomer of, fungichromin, and was very similar in structure to the filipins [2]. The equilibrium constants for association of the polyene antibiotics with aqueous suspensions of cholesterol follow the order filipin IIl > amphotericin B > nystatin > lagosin, in agreement with the order reported for the extent of damage these antibiotics cause in natural and model membranes [2].
    
    [1] Pandey R C, Guenther E C, AszALos A A, et al. Physicochemical and biological comparison of polyene macrolide antibiotics fungichromin, lagosin and cogomycin[J]. The Journal of antibiotics, 1982, 35(8): 988-996.
    [2] Bittman R, Fischkoff S A. Fluorescence studies of the binding of the polyene antibiotics filipin III, amphotericin B, nystatin, and lagosin to cholesterol[J]. Proceedings of the National Academy of Sciences, 1972, 69(12): 3795-3799.
- Properties
  - Categories
    
    polyene macrolide antibiotic
    
    Alternative Name
    
    Antibiotic A 246,14-hydroxy Filipin,NSC 105388,NSC 276732; (3R,4S,6S,8S,10R,12R,14R,15R,16R,17E,19E,21E,23E,25E,27S,28R)-4,6,8,10,12,14,15,16,27-nonahydroxy-3-[(1R)-1-hydroxyhexyl]-17,28-dimethyl-oxacyclooctacosa-17,19,21,23,25-pentaen-2-one
    
    CAS Number
    
    6834-98-6
    
    Molecular Formula
    
    C35H58O12
    
    Molecular Weight
    
    670.8
    
    Appearance
    
    A solid
    
    Purity
    
    Purity ≥95.00%
    
    Solubility
    
    Soluble in DMSO
    
    Storage
    
    Store at -20°C
    
    SMILES
    
    C/C1=C\C=C\C=C\C=C\C=C\[[email protected]](O)[[email protected]@H](C)OC([[email protected]@]([[email protected]](O)CCCCC)([H])[[email protected]@H](O)C[[email protected]@H](O)C[[email protected]@H](O)C[[email protected]@H](O)C[[email protected]@H](O)C[[email protected]@H](O)[[email protected]@H](O)[[email protected]@H]1O)=O
    
    * For Research Use Only