Filipin interaction with

The macrolide antibiotic filipin interacts with 3-p-hydroxysterols such as cholesterol in the plasma membrane to form filipin-sterol complexes (59). Subsequently, the filamentous caveolin-l-coat rapidly disassembles, which... 

Filipin (315) is a polyene antibiotic that is capable of interaction with sterols in liposomes and biological membranes, leading to alteration of... 

These polyenes injure fungi by binding to the ergosterol and sitosterol of the plasma membranes (Hamilton-Miller, 1973). Mycoplasma laidlawii was unaffected by filipin when grown in the absence of the sterol, but lysed when grown in its presence (Weber and Kinsky, 1965). When polyene antibiotics were injected under mixed lipids, present as a monolayer in a surface-trough, it was found that the polyene interpenetrated the film and increased its area. Reorientation of the sterol component, caused by interaction with the polyene, seemed to make the film leaky (Demel, Van Deenen and Kinsky, 1965). Mitochondrial and nuclear membranes are not affected by the polyenes, nor is the cell wall (Kinsky, 1962). 

The stoichiometry of the polyene antibiotic—cholesterol interaction has been measured in various systems with different techniques. The filipin—cholesterol interaction has been the subject of extensive study and the results suggest this interaction is equimolar. The data on other polyenes is not so definite, but suggests that only a small number of sterol molecules interact with one polyene antibiotic molecule. 

Sterol-supplemented liposomes were able to bind and alter the UV absorption spectra of filipin, etruscomycin and amphotericin B but not those of nystatin or pimaricin [146]. The presence of a 30-hydroxyl group in the sterol incorporated into the liposome appeared to be a prerequisite for interaction with polyene antibiotics. Sterol-containing liposomes have been shown to enhance the fluorescence intensity of filipin and etruscomycin [157,186]. 

Other studies [215] have suggested that the lecithin in the dispersion interacts with filipin thereby providing a matrix for interaction of the antibiotic with the sterol. There was no evidence (from infra-red spectroscopy) for hydrogen... 

Norman A.W, Demel R.A., DeKmyff B., Geiuts Van Kessel W.S.M. Van Deenen L.L.M. (1972) Studies on the biological properties of polyene antibiotics comparison of the other polyenes widi filipin in their ability to interact specifically with sterol. Biochim BiophysActa, 290, 1-14. 

A combination of 2H-NMR, CD, fluorescence, and electron absorption techniques has been used to investigate the interaction of the pentene antibiotic filipin with dimyristoylphosphatidylcholine [168]. 

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