Interaction of Amphotericin B with a synthetic glycolipid in Langmuir monolayers

PINZÓN BARRANTES, JOHN JAIRO; ANGELONI, GENARO; VICO, RAQUEL V.

Ciudad Autónoma de Buenos Aires

Encuentro; Reunión Conjunta de Sociedades de Biociencias; 2017

Sociedades de Biociencias

Amphotericin B (AmB) is an amphipathic polyene antibiotic used to treat systemic fungal infections. The therapeutic action as well as the toxic side effects of AmB depends directly on the molecular organization of the drug. AmB posses very low solubility in aqueous media and new alternatives for its administration are needed. An interesting strategy is the use of surfactants to transport hydrophobic drugs. In previous work we have synthesized a glycolipid formed by b-cyclodextrin and an alkyl chain (bCDanf). The surface behavior at the air-water interface of bCDanf, alone and in the presence of other amphiphiles, is well known. As this glycolipid could offer an alternative to transport AmB our aim was to get inside about the interactions established among them. For this purpose, Langmuir monolayers of films formed by AmB and AmB/bCDanf were studied at the air-water interface and their topography accessed by Brewster angle microscopy (BAM). Also spectroscopic techniques such as NMR, circular dichroism and FT-IR were performed to elucidate the interactions. Our study indicates that strong interactions take place among AmB/bCDanf mainly through the sugar moieties. Also, the organization acquired by AmB at the interface varies considerable due the presence of bCDanf. The presence of bCDanf favors the monomeric form of the drug which highly desirably for clinical use.