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Ultraviolet and Light Absorption Spectrometry
Published in Adorjan Aszalos, Modern Analysis of Antibiotics, 2020
Zoltan M. Dinya, Ferenc J. Sztaricskai
The class of heptaene macrolide antibiotics can be divided into two subgroups [281—286] on the basis of the properties of the products formed upon acid or alkaline hydrolysis: Heptaene macrolides containing no aromatic unit (such as amphotericin B, candidin, candidoin, and mycoheptin) and bearing only a mycosa-mine moiety.Heptaene macrolides with an aromatic moiety (including trichomycin, candicidin, perimycin, levorin, hamycin, and aureofungin). The aromatic unit of these antibiotics is usually p-aminoacetophenone or p-aminophenylacetone and their substituted analogs. These antibiotics also contain amino sugar moiety, such as mycosamine or perosamine (4-amino-4,6-dideoxy-D-mannose).
Amphotericin B Deoxycholate
Published in M. Lindsay Grayson, Sara E. Cosgrove, Suzanne M. Crowe, M. Lindsay Grayson, William Hope, James S. McCarthy, John Mills, Johan W. Mouton, David L. Paterson, Kucers’ The Use of Antibiotics, 2017
Neil R. H. Stone, Tihana Bicanic
Amphotericin B deoxycholate (AMB, Fungizone, Bristol-Myers Squibb, New York, NY) is a polyene antibiotic with primarily antifungal and antiparasitic activity. Its molecular formula is C47H73NO17 with molecular weight of 924.08 daltons. It is most often used in the treatment of pathogenic yeasts and molds, as well as the protozoan parasite Leishmania spp. In common with other polyenes, AMB is composed of a ring of carbon atoms with a series of conjugated carbon–carbon double bonds on one side and hydroxyl groups on the other side (Hamilton-Miller, 1973). It has a mycosamine ring bonded to the molecule. The structure of amphotericin B is shown in Figure 141.1.
Potential lipid-based strategies of amphotericin B designed for oral administration in clinical application
Published in Drug Delivery, 2023
Xiaoming Zhong, Jianqiong Yang, Hongyan Liu, Zhiwen Yang, Ping Luo
AmB has a molecular weight of 924 Da (Cuddihy et al., 2019; Liu et al., 2017). Molecular structure of AmB is comprised of a macrolactone ring and non-polar heptene group (Figure 1). The ring is β-glycosylated at C19 with a mycosamine group, exhibiting an almost flat chromophore with seven conjugated double bonds in the trans conformation. At C13 and C17, the macrolactone ring also contains a hemiketal ring. The presence of an amino group in the mycosamine head group and a carboxyl group at C16 determines the amphoteric nature of AmB (Cuddihy et al., 2019; Liu et al., 2017). Additionally, the specific three-dimensional structure of this molecule is determined to own hydrophobic and hydrophilic regions, further conferring its amphipathic properties (Cuddihy et al., 2019; Liu et al., 2017). Consequently, AmB is responsible for poorly soluble in highly polar and nonpolar solvents (Cuddihy et al., 2019; Liu et al., 2017; Ciesielski et al., 2016).
Recent advances in amphotericin B delivery strategies for the treatment of leishmaniases
Published in Expert Opinion on Drug Delivery, 2019
Juliane S. Lanza, Sébastien Pomel, Philippe M. Loiseau, Frédéric Frézard
In addition to amphoteric features, its cyclic and asymmetric structure, the AmB molecule exhibits hydrophilic and lipophilic chains conferring amphiphilic character, also resulting in poor solubility in water and most of organic solvents. It is a semi-rigid molecule in which two moieties – the macrolidic ring and the mycosamine sugar ring – are able to rotate around the β-glycosidic bond (Figure 1).