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Review
. 2022 Jun 30;12(7):681.
doi: 10.3390/membranes12070681.

Polyene Antibiotics Physical Chemistry and Their Effect on Lipid Membranes; Impacting Biological Processes and Medical Applications

Tammy Haro-Reyes  1 , Lucero Díaz-Peralta  1 , Arturo Galván-Hernández  1 , Anahi Rodríguez-López  2 , Lourdes Rodríguez-Fragoso  2 , Iván Ortega-Blake  1
Affiliations
Review

Polyene Antibiotics Physical Chemistry and Their Effect on Lipid Membranes; Impacting Biological Processes and Medical Applications

Tammy Haro-Reyes et al. Membranes (Basel). .

Abstract

This review examined a collection of studies regarding the molecular properties of some polyene antibiotic molecules as well as their properties in solution and in particular environmental conditions. We also looked into the proposed mechanism of action of polyenes, where membrane properties play a crucial role. Given the interest in polyene antibiotics as therapeutic agents, we looked into alternative ways of reducing their collateral toxicity, including semi-synthesis of derivatives and new formulations. We follow with studies on the role of membrane structure and, finally, recent developments regarding the most important clinical applications of these compounds.

Keywords: chemical properties; clinical applications; liposomal formulation; mechanism of action; membrane structure; polyenes; semi-synthetic derivatives.

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Conflict of interest statement

The authors declare no conflict of interest. The funders had no role in the design of the study; in the collection, analyses, or interpretation of data; in the writing of the manuscript, or in the decision to publish the results.

Figures

Figure 1
Figure 1
General structure of polyene antibiotics.
Figure 2
Figure 2
Structure of Nystatin 2.
Figure 3
Figure 3
Structure of Amphotericin B 1.
Figure 4
Figure 4
Structure of Filipin III 3.
Figure 5
Figure 5
Structure of Natamycin 4.
Figure 6
Figure 6
Chemical structure of oxidized amphotericin B form (AmB-ox, n = 5), where n is the number of double bonds in the hydrophobic chain.
Figure 7
Figure 7
(A)—Absorption spectra of Amphotericin B in PBS at pH 7.4 and exposed to air at ambient conditions as a function of time and illumination (2000 luxes). (B)—Spectra of the LED lamp used for illumination.
Figure 8
Figure 8
The N,N-di-(3-aminopropyl) AmB derivative 5.
Figure 9
Figure 9
The amide N,N-dialkyl derivative 6.
Figure 10
Figure 10
Chemical structure of AmB urea derivative 7.
Figure 11
Figure 11
Structure of A21, an amphotericin B derivative 8.
Figure 12
Figure 12
Amphamide salt form with glutamate 9.
Figure 13
Figure 13
Topographic images of supported lipid bilayers composed of POPC:ESM 1:1 mol:mol + 20 mol% ergosterol in the presence (B,D) or absence of polyenes (A–C). Polyenes were added by increments of 0.5 μM until a clear effect was observed. For AmB (B), this occurred at 1 μM; for A21 at 2 μM. (E–H) show height profiles corresponding to the lines drawn on the topographic image.
Figure 14
Figure 14
Topographic images of supported lipid bilayers composed of POPC:ESM 1:1 mol:mol + 20 mol% cholesterol in the presence (B,C) or absence of polyenes (A). Polyenes were added by increments of 0.5 μM until a clear effect was observed. For AmB (B) this occurred at 2 μM; for A21 at 5 μM. (D–F) show height profiles corresponding to the lines drawn on the topographic image. White arrows indicate regions where nano-defects or lesions are clearly visible.
See this image and copyright information in PMC

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