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Antifungal Agents

Antifungal Agents

Amphotericin B is a broad-spectrum antifungal agent that exploits structural differences between fungal and mammalian cell membranes. Its amphipathic structure—featuring a hydrophobic polyene-lactone ring and a hydrophilic region containing mycosamine and carboxylic acid groups—enables selective binding to ergosterol, a sterol predominantly found in fungal plasma membranes. This selective interaction underlies the drug’s antifungal activity, although weak binding to cholesterol contributes to...

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Automation of Bio-Atomic Force Microscope Measurements on Hundreds of C. albicans Cells

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Conformational analysis of Amphotericin B.

M Baginski¹, P Gariboldi, P Bruni

¹Department of Pharmaceutical Technology and Biochemistry, Technical University of Gdansk, Narutowicza St. 11/12, 80-952 Gdansk, Poland. maciekb@altis.chem.pg.gda.pl

Biophysical Chemistry

|April 22, 1997

Summary

Computational analysis explored Amphotericin B (AmB) conformations, revealing new molecular shapes crucial for its antifungal activity. These findings aid in understanding AmB-target interactions and developing improved antifungal drugs.

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Area of Science:

* Pharmaceutical Chemistry
* Computational Chemistry
* Mycology

Background:

* Amphotericin B (AmB) is a vital antifungal agent.
* Its mechanism of action is linked to molecular conformation.
* Understanding AmB's structure is key to optimizing its efficacy.

Purpose of the Study:

* To perform a theoretical conformational analysis of Amphotericin B.
* To investigate the influence of molecular shape on antifungal action.
* To identify potential new conformations relevant to AmB's function.

Main Methods:

* Employed MM2P and AM1 computational methods for conformational analysis.
* Analyzed the orientation of macrolidic and glycosidic fragments using phi and psi angles.
* Generated steric energy and population maps for AmB conformers.

Main Results:

* Identified multiple AmB conformers, including two previously observed experimentally.
* Proposed novel, unobserved conformers that may exist within AmB channel structures.
* Correlated computational findings with existing experimental Nuclear Magnetic Resonance (NMR) data.

Conclusions:

* New structural insights into Amphotericin B were obtained.
* Findings provide a basis for molecular modeling of AmB-target interactions.
* Results will guide the design of novel Amphotericin B derivatives.