ArticleAntimicrobial agents and chemotherapy2013
Structure-antifungal activity relationships of polyene antibiotics of the amphotericin B group.
Article in Antimicrobial agents and chemotherapy, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 38 papers.
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Who cites it
38 citing papers in PubMed, 86 citations in OpenAlex.
- A Cationic Supramolecule With Potent Antifungal Activity, Single-Species Selectivity, and Strong Synergy With Echinocandins.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026Article
- Targeting the polyene chain represents an adjuvant strategy for optimizing polyene antifungals.Proceedings of the National Academy of Sciences of the United States of America · 2026Article
- Advancing fungal keratitis treatment: transitioning from conventional amphotericin B therapy to nanocarrier-based delivery systems.Naunyn-Schmiedeberg's archives of pharmacology · 2025Review
- Pharmaco-Technological Characterization, Structural Analysis, and Toxicological Evaluation of the Novel Polyene Antibiotic Roseofungin for Drug Development.Pharmaceutics · 2025Article
- Article
- Polyene-Based Derivatives with Antifungal Activities.Pharmaceutics · 2024Review
- Advancements and challenges in antifungal therapeutic development.Clinical microbiology reviews · 2024Review
- Antifungal Constituents ofMolecules (Basel, Switzerland) · 2023Article
- One Platform Comparison of Polymeric and Lipidic Nanoparticles for the Delivery of Amphotericin B.AAPS PharmSciTech · 2023Article
- Selected Gut Bacteria from Water Monitor Lizard Exhibit Effects against PathogenicMicroorganisms · 2023Article
- Natural products and their semi-synthetic derivatives against antimicrobial-resistant human pathogenic bacteria and fungi.Saudi journal of biological sciences · 2022Review
- Polyene Antibiotics Physical Chemistry and Their Effect on Lipid Membranes; Impacting Biological Processes and Medical Applications.Membranes · 2022Review
- Water-Soluble Nystatin and Derivative.ACS medicinal chemistry letters · 2022Article
- Synthesis and mechanism-of-action of a novel synthetic antibiotic based on a dendritic system with bow-tie topology.Frontiers in microbiology · 2022Article
- Antifungal Macrocycle Antibiotic Amphotericin B-Its Present and Future. Multidisciplinary Perspective for the Use in the Medical Practice.Biochemistry (Moscow) Supplement. Series B, Biomedical chemistry · 2022Article
- Synthetic Biology Advanced Natural Product Discovery.Metabolites · 2021Review
- Antibacterial polyene-polyol macrolides and cyclic peptides from the marine-derived Streptomyces sp. MS110128.Applied microbiology and biotechnology · 2021Article
- Bluemomycin, a new naphthoquinone derivative from Streptomyces sp. with antimicrobial and cytotoxic properties.Biotechnology letters · 2021Article
- Amphotericin B-loaded deformable lipid vesicles for topical treatment of cutaneous leishmaniasis skin lesions.Drug delivery and translational research · 2021Article
- Natural products in drug discovery: advances and opportunities.Nature reviews. Drug discovery · 2021Review
Corrections and comments
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Authors and funding
13 authors at 2 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
A comprehensive comparative analysis of the structure-antifungal activity relationships for the series of biosynthetically engineered nystatin analogues and their novel semisynthetic derivatives, as well as amphotericin B (AMB) and its semisynthetic derivatives, was performed. The data obtained revealed the significant influence of the structure of the C-7 to C-10 polyol region on the antifungal activity of these polyene antibiotics. Comparison of positions of hydroxyl groups in the antibiotics and in vitro antifungal activity data showed that the most active are the compounds in which hydroxyl groups are in positions C-8 and C-9 or positions C-7 and C-10. Antibiotics with OH groups at both C-7 and C-9 had the lowest activity. The replacement of the C-16 carboxyl with methyl group did not significantly affect the in vitro antifungal activity of antibiotics without modifications at the amino group of mycosamine. In contrast, the activity of the N-modified derivatives was modulated both by the presence of CH3 or COOH group in the position C-16 and by the structure of the modifying substituent. The most active compounds were tested in vivo to determine the maximum tolerated doses and antifungal activity on the model of candidosis sepsis in leukopenic mice (cyclophosphamide-induced). Study of our library of semisynthetic polyene antibiotics led to the discovery of compounds, namely, N-(L-lysyl)-BSG005 (compound 3n) and, especially, L-glutamate of 2-(N,N-dimethylamino)ethyl amide of S44HP (compound 2j), with high antifungal activity that were comparable in in vitro and in vivo tests to AMB and that have better toxicological properties.
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