Iso-Partricin, an Aromatic Analogue of Amphotericin B: How Shining Light on Old Drugs Might Help Create New Ones

• Main Authors: Paweł Szczeblewski (Author), Justyna Górska (Author), Witold Andrałojć (Author), Patryk Janke (Author), Karolina Wąsik (Author), Tomasz Laskowski (Author)
• Format: Book
• Published: MDPI AG, 2021-09-01T00:00:00Z.
• Subjects: article
• Online Access: Connect to this object online.
• Notes: 10.3390/antibiotics10091102; 2079-6382
• Keywords: partricin; aureofacin; polyene macrolides; photoisomerization; selective toxicity; structural studies; Therapeutics. Pharmacology; RM1-950
• Source: Antibiotics, Vol 10, Iss 9, p 1102 (2021)

Partricin is a heptaene macrolide antibiotic complex that exhibits exceptional antifungal activity, yet poor selective toxicity, in the pathogen/host system. It consists of two compounds, namely partricin A and B, and both of these molecules incorporate two <i>cis</i>-type bonds within their heptaenic chromophores: 28<i>Z</i> and 30<i>Z</i>. In this contribution, we have proven that partricins are susceptible to a chromophore-straightening photoisomerization process. The occurring 28<i>Z</i>→28<i>E</i> and 30<i>Z</i>→30<i>E</i> switches are irreversible in given conditions, and they are the only structural changes observed during the experiment. The obtained <i>all-trans</i> partricin's derivatives, namely iso-partricins A and B, exhibit very promising features, potentially resulting in the improvement of their selective toxicity.