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

  • Antibiotics (Basel). 2021 Sep 13;10(9):1102. doi: 10.3390/antibiotics10091102.
Paweł Szczeblewski  1 ,  Justyna Górska  1 ,  Witold Andrałojć  2 ,  Patryk Janke  1 ,  Karolina Wąsik  1 ,  Tomasz Laskowski  1
Affiliations
  • 1. Department of Pharmaceutical Technology and Biochemistry and BioTechMed Centre, Faculty of Chemistry, Gdańsk University of Technology, Gabriela Narutowicza Str. 11/12, 80-233 Gdańsk, Poland.
  • 2. Institute of Bioorganic Chemistry, Polish Academy of Sciences, Zygmunta Noskowskiego Str. 12/14, 61-704 Poznań, Poland.
PMID: 34572684 DOI: 10.3390/antibiotics10091102
Abstract

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 cis-type bonds within their heptaenic chromophores: 28Z and 30Z. In this contribution, we have proven that partricins are susceptible to a chromophore-straightening photoisomerization process. The occurring 28Z→28E and 30Z→30E switches are irreversible in given conditions, and they are the only structural changes observed during the experiment. The obtained all-trans partricin's derivatives, namely iso-partricins A and B, exhibit very promising features, potentially resulting in the improvement of their selective toxicity.

Keywords
NMR; aureofacin; partricin; photoisomerization; polyene macrolides; selective toxicity; structural studies.
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