Iso-Partricin, an Aromatic Analogue of Amphotericin B: How Shining Light on Old Drugs Might Help Create New Ones
Paweł Szczeblewski,
Justyna Górska,
Witold Andrałojć,
Patryk Janke,
Karolina Wąsik,
Tomasz Laskowski
Affiliations
Paweł Szczeblewski
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
Justyna Górska
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
Witold Andrałojć
Institute of Bioorganic Chemistry, Polish Academy of Sciences, Zygmunta Noskowskiego Str. 12/14, 61-704 Poznań, Poland
Patryk Janke
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
Karolina Wąsik
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
Tomasz Laskowski
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
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.
