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

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

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 t...

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Main Authors: Paweł Szczeblewski, Justyna Górska, Witold Andrałojć, Patryk Janke, Karolina Wąsik, Tomasz Laskowski
Format: Article
Language:English
Published: MDPI AG 2021-09-01
Series:Antibiotics
Subjects:
partricin
aureofacin
polyene macrolides
photoisomerization
selective toxicity
structural studies
Online Access:https://www.mdpi.com/2079-6382/10/9/1102
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spelling doaj-30e8aba704074e609968310e9626c43d2021-09-25T23:37:29ZengMDPI AGAntibiotics2079-63822021-09-01101102110210.3390/antibiotics10091102Iso-Partricin, an Aromatic Analogue of Amphotericin B: How Shining Light on Old Drugs Might Help Create New OnesPaweł Szczeblewski0Justyna Górska1Witold Andrałojć2Patryk Janke3Karolina Wąsik4Tomasz Laskowski5Department of Pharmaceutical Technology and Biochemistry and BioTechMed Centre, Faculty of Chemistry, Gdańsk University of Technology, Gabriela Narutowicza Str. 11/12, 80-233 Gdańsk, PolandDepartment of Pharmaceutical Technology and Biochemistry and BioTechMed Centre, Faculty of Chemistry, Gdańsk University of Technology, Gabriela Narutowicza Str. 11/12, 80-233 Gdańsk, PolandInstitute of Bioorganic Chemistry, Polish Academy of Sciences, Zygmunta Noskowskiego Str. 12/14, 61-704 Poznań, PolandDepartment of Pharmaceutical Technology and Biochemistry and BioTechMed Centre, Faculty of Chemistry, Gdańsk University of Technology, Gabriela Narutowicza Str. 11/12, 80-233 Gdańsk, PolandDepartment of Pharmaceutical Technology and Biochemistry and BioTechMed Centre, Faculty of Chemistry, Gdańsk University of Technology, Gabriela Narutowicza Str. 11/12, 80-233 Gdańsk, PolandDepartment of Pharmaceutical Technology and Biochemistry and BioTechMed Centre, Faculty of Chemistry, Gdańsk University of Technology, Gabriela Narutowicza Str. 11/12, 80-233 Gdańsk, PolandPartricin 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.https://www.mdpi.com/2079-6382/10/9/1102partricinaureofacinpolyene macrolidesphotoisomerizationselective toxicitystructural studies
collection DOAJ
language English
format Article
sources DOAJ
author Paweł Szczeblewski
Justyna Górska
Witold Andrałojć
Patryk Janke
Karolina Wąsik
Tomasz Laskowski
spellingShingle Paweł Szczeblewski
Justyna Górska
Witold Andrałojć
Patryk Janke
Karolina Wąsik
Tomasz Laskowski
Iso-Partricin, an Aromatic Analogue of Amphotericin B: How Shining Light on Old Drugs Might Help Create New Ones
Antibiotics
partricin
aureofacin
polyene macrolides
photoisomerization
selective toxicity
structural studies
author_facet Paweł Szczeblewski
Justyna Górska
Witold Andrałojć
Patryk Janke
Karolina Wąsik
Tomasz Laskowski
author_sort Paweł Szczeblewski
title Iso-Partricin, an Aromatic Analogue of Amphotericin B: How Shining Light on Old Drugs Might Help Create New Ones
title_short Iso-Partricin, an Aromatic Analogue of Amphotericin B: How Shining Light on Old Drugs Might Help Create New Ones
title_full Iso-Partricin, an Aromatic Analogue of Amphotericin B: How Shining Light on Old Drugs Might Help Create New Ones
title_fullStr Iso-Partricin, an Aromatic Analogue of Amphotericin B: How Shining Light on Old Drugs Might Help Create New Ones
title_full_unstemmed Iso-Partricin, an Aromatic Analogue of Amphotericin B: How Shining Light on Old Drugs Might Help Create New Ones
title_sort iso-partricin, an aromatic analogue of amphotericin b: how shining light on old drugs might help create new ones
publisher MDPI AG
series Antibiotics
issn 2079-6382
publishDate 2021-09-01
description 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.
topic partricin
aureofacin
polyene macrolides
photoisomerization
selective toxicity
structural studies
url https://www.mdpi.com/2079-6382/10/9/1102
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