Thiazolide Prodrug Esters and Derived Peptides: Synthesis and Activity.

Stachulski, Andrew V ORCID: 0000-0002-5100-8884, Rossignol, Jean-Francois, Pate, Sophie, Taujanskas, Joshua, Iggo, Jonathan A ORCID: 0000-0001-8070-1226, Aerts, Rudi, Pascal, Etienne, Piacentini, Sara, La Frazia, Simone, Santoro, M Gabriella
et al (show 5 more authors) (2023) Thiazolide Prodrug Esters and Derived Peptides: Synthesis and Activity. ACS bio & med chem Au, 3 (4). pp. 327-334.

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Amino acid ester prodrugs of the thiazolides, introduced to improve the pharmacokinetic parameters of the parent drugs, proved to be stable as their salts but were unstable at pH > 5. Although some of the instability was due to simple hydrolysis, we have found that the main end products of the degradation were peptides formed by rearrangement. These peptides were stable solids: they maintained significant antiviral activity, and in general, they showed improved pharmacokinetics (better solubility and reduced clearance) compared to the parent thiazolides. We describe the preparation and evaluation of these peptides.

Item Type: Article
Divisions: Faculty of Science and Engineering > School of Physical Sciences
Depositing User: Symplectic Admin
Date Deposited: 05 Jun 2023 13:29
Last Modified: 19 Sep 2023 18:28
DOI: 10.1021/acsbiomedchemau.2c00083
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