Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 60, Issue 23, Pages 12829-12834Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202103477
Keywords
corroles; drug design; iron; serum; water solubility
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Funding
- Israel Science Foundation
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A new class of corroles that meet drug likeness criteria have been synthesized using a straightforward method based on trifluoromethyl hydrolysis. These corroles demonstrate the ability to affect their association with plasma proteins and show excellent performance for catalase-like decomposition of hydrogen peroxide.
Heme-like metal-chelating macrocycles, including expanded and contracted porphyrins, are of everlasting interest as drug candidates for numerous diseases. Still, all reported corrole derivatives (and most other heme analogues) do not fulfill the most basic standards expected for oral drug administration: a combination of low molecular weight and reasonable water solubility. We now disclose a very straightforward synthetic method that relies on surprisingly facile trifluoromethyl hydrolysis for gaining access to a new class of corroles that do satisfy all druglikeness criteria. The relevance is briefly exemplified for the iron corroles by demonstrating the ability to affect their association with plasma proteins and their performance for catalase-like decomposition of hydrogen peroxide.
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