Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 60, Issue 20, Pages 11288-11293Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202102706
Keywords
large-sized macrocycles; peptides; host– guest complexation; hemolysis; metabolic stability
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Funding
- National Natural Science Foundation of China [21772118, 21971192, 81573354]
- Natural Science Foundation of Tianjin City [20JCZDJC00200]
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Water-soluble large-sized quaterphen[n]arenes (WQPns, n=3, 4) were designed and synthesized with significantly distinct recognition abilities for the antimicrobial peptide pexiganan. The complexation of pexiganan by WQP3 and WQP4 effectively decreased its hemolysis in rabbit red blood cells and enhanced its metabolic stability in the presence of proteinase K, rat plasma, and liver or kidney homogenates.
Traditional macrocyclic hosts have finite cavity sizes, generally 5-10 angstrom, which are commonly adaptive to recognize small guests rather than biological macromolecules. Here two water-soluble large-sized quaterphen[n]arenes (WQPns, n=3, 4) were designed and synthesized. These two hosts present significantly distinct recognition abilities. Specifically, they could strongly complex an antimicrobial peptide, pexiganan (PXG) with the association constants (K-a) of (4.20 +/- 0.23)x10(4) M-1 for PXG/WQP3 and (2.46 +/- 0.44)x10(5) M-1 for PXG/WQP4. Complexation of PXG by WQP3 and WQP4 served to decrease the hemolysis of PXG in rabbit red blood cells in a statistically significant way. Furthermore, host-guest complexation was shown to substantially enhance metabolic stability of PXG in presence of proteinase K, rat plasma and liver or kidney homogenates.
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