Double Orthogonal Click Reactions for the Development of Antimicrobial Peptide Nanotubes |
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Authors: | Dr Eva González-Freire Dr Federica Novelli Antonio Pérez-Estévez Prof?Dr Rafael Seoane Dr Manuel Amorín Prof?Dr Juan R Granja |
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Institution: | 1. Centro Singular de Investigación en Química Biolóxica e, Materiais Moleculares (CIQUS), Departamento de Química Orgánica, Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Spain;2. Department of Microbiology and Parasitology, Medical School, University of Santiago de Compostela, 15782 Santiago de Compostela, Spain |
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Abstract: | A new class of amphipathic cyclic peptides, which assemble in bacteria membranes to form polymeric supramolecular nanotubes giving them antimicrobial properties, is described. The method is based on the use of two orthogonal clickable transformations to incorporate different hydrophobic or hydrophilic moieties in a simple, regioselective, and divergent manner. The resulting cationic amphipathic cyclic peptides described in this article exhibit strong antimicrobial properties with a broad therapeutic window. Our studies suggest that the active form is the nanotube resulted from the parallel stacking of the cyclic peptide precursors. Several techniques, CD, FTIR, fluorescence, and STEM, among others, confirm the nanotube formation. |
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Keywords: | antimicrobial cyclic peptides orthogonal clicking self-assembly supramolecular medicines |
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