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Double Orthogonal Click Reactions for the Development of Antimicrobial Peptide Nanotubes
Author(s) -
GonzálezFreire Eva,
Novelli Federica,
PérezEstévez Antonio,
Seoane Rafael,
Amorín Manuel,
Granja Juan R.
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202004127
Subject(s) - amphiphile , supramolecular chemistry , antimicrobial , nanotube , cationic polymerization , combinatorial chemistry , peptide , membrane , stacking , cyclic peptide , regioselectivity , click chemistry , chemistry , materials science , nanotechnology , organic chemistry , copolymer , molecule , polymer , biochemistry , carbon nanotube , catalysis
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.