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Fluorescence and Morphology of Self‐Assembled Nucleobases and Their Diphenylalanine Hybrid Aggregates
Author(s) -
Avitabile Concetta,
Diaferia Carlo,
Roviello Valentina,
Altamura Davide,
Giannini Cinzia,
Vitagliano Luigi,
Accardo Antonella,
Romanelli Alessandra
Publication year - 2019
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.201902709
Subject(s) - nucleobase , dipeptide , nucleic acid , biomolecule , peptide nucleic acid , monomer , chemistry , fluorescence , peptide , structural motif , self assembly , combinatorial chemistry , biochemistry , dna , organic chemistry , polymer , physics , quantum mechanics
Studies carried out in recent decades have revealed that the ability to self‐assemble is a widespread property among biomolecules. Small nucleic acid moieties or very short peptides are able to generate intricate assemblies endowed with remarkable structural and spectroscopic properties. Herein, the structural/spectroscopic characterization of aggregates formed by nucleobases and peptide nucleic acid (PNA)–peptide conjugates are reported. At high concentration, all studied nucleobases form aggregates characterized by previously unreported fluorescence properties. The conjugation of these bases, as PNA derivatives, to the dipeptide Phe–Phe leads to the formation of novel hybrid assemblies, which are characterized by an amyloid‐like association of the monomers. Although these compounds share the same basic cross‐β motif, the nature and number of PNA units have an important impact on both the level of structural order and the intrinsic fluorescence of the self‐assembled nanostructure.