Abstract
Peptides and their synthetic analogs are a class of molecules with enormous relevance as therapeutics for their ability to interact with biomacromolecules like nucleic acids and proteins, potentially interfering with biological pathways often involved in the onset and progression of pathologies of high social impact. Nucleobase-bearing peptides (nucleopeptides) and pseudopeptides (PNAs) offer further interesting possibilities related to their nucleobase-decorated nature for diagnostic and therapeutic applications, thanks to their reported ability to target complementary DNA and RNA strands. In addition, these chimeric compounds are endowed with intriguing self-assembling properties, which are at the heart of their investigation as self-replicating materials in prebiotic chemistry, as well as their application as constituents of innovative drug delivery systems and, more generally, as novel nanomaterials to be employed in biomedicine. Herein we describe the properties of nucleopeptides, PNAs and related supramolecular systems, and summarize some of the most relevant applications of these systems.
Highlights
Among the nucleic acid mimetics, nucleopeptides—i.e., natural or synthetic compounds composed of nucleobases inserted on a peptide backbone (Figure 1a)—show interesting features deriving from their experimentally proven capacity to bind complementaryRNA and DNA sequences [1,2,3,4,5,6,7,8,9]
Triphenyl pyridine- or triphenylamine-functionalized polytyrosine showed a similar aggregation-induced emission (AIE) behavior, which was explained as a consequence of the restriction of the intramolecular rotation mechanism for chromophoric compounds when attached to the polypeptides featured by a rigid-rod conformation [127,128]
Both single- and oligo-nucleobase-bearing peptides are interesting, conjugated compounds whose self-assembling behavior is significant in numerous research fields, ranging from prebiotic chemistry to biomedicine and nanomaterials science
Summary
Among the nucleic acid mimetics, nucleopeptides—i.e., natural or synthetic compounds composed of nucleobases inserted on a peptide backbone (Figure 1a)—show interesting features deriving from their experimentally proven capacity to bind complementary. The H-bonding ability between the complementary bases of the nucleic acid and the nucleopeptide can be reinforced by other kinds of binding interactions, such as the electrostatic ones (Figure 1b,c). This is the case, for example, of cationic nucleopeptides obtained by the sequential oligomerization of diamino acids, in the form of nucleobase-bearing and base-free units (Figure 1b) [1,2,4]. It is worth mentioning that, even though, to the best of our knowledge, no examples of nucleopeptide sequences fully based on nucleoamino acids have been found in natural sources to date, excluding the short willardiine nucleopeptides [38], no other DNA analog has monomers of natural origin
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