New insight into nucleo α-amino acids – Synthesis and SAR studies on cytotoxic activity of β-pyrimidine alanines

Ignatowska, Jolanta; Mironiuk‐Puchalska, Ewa; Grześkowiak, Piotr; Wińska, Patrycja; Wielechowska, Monika; Bretner, Maria; Karatsai, Olena; Rędowicz, Maria Jolanta; Koszytkowska‐Stawińska, Mariola

doi:10.1016/j.bioorg.2020.103864

Cited by 6 publications

(3 citation statements)

References 42 publications

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“…Nucleobase-containing amino acids, also known as nucleoamino acids [29], consist of amino acid residues linked to DNA or RNA bases through diverse connecting moieties referred to as linkers. These hybrid derivatives, featuring heteroaromatic rings fused with amino acid-based structures, are sourced from nature or synthesized by means of chemical procedures in a laboratory.…”

Section: Nucleobase-bearing Amino Acid Systems and Self-assemblymentioning

confidence: 99%

Dancing with Nucleobases: Unveiling the Self-Assembly Properties of DNA and RNA Base-Containing Molecules for Gel Formation

Scognamiglio,

Vicidomini,

Roviello

2023

Gels

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Nucleobase-containing molecules are compounds essential in biology due to the fundamental role of nucleic acids and, in particular, G-quadruplex DNA and RNA in life. Moreover, some molecules different from nucleic acids isolated from different vegetal sources or microorganisms show nucleobase moieties in their structure. Nucleoamino acids and peptidyl nucleosides belong to this molecular class. Closely related to the above, nucleopeptides, also known as nucleobase-bearing peptides, are chimeric derivatives of synthetic origin and more rarely isolated from plants. Herein, the self-assembly properties of a vast number of structures, belonging to the nucleic acid and nucleoamino acid/nucleopeptide family, are explored in light of the recent scientific literature. Moreover, several technologically relevant properties, such as the hydrogelation ability of some of the nucleobase-containing derivatives, are reviewed in order to make way for future experimental investigations of newly devised nucleobase-driven hydrogels. Nucleobase-containing molecules, such as mononucleosides, DNA, RNA, quadruplex (G4)-forming oligonucleotides, and nucleopeptides are paramount in gel and hydrogel formation owing to their distinctive molecular attributes and ability to self-assemble in biomolecular nanosystems with the most diverse applications in different fields of biomedicine and nanotechnology. In fact, these molecules and their gels present numerous advantages, underscoring their significance and applicability in both material science and biomedicine. Their versatility, capability for molecular recognition, responsiveness to stimuli, biocompatibility, and biodegradability collectively contribute to their prominence in modern nanotechnology and biomedicine. In this review, we emphasize the critical role of nucleobase-containing molecules of different nature in pioneering novel materials with multifaceted applications, highlighting their potential in therapy, diagnostics, and new nanomaterials fabrication as required for addressing numerous current biomedical and nanotechnological challenges.

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Section: Nucleobase-bearing Amino Acid Systems and Self-assemblymentioning

confidence: 99%

Dancing with Nucleobases: Unveiling the Self-Assembly Properties of DNA and RNA Base-Containing Molecules for Gel Formation

Scognamiglio,

Vicidomini,

Roviello

2023

Gels

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“…Refs. [ 82 , 83 , 84 , 85 ] Nonetheless, nucleoamino acid moieties are found in the natural peptidyl nucleosides [ 86 ], molecules that play a key role in biology and therapy, while a plethora of synthetic nucleoamino acids were developed as building blocks of nucleopeptides [ 87 , 88 , 89 , 90 , 91 , 92 ].…”

Section: Willardiine In Peptide Structuresmentioning

confidence: 99%

Willardiine and Its Synthetic Analogues: Biological Aspects and Implications in Peptide Chemistry of This Nucleobase Amino Acid

et al. 2022

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Willardiine is a nonprotein amino acid containing uracil, and thus classified as nucleobase amino acid or nucleoamino acid, that together with isowillardiine, forms the family of uracilylalanines isolated more than six decades ago in higher plants. Willardiine acts as a partial agonist of ionotropic glutamate receptors and more in particular it agonizes the non-N-methyl-D-aspartate (non-NMDA) receptors of L-glutamate: ie. the α-amino-3-hydroxy-5-methyl-4-isoxazole-propionic acid (AMPA) and kainate receptors. Several analogues and derivatives of willardiine have been synthesised in the laboratory in the last decades and these compounds show different binding affinities for the non-NMDA receptors. More in detail, the willardiine analogues have been employed not only in the investigation of the structure of AMPA and kainate receptors, but also to evaluate the effects of receptor activation in the various brain regions. Remarkably, there are a number of neurological diseases determined by alterations in glutamate signaling, and thus, ligands for AMPA and kainate receptors deserve attention as potential neurodrugs. In fact, similar to willardiine its analogues often act as agonists of AMPA and kainate receptors. A particular importance should be recognized to willardiine and its thymine-based analogue AlaT also in the peptide chemistry field. In fact, besides the naturally-occurring short nucleopeptides isolated from plant sources, there are different examples in which this class of nucleoamino acids was investigated for nucleopeptide development. The applications are various ranging from the realization of nucleopeptide/DNA chimeras for diagnostic applications, and nucleoamino acid derivatization of proteins for facilitating protein-nucleic acid interaction, to nucleopeptide-nucleopeptide molecular recognition for nanotechnological applications. All the above aspects on both chemistry and biotechnological applications of willardine/willardine-analogues and nucleopeptide will be reviewed in this work.

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“…Nucleopeptide monomers, i.e., nucleoamino acids [9], can be (i) naturally occurring compounds such as willardiine and others [16][17][18][19], (ii) mimics of natural molecules, or (iii) synthetic building blocks. Since modified nucleosides containing nucleobase modifications are interesting scaffolds featured by several biological properties, e.g., antiviral or antitumor activities [20][21][22][23][24][25][26][27], the wide range of these modified nucleobases can be combined with amino acidic units to obtain new bioactive nucleoamino acids, also constituting useful synthetic building blocks for novel nucleopeptides.…”

Section: Introductionmentioning

confidence: 99%

From Prebiotic Chemistry to Supramolecular Biomedical Materials: Exploring the Properties of Self-Assembling Nucleobase-Containing Peptides

et al. 2021

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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.

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New insight into nucleo α-amino acids – Synthesis and SAR studies on cytotoxic activity of β-pyrimidine alanines

Cited by 6 publications

References 42 publications

Dancing with Nucleobases: Unveiling the Self-Assembly Properties of DNA and RNA Base-Containing Molecules for Gel Formation

Dancing with Nucleobases: Unveiling the Self-Assembly Properties of DNA and RNA Base-Containing Molecules for Gel Formation

Willardiine and Its Synthetic Analogues: Biological Aspects and Implications in Peptide Chemistry of This Nucleobase Amino Acid

From Prebiotic Chemistry to Supramolecular Biomedical Materials: Exploring the Properties of Self-Assembling Nucleobase-Containing Peptides

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