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Nucleobase-containing peptides (nucleopeptides) represent a unique class of biohybrid molecules that combine the structural versatility of peptides with the functional properties of nucleobases, enabling programmable self-assembly and selective molecular interactions. These features position nucleopeptides as promising tools for biomedical and supramolecular applications. Here, we report the synthesis and characterization of a novel nucleopeptide derived from a tryptophan dipeptide (WW) functionalized with a thymine (T) base, termed WWT. Circular Dichroism and UV-Vis spectroscopy revealed distinctive spectral features and supramolecular organization in solution, confirmed by Dynamic Light Scattering. Binding studies showed no detectable interaction with DNA or RNA, whereas measurable spectral perturbations indicated affinity for bovine serum albumin. Metal-binding experiments with Ni(II) and Cu(II) further highlighted the influence of these ions on the modulation of WWT's optical properties, while computational modelling using HDOCK complemented the experimental data by predicting aggregation modes and protein-binding interfaces. To explore biological relevance, we integrated controlled exposure of IMR-90 human fibroblasts and Jurkat T lymphocytes with proteomics and metabolomics, identifying time-dependent modulation of pathways linked to metabolism, RNA/DNA processing, and T-cell signaling. Functionally, WWT enhanced fibroblast migration without altering lysosomal, mitochondrial, or cytoskeletal organization. Overall, this study provides the first combined synthetic, spectroscopic, computational, and multi-omics evaluation of WWT properties and effects, revealing its organized supramolecular behaviour, selective biomolecular interactions, and potential pro-regenerative properties.