{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,16]],"date-time":"2026-04-16T03:06:02Z","timestamp":1776308762337,"version":"3.50.1"},"reference-count":39,"publisher":"Springer Science and Business Media LLC","issue":"1","license":[{"start":{"date-parts":[[2017,3,22]],"date-time":"2017-03-22T00:00:00Z","timestamp":1490140800000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0"},{"start":{"date-parts":[[2017,3,22]],"date-time":"2017-03-22T00:00:00Z","timestamp":1490140800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0"}],"content-domain":{"domain":["link.springer.com"],"crossmark-restriction":false},"short-container-title":["Sci Rep"],"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Very recently we proposed novel di- and tetra-phenylalanine peptides derivatized with gadolinium complexes as potentials supramolecular diagnostic agents for applications in MRI (Magnetic Resonance Imaging). It was observed that in very short FF dipeptide building blocks, the propensity to aggregate decreases significantly after modification with bulky moiety such as Gd-complexes, thus limiting their potential as CAs. We hypothesized that the replacement of the Phe side chain with more extended aromatic groups could improve the self-assembling. Here we describe the synthesis, structural and relaxometric behavior of a novel water soluble self-assembled peptide CA based on 2-naphthylalanine (2Nal). The peptide conjugate Gd-DOTA-L<jats:sub>6<\/jats:sub>-(2Nal)<jats:sub>2<\/jats:sub> is able to self-assemble in long fibrillary nanostructures in water solution (up to 1.0\u2009mg\/mL). CD and FTIR spectroscopies indicate a \u03b2 sheet secondary structure with an antiparallel orientation of single strands. All data are in good agreement with WAXS and SAXS characterizations that show the typical \u201ccross-\u03b2 pattern\u201d for fibrils at the solid state. Molecular modeling indicates the three-dimensional structure of the peptide spine of aggregates is essentially constituted by extended \u03b2-sheet motifs stabilized by hydrogen bonds and hydrophobic interactions. The high relaxivity of nanoaggregates (12.3\u2009mM<jats:sup>\u22121<\/jats:sup> s<jats:sup>\u22121<\/jats:sup> at 20\u2009MHz) and their capability to encapsulate doxorubicin suggest their potential application as supramolecular theranostic agents.<\/jats:p>","DOI":"10.1038\/s41598-017-00332-3","type":"journal-article","created":{"date-parts":[[2017,3,16]],"date-time":"2017-03-16T10:38:46Z","timestamp":1489660726000},"update-policy":"https:\/\/doi.org\/10.1007\/springer_crossmark_policy","source":"Crossref","is-referenced-by-count":28,"title":["Cross-beta nanostructures based on dinaphthylalanine Gd-conjugates loaded with doxorubicin"],"prefix":"10.1038","volume":"7","author":[{"given":"Carlo","family":"Diaferia","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Eliana","family":"Gianolio","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Teresa","family":"Sibillano","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Flavia Anna","family":"Mercurio","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Marilisa","family":"Leone","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Cinzia","family":"Giannini","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Nicole","family":"Balasco","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Luigi","family":"Vitagliano","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Giancarlo","family":"Morelli","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Antonella","family":"Accardo","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"297","published-online":{"date-parts":[[2017,3,22]]},"reference":[{"key":"332_CR1","doi-asserted-by":"publisher","first-page":"6881","DOI":"10.1039\/C4CS00164H","volume":"43","author":"L Adler-Abramovich","year":"2014","unstructured":"Adler-Abramovich, L. & Gazit, E. The physical properties of supramolecular peptide assemblies: from building block association to technological applications. Chem Soc Rev \n                           43, 6881\u20136893, doi:10.1039\/c4cs00164h (2014).","journal-title":"Chem Soc Rev"},{"key":"332_CR2","doi-asserted-by":"publisher","first-page":"1877","DOI":"10.1039\/b915765b","volume":"39","author":"X Yan","year":"2010","unstructured":"Yan, X., Zhu, P. & Li, J. Self-assembly and application of diphenylalanine-based nanostructures. Chem Soc Rev \n                           39, 1877\u20131890, doi:10.1039\/b915765b (2010).","journal-title":"Chem Soc Rev"},{"key":"332_CR3","doi-asserted-by":"publisher","first-page":"1460","DOI":"10.1021\/la903571y","volume":"26","author":"G Demirel","year":"2010","unstructured":"Demirel, G., Malvadkar, N. & Demirel, M. C. Control of protein adsorption onto core-shell tubular and vesicular structures of diphenylalanine\/parylene. 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Chemistry-a European Journal \n                           7, 5153\u20135159, doi:10.1002\/1521-3765(20011203)7:23<5153::Aid-Chem5153>3.0.Co;2-N (2001).","journal-title":"Chemistry-a European Journal"},{"key":"332_CR8","doi-asserted-by":"publisher","first-page":"5020","DOI":"10.1016\/j.bpj.2009.03.026","volume":"96","author":"P Tamamis","year":"2009","unstructured":"Tamamis, P. et al. Self-Assembly of Phenylalanine Oligopeptides: Insights from Experiments and Simulations. Biophysical Journal \n                           96, 5020\u20135029, doi:10.1016\/j.bpj.2009.03.026 (2009).","journal-title":"Biophysical Journal"},{"key":"332_CR9","doi-asserted-by":"publisher","first-page":"3907","DOI":"10.1021\/nn300015g","volume":"6","author":"C Guo","year":"2012","unstructured":"Guo, C., Luo, Y., Zhou, R. H. & Wei, G. H. Probing the Self-Assembly Mechanism of Diphenylalanine-Based Peptide Nanovesicles and Nanotubes. 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