The synthesis and the structural characterization of dipeptides composed of unnatural fluorine-substituted β(2,3)-diarylamino acid and l-alanine are reported. Depending on the stereochemistry of the β amino acid, these dipeptides are able to self-assemble into proteolytic stable nanotubes. These architectures were able to enter the cell and locate in the cytoplasmic/perinuclear region and represent interesting candidates for biomedical applications.

Dipeptide Nanotubes Containing Unnatural Fluorine-Substituted beta(2,3)-Diarylamino Acid and L-Alanine as Candidates for Biomedical Applications / A. Bonetti, S. Pellegrino, P. Das, S. Yuran, R. Bucci, N. Ferri, F. Meneghetti, C. Castellano, M. Reches, M.L. Gelmi. - In: ORGANIC LETTERS. - ISSN 1523-7060. - 17:18(2015 Sep 18), pp. 4468-4471. [10.1021/acs.orglett.5b02132]

Dipeptide Nanotubes Containing Unnatural Fluorine-Substituted beta(2,3)-Diarylamino Acid and L-Alanine as Candidates for Biomedical Applications

A. Bonetti
Secondo
;
S. Pellegrino
Primo
;
R. Bucci;N. Ferri;F. Meneghetti;C. Castellano;M.L. Gelmi
Ultimo
2015

Abstract

The synthesis and the structural characterization of dipeptides composed of unnatural fluorine-substituted β(2,3)-diarylamino acid and l-alanine are reported. Depending on the stereochemistry of the β amino acid, these dipeptides are able to self-assemble into proteolytic stable nanotubes. These architectures were able to enter the cell and locate in the cytoplasmic/perinuclear region and represent interesting candidates for biomedical applications.
Drug-delivery system; peptide nanotubes; amino-acid; nanostructures; derivatives; helix; inducer; ph
Settore CHIM/06 - Chimica Organica
18-set-2015
Article (author)
File in questo prodotto:
File Dimensione Formato  
acs.orglett.pdf

accesso riservato

Tipologia: Publisher's version/PDF
Dimensione 1.7 MB
Formato Adobe PDF
1.7 MB Adobe PDF   Visualizza/Apri   Richiedi una copia
2ndREVISION_main text.pdf

accesso aperto

Tipologia: Post-print, accepted manuscript ecc. (versione accettata dall'editore)
Dimensione 847.68 kB
Formato Adobe PDF
847.68 kB Adobe PDF Visualizza/Apri
Pubblicazioni consigliate

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/314949
Citazioni
  • ???jsp.display-item.citation.pmc??? 10
  • Scopus 47
  • ???jsp.display-item.citation.isi??? 44
social impact