Utilize este identificador para referenciar este registo:
https://hdl.handle.net/1822/38228
Registo completo
Campo DC | Valor | Idioma |
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dc.contributor.author | Vilaça, Helena | por |
dc.contributor.author | Hortelão, Ana C. L. | por |
dc.contributor.author | Castanheira, Elisabete M. S. | por |
dc.contributor.author | Queiroz, Maria João R. P. | por |
dc.contributor.author | Hilliou, L. | por |
dc.contributor.author | Hamley, Ian W. | por |
dc.contributor.author | Martins, José A | por |
dc.contributor.author | Ferreira, Paula M. T. | por |
dc.date.accessioned | 2015-11-17T12:12:46Z | - |
dc.date.issued | 2015-10-07 | - |
dc.identifier.issn | 0024-9297 | por |
dc.identifier.uri | https://hdl.handle.net/1822/38228 | - |
dc.description.abstract | In this work, we introduce dipeptides containing tryptophan N-capped with the nonsteroidal anti-inflammatory drug naproxen and C-terminal dehydroamino acids, dehydrophenylalanine (ΔPhe), dehydroaminobutyric acid (ΔAbu), and dehydroalanine (ΔAla) as efficacious protease resistant hydrogelators. Optimized conditions for gel formation are reported. Transmission electron microscopy experiments revealed that the hydrogels consist of networks of micro/nanosized fibers formed by peptide self-assembly. Fluorescence and circular dichroism spectroscopy indicate that the self-assembly process is driven by stacking interactions of the aromatic groups. The naphthalene groups of the naproxen moieties are highly organized in the fibers through chiral stacking. Rheological experiments demonstrated that the most hydrophobic peptide (containing C-terminal ΔPhe) formed more elastic gels at lower critical gelation concentrations. This gel revealed irreversible breakup, while the C-terminal ΔAbu and ΔAla gels, although less elastic, exhibited structural recovery and partial healing of the elastic properties. A potential antitumor thieno[3,2-b]pyridine derivative was incorporated (noncovalently) into the gel formed by the hydrogelator containing C-terminal ΔPhe residue. Fluorescence and Förster resonance energy transfer measurements indicate that the drug is located in a hydrophobic environment, near/associated with the peptide fibers, establishing this type of hydrogel as a good drug-nanocarrier candidate. | por |
dc.description.sponsorship | FCT-Portugal and FEDER/COMPETE through CQ-UM, National NMR Network (Bruker 400), and I3N Strategic Project LA 25:2011-2012. Additional funds by Programa Operacional Regional do Norte (ON.2) through the project Matepro-Optimizing Materials and Processes, with reference NORTE-07-0124-FEDER-000037 FEDER COMPETE are also acknowledged. H.V. also thanks FCT for the PhD grant (SFRH/BD/72651/2010) cofunded by the European Social Fund. | por |
dc.language.iso | eng | por |
dc.publisher | ACS Publications | por |
dc.relation | FCT funds for I3N Strategic Project LA 25:2011-2012 | por |
dc.relation | Programa Operacional Regional do Norte (ON.2) through the project MateproOptimizing Materials and Processes, with reference NORTE-07-0124-FEDER-000037 FEDER COMPETE | por |
dc.rights | restrictedAccess | por |
dc.rights.uri | http://creativecommons.org/licenses/by/4.0/ | por |
dc.subject | Peptide | por |
dc.subject | Hydrogel | por |
dc.title | Dehydrodipeptide hydrogelators containing naproxen N-capped tryptophan: self-assembly, hydrogel characterization, and evaluation as potential drug nanocarriers | por |
dc.type | article | - |
dc.peerreviewed | yes | por |
sdum.publicationstatus | published | por |
oaire.citationStartPage | 3562 | por |
oaire.citationEndPage | 3573 | por |
oaire.citationIssue | 11 | por |
oaire.citationTitle | Biomacromolecules | por |
oaire.citationVolume | 16 | por |
dc.identifier.doi | 10.1021/acs.biomac.5b01006 | por |
dc.identifier.pmid | 26443892 | por |
dc.subject.fos | Ciências Naturais::Ciências Químicas | por |
dc.subject.wos | Science & Technology | por |
sdum.journal | Biomacromolecules | por |
Aparece nas coleções: | CDF - FAMO - Artigos/Papers (with refereeing) CDQuim - Artigos (Papers) IPC - Artigos em revistas científicas internacionais com arbitragem |
Ficheiros deste registo:
Ficheiro | Descrição | Tamanho | Formato | |
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biomac2015 gels helena1.pdf Acesso restrito! | 7,46 MB | Adobe PDF | Ver/Abrir |
Este trabalho está licenciado sob uma Licença Creative Commons