Publicação
Aryl-capped lysine-dehydroamino acid dipeptide supergelators as potential drug release systems
| Resumo: | Employing amino acids and peptides as molecular building blocks provides unique opportunities for generating supramolecular hydrogels, owing to their inherent biological origin, bioactivity, biocompatibility, and biodegradability. However, they can suffer from proteolytic degradation. Short peptides (<8 amino acids) attached to an aromatic capping group are particularly attractive alternatives for minimalistic low molecular weight hydrogelators. Peptides with low critical gelation concentrations (CGCs) are especially desirable, as the low weight percentage required for gelation makes them more cost-effective and reduces toxicity. In this work, three dehydrodipeptides were studied for their self-assembly properties. The results showed that all three dehydrodipeptides can form self-standing hydrogels with very low critical gelation concentrations (0.050.20 wt%) using a pH trigger. Hydrogels of all three dehydrodipeptides were characterised by scanning tunnelling emission microscopy (STEM), rheology, fluorescence spectroscopy, and circular dichroism (CD) spectroscopy. Molecular modelling was performed to probe the structural patterns and interactions. The cytotoxicity of the new compounds was tested using human keratinocytes (HaCaT cell line). In general, the results suggest that all three compounds are non-cytotoxic, although one of the peptides shows a small impact on cell viability. In sustained release assays, the effect of the charge of the model drug compounds on the rate of cargo release from the hydrogel network was evaluated. The hydrogels provide a sustained release of methyl orange (anionic) and ciprofloxacin (neutral), while methylene blue (cationic) was retained by the network. |
|---|---|
| Autores principais: | Oliveira, Carlos B. P. |
| Outros Autores: | Pereira, Renato B.; Pereira, David M.; Hilliou, L.; Castro, Tarsila Gabriel; Martins, J. A. R.; Jervis, Peter John; Ferreira, Paula M. T. |
| Assunto: | critical gelation concentration dehydrodipeptides drug delivery systems lysine self-assembly supramolecular hydrogels |
| Ano: | 2022 |
| País: | Portugal |
| Tipo de documento: | artigo |
| Tipo de acesso: | acesso aberto |
| Instituição associada: | Universidade do Minho |
| Idioma: | inglês |
| Origem: | RepositóriUM - Universidade do Minho |
| _version_ | 1864250629948440576 |
|---|---|
| author | Oliveira, Carlos B. P. |
| author2 | Pereira, Renato B. Pereira, David M. Hilliou, L. Castro, Tarsila Gabriel Martins, J. A. R. Jervis, Peter John Ferreira, Paula M. T. |
| author2_role | author author author author author author author |
| author_facet | Oliveira, Carlos B. P. Pereira, Renato B. Pereira, David M. Hilliou, L. Castro, Tarsila Gabriel Martins, J. A. R. Jervis, Peter John Ferreira, Paula M. T. |
| author_role | author |
| contributor_name_str_mv | Universidade do Minho |
| country_str | PT |
| creators_json_str | [{\"Person.name\":\"Oliveira, Carlos B. P.\"},{\"Person.name\":\"Pereira, Renato B.\"},{\"Person.name\":\"Pereira, David M.\"},{\"Person.name\":\"Hilliou, L.\"},{\"Person.name\":\"Castro, Tarsila Gabriel\"},{\"Person.name\":\"Martins, J. A. R.\"},{\"Person.name\":\"Jervis, Peter John\"},{\"Person.name\":\"Ferreira, Paula M. T.\"}] |
| datacite.contributors.contributor.contributorName.fl_str_mv | Universidade do Minho |
| datacite.creators.creator.creatorName.fl_str_mv | Oliveira, Carlos B. P. Pereira, Renato B. Pereira, David M. Hilliou, L. Castro, Tarsila Gabriel Martins, J. A. R. Jervis, Peter John Ferreira, Paula M. T. |
| datacite.date.Accepted.fl_str_mv | 2022-10-05T00:00:00Z |
| datacite.date.available.fl_str_mv | 2022-10-28T10:27:59Z |
| datacite.date.embargoed.fl_str_mv | 2022-10-28T10:27:59Z |
| datacite.rights.fl_str_mv | http://purl.org/coar/access_right/c_abf2 |
| datacite.subjects.subject.fl_str_mv | critical gelation concentration dehydrodipeptides drug delivery systems lysine self-assembly supramolecular hydrogels |
| datacite.titles.title.fl_str_mv | Aryl-capped lysine-dehydroamino acid dipeptide supergelators as potential drug release systems |
| dc.contributor.none.fl_str_mv | Universidade do Minho |
| dc.creator.none.fl_str_mv | Oliveira, Carlos B. P. Pereira, Renato B. Pereira, David M. Hilliou, L. Castro, Tarsila Gabriel Martins, J. A. R. Jervis, Peter John Ferreira, Paula M. T. |
| dc.date.Accepted.fl_str_mv | 2022-10-05T00:00:00Z |
| dc.date.available.fl_str_mv | 2022-10-28T10:27:59Z |
| dc.date.embargoed.fl_str_mv | 2022-10-28T10:27:59Z |
| dc.format.none.fl_str_mv | application/pdf |
| dc.identifier.none.fl_str_mv | https://hdl.handle.net/1822/80373 |
| dc.language.none.fl_str_mv | eng |
| dc.publisher.none.fl_str_mv | MDPI |
| dc.rights.none.fl_str_mv | http://purl.org/coar/access_right/c_abf2 |
| dc.subject.none.fl_str_mv | critical gelation concentration dehydrodipeptides drug delivery systems lysine self-assembly supramolecular hydrogels |
| dc.title.fl_str_mv | Aryl-capped lysine-dehydroamino acid dipeptide supergelators as potential drug release systems |
| dc.type.none.fl_str_mv | http://purl.org/coar/resource_type/c_6501 |
| description | Employing amino acids and peptides as molecular building blocks provides unique opportunities for generating supramolecular hydrogels, owing to their inherent biological origin, bioactivity, biocompatibility, and biodegradability. However, they can suffer from proteolytic degradation. Short peptides (<8 amino acids) attached to an aromatic capping group are particularly attractive alternatives for minimalistic low molecular weight hydrogelators. Peptides with low critical gelation concentrations (CGCs) are especially desirable, as the low weight percentage required for gelation makes them more cost-effective and reduces toxicity. In this work, three dehydrodipeptides were studied for their self-assembly properties. The results showed that all three dehydrodipeptides can form self-standing hydrogels with very low critical gelation concentrations (0.050.20 wt%) using a pH trigger. Hydrogels of all three dehydrodipeptides were characterised by scanning tunnelling emission microscopy (STEM), rheology, fluorescence spectroscopy, and circular dichroism (CD) spectroscopy. Molecular modelling was performed to probe the structural patterns and interactions. The cytotoxicity of the new compounds was tested using human keratinocytes (HaCaT cell line). In general, the results suggest that all three compounds are non-cytotoxic, although one of the peptides shows a small impact on cell viability. In sustained release assays, the effect of the charge of the model drug compounds on the rate of cargo release from the hydrogel network was evaluated. The hydrogels provide a sustained release of methyl orange (anionic) and ciprofloxacin (neutral), while methylene blue (cationic) was retained by the network. |
| dirty | 0 |
| eu_rights_str_mv | openAccess |
| format | article |
| fulltext.url.fl_str_mv | https://prod-dspace.uminho.pt/bitstreams/b660d6ba-5599-43e4-aa40-3fb6272d5012/download |
| id | rum_7cf24dfbcd8b56136cdc130d0bb7d1bb |
| identifier.url.fl_str_mv | https://hdl.handle.net/1822/80373 |
| instacron_str | repositorium |
| institution | Universidade do Minho |
| instname_str | Universidade do Minho |
| language | eng |
| network_acronym_str | rum |
| network_name_str | RepositóriUM - Universidade do Minho |
| oai_identifier_str | oai:repositorium.uminho.pt:1822/80373 |
| organization_str_mv | urn:organizationAcronym:repositorium |
| person_str_mv | Oliveira, Carlos B. P. Pereira, Renato B. Pereira, David M. Hilliou, L. Castro, Tarsila Gabriel Martins, J. A. R. Jervis, Peter John Ferreira, Paula M. T. |
| publishDate | 2022 |
| publisher.none.fl_str_mv | MDPI |
| reponame_str | RepositóriUM - Universidade do Minho |
| repository_id_str | urn:repositoryAcronym:rum |
| service_str_mv | urn:repositoryAcronym:rum |
| spelling | engMDPIporEmploying amino acids and peptides as molecular building blocks provides unique opportunities for generating supramolecular hydrogels, owing to their inherent biological origin, bioactivity, biocompatibility, and biodegradability. However, they can suffer from proteolytic degradation. Short peptides (<8 amino acids) attached to an aromatic capping group are particularly attractive alternatives for minimalistic low molecular weight hydrogelators. Peptides with low critical gelation concentrations (CGCs) are especially desirable, as the low weight percentage required for gelation makes them more cost-effective and reduces toxicity. In this work, three dehydrodipeptides were studied for their self-assembly properties. The results showed that all three dehydrodipeptides can form self-standing hydrogels with very low critical gelation concentrations (0.050.20 wt%) using a pH trigger. Hydrogels of all three dehydrodipeptides were characterised by scanning tunnelling emission microscopy (STEM), rheology, fluorescence spectroscopy, and circular dichroism (CD) spectroscopy. Molecular modelling was performed to probe the structural patterns and interactions. The cytotoxicity of the new compounds was tested using human keratinocytes (HaCaT cell line). In general, the results suggest that all three compounds are non-cytotoxic, although one of the peptides shows a small impact on cell viability. In sustained release assays, the effect of the charge of the model drug compounds on the rate of cargo release from the hydrogel network was evaluated. The hydrogels provide a sustained release of methyl orange (anionic) and ciprofloxacin (neutral), while methylene blue (cationic) was retained by the network.application/pdfporAryl-capped lysine-dehydroamino acid dipeptide supergelators as potential drug release systemsOliveira, Carlos B. P.Pereira, Renato B.Pereira, David M.Hilliou, L.Castro, Tarsila GabrielMartins, J. A. R.Jervis, Peter JohnFerreira, Paula M. T.HostingInstitutionOrganizationalUniversidade do Minhoe-mailmailto:repositorium@usdb.uminho.ptrepositorium@usdb.uminho.ptISBNIsPartOf1424-6783ISSNIsPartOf1661-6596DOIIsPartOf10.3390/ijms2319118112022-10-28T10:27:59Z2022-10-052022-10-28T08:25:21Z2022-10-05T00:00:00ZHandlehttps://hdl.handle.net/1822/80373http://purl.org/coar/access_right/c_abf2open accesscritical gelation concentrationdehydrodipeptidesdrug delivery systemslysineself-assemblysupramolecular hydrogels6121395 bytesliteraturehttp://purl.org/coar/resource_type/c_6501journal articlehttp://purl.org/coar/access_right/c_abf2application/pdffulltexthttps://prod-dspace.uminho.pt/bitstreams/b660d6ba-5599-43e4-aa40-3fb6272d5012/download |
| spellingShingle | Aryl-capped lysine-dehydroamino acid dipeptide supergelators as potential drug release systems Oliveira, Carlos B. P. critical gelation concentration dehydrodipeptides drug delivery systems lysine self-assembly supramolecular hydrogels |
| subject.fl_str_mv | critical gelation concentration dehydrodipeptides drug delivery systems lysine self-assembly supramolecular hydrogels |
| title | Aryl-capped lysine-dehydroamino acid dipeptide supergelators as potential drug release systems |
| title_full | Aryl-capped lysine-dehydroamino acid dipeptide supergelators as potential drug release systems |
| title_fullStr | Aryl-capped lysine-dehydroamino acid dipeptide supergelators as potential drug release systems |
| title_full_unstemmed | Aryl-capped lysine-dehydroamino acid dipeptide supergelators as potential drug release systems |
| title_short | Aryl-capped lysine-dehydroamino acid dipeptide supergelators as potential drug release systems |
| title_sort | Aryl-capped lysine-dehydroamino acid dipeptide supergelators as potential drug release systems |
| topic | critical gelation concentration dehydrodipeptides drug delivery systems lysine self-assembly supramolecular hydrogels |
| topic_facet | critical gelation concentration dehydrodipeptides drug delivery systems lysine self-assembly supramolecular hydrogels |
| url | https://hdl.handle.net/1822/80373 |
| visible | 1 |