Poly(ester amide)s based on (L)-lactic acid oligomers and α-amino acids: influence of the α-amino acid side chain in the poly(ester amide)s properties
Autor(a) principal: | |
---|---|
Data de Publicação: | 2013 |
Outros Autores: | , , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
Texto Completo: | http://hdl.handle.net/10400.6/4639 |
Resumo: | Novel biodegradable and low cytotoxic poly(ester amide)s (PEAs) based on α-amino acids and (L)-lactic acid (L-LA) oligomers were successfully synthesized by interfacial polymerization. The chemical structure of the new polymers was confirmed by spectroscopic analyses. Further characterization suggests that the α-amino acid plays a critical role on the final properties of the PEA. L-phenylalanine provides PEAs with higher glass transition temperature, whereas glycine enhances the crystallinity. The hydrolytic degradation in PBS (pH = 7.4) at 37 °C also depends on the α-amino acid, being faster for glycine-based PEAs. The cytotoxic profiles using fibroblast human cells indicate that the PEAs did not elicit an acute cytotoxic effect. The strategy presented in this work opens the possibility of synthesizing biodegradable PEAs with low citotoxicity by an easy and fast method. It is worth to mention also that the properties of these materials can be fine-tuned only by changing the α-amino acid. |
id |
RCAP_5ee2fd9672beaa8cd74f62f3222d4532 |
---|---|
oai_identifier_str |
oai:ubibliorum.ubi.pt:10400.6/4639 |
network_acronym_str |
RCAP |
network_name_str |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
repository_id_str |
7160 |
spelling |
Poly(ester amide)s based on (L)-lactic acid oligomers and α-amino acids: influence of the α-amino acid side chain in the poly(ester amide)s propertiesα-amino acids(L)-lactic acid oligomersInterfacial polycondensationDegradationBiocompatibilityNovel biodegradable and low cytotoxic poly(ester amide)s (PEAs) based on α-amino acids and (L)-lactic acid (L-LA) oligomers were successfully synthesized by interfacial polymerization. The chemical structure of the new polymers was confirmed by spectroscopic analyses. Further characterization suggests that the α-amino acid plays a critical role on the final properties of the PEA. L-phenylalanine provides PEAs with higher glass transition temperature, whereas glycine enhances the crystallinity. The hydrolytic degradation in PBS (pH = 7.4) at 37 °C also depends on the α-amino acid, being faster for glycine-based PEAs. The cytotoxic profiles using fibroblast human cells indicate that the PEAs did not elicit an acute cytotoxic effect. The strategy presented in this work opens the possibility of synthesizing biodegradable PEAs with low citotoxicity by an easy and fast method. It is worth to mention also that the properties of these materials can be fine-tuned only by changing the α-amino acid.A.C. Fonseca acknowledges “Fundação para a Ciência e Tecnologia”, Grant: SFRH/BD/41305/2007. The 1 H NMR data were obtained from Rede Nacional de RMN in the University of Coimbra, Portugal. The Varian VNMRS 600 MHz spectrometer is part of the National NMR Network and was purchased in the framework of the National Program for Scientific Re-equipment (contract REDE/1517/RMN/2005, with funds from POCI 2010 (FEDER) and Fundação para a Ciência e Tecnologia (FCT)). I.J. Correia acknowledges the project PTDC/EME-TME/103375/2008 for financial support.Taylor & FrancisuBibliorumFonseca, AnaCoelho, JorgeValente, JoanaCorreia, Tiago R.Correia, Ilídio Joaquim SobreiraGil, MariaSimões, Pedro2018-03-20T09:16:18Z2013-01-252013-01-25T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10400.6/4639engFonseca, A.C. Coelho, J. F.J., Valente, J. F.A., Correia, T. R., Correia, I.J., Gil, M. H. e Simões, P. N. (2013) "Poly(ester amide)s based on (L)-lactic acid oligomers and alpha-amino acids: influence of the alpha-amino acid side chain in the poly(ester amide)s properties", Journal of Biomaterials Science Polymer Edition, Vol. 24(12), pp. 1391-140910.1080/09205063.2012.762293metadata only accessinfo:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2023-12-15T09:41:49Zoai:ubibliorum.ubi.pt:10400.6/4639Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-20T00:45:42.072321Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse |
dc.title.none.fl_str_mv |
Poly(ester amide)s based on (L)-lactic acid oligomers and α-amino acids: influence of the α-amino acid side chain in the poly(ester amide)s properties |
title |
Poly(ester amide)s based on (L)-lactic acid oligomers and α-amino acids: influence of the α-amino acid side chain in the poly(ester amide)s properties |
spellingShingle |
Poly(ester amide)s based on (L)-lactic acid oligomers and α-amino acids: influence of the α-amino acid side chain in the poly(ester amide)s properties Fonseca, Ana α-amino acids (L)-lactic acid oligomers Interfacial polycondensation Degradation Biocompatibility |
title_short |
Poly(ester amide)s based on (L)-lactic acid oligomers and α-amino acids: influence of the α-amino acid side chain in the poly(ester amide)s properties |
title_full |
Poly(ester amide)s based on (L)-lactic acid oligomers and α-amino acids: influence of the α-amino acid side chain in the poly(ester amide)s properties |
title_fullStr |
Poly(ester amide)s based on (L)-lactic acid oligomers and α-amino acids: influence of the α-amino acid side chain in the poly(ester amide)s properties |
title_full_unstemmed |
Poly(ester amide)s based on (L)-lactic acid oligomers and α-amino acids: influence of the α-amino acid side chain in the poly(ester amide)s properties |
title_sort |
Poly(ester amide)s based on (L)-lactic acid oligomers and α-amino acids: influence of the α-amino acid side chain in the poly(ester amide)s properties |
author |
Fonseca, Ana |
author_facet |
Fonseca, Ana Coelho, Jorge Valente, Joana Correia, Tiago R. Correia, Ilídio Joaquim Sobreira Gil, Maria Simões, Pedro |
author_role |
author |
author2 |
Coelho, Jorge Valente, Joana Correia, Tiago R. Correia, Ilídio Joaquim Sobreira Gil, Maria Simões, Pedro |
author2_role |
author author author author author author |
dc.contributor.none.fl_str_mv |
uBibliorum |
dc.contributor.author.fl_str_mv |
Fonseca, Ana Coelho, Jorge Valente, Joana Correia, Tiago R. Correia, Ilídio Joaquim Sobreira Gil, Maria Simões, Pedro |
dc.subject.por.fl_str_mv |
α-amino acids (L)-lactic acid oligomers Interfacial polycondensation Degradation Biocompatibility |
topic |
α-amino acids (L)-lactic acid oligomers Interfacial polycondensation Degradation Biocompatibility |
description |
Novel biodegradable and low cytotoxic poly(ester amide)s (PEAs) based on α-amino acids and (L)-lactic acid (L-LA) oligomers were successfully synthesized by interfacial polymerization. The chemical structure of the new polymers was confirmed by spectroscopic analyses. Further characterization suggests that the α-amino acid plays a critical role on the final properties of the PEA. L-phenylalanine provides PEAs with higher glass transition temperature, whereas glycine enhances the crystallinity. The hydrolytic degradation in PBS (pH = 7.4) at 37 °C also depends on the α-amino acid, being faster for glycine-based PEAs. The cytotoxic profiles using fibroblast human cells indicate that the PEAs did not elicit an acute cytotoxic effect. The strategy presented in this work opens the possibility of synthesizing biodegradable PEAs with low citotoxicity by an easy and fast method. It is worth to mention also that the properties of these materials can be fine-tuned only by changing the α-amino acid. |
publishDate |
2013 |
dc.date.none.fl_str_mv |
2013-01-25 2013-01-25T00:00:00Z 2018-03-20T09:16:18Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://hdl.handle.net/10400.6/4639 |
url |
http://hdl.handle.net/10400.6/4639 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
Fonseca, A.C. Coelho, J. F.J., Valente, J. F.A., Correia, T. R., Correia, I.J., Gil, M. H. e Simões, P. N. (2013) "Poly(ester amide)s based on (L)-lactic acid oligomers and alpha-amino acids: influence of the alpha-amino acid side chain in the poly(ester amide)s properties", Journal of Biomaterials Science Polymer Edition, Vol. 24(12), pp. 1391-1409 10.1080/09205063.2012.762293 |
dc.rights.driver.fl_str_mv |
metadata only access info:eu-repo/semantics/openAccess |
rights_invalid_str_mv |
metadata only access |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
application/pdf |
dc.publisher.none.fl_str_mv |
Taylor & Francis |
publisher.none.fl_str_mv |
Taylor & Francis |
dc.source.none.fl_str_mv |
reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação instacron:RCAAP |
instname_str |
Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
instacron_str |
RCAAP |
institution |
RCAAP |
reponame_str |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
collection |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
repository.name.fl_str_mv |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
repository.mail.fl_str_mv |
|
_version_ |
1799136354432450560 |