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

Detalhes bibliográficos
Autor(a) principal: Fonseca, Ana
Data de Publicação: 2013
Outros Autores: Coelho, Jorge, Valente, Joana, Correia, Tiago R., Correia, Ilídio Joaquim Sobreira, Gil, Maria, Simões, Pedro
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.
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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
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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)
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