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- Towards the development of electrospun mats from poly(ε-caprolactone)/poly(ester amide)s miscible blendsPublication . Lamas, Miguel; Lima, Mafalda S.; Pinho, AC; Tugushi, David; Katsarava, Ramaz; Costa, Elisabete C.; Correia, Ilídio Joaquim Sobreira; Serra, Armenio; Coelho, Jorge; Fonseca, Ana C.In this work, electrospun mats made from miscible poly(ε-caprolactone) (PCL)/poly(ester amide) (PEA) blends were prepared, for the first time. The well-known immiscibility issues between these two type of polymers were overcome through the synthesis of a novel tailor-made compatibilizer blocky PEA, comprising well defined PCL and PEA8L6 blocks (PCL-PEA8L6). The PCL-PEA8L6 was synthesized for the first time in this work and was characterized in terms of its chemical structure and thermal properties. Regarding the mats, it was found that their properties (morphology, porosity, wettability, thermomechanical) can be easily adjusted by the ratio of the components of the mixture to be electrospun. Increasing amounts of PEA led to more hydrophilic mats, with enhanced in vitro degradability, both hydrolytic and enzymatic. The in vitro cytotoxicity tests carried out with normal human dermal fibroblasts (NHDF) revealed that the samples do not elicit any acute adverse effect on the cells. Moreover, the NHDF were able to grow and proliferate in the surface of the electrospun mats. The data presented in this contribution is a proof-of-concept that can be used to address immiscibility issues between different types of polymers broadly used in biomedical applications.
- Preparation of well-defined brush-like block copolymers for gene delivery applications under biorelevant reaction conditionsPublication . Góis, Joana R.; Reis, Fábio; Almeida, Ana Margarida; Pereira, Patrícia; Sousa, Fani; Serra, Armenio; Coelho, JorgeWell-defined oligo(ethylene glycol) methyl ether methacrylate (OEOMA) based block copolymers with cationic segments composed by N,N-(dimethylamino) ethyl methacrylate (DMAEMA) and/or 2-(diisopropylamino) ethyl methacrylate (DPA) were developed under biorelevant reaction conditions. These brush-type copolymers were synthesized through supplemental activator and reducing agent (SARA) atom transfer radical polymerization (ATRP) using sodium dithionite as SARA agent. The synthesis was carried out using an eco-friendly solvent mixture, very low copper catalyst concentration, and mild reaction conditions. The structure of the block copolymers was characterized by size exclusion chromatography (SEC) analysis and 1H nuclear magnetic resonance (NMR) spectroscopy. The pH-dependent protonation of these copolymers enables the efficient complexation with plasmid DNA (pDNA), yielding polyplexes with sizes ranging from 200 up to 700 nm, depending on the molecular weight of the copolymers, composition and concentration used. Agarose gel electrophoresis confirmed the successful pDNA encapsulation. No cytotoxicity effect was observed, even for N/P ratios higher than 50, for human fibroblasts and cervical cancer cell lines cells. The in vitro cellular uptake experiments demonstrated that the pDNA-loaded block copolymers were efficiently delivered into nucleus of cervical cancer cells. The polymerization approach, the unique structure of the block copolymers and the efficient DNA encapsulation presented can open new avenues for development of efficient tailor made gene delivery systems under biorelevant conditions.
- 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 propertiesPublication . Fonseca, Ana; Coelho, Jorge; Valente, Joana; Correia, Tiago R.; Correia, Ilídio Joaquim Sobreira; Gil, Maria; Simões, PedroNovel 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.