Synthesis, characterization of 2-(methacryloyloxy)ethyl-(di-) l-lactate and their application in dextran-based hydrogels

Cadée, Jenny A.; Kerf, M De; Groot, Cornelis J. De; Otter, W. Den; Hennink, Wim E.

doi:10.1016/s0032-3861(99)00354-7

Cited by 30 publications

(35 citation statements)

References 20 publications

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“…Oligolactate esters of 2-hydroxyethyl methacrylate (HEMA-lactate n ), (n=number of lactate units in oligolactate) were synthesized by ring-opening oligomerization of lactide using HEMA as the initiator and stannous octoate as a catalyst as described by Cadee et al [9]. In brief, a mixture of lactide and HEMA was stirred at 110°C under nitrogen purging until the lactide was molten.…”

Section: Synthesismentioning

confidence: 99%

A polymeric micelle system with a hydrolysable segment for drug delivery

Zeng

Pitt²

2006

Journal of Biomaterials Science, Polymer Edition

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A potential anticancer drug delivery polymeric micelle system with an in vitro degradation half-life of about 48 hours that releases its drug upon application of ultrasound was synthesized. This vehicle was composed of an amphiphilic copolymer poly(ethylene oxide)-b-poly(N-isopropylacrylamideco-2-hydroxyethyl methacrylate-lactate n ). The degree of polymerization of lactate side group, n, was 0, 3 or 5. The molar ratio of NIPAAm to HEMA-lactate n to PEO in polymerization was optimized to produce an in vitro polymeric micelle half-life of about 48 hour at 40°C. 1,6-diphenyl-1,3,5-hexatriene (DPH) was used as a fluorescent probe to study the hydrophobicity of the cores of the polymeric micelles. The results showed that the cores of the polymeric micelles were hydrophobic enough to sequester DPH and the anti-cancer drug Doxorubicin (Dox). Dox was encapsulated into the polymeric micelles having molar feed ratio of NIPAAm to HEMA-lactate 3 to PEO equal to 20 : 5 : 1; this drug was released upon the application of low-frequency ultrasound. The Dox release was about 2 % at room temperature and 4 % at body temperature, and the drug returned to the polymeric micelles when insonation ceased.

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Section: Synthesismentioning

confidence: 99%

A polymeric micelle system with a hydrolysable segment for drug delivery

Zeng

Pitt²

2006

Journal of Biomaterials Science, Polymer Edition

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“…Notably, experiments 1-1, 1-2, and 1-3 were carried out at different reaction periods (6,12, and 24 h). In Figure 2 FTIR spectra of (a) dextran and (b) dextranAaM gel.…”

Section: Resultsmentioning

confidence: 99%

“…Recently there have been considerable efforts to synthesis hydrogels from dextran by many different methods. 5,6 Dextran-based hydrogels have usually been prepared by using functionalized dextran with polymerizable double bonds (methacrylate etc.). 7,8 van Dijk-Wolthius et al had synthesized glycidyl methacrylate derivatized dextran and polymerized this compound by ammonium persulfate (APS) and N,N,N 0 ,N 0 -tetrametiletilendiamin (TEMED) to form a hydrogel.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of new dextran‐acrylamide gels

Abdurrahmanoğlu

Firat

2007

J of Applied Polymer Sci

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Dextran-acrylamide gels were synthesized in a single step reaction by using 4,4 0 -azobis(4-cynovaleric acid) as bi-functional initiator at 608C. Corresponding acrylamide (AaM) gels in the absence of dextran were also prepared for comparison. Several parameters such as reaction period (6, 12, and 24 h), monomer and crosslinker concentrations were varied and their effects on the properties of gels were investigated. Gels were characterized by their mechanical and swelling behaviors and in terms of structural changes using SEM. It was observed that swelling degree decreased by increasing the monomer concentration due to formation of more crosslinking points that cause tighter network structure. Mechanical measurements showed that elastic modulus of AaM gels was higher than that of dextran-AaM gel which indicating the importance of dextran concentration on the flexibility of the network.

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“…18 However, because of its high biostability, 16 PHEMA has not been successfully used as a biodegradable hydrogel yet, despite several studies have focused on this aspect. 6,17,[19][20][21][22] Although some of the proposed structures presented degradation capabilities to some extent, the resulting hydrogels had two major deficiencies. First, as expected they showed very poor mechanical properties due to the structure of the cross-linker used 11,22 or to the mechanism of cross-linking.…”

Section: Introductionmentioning

confidence: 99%

Biodegradable HEMA‐based hydrogels with enhanced mechanical properties

Moghadam

Pioletti

2015

J Biomed Mater Res

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Hydrogels are widely used in the biomedical field. Their main purposes are either to deliver biological active agents or to temporarily fill a defect until they degrade and are followed by new host tissue formation. However, for this latter application, biodegradable hydrogels are usually not capable to sustain any significant load. The development of biodegradable hydrogels presenting load-bearing capabilities would open new possibilities to utilize this class of material in the biomedical field. In this work, an original formulation of biodegradable photo-crosslinked hydrogels based on hydroxyethyl methacrylate (HEMA) is presented. The hydrogels consist of short-length poly(2-hydroxyethyl methacrylate) (PHEMA) chains in a star shape structure, obtained by introducing a tetra-functional chain transfer agent in the backbone of the hydrogels. They are cross-linked with a biodegradable N,O-dimethacryloyl hydroxylamine (DMHA) molecule sensitive to hydrolytic cleavage. We characterized the degradation properties of these hydrogels submitted to mechanical loadings. We showed that the developed hydrogels undergo long-term degradation and specially meet the two essential requirements of a biodegradable hydrogel suitable for load bearing applications: enhanced mechanical properties and low molecular weight degradation products.

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Synthesis, characterization of 2-(methacryloyloxy)ethyl-(di-) l-lactate and their application in dextran-based hydrogels

Cited by 30 publications

References 20 publications

A polymeric micelle system with a hydrolysable segment for drug delivery

A polymeric micelle system with a hydrolysable segment for drug delivery

Synthesis and characterization of new dextran‐acrylamide gels

Biodegradable HEMA‐based hydrogels with enhanced mechanical properties

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