Preparation and characterization of hydrogels based on acryloyl end-capped four-arm star-shaped poly(ethylene glycol)-branched-oligo(l-lactide) via Michael-type addition reaction
-
Huai-Qing Yu
and
Rimin Cong
Abstract
An acryloyl end-capped four-arm star-shaped poly(ethylene glycol)-branched-oligo(l-lactide) (4A-PEG-PLA) macromer was firstly prepared. A novel kind of hydrogels was synthesized via the Michael-type addition reaction between (2S,3S)-1,4-bis-sulfanylbutane-2,3-diol (dithiothreitol) and this macromer. Gelation time was determined visually as the time when the precursor solution did not flow on inverting the vials. Hydrogel structure was characterized by FTIR analysis, swelling and degradation tests. It was found that colorless and transparent hydrogels were quickly generated in situ. The gelation time, swelling and degradation behaviors of this kind of hydrogels could be adjusted by changing the concentration of the macromer solution in PBS buffer (pH 7.4). This novel hydrogel is expected to be used as a biomedical material.
[1] Bočková, J., Vojtová L., Přikryl, R., Čechal, J., & Jančř J. (2008). Collagen-grafted ultra-high molecular weight polyethylene for biomedical applications. Chemical Papers, 62, 580–588. DOI: do]10.2478/s11696-008-0076-1. http://dx.doi.org/10.2478/s11696-008-0076-110.2478/s11696-008-0076-1Search in Google Scholar
[2] Cai, S., Liu, Y., Shu, X. Z., & Prestwich, G. D. (2005). Injectable glycosaminoglycan hydrogels for controlled release of human basic fibroblast growth factor. Biomaterials, 26, 6054–6067. DOI: 10.1016/j.biomaterials.2005.03.012. http://dx.doi.org/10.1016/j.biomaterials.2005.03.01210.1016/j.biomaterials.2005.03.012Search in Google Scholar
[3] Chenite, A., Chaput, C., Wang, D., Combes, C., Buschmann, M. D., Hoemann, C. D., Leroux, J. C., Atkinson, B. L., Binette, F., & Selmani, A. (2000). Novel injectable neutral so lutions of chitosan form biodegradable gels in situ. Biomaterials, 21, 2155–2161. DOI: 10.1016/S0142-9612(00)00116-2. http://dx.doi.org/10.1016/S0142-9612(00)00116-210.1016/S0142-9612(00)00116-2Search in Google Scholar
[4] de Jong, S. J., De Smedt, S. C., Demeester, J., van Nostrum, C. F., Kettenes-van den Bosch, J. J., & Hennink, W. E. (2001). Biodegradable hydrogels based on stereocomplex formation between lactic acid oligomers grafted to dextran. Journal of Controlled Release, 72, 47–56. DOI: 10.1016/S0168-3659(01)00261-9. http://dx.doi.org/10.1016/S0168-3659(01)00261-910.1016/S0168-3659(01)00261-9Search in Google Scholar
[5] Elbert, D. L., Pratt, A. B., Lutolf, M. P., Halstenberg, S., & Hubbell, J. A. (2001). Protein delivery from materials formed by self-selective conjugate addition reactions. Journal of Controlled Release, 76, 11–25. DOI: 10.1016/S0168-3659(01)00398-4. http://dx.doi.org/10.1016/S0168-3659(01)00398-410.1016/S0168-3659(01)00398-4Search in Google Scholar
[6] Friedman, M., Cavins, J. F., & Wall, J. S. (1965). Relative nucleophilic reactivities of amino groups and mercaptide ions in addition reactions with α,β-unsaturated compounds. Journal of the American Chemical Society, 87, 3672–3682. DOI: 10.1021/ja01094a025. http://dx.doi.org/10.1021/ja01094a02510.1021/ja01094a025Search in Google Scholar
[7] Hennink, W. E., & van Nostrum, C. F. (2002). Novel crosslinking methods to design hydrogels. Advanced Drug Delivery Reviews, 54, 13–36. DOI: 10.1016/S0169-409X(01)00240-X. http://dx.doi.org/10.1016/S0169-409X(01)00240-X10.1016/S0169-409X(01)00240-XSearch in Google Scholar
[8] Kissel, T., Li, Y., & Unger, F. (2002). ABA-triblock copolymers from biodegradable polyester A-blocks and hydrophilic poly(ethylene oxide) B-blocks as a candidate for in situ forming hydrogel delivery systems for proteins. Advanced Drug Delivery Reviews, 54, 99–134. DOI: 10.1016/S0169-409X(01)00244-7. http://dx.doi.org/10.1016/S0169-409X(01)00244-710.1016/S0169-409X(01)00244-7Search in Google Scholar
[9] Lutolf, M. P., & Hubbell, J. A. (2003). Synthesis and physicochemical characterization of end-linked poly(ethylene glycol)-co-peptide hydrogels formed by Michael-type addition. Biomacromolecules, 4, 713–722. DOI: 10.1021/bm025744e. http://dx.doi.org/10.1021/bm025744e10.1021/bm025744eSearch in Google Scholar PubMed
[10] Mather, B. D., Viswanathan, K., Miller, K. M., & Long, T. E. (2006). Michael addition reactions in macromolecular design for emerging technologies. Progress in Polymer Science, 31, 487–531. DOI: 10.1016/j.progpolymsci.2006.03.001. http://dx.doi.org/10.1016/j.progpolymsci.2006.03.00110.1016/j.progpolymsci.2006.03.001Search in Google Scholar
[11] Metters, A., & Hubbell, J. (2005). Network formation and degradation behavior of hydrogels formed by Michael-type addition reactions. Biomacromolecules, 6, 290–301. DOI: 10.1021/bm049607o. http://dx.doi.org/10.1021/bm049607o10.1021/bm049607oSearch in Google Scholar PubMed
[12] Peppas, N. A., Bures, P., Leobandun, W., & Ichikawa, H. (2000). Hydrogels in pharmaceutical formulations. European Journal of Pharmaceutics and Biopharmaceutics, 50, 27–46. DOI: 10.1016/S0939-6411(00)00090-4. http://dx.doi.org/10.1016/S0939-6411(00)00090-410.1016/S0939-6411(00)00090-4Search in Google Scholar
[13] Sawhney, A. S., Pathak, C. P., & Hubbell, J. A. (1993). Bioerodible hydrogels based on photopolymerized poly(ethylene glycol)-co-poly(α-hydroxy acid) diacrylate macromers. Macromolecules, 26, 581–587. DOI: 10.1021/ma00056a005. http://dx.doi.org/10.1021/ma00056a00510.1021/ma00056a005Search in Google Scholar
[14] Schoenmakers, R. G., van de Wetering, P., Elbert, D. L., & Hubbell, J. A. (2004). The effect of the linker on the hydrolysis rate of drug-linked ester bonds. Journal of Controlled Release, 95, 291–300. DOI: 10.1016/j.jconrel.2003.12.009. http://dx.doi.org/10.1016/j.jconrel.2003.12.00910.1016/j.jconrel.2003.12.009Search in Google Scholar PubMed
[15] Veverková, E., Droppová, R., & Toma, Š. (2006). Comparison of betaine and l-stachydrine as phase-transfer catalysts in Michael addition and Darzens reaction. Chemical Papers, 60, 333–337. DOI: do]10.2478/s11696-006-0061-5. http://dx.doi.org/10.2478/s11696-006-0061-510.2478/s11696-006-0061-5Search in Google Scholar
© 2010 Institute of Chemistry, Slovak Academy of Sciences
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Articles in the same Issue
- A deuterium-palladium electrode as a new sensor in non-aqueous solutions: potentiometric titration of weak acids in acetonitrile and benzonitrile
- Chemical variability of Artemisia herba-alba Asso essential oils from East Morocco
- Ag and Cu loaded on TiO2/graphite as a catalyst for Escherichia coli-contaminated water disinfection
- Direct electrochemistry and electrocatalysis of horseradish peroxidase immobilized in hyaluronic acid and single walled carbon nanotubes composite film
- Biological buffered saline solution as solvent in agar-carbomer hydrogel synthesis
- GC/MS analysis of gaseous degradation products formed during extrusion blow molding process of PE films
- Preparation, spectral, thermal, and biological properties of zinc(II) 4-chloro- and 5-chlorosalicylate complexes with methyl 3-pyridylcarbamate and phenazone
- Polyamidoamine dendrimer and dextran conjugates: preparation, characterization, and in vitro and in vivo evaluation
- Morphological characteristics of modified freeze-dried poly(N-isopropylacrylamide) microspheres studied by optical microscopy, SEM, and DLS
- Photophysical properties of novel ferrocenyl quinoline derivatives with red emission in solutions and polymeric matrices
- Preparation and characterization of hydrogels based on acryloyl end-capped four-arm star-shaped poly(ethylene glycol)-branched-oligo(l-lactide) via Michael-type addition reaction
- ArF laser photolytic deposition and thermal modification of an ultrafine chlorohydrocarbon
- Asymmetric synthesis of machilin C and its analogue
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- Single crystal X-ray structure and optical properties of anthraquinone-based dyes
- Low-density polyethylene in mixtures of hexane and benzene derivates
- Factors influencing aggregation behavior of poly(γ-benzyl l-glutamate)-graft-poly(ethylene glycol) copolymer in mixed solvents
- Chemical evaluation of Fallopia species leaves and antioxidant properties of their non-cellulosic polysaccharides
- Rapid synthesis and bioactivities of 3-(nitromethylene)indolin-2-one analogues
- ZnO nanorods catalyzed N-alkylation of piperidin-4-one, 4(3H)-pyrimidone, and ethyl 6-chloro-1,2-dihydro-2-oxo-4-phenylquinoline-3-carboxylate
