| Synthesis of biocompatible segmented polyurethanes from aliphatic diisocyanates and diurea diol chain extenders. | |
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MedLine Citation:
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PMID: 16701828 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Many polyurethane elastomers display excellent mechanical properties and adequate biocompatibility. However, many medical-grade polyurethanes are prepared from aromatic diisocyanates and can degrade in vivo to carcinogenic aromatic diamines, although the question of whether the concentrations of these harmful degradation products attain physiologically relevant levels is currently unresolved and strongly debated. It is therefore desirable to synthesize new medical-grade polyurethanes from less toxic aliphatic diisocyanates. In this paper, biocompatible segmented polyurethane elastomers were synthesized from aliphatic diisocyanates (1,4-diisocyanatobutane (BDI) and lysine methyl ester diisocyanate (LDI)), novel diurea diol chain extenders based on tyrosine and tyramine, and a model poly(ethylene glycol) (PEG) diol soft segment. The objectives were to design a hard segment similar in structure to that of MDI-based polyurethanes and also investigate the effects of systematic changes in structure on mechanical and biological properties. The non-branched, symmetric polyurethane prepared from BDI and a tyramine-based chain extender had the highest modulus at 37 degrees C. Introduction of symmetric short-chain branches (SCBs) incorporated in the tyrosine-based chain extender lowered the modulus by an order of magnitude. Polyurethanes prepared from LDI were soft polymers that had a still lower modulus due to the asymmetric SCBs that hindered hard segment packing. Polyurethanes prepared from tyramine and tyrosine chain extenders thermally degraded at temperatures ranging from 110 to 150 degrees C, which are lower than that reported previously for phenyl urethanes. All four polyurethanes supported the attachment, proliferation, and high viability of MG-63 human osteoblast-like cells in vitro. Therefore, the non-cytotoxic chemistry of these polyurethanes make them good candidates for further development as biomedical implants. |
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Authors:
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Scott A Guelcher; Katie M Gallagher; Jonathan E Didier; Derek B Klinedinst; John S Doctor; Aaron S Goldstein; Garth L Wilkes; Eric J Beckman; Jeffrey O Hollinger |
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Publication Detail:
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Type: Evaluation Studies; Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, Non-P.H.S. Date: 2005-03-31 |
Journal Detail:
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Title: Acta biomaterialia Volume: 1 ISSN: 1742-7061 ISO Abbreviation: - Publication Date: 2005 Jul |
Date Detail:
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Created Date: 2006-05-16 Completed Date: 2006-06-06 Revised Date: 2007-11-14 |
Medline Journal Info:
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Nlm Unique ID: 101233144 Medline TA: Acta Biomater Country: England |
Other Details:
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Languages: eng Pagination: 471-84 Citation Subset: IM |
Affiliation:
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Department of Biomedical Engineering, Bone Tissue Engineering Center, Carnegie Mellon University, Pittsburgh, PA 15213-3890, USA. sg@andrew.cmu.edu |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Biocompatible Materials
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chemistry* Cell Culture Techniques / methods Cell Line, Tumor Cell Proliferation Cell Survival Cross-Linking Reagents / chemistry Humans Isocyanates / chemistry* Osteosarcoma / pathology*, physiopathology* Polyurethanes / chemistry* Tissue Engineering / methods* Urea / chemistry* |
| Grant Support | |
ID/Acronym/Agency:
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T32EB00424/EB/NIBIB NIH HHS |
| Chemical | |
Reg. No./Substance:
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0/Biocompatible Materials; 0/Cross-Linking Reagents; 0/Isocyanates; 0/Polyurethanes; 57-13-6/Urea |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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