Synthesis of OH-group-containing, biodegradable polyurethane and protein fixation on its surface.

Abstract

A series of biodegradable polyurethanes containing free side hydroxyl groups (PUOH) were synthesized successfully in two steps: (1) PLA diol as soft segment, hexamethylene diisocyanate (HDI) as hard segment, and benzalpentaerythritol (BPO) as a chain extender were used to synthesize PUs with protected OH groups; (2) CF(3)COOH was used as a deprotection agent to remove the benzal groups on PU to prepare PUOH. The properties of PU and PUOH were characterized by Fourier transform infrared spectroscopy (FT-IR), nuclear magnetic resonance (NMR), differential scanning calorimetry (DSC), water contact angle measurement, and gel permeation chromatography (GPC). The benzal groups were removed completely in 15 min without detrimental effect on PU main chains to obtain PUOHs. 4-Azidobenzoic acid was conjugated to PUOH through its esterification with the free OH groups on PUOH. The results of immunofluorescence assay showed that the phenyl azide groups formed were capable of binding mouse IgG under UV (254 nm) irradiation in 3 min; the bound mouse IgG retained its own biological activity and could further bind the FITC-labeled anti(mouse IgG). Therefore, this material has a potential in immunofluorescence assay and related fields.

• Authors: Lixin Yang, Jizheng Wei, Lesan Yan, Yubin Huang, Xiabin Jing
• Journal: Biomacromolecules (Biomacromolecules) Vol. 12 Issue 6 Pg. 2032-8 (Jun 13 2011) ISSN: 1526-4602 [Electronic] United States
• PMID: 21488702 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Antibodies, Anti-Idiotypic
• Azides
• Biocompatible Materials
• Cyanates
• Hydroxides
• Immunoglobulin G
• Isocyanates
• Polyurethanes
• Propylene Glycols
• 1,6-hexamethylene diisocyanate
• 4-azidobenzoic acid
• hydroxide ion
• Fluorescein-5-isothiocyanate
• pentaerythritol

Topics

• Animals
• Antibodies, Anti-Idiotypic (immunology, metabolism)
• Azides (chemistry)
• Biocompatible Materials (chemical synthesis, metabolism)
• Biodegradation, Environmental
• Calorimetry, Differential Scanning
• Chromatography, Gel
• Cyanates (chemistry)
• Fluorescein-5-isothiocyanate (analysis)
• Hydroxides (chemistry)
• Immunoassay (methods)
• Immunoglobulin G (immunology, metabolism)
• Isocyanates
• Magnetic Resonance Spectroscopy
• Mice
• Polyurethanes (chemical synthesis, metabolism)
• Propylene Glycols (chemistry)
• Protein Binding
• Spectroscopy, Fourier Transform Infrared