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Molecules 2011, 16(10), 8181-8197; doi:10.3390/molecules16108181

Synthesis and Evaluation of Poly(hexamethylene-urethane) and PEG-Poly(hexamethylene-urethane) and Their Cholesteryl Oleyl Carbonate Composites for Human Blood Biocompatibility

1
Department of Pharmacy, Chia Nan University of Pharmacy and Science, 60 Erh-Jen Rd., Sec. 1,Tainan 717, Taiwan
2
Department of Life Science, Chia Nan University of Pharmacy and Science, 60 Erh-Jen Rd., Sec. 1, Tainan 717, Taiwan
3
Department of Pharmacy Practice, Tri-service General Hospital, Taipei 114, Taiwan
4
Department of Chemistry and Biochemistry, National Chung Cheng University, 168 University Rd., Chia-Yi 621, Taiwan
These authors contributed equally to this work.
*
Author to whom correspondence should be addressed.
Received: 19 August 2011 / Revised: 19 September 2011 / Accepted: 22 September 2011 / Published: 28 September 2011
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Abstract

Two new urethane-based acrylates (UAA and PEG-UAA) were synthesized as polymer blocks. The chemical composition of the two monomers was confirmed by IR and NMR. After cross-linking these blockers by radical polymerization, “hexamethylene PU” [poly(hexamethylene-urethane)] and “PEG-hexamethylene PU” [PEG-poly(hexa-methylene-urethane)] were obtained. The platelet adhesion and platelet activation of these polymers were evaluated in the presence of Platelet Rich Plasma (PRP) blood. The relative blood clotting indexes of the polymers were determined to measure their capability of reducing thrombogenicity. The hemolysis of red blood cells was also assessed to examine the haemocompatibility of the polymers. The hexamethylene PU and PEG-hexamethylene PU showed less platelet adhesion, platelet activation, blood clotting and hemolysis than a commercial PU (Tecoflex). The liquid crystal molecule, cholesteryl oleyl carbonate (COC), showed further improved biocompatibility to human blood, after COC was embedded in the PU polymers. PEG-hexamethylene PU + 10% COC demonstrated the best activity in reducing thrombogenicity and the best haemocompatibility. The inclusion of PEG segments into the PEG-UAA structure increased its hydrophilicity. The methylene bis(cyclohexyl) segments in Tecoflex PU decreased haemocompatibility. These observations are in good agreement with performed contact angle measurements. The PEG-hexamethylene PU loaded with COC might be a promising material for applications in bioengineering.
Keywords: polymer; cholesteryl oleyl carbonate; platelet; blood compatibility polymer; cholesteryl oleyl carbonate; platelet; blood compatibility
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Shih, M.F.; Shau, M.D.; Hsieh, C.C.; Cherng, J.Y. Synthesis and Evaluation of Poly(hexamethylene-urethane) and PEG-Poly(hexamethylene-urethane) and Their Cholesteryl Oleyl Carbonate Composites for Human Blood Biocompatibility. Molecules 2011, 16, 8181-8197.

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