Synthesis, Characterization, and Electrospinning of a Functionalizable, Polycaprolactone-Based Polyurethane for Soft Tissue Engineering
We synthesized a biodegradable, elastomeric, and functionalizable polyurethane (PU) that can be electrospun for use as a scaffold in soft tissue engineering. The PU was synthesized from polycaprolactone diol, hexamethylene diisocyanate, and dimethylolpropionic acid (DMPA) chain extender using two-st...
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MDPI AG
2021-05-01
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| Series: | Polymers |
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| Online Access: | https://www.mdpi.com/2073-4360/13/9/1527 |
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| author | Jin-Jia Hu Chia-Chi Liu Chih-Hsun Lin Ho-Yi Tuan-Mu |
| author_facet | Jin-Jia Hu Chia-Chi Liu Chih-Hsun Lin Ho-Yi Tuan-Mu |
| author_sort | Jin-Jia Hu |
| collection | DOAJ |
| description | We synthesized a biodegradable, elastomeric, and functionalizable polyurethane (PU) that can be electrospun for use as a scaffold in soft tissue engineering. The PU was synthesized from polycaprolactone diol, hexamethylene diisocyanate, and dimethylolpropionic acid (DMPA) chain extender using two-step polymerization and designated as PU-DMPA. A control PU using 1,4-butanediol (1,4-BDO) as a chain extender was synthesized similarly and designated as PU-BDO. The chemical structure of the two PUs was verified by FT-IR and <sup>1</sup>H-NMR. The PU-DMPA had a lower molecular weight than the PU-BDO (~16,700 Da vs. ~78,600 Da). The melting enthalpy of the PU-DMPA was greater than that of the PU-BDO. Both the PUs exhibited elastomeric behaviors with a comparable elongation at break (<inline-formula><math xmlns="http://www.w3.org/1998/Math/MathML" display="inline"><semantics><mrow><mi>λ</mi><mo>=</mo><mrow><mi>L</mi><mo>/</mo><mrow><msub><mi>L</mi><mn>0</mn></msub><mo>=</mo></mrow></mrow></mrow></semantics></math></inline-formula> 13.2). The PU-DMPA had a higher initial modulus (19.8 MPa vs. 8.7 MPa) and a lower linear modulus (0.7 MPa vs. 1.2 MPa) and ultimate strength (9.5 MPa vs. 13.8 MPa) than the PU-BDO. The PU-DMPA had better hydrophilicity than the PU-BDO. Both the PUs displayed no cytotoxicity, although the adhesion of human umbilical artery smooth muscle cells on the PU-DMPA surface was better. Bead free electrospun PU-DMPA membranes with a narrow fiber diameter distribution were successfully fabricated. As a demonstration of its functionalizability, gelatin was conjugated to the electrospun PU-DMPA membrane using carbodiimide chemistry. Moreover, hyaluronic acid was immobilized on the amino-functionalized PU-DMPA. In conclusion, the PU-DMPA has the potential to be used as a scaffold material for soft tissue engineering. |
| first_indexed | 2024-03-10T11:34:22Z |
| format | Article |
| id | doaj.art-1adc0546357045198899eddcf545e757 |
| institution | Directory Open Access Journal |
| issn | 2073-4360 |
| language | English |
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| spelling | doaj.art-1adc0546357045198899eddcf545e7572023-11-21T18:59:08ZengMDPI AGPolymers2073-43602021-05-01139152710.3390/polym13091527Synthesis, Characterization, and Electrospinning of a Functionalizable, Polycaprolactone-Based Polyurethane for Soft Tissue EngineeringJin-Jia Hu0Chia-Chi Liu1Chih-Hsun Lin2Ho-Yi Tuan-Mu3Department of Mechanical Engineering, National Yang Ming Chiao Tung University, Hsinchu 300, TaiwanDepartment of Biomedical Engineering, National Cheng Kung University, Tainan 701, TaiwanDivision of Plastic and Reconstructive Surgery, Department of Surgery, Taipei Veterans General Hospital, Taipei 112, TaiwanDepartment of Physical Therapy, Tzu Chi University, Hualien 970, TaiwanWe synthesized a biodegradable, elastomeric, and functionalizable polyurethane (PU) that can be electrospun for use as a scaffold in soft tissue engineering. The PU was synthesized from polycaprolactone diol, hexamethylene diisocyanate, and dimethylolpropionic acid (DMPA) chain extender using two-step polymerization and designated as PU-DMPA. A control PU using 1,4-butanediol (1,4-BDO) as a chain extender was synthesized similarly and designated as PU-BDO. The chemical structure of the two PUs was verified by FT-IR and <sup>1</sup>H-NMR. The PU-DMPA had a lower molecular weight than the PU-BDO (~16,700 Da vs. ~78,600 Da). The melting enthalpy of the PU-DMPA was greater than that of the PU-BDO. Both the PUs exhibited elastomeric behaviors with a comparable elongation at break (<inline-formula><math xmlns="http://www.w3.org/1998/Math/MathML" display="inline"><semantics><mrow><mi>λ</mi><mo>=</mo><mrow><mi>L</mi><mo>/</mo><mrow><msub><mi>L</mi><mn>0</mn></msub><mo>=</mo></mrow></mrow></mrow></semantics></math></inline-formula> 13.2). The PU-DMPA had a higher initial modulus (19.8 MPa vs. 8.7 MPa) and a lower linear modulus (0.7 MPa vs. 1.2 MPa) and ultimate strength (9.5 MPa vs. 13.8 MPa) than the PU-BDO. The PU-DMPA had better hydrophilicity than the PU-BDO. Both the PUs displayed no cytotoxicity, although the adhesion of human umbilical artery smooth muscle cells on the PU-DMPA surface was better. Bead free electrospun PU-DMPA membranes with a narrow fiber diameter distribution were successfully fabricated. As a demonstration of its functionalizability, gelatin was conjugated to the electrospun PU-DMPA membrane using carbodiimide chemistry. Moreover, hyaluronic acid was immobilized on the amino-functionalized PU-DMPA. In conclusion, the PU-DMPA has the potential to be used as a scaffold material for soft tissue engineering.https://www.mdpi.com/2073-4360/13/9/1527polyurethanestwo-step reactionelastomerfunctionalizationelectrospinning2,2-bis(hydroxymethyl)propionic acid |
| spellingShingle | Jin-Jia Hu Chia-Chi Liu Chih-Hsun Lin Ho-Yi Tuan-Mu Synthesis, Characterization, and Electrospinning of a Functionalizable, Polycaprolactone-Based Polyurethane for Soft Tissue Engineering Polymers polyurethanes two-step reaction elastomer functionalization electrospinning 2,2-bis(hydroxymethyl)propionic acid |
| title | Synthesis, Characterization, and Electrospinning of a Functionalizable, Polycaprolactone-Based Polyurethane for Soft Tissue Engineering |
| title_full | Synthesis, Characterization, and Electrospinning of a Functionalizable, Polycaprolactone-Based Polyurethane for Soft Tissue Engineering |
| title_fullStr | Synthesis, Characterization, and Electrospinning of a Functionalizable, Polycaprolactone-Based Polyurethane for Soft Tissue Engineering |
| title_full_unstemmed | Synthesis, Characterization, and Electrospinning of a Functionalizable, Polycaprolactone-Based Polyurethane for Soft Tissue Engineering |
| title_short | Synthesis, Characterization, and Electrospinning of a Functionalizable, Polycaprolactone-Based Polyurethane for Soft Tissue Engineering |
| title_sort | synthesis characterization and electrospinning of a functionalizable polycaprolactone based polyurethane for soft tissue engineering |
| topic | polyurethanes two-step reaction elastomer functionalization electrospinning 2,2-bis(hydroxymethyl)propionic acid |
| url | https://www.mdpi.com/2073-4360/13/9/1527 |
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