Microbial degradation, cytotoxicity and antibacterial activity of polyurethanes based on modified castor oil and polycaprolactone

References

• Alishiri M, Shojaei A, Abdekhodaie MJ, et al. Synthesis and characterization of biodegradable acrylated polyurethane based on poly(ε-caprolactone) and 1,6-hexamethylene diisocyanate. Mater. Sci. Eng. C: Mater. Biol. Appl. 2014;42:763–773.10.1016/j.msec.2014.05.056
   PubMed Web of Science ®Google Scholar
• Jing Q, Law JY, Tan LP, et al. Preparation, characterization and properties of polycaprolactone diol-functionalized multi-walled carbon nanotube/thermoplastic polyurethane composite. Compos. Part A: Appl. Sci. Manuf. 2015;70:8–15.10.1016/j.compositesa.2014.10.028
   Web of Science ®Google Scholar
• Zia KM, Bhatti HN, Bhatti IA. Methods for polyurethane and polyurethane composites, recycling and recovery: a review. React. Funct. Polym. 2007;67:675–692.10.1016/j.reactfunctpolym.2007.05.004
   Web of Science ®Google Scholar
• Cho SM, Kim BK. Thermo-sensitive hydrogels based on interpenetrating polymer networks made of poly(N-isopropylacrylamide) and polyurethane. J. Biomater. Sci. Polym. Ed. 2010;21:1051–1068.10.1163/092050609X12457428830438
   PubMed Web of Science ®Google Scholar
• Gunatillake P, Mayadunne R, Adhikari R. Recent developments in biodegradable synthetic polymers. Biotechnol. Annu. Rev. 2006;12:301–347.10.1016/S1387-2656(06)12009-8
   PubMedGoogle Scholar
• Vroman I, Tighzert L. Biodegradable polymers. Materials. 2009;2:307–344.
   Web of Science ®Google Scholar
• Chashmejahanbin MR, Daemi H, Barikani M, et al. Noteworthy impacts of polyurethane-urea ionomers as the efficient polar coatings on adhesion strength of plasma treated polypropylene. Appl. Surf. Sci. 2014;317:688–695.10.1016/j.apsusc.2014.08.094
   Web of Science ®Google Scholar
• Bat E, Zhang Z, Feijen J, et al. Biodegradable elastomers for biomedical applications and regenerative medicine. Regen. Med. 2014;9:385–398.10.2217/rme.14.4
   PubMed Web of Science ®Google Scholar
• Pergal MV, Antic VV, Tovilovic G, et al. In vitro biocompatibility evaluation of novel urethane-siloxane co-polymers based on poly(-caprolactone)-block-poly(dimethylsiloxane)-block-poly(-caprolactone). J. Biomater. Sci. Polym. Ed. 2012;23:1629–1657.
   PubMed Web of Science ®Google Scholar
• Liu Y, Inoue Y, Sakata S, et al. Effects of molecular architecture of phospholipid polymers on surface modification of segmented polyurethanes. J. Biomater. Sci. Polym. Ed. 2014;25:474–486.10.1080/09205063.2013.873282
   PubMed Web of Science ®Google Scholar
• He W, Benson R. Polymeric biomaterials. In: Kutz M, editor. Applied plastics engineering handbook. 1st ed. New York (NY): Elsevier; 2011. p. 87–107.10.1016/B978-1-4377-3514-7.10010-8
   Google Scholar
• Murray KA, Kennedy JE, McEvoy B, et al. The influence of electron beam irradiation conducted in air on the thermal, chemical, structural and surface properties of medical grade polyurethane. Eur. Polym. J. 2013;49:1782–1795.10.1016/j.eurpolymj.2013.03.034
   Web of Science ®Google Scholar
• Bakhshi H, Yeganeh H, Yari A, et al. Castor oil-based polyurethane coatings containing benzyl triethanol ammonium chloride: synthesis, characterization, and biological properties. J. Mater. Sci. 2014;49:5365–5377.10.1007/s10853-014-8244-x
   Web of Science ®Google Scholar
• Estrada A, Herrera J. Síntesis de materiales a base de uretano reforzados con nanopartículas metálicas. I. Síntesis y caracterización [Synthesis of nanocomposites of a urethane–type polymer incorporated with metalic nanoparticles. I. Synthesis and characterization]. Rev Iberoam Polímeros. 2013;14:28–38.
   Google Scholar
• Kucinska-Lipka J, Gubanska I, Janik H, et al. Fabrication of polyurethane and polyurethane based composite fibres by the electrospinning technique for soft tissue engineering of cardiovascular system. Mater. Sci. Eng. C: Mater. Biol. Appl. 2015;46:166–176.10.1016/j.msec.2014.10.027
   PubMed Web of Science ®Google Scholar
• Li Y, Shimizu H. Toughening of polylactide by melt blending with a biodegradable poly(ether)urethane elastomer. Macromol. Biosci. 2007;7:921–928.10.1002/(ISSN)1616-5195
   PubMed Web of Science ®Google Scholar
• van Minnen B, Stegenga B, van Leeuwen MB, et al. A long-term in vitro biocompatibility study of a biodegradable polyurethane and its degradation products. J. Biomed. Mater. Res. A. 2006;76A:377–385.10.1002/(ISSN)1552-4965
   Web of Science ®Google Scholar
• Park H, Gong M-S, Park J-H, et al. Silk fibroin-polyurethane blends: physical properties and effect of silk fibroin content on viscoelasticity, biocompatibility and myoblast differentiation. Acta Biomater. 2013;9:8962–8971.10.1016/j.actbio.2013.07.013
   PubMed Web of Science ®Google Scholar
• Tsai M-C, Hung K-C, Hung S-C, et al. Evaluation of biodegradable elastic scaffolds made of anionic polyurethane for cartilage tissue engineering. Colloids Surf. B. 2015;125:34–44.10.1016/j.colsurfb.2014.11.003
   PubMed Web of Science ®Google Scholar
• Wang W, Guo Y, Otaigbe J. Synthesis and characterization of novel biodegradable and biocompatible poly(ester-urethane) thin films prepared by homogeneous solution polymerization. Polymer. 2008;49:4393–4398.10.1016/j.polymer.2008.07.057
   Web of Science ®Google Scholar
• Zhou L, Liang D, He X, et al. The degradation and biocompatibility of pH-sensitive biodegradable polyurethanes for intracellular multifunctional antitumor drug delivery. Biomaterials. 2012;33:2734–2745.10.1016/j.biomaterials.2011.11.009
   PubMed Web of Science ®Google Scholar
• Chen R, Zhang C, Kessler MR. Polyols and polyurethanes prepared from epoxidized soybean oil ring-opened by polyhydroxy fatty acids with varying OH numbers. J. Appl. Polym. Sci. 2014;132:1–10.
   Google Scholar
• St John KR. The use of compliant layer prosthetic components in orthopedic joint repair and replacement: a review. J. Biomed. Mater. Res. Part. B. Appl. Biomater. 2014;102:1332–1341.10.1002/jbm.b.v102.6
   PubMed Web of Science ®Google Scholar
• Adolph EJ, Pollins AC, Cardwell NL, et al. Biodegradable lysine-derived polyurethane scaffolds promote healing in a porcine full-thickness excisional wound model. J. Biomater. Sci. Polym. Ed. 2014;25:1973–1985.10.1080/09205063.2014.965997
   PubMed Web of Science ®Google Scholar
• Rajan KP, Al-Ghamdi A, Parameswar R, et al. Blends of thermoplastic polyurethane and polydimethylsiloxane rubber: assessment of biocompatibility and suture holding strength of membranes. Int. J. Biomater. 2013;2013:1–7.10.1155/2013/240631
   Google Scholar
• Rocco KA, Maxfield MW, Best CA, et al. In vivo applications of electrospun tissue-engineered vascular grafts: a review. Tissue Eng. Part. B. 2014;20:628–640.10.1089/ten.teb.2014.0123
   PubMed Web of Science ®Google Scholar
• Rodríguez-Galán A, Franco L, Puiggal J. Biodegradable polyurethanes and poly(ester amide)s. In: Lendlein A, Sisson A, editors. Handbook of biodegradable polymers. Weinheim: Wiley-VCH Verlag GmbH & Co. KGaA; 2011. p. 133–154.10.1002/9783527635818
   Google Scholar
• Rodríguez A, Rodríguez Y. Biodegradación de poliuretao mediante el uso del hongo Pestalotiopsis microspora [Polyurethane degradation using the mushroom Pestalotiopsis microspora] [ research]. Santander (CO): Instituto Universitario de la Paz; 2015.
   Google Scholar
• McBane JE, Sharifpoor S, Cai K, et al. Biodegradation and in vivo biocompatibility of a degradable, polar/hydrophobic/ionic polyurethane for tissue engineering applications. Biomaterials. 2011;32:6034–6044.10.1016/j.biomaterials.2011.04.048
   PubMed Web of Science ®Google Scholar
• da Silva GR, da Silva-Cunha Jr. A, Behar-Cohen F, et al. Biodegradation of polyurethanes and nanocomposites to non-cytotoxic degradation products. Polym. Degrad. Stab. 2010;95:491–499.10.1016/j.polymdegradstab.2010.01.001
   Web of Science ®Google Scholar
• Han J, Chen B, Ye L, et al. Synthesis and characterization of biodegradable polyurethane based on poly(e-caprolactone) and L-lysine ethyl ester diisocyanate. Front. Mater. Sci. Chin. 2009;3:25–32.10.1007/s11706-009-0013-4
   Google Scholar
• Sosnik A, Gotelli G. Aplicaciones de la tecnología de radiación de microondas en la síntesis de biomateriales [Technology applications of microwave radiation in the synthesis of biomaterials]. In: Coimbra University, editor. Biomateriales aplicados al diseño de sistemas terapéuticos avanzados. Argentina; 2015. p. 55.
   Google Scholar
• Vatankhah E, Semnani D, Prabhakaran MP, et al. Artificial neural network for modeling the elastic modulus of electrospun polycaprolactone/gelatin scaffolds. Acta Biomater. 2014;10:709–721.10.1016/j.actbio.2013.09.015
   PubMed Web of Science ®Google Scholar
• Larraza Í. Desarrollo de nuevas estrategias para la preparación de nanocomposites con propriedades antimicrobianas [Development of new strategies for the preparation of nanocomposites with antimicrobial properties] [dissertation]. Madrid (ES): Universidad Autónoma de Madrid; 2012.
   Google Scholar
• Wang Y, Yu Y, Zhang L, et al. One-step surface modification of polyurethane using affinity binding peptides for enhanced fouling resistance. J. Biomater. Sci. Polym. Ed. 2015;26:459–467.10.1080/09205063.2015.1023242
   PubMed Web of Science ®Google Scholar
• Han J, Cao R-W, Chen B, et al. Electrospinning and biocompatibility evaluation of biodegradable polyurethanes based on L-lysine diisocyanate and L-lysine chain extender. J. Biomed. Mater. Res. A. 2011;96A:705–714.10.1002/jbm.a.33023
   Web of Science ®Google Scholar
• Valero MF, Ortegón Y. Polyurethane elastomers-based modified castor oil and poly(e-caprolactone) for surface-coating applications: synthesis, characterization, and in vitro degradation. J. Elastomers. Plast. 2015;47:360–369.
   Web of Science ®Google Scholar
• Kanmani P, Rhim J-W. Physical, mechanical and antimicrobial properties of gelatin based active nanocomposite films containing AgNPs and nanoclay. Food Hydrocoll. 2014;35:644–652.
   Web of Science ®Google Scholar
• Pignatello R, Impallomeni G, Pistarà V, et al. New amphiphilic derivatives of poly(ethylene glycol) (PEG) as surface modifiers of colloidal drug carriers. III. Lipoamino acid conjugates with carboxy- and amino-PEG(5000) polymers. Mater. Sci. Eng. C. 2015;46:470–481.10.1016/j.msec.2014.10.054
   PubMed Web of Science ®Google Scholar
• Bakhshi H, Yeganeh H, Mehdipour-Ataei S. Synthesis and evaluation of antibacterial polyurethane coatings made from soybean oil functionalized with dimethylphenylammonium iodide and hydroxyl groups. J. Biomed. Mater. Res. A. 2013;101:1599–1611.
   PubMed Web of Science ®Google Scholar
• Han W, Tu M, Zeng R, et al. Preparation, characterization and cytocompatibility of polyurethane/cellulose based liquid crystal composite membranes. Carbohydr. Polym. 2012;90:1353–1361.10.1016/j.carbpol.2012.07.004
   PubMed Web of Science ®Google Scholar
• Calvo-Correas T, Santamaria-Echart A, Saralegi A, et al. Thermally-responsive biopolyurethanes from a biobased diisocyanate. Eur. Polym. J. 2015;70:173–185.10.1016/j.eurpolymj.2015.07.022
   Web of Science ®Google Scholar
• Guan J, Sacks MS, Beckman EJ, et al. Biodegradable poly(ether ester urethane)urea elastomers based on poly(ether ester) triblock copolymers and putrescine: synthesis, characterization and cytocompatibility. Biomaterials. 2004;25:85–96.10.1016/S0142-9612(03)00476-9
   PubMed Web of Science ®Google Scholar
• Kara F, Aksoy EA, Yuksekdag Z, et al. Synthesis and surface modification of polyurethanes with chitosan for antibacterial properties. Carbohydr. Polym. 2014;112:39–47.10.1016/j.carbpol.2014.05.019
   PubMed Web of Science ®Google Scholar
• Zhang C, Ding R, Kessler MR. Reduction of epoxidized vegetable oils: a novel method to prepare bio-based polyols for polyurethanes. Macromol. Raopid. Commun. 2014;35:1068–1074.
   PubMed Web of Science ®Google Scholar
• Yilgör E, Isik M, Söz CK, et al. Synthesis and structure-property behavior of polycaprolactone-polydimethylsiloxane-polycaprolactone triblock copolymers. Polymer. 2016;83:138–153.
   Web of Science ®Google Scholar
• Wu G-H, Hsu S. Synthesis of water-based cationic polyurethane for antibacterial and gene delivery applications. Colloids Surf. B. 2016;146:825–832.
   PubMed Web of Science ®Google Scholar
• Sivakumar PM, Cometa S, Alderighi M, et al. Chalcone embedded polyurethanes as a biomaterial: Synthesis, characterization and antibacterial adhesion. Carbohydr. Polym. 2012;87:353–360.
   Web of Science ®Google Scholar
• Hill MJ, Cheah C, Sarkar D. Interfacial energetics approach for analysis of endothelial cell and segmental polyurethane interactions. Colloids Surf. B. 2016;144:46–56.
   PubMed Web of Science ®Google Scholar
• Touchet TJ. Hierarchal structure–property relationships of segmented polyurethanes. In: Stuart L. Cooper, editor. Advances in Polyurethane Biomaterials. Dublin (IR); 2016. p. 3.
   Google Scholar
• Ibarboure E, Baron A, Papon E, et al. Self-assembly of graft polyurethanes having both crystallizable poly(ε-caprolactone) blocks and soft poly(n-butyl acrylate) segments. Thin. Solid. Films. 2009;517:3281–3286.
   Web of Science ®Google Scholar
• Valério A, Conti DS, Araújo PHH, et al. Synthesis of PEG-PCL-based polyurethane nanoparticles by miniemulsion polymerization. Colloids Surf. B. 2015;135:35–41.
   PubMed Web of Science ®Google Scholar
• Gogoi S, Barua S, Karak N. Biodegradable and thermostable synthetic hyperbranched poly(urethane-urea)s as advanced surface coating materials. Prog. Org. Coat. 2014;77:1418–1427.10.1016/j.porgcoat.2014.04.021
   Web of Science ®Google Scholar
• Chen Q, Liang S, Thouas GA. Elastomeric biomaterials for tissue engineering. Prog. Polym. Sci. 2013;38:584–671.
   Web of Science ®Google Scholar
• Spontón M, Casis N, Mazo P, et al. Biodegradation study by Pseudomonas sp. of flexible polyurethane foams derived from castor oil. Int. Biodeterior. Biodegrad. 2013;85:85–94.10.1016/j.ibiod.2013.05.019
   Web of Science ®Google Scholar
• Cherng JY, Hou TY, Shih MF, et al. Polyurethane-based drug delivery systems. Int. J. Pharm. 2013;450:145–162.10.1016/j.ijpharm.2013.04.063
   PubMed Web of Science ®Google Scholar
• Abedalwafa M, Wang F, Wang L, et al. Biodegradable poly-ε-caprolactone (PCL) for tissue engineering applications: a review. Rev. Adv. Mater. Sci. 2013;34:123–140.
   Web of Science ®Google Scholar
• Reddy TT, Kano A, Maruyama A, et al. Synthesis, characterization and drug release of biocompatible/biodegradable non-toxic poly(urethane urea)s based on poly(ε-caprolactone)s and lysine-based diisocyanate. J. Biomater. Sci. Polym. Ed. 2010;21:1483–1502.10.1163/092050609X12518804794785
   PubMed Web of Science ®Google Scholar
• Cauich-Rodríguez JV, Chan-Chan LH, Hernández-Sánchez F, et al. Degradation of polyurethanes for cardiovascular applications. In: Pignatello R, editor. Advances in biomaterials science and biomedical applications. Mexico: InTech; 2012. p. 51–82.
   Google Scholar
• Woźniak P, Bil M, Ryszkowska J, et al. Candidate bone-tissue-engineered product based on human-bone-derived cells and polyurethane scaffold. Acta Biomater. 2010;6:2484–2493.10.1016/j.actbio.2009.10.022
   PubMed Web of Science ®Google Scholar
• Ortegón Y. Síntesis, caracterización y análisis de la degradabilidad de adhesivos tipo poliuretano obtenidos a partir del aceite de higuerilla modificado [Synthesis, characterization and analysis of degradability type polyurethane adhesives obtained from the modified castor oil] [master’s thesis]. Chía: Universidad de La Sabana; 2014.
   Google Scholar
• Caixeta DS, Scarpa TH, Brugnera DF, et al. Chemical sanitizers to control biofilms formed by two Pseudomonas species on stainless steel surface. Ciência e Tecnol. Aliment. 2012;32:142–150.10.1590/S0101-20612012005000008
   Google Scholar
• Perales-Alcacio JL, Santa-Olalla Tapia J, Mojica-Cardoso C, et al. HUVEC biocompatibility and platelet activation of segmented polyurethanes prepared with either glutathione or its amino acids as chain extenders. J. Biomater. Sci. Polym. Ed. 2013;24:1601–1617.10.1080/09205063.2013.782804
   PubMed Web of Science ®Google Scholar
• Bakhshi H, Yeganeh H, Mehdipour-Ataei S, et al. Synthesis and characterization of antibacterial polyurethane coatings from quaternary ammonium salts functionalized soybean oil based polyols. Mater. Sci. Eng. C. 2013;33:153–164.10.1016/j.msec.2012.08.023
   PubMed Web of Science ®Google Scholar
• Domanska A, Boczkowska A. Biodegradable polyurethanes from crystalline prepolymers. Polym. Degrad. Stab. 2014;108:175–181.
   Web of Science ®Google Scholar
• Tijing LD, Ruelo MTG, Amarjargal A, et al. One-step fabrication of antibacterial (silver nanoparticles/poly(ethylene oxide)) - Polyurethane bicomponent hybrid nanofibrous mat by dual-spinneret electrospinning. Mater. Chem. Phys. 2012;134:557–561.10.1016/j.matchemphys.2012.03.037
   Web of Science ®Google Scholar
• Clauss M, Trampuz A, Borens O, et al. Biofilm formation on bone grafts and bone graft substitutes: comparison of different materials by a standard in vitro test and microcalorimetry. Acta Biomater. 2010;6:3791–3797.10.1016/j.actbio.2010.03.011
   PubMed Web of Science ®Google Scholar
• Francolini I, Piozzi A. 12 – Antimicrobial polyurethanes for intravascular medical devices. Adv. Polyurethane Biomater. 2016:349–385.
   Google Scholar
• Xue Y, Xiao H, Zhang Y. Antimicrobial polymeric materials with quaternary ammonium and phosphonium salts. Int. J. Mol. Sci. 2015;16:3626–3655.
   PubMed Web of Science ®Google Scholar