Modification of polycarbonateurethane surface with poly(ethylene glycol) monoacrylate and phosphorylcholine glyceraldehyde for anti-platelet adhesion

Jing YANG, Juan LV, Bin GAO, Li ZHANG, Dazhi YANG, Changcan SHI, Jintang GUO, Wenzhong LI, Yakai FENG

PDF(756 KB)
PDF(756 KB)
Front. Chem. Sci. Eng. ›› 2014, Vol. 8 ›› Issue (2) : 188-196. DOI: 10.1007/s11705-014-1414-1
RESEARCH ARTICLE
RESEARCH ARTICLE

Modification of polycarbonateurethane surface with poly(ethylene glycol) monoacrylate and phosphorylcholine glyceraldehyde for anti-platelet adhesion

Author information +
History +

Abstract

Poly(ethylene glycol) monoacrylate (PEGMA) is grafted onto polycarbonateurethane (PCU) surface via ultraviolet initiated photopolymerization. The hydroxyl groups of poly(PEGMA) on the surface react with one NCO group of isophorone diisocyanate (IPDI) and another NCO group of IPDI is then hydrolyzed to form amino terminal group, which is further grafted with phosphorylcholine glyceraldehyde to establish a biocompatible hydrophilic structure on the surface. Fourier transform infrared spectroscopy and X-ray photoelectron spectroscopy confirm the successful grafting of both PEG and phosphorylcholine functional groups on the surface. The decrease of the water contact angle for the modified film is caused by synergic effect of PEG and phosphorylcholine, which both have the high hydrophilicity. Furthermore, the number of platelets adhered is relative low on the synergetically modified PCU film compared with the PCU film modified only by poly(PEGMA). Our synergic modification method using both PEG and phosphorylcholine may be applied in surface modification of blood-contacting biomaterials and some relevant devices.

Keywords

poly(ethylene glycol) monoacrylate / phosphorylcholine / polycarbonateurethane / surface modification / anti-platelet adhesion / biomaterials

Cite this article

Download citation ▾
Jing YANG, Juan LV, Bin GAO, Li ZHANG, Dazhi YANG, Changcan SHI, Jintang GUO, Wenzhong LI, Yakai FENG. Modification of polycarbonateurethane surface with poly(ethylene glycol) monoacrylate and phosphorylcholine glyceraldehyde for anti-platelet adhesion. Front. Chem. Sci. Eng., 2014, 8(2): 188‒196 https://doi.org/10.1007/s11705-014-1414-1

References

[1]
KushwahaM, AndersonJ M, BosworthC A, AndukuriA, MinorW P, LancasterJ R J Jr, AndersonP G, BrottB C, JunH W. A nitric oxide releasing, self assembled peptide amphiphile matrix that mimics native endothelium for coating implantable cardiovascular devices. Biomaterials, 2010, 31(7): 1502–1508
CrossRef Google scholar
[2]
OkoshiT, SoldaniG, GoddardM, GallettiP M. Very small diameter polyurethane vascular prostheses with rapid endothelialization for coronary artery bypass grafting. Journal of Thoracic and Cardiovascular Surgery, 1993, 105(5): 791–795
[3]
IsenbergB C, WilliamsC, TranquilloR T. Small-diameter artificial arteries engineered in vitro. Circulation Research, 2006, 98(1): 25–35
CrossRef Google scholar
[4]
WangH Y, FengY K, BehlM, LendleinA, ZhaoH Y, XiaoR F, LuJ, ZhangL, GuoJ T. Hemocompatible PU/gelatin-heparin nanofibrous scaffolds as potential artificial blood vessels by bi-layer electrospinning technique. Frontiers of Chemical Science and Engineering, 2011, 5(3): 392–400
CrossRef Google scholar
[5]
FengY K, MengF R, XiaoR F, ZhaoH Y, GuoJ T. Electrospinning of polycarbonate urethane biomaterials. Frontiers of Chemical Science and Engineering, 2011, 5(1): 11–18
CrossRef Google scholar
[6]
FengY K, XueY, GuoJ T, ChengL, JiaoL C, ZhangL, YueJ L. Synthesis and characterization of poly(carbonate urethane) networks with shape-memory properties. Journal of Applied Polymer Science, 2009, 112(1): 473–478
CrossRef Google scholar
[7]
BehlM, RidderU, FengY K, KelchS, LendleinA. Shape-memory capability of binary multiblock copolymer blends with hard and switching domains provided by different components. Soft Matter, 2009, 5(3): 676–684
CrossRef Google scholar
[8]
GuoJ T, YinJ W, FengY K. Synthesis and characterization of HDI/MDI-polycarbonate urethanes. Transaction of Tianjin University, 2010, 16(5): 317–321
CrossRef Google scholar
[9]
HsuS H, KaoY C, LinZ C. Enhanced biocompatibility in biostable poly(carbonate)urethane. Macromolecular Bioscience, 2004, 19, 4(4): 464–470
[10]
SeifalianA M, SalacinskiH J, TiwariA, EdwardsA, BowaldS, HamiltonG. In vivo biostability of a poly(carbonate-urea)urethane graft. Biomaterials, 2003, 24(14): 2549–2557
CrossRef Google scholar
[11]
ChandyT, VanH J, NettekovenW, JohnsonJ. Long-term in vitro stability assessment of polycarbonate urethane micro catheters: resistance to oxidation and stress cracking. Journal of Biomedical Materials Research Part B: Applied Biomaterials, 2009, 89(2): 314–324
[12]
JohnB J, FurukawaM. Enhanced mechanical properties of polyamide 6 fibers coated with a polyurethane thin film. Polymer Engineering and Science, 2009, 49(10): 1970–1978
CrossRef Google scholar
[13]
AjiliS H, EbrahimiN G, KhorasaniM T. Study on thermoplastic polyurethane/polypropylene (TPU/PP) blend as a blood bag material. Journal of Applied Polymer Science, 2003, 89(9): 2496–2501
CrossRef Google scholar
[14]
FengY K, ZhangS F, WangH Y, ZhaoH Y, LuJ, GuoJ T, BehlM, LendleinA. Drug release from biodegradable polyesterurethanes with shape-memory effect. Journal of Controlled Release, 2011, 152(Suppl 1): e20–e21
CrossRef Google scholar
[15]
WeiY, JiY, XiaoL L, LinQ K, XuJ P, RenK F, JiJ. Surface engineering of cardiovascular stent with endothelial cell selectivity for in vivo re-endothelialisation. Biomaterials, 2013, 34(11): 2588–2599
CrossRef Google scholar
[16]
GuoJ T, FengY K, YeY Q, ZhaoH Y. Construction of hemocompatible polycarbonate urethane with sulfoammonium zwitterionic polyethylene glycol. Journal of Applied Polymer Science, 2011, 122(2): 1084–1091
CrossRef Google scholar
[17]
WuZ Q, ChenH, HuangH, ZhaoT L, LiuX L, LiD, YuQ. A facile approach to modify polyurethane surfaces for biomaterial applications. Macromolecular Bioscience, 2009, 9(12): 1165–1168
CrossRef Google scholar
[18]
LiJ, LinF, LiL D, LiJ, LiuS. Surface engineering of poly(ethylene terephthalate) for durable hemocompatibility via a surface interpenetrating network technique. Macromolecular Chemistry and Physics, 2012, 213(20): 2120–2129
CrossRef Google scholar
[19]
MelA D, JellG, StevensM M, SeifalianA M. Biofunctionalization of biomaterials for accelerated in situ endothelialization: A review. Biomacromolecules, 2008, 9(11): 2969–2979
CrossRef Google scholar
[20]
ZhuH G, JiJ, ShenJ C. Surface engineering of poly(DL-lactic acid) by entrapment of biomacromolecules. Macromolecular Rapid Communications, 2002, 23(14): 819–823
CrossRef Google scholar
[21]
KhanM, FengY K, YangD Z, ZhouW, TianH, HanY, ZhangL, YuanW J, ZhangJ, GuoJ T, ZhangW C. Biomimetic design of amphiphilic polycations and surface grafting onto polycarbonate urethane film as effective antibacterial agents with controlled hemocompatibility. Journal of Polymer Science. Part A, Polymer Chemistry, 2013, 51(15): 3166–3176
CrossRef Google scholar
[22]
GonçalvesaS, LeirósaA, KootenbT V, DouradoaF, RodriguesL R. Physicochemical and biological evaluation of poly(ethylene glycol) methacrylate grafted onto poly(dimethyl siloxane) surfaces for prosthetic devices. Colloids and Surfaces. B, Biointerfaces, 2013, 109(1): 228–235
CrossRef Google scholar
[23]
JiJ, FengL X, QiuY X, YuX J. Stearyl poly(ethylene oxide) grafted surface for preferential adsorption of part 2.The effect of the molecule mobility onto protein adsorption. Polymer, 2000, 41(10): 3713–3718
CrossRef Google scholar
[24]
SeongbongJ, KinamP. Surface modification using silanated poly(ethylene glycol)s. Biomaterials, 2000, 21(6): 605–616
[25]
WangH Y, FengY K, FangZ C, YuanW J, KhanM. Co-electrospun blends of PU and PEG as potential biocompatible scaffolds for small-diameter vascular tissue engineering. Materials Science and Engineering C, 2012, 32(8): 2306–2315
CrossRef Google scholar
[26]
ZhaoH Y, FengY K, GuoJ T. Grafting of poly(ethylene glycol) monoacrylate onto polycarbonateurethane surfaces by ultraviolet radiation grafting polymerization to control hydrophilicity. Journal of Applied Polymer Science, 2011, 119(6): 3717–3727
CrossRef Google scholar
[27]
YuanW J, FengY K, WangH Y, YangD Z, AnB, ZhangW C, KhanM, GuoJ T. Hemocompatible surface of electrospun nanofibrous scaffolds by ATRP modification. Materials Science and Engineering: C, 2013, 33(7): 3644–3651
[28]
PerttuaE K, SzokaF C. Zwitterionic sulfobetaine lipids that form vesicles with salt-dependent thermotropic properties. Chemical Communications, 2011, 47(47): 12613–12615
CrossRef Google scholar
[29]
FengY K, YangD Z, BehlM, LendleinA, ZhaoH Y, GuoJ T. The influence of zwitterionic phospholipid brushes grafted via UV-initiated or SI-ATR polymerization on the hemocompatibility of polycarbonateurethane. Macromolecular Symposia, 2011, 309–310(1): 6–15
CrossRef Google scholar
[30]
FengY K, YangD Z, ZhaoH Y, GuoJ T, ChenQ L, LiuJ S. Grafting sulfoammonium zwitterionic brushes onto polycarbonateurethane surface to improve hemocompatibility. Advanced Materials Research, 2011, 306–307: 1631–1634
CrossRef Google scholar
[31]
ShihY J, LaiC J, KungH H, JiangS Y. Blood-inert surfaces via ion-pair anchoring of zwitterionic copolymer brushes in human whole blood. Advanced Functional Materials, 2013, 23(9): 1100–1110
CrossRef Google scholar
[32]
ShihY J, ChangY. Tunable blood compatibility of polysulfobetaine from controllable molecular-weight dependence of zwitterionic nonfouling nature in aqueous solution. Langmuir, 2010, 26(22): 17286–17294
CrossRef Google scholar
[33]
WangM, YuanJ, HuangX, CaiX, LiL, ShenJ. Grafting of carboxybetaine brush onto cellulose membranes via surface-initiated ARGET-ATRP for improving blood compatibility. Colloids and Surfaces. B, Biointerfaces, 2013, 103: 52–58
CrossRef Google scholar
[34]
LiuG Y, HuX F, ChenC J, JiJ. Construct biomimetic giant vesicles via self-assembly of poly(2-methacryloyloxyethyl phosphorylcholine)- block-poly (D,L- lactide). Journal of Applied Polymer Science, 2010, 118(6): 3197–3202
CrossRef Google scholar
[35]
GaoB, FengY K, LuJ, ZhangL, ZhaoM, ShiC C, KhanM, GuoJ T. Grafting of phosphorylcholine functional groups on polycarbonate urethane surface for resisting platelet adhesion. Materials Science and Engineering C, 2013, 33(5): 2871–2878
CrossRef Google scholar
[36]
LuJ, FengY K, GaoB, GuoJ T. Preparation and characterization of phosphorylcholine glyceraldehyde grafted polycarbonateurethane films. Journal of Polymer Research, 2012, 19(9): 9959–9969
CrossRef Google scholar
[37]
GaoW, FengY K, LuJ, KhanM, GuoJ T. Biomimetic surface modification of polycarbonateurethane film via phosphorylcholine-graft for resisting platelet adhesion. Macromolecular Research, 2012, 20(10): 1063–1069
CrossRef Google scholar
[38]
TanM Q, FengY K, WangH Y, ZhangL, KhanM, GuoJ T, ChenQ L, LiuJ S. Immobilized bioactive agents onto polyurethane surface with heparin and phosphorylcholine group. Macromolecular Research, 2013, 21(5): 541–549
CrossRef Google scholar
[39]
LuJ, FengY K, GaoB, GuoJ T. Grafting of a novel phosphorylcholine-containing vinyl monomer onto polycarbonateurethane surfaces by ultraviolet radiation grafting polymerization. Macromolecular Research, 2012, 20(7): 693–702
CrossRef Google scholar
[40]
AlbrechtW, SeifertB, WeigelT, SchossigM, HolländerA, GrothT, HilkeR. Amination of poly(ether imide) membranes using di- and multivalent amines. Macromolecular Chemistry and Physics, 2003, 204(3): 510–521
CrossRef Google scholar
[41]
JiangH, WangX B, LiC Y, LiJ S, XuF J, MaoC, YangW T, ShenJ. Improvement of hemocompatibility of polycaprolactone film surfaces with zwitterionic polymer brushes. Langmuir, 2011, 27(18): 11575–11581
CrossRef Google scholar
[42]
LiD, ChenH, McClungW G, BrashJ L. Lysine-PEG-modified polyurethane as a fibrinolytic surface: Effect of PEG chain length on protein interactions, platelet interactions and clotlysis. Acta Biomaterialia, 2009, 5(6): 1864–1871
CrossRef Google scholar
[43]
FengY K, ZhaoH Y, BehlM, LendleinA, GuoJ T, YangD Z. Grafting of poly(ethylene glycol) monoacrylates on polycarbonateurethane by UV initiated polymerization for improving hemocompatibility. Journal of Materials Science. Materials in Medicine, 2013, 24(1): 61–70
CrossRef Google scholar
[44]
LomölderR, PlogmannF, SpeierP. Selectivity of isophorone diisocyanate in the urethane reaction influence of temperature, catalysis, and reaction partners. Journal of Coatings Technology, 1997, 69(868): 51–57
CrossRef Google scholar
[45]
MiyazawaK, WinnikF M, MiyazawaK, WinnikF O M. Solution properties of phosphorylcholine-based hydrophobically modified polybetaines in water and mixed solvents. Macromolecules, 2002, 35(25): 9536–9544
CrossRef Google scholar

Acknowledgements

This work has been financially supported by Ministry of Science and Technology of China (Grants No. 2013DFG52040 and 2008DFA51170), National Natural Science Foundation of China (Grant No. 31370969), and Ph.D. Programs Foundation of Ministry of Education of China (No. 20120032110073).

RIGHTS & PERMISSIONS

2014 Higher Education Press and Springer-Verlag Berlin Heidelberg
AI Summary AI Mindmap
PDF(756 KB)

Accesses

Citations

Detail

Sections
Recommended

/