Self-Assembled Amphiphilic Macromolecule Coatings: Comparison of Grafting-From and Grafting-To Approaches for Bioactive Delivery

Langmuir

Volumn 32, Issue 20, 2016, Pages 5038-5047

  Chan, Jennifer W ^a   Huang, Amy ^b   Uhrich, Kathryn E ^a,b  

^a RUTGERS UNIVERSITY   (United States)

^b RUTGERS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADHESION; BIOACTIVITY; COATINGS; COORDINATION REACTIONS; HYDROPHILICITY; HYDROPHOBICITY; MACROMOLECULES; PLATELETS; POLYETHYLENE GLYCOLS; STAINLESS STEEL; STENTS;

AMPHIPHILIC MACROMOLECULES; ANTI-PLATELET ACTIVITIES; CARBODIIMIDE COUPLINGS; FUNCTIONAL END GROUPS; GRAFTING FROM METHOD; HYDROPHOBIC AND HYDROPHILIC; SURFACE FUNCTIONALIZATION; THERAPEUTIC DELIVERY;

GRAFTING (CHEMICAL);

BIOCOMPATIBLE COATED MATERIAL; DRUG CARRIER; MACROGOL DERIVATIVE;

ADSORPTION; CELL PROLIFERATION; CHEMICAL PHENOMENA; CHEMISTRY; COMPARATIVE STUDY; CYTOLOGY; DRUG EFFECT; HUMAN; SMOOTH MUSCLE CELL; THROMBOCYTE ADHESION;

ADSORPTION; CELL PROLIFERATION; COATED MATERIALS, BIOCOMPATIBLE; DRUG CARRIERS; HUMANS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; MYOCYTES, SMOOTH MUSCLE; PLATELET ADHESIVENESS; POLYETHYLENE GLYCOLS;

EID: 84971254921     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/acs.langmuir.6b00524     Document Type: Article

References (54)

1. Alcantar, N. A.; Aydil, E. S.; Israelachvili, J. N. Polyethylene glycol-coated biocompatible surfaces J. Biomed. Mater. Res. 2000, 51 (3) 343-51 10.1002/1097-4636(20000905)51:3<343::AID-JBM7>3.0.CO;2-D
2. Gawalt, E. S.; Avaltroni, M. J.; Danahy, M. P.; Silverman, B. M.; Hanson, E. L.; Midwood, K. S.; Schwarzbauer, J. E.; Schwartz, J. Bonding organics to Ti alloys: Facilitating human osteoblast attachment and spreading on surgical implant materials Langmuir 2003, 19 (1) 200-204 10.1021/la0203436
3. Kingshott, P.; Thissen, H.; Griesser, H. J. Effects of cloud-point grafting, chain length, and density of PEG layers on competitive adsorption of ocular proteins Biomaterials 2002, 23 (9) 2043-2056 10.1016/S0142-9612(01)00334-9
4. Love, J. C.; Estroff, L. A.; Kriebel, J. K.; Nuzzo, R. G.; Whitesides, G. M. Self-assembled monolayers of thiolates on metals as a form of nanotechnology Chem. Rev. 2005, 105 (4) 1103-1170 10.1021/cr0300789
5. Henze, M.; Mädge, D.; Prucker, O.; Rühe, J. Grafting Through": Mechanistic Aspects of Radical Polymerization Reactions with Surface-Attached Monomers Macromolecules 2014, 47 (9) 2929-2937 10.1021/ma402607d
6. Tugulu, S.; Klok, H.-A. Stability and Nonfouling Properties of Poly(poly(ethylene glycol) methacrylate) Brushes under Cell Culture Conditions Biomacromolecules 2008, 9 (3) 906-912 10.1021/bm701293g
7. Popelka, Š.; Houska, M.; Havlíková, J.; Proks, V.; Kučka, J.; Šturcová, A.; Bačáková, L.; Rypáček, F. Poly(ethylene oxide) brushes prepared by the "grafting to" method as a platform for the assessment of cell receptor-ligand binding Eur. Polym. J. 2014, 58, 11-22 10.1016/j.eurpolymj.2014.06.004
8. Zdyrko, B.; Luzinov, I. Polymer brushes by the "grafting to" method Macromol. Rapid Commun. 2011, 32 (12) 859-69 10.1002/marc.201100162
9. Minko, S. Grafting on Solid Surfaces: "Grafting to" and "Grafting from" Methods. In Polymer Surfaces and Interfaces; Stamm, M., Ed.; Springer: Berlin, 2008; pp 215-234.
10. Bielecki, R.; Doll, P.; Spencer, N. Ultrathin, Oil-Compatible, Lubricious Polymer Coatings: A Comparison of Grafting-To and Grafting-From Strategies Tribol. Lett. 2013, 49 (1) 273-280 10.1007/s11249-012-0065-y
11. Basuki, J. S.; Esser, L.; Zetterlund, P. B.; Whittaker, M. R.; Boyer, C.; Davis, T. P. Grafting of P(OEGA) Onto Magnetic Nanoparticles Using Cu(0) Mediated Polymerization: Comparing Grafting "from" and "to" Approaches in the Search for the Optimal Material Design of Nanoparticle MRI Contrast Agents Macromolecules 2013, 46 (15) 6038-6047 10.1021/ma401250f
12. Acharya, G.; Park, K. Mechanisms of controlled drug release from drug-eluting stents Adv. Drug Delivery Rev. 2006, 58 (3) 387-401 10.1016/j.addr.2006.01.016
13. Akin, I.; Schneider, H.; Ince, H.; Kische, S.; Rehders, T. C.; Chatterjee, T.; Nienaber, C. A. Second- and third-generation drug-eluting coronary stents: progress and safety Herz 2011, 36 (3) 190-6 10.1007/s00059-011-3458-z
14. Inoue, T.; Croce, K.; Morooka, T.; Sakuma, M.; Node, K.; Simon, D. I. Vascular inflammation and repair implications for re-endothelialization, restenosis, and stent thrombosis JACC: Cardiovascular Interventions 2011, 4 (10) 1057-1066 10.1016/j.jcin.2011.05.025
15. Otsuka, Y.; Chronos, N.; Apkarian, R. P.; Robinson, K. A. Scanning electron microscopic analysis of defects in polymer coatings of three commercially available stents: Comparison of BiodivYsio, Taxus and Cypher stents J. Invasive Cardiol. 2007, 19 (2) 71-76
16. Virmani, R.; Guagliumi, G.; Farb, A.; Musumeci, G.; Grieco, N.; Motta, T.; Mihalcsik, L.; Tespili, M.; Valsecchi, O.; Kolodgie, F. D. Localized hypersensitivity and late coronary thrombosis secondary to a sirolimus-eluting stent: Should we be cautious? Circulation 2004, 109 (6) 701-705 10.1161/01.CIR.0000116202.41966.D4
17. Chan, J. W.; Zhang, Y.; Uhrich, K. E. Amphiphilic Macromolecule Self-Assembled Monolayers Suppress Smooth Muscle Cell Proliferation Bioconjugate Chem. 2015, 26 (7) 1359-1369 10.1021/acs.bioconjchem.5b00208
18. Chan, J. W.; Lewis, D. R.; Petersen, L. K.; Moghe, P. V.; Uhrich, K. E. Amphiphilic macromolecule nanoassemblies suppress smooth muscle cell proliferation and platelet adhesion Biomaterials 2016, 84, 219-229 10.1016/j.biomaterials.2015.12.033
19. Chnari, E.; Lari, H. B.; Tian, L.; Uhrich, K. E.; Moghe, P. V. Nanoscale anionic macromolecules for selective retention of low-density lipoproteins Biomaterials 2005, 26 (17) 3749-58 10.1016/j.biomaterials.2004.09.038
20. Tian, L.; Yam, L.; Zhou, N.; Tat, H.; Uhrich, K. E. Amphiphilic Scorpion-like Macromolecules: Design, Synthesis, and Characterization Macromolecules 2004, 37 (2) 538-543 10.1021/ma030411a
21. Sparks, S. M. Design, synthesis, and utility of fuctionalized nanoscale amphiphilic macromolecules for biomedical applications. Thesis. Rutgers University, 2011, (Department of Chemistry and Chemical Biology).
22. Djordjevic, J.; Del Rosario, L. S.; Jinzhong, W.; Uhrich, K. E. Amphiphilic Scorpion-like Macromolecules as Micellar Nanocarriers J. Bioact. Compat. Polym. 2008, 23 (6) 532-551 10.1177/0883911508097498
23. Hanson, E. L.; Schwartz, J.; Nickel, B.; Koch, N.; Danisman, M. F. Bonding self-assembled, compact organophosphonate monolayers to the native oxide surface of silicon J. Am. Chem. Soc. 2003, 125 (51) 16074-16080 10.1021/ja035956z
24. Palik, E. D. Handbook of Optical Constants of Solids; Academic Press: 1998; Vol. 3.
25. Sofia, S. J.; Premnath, V.; Merrill, E. W. Poly(ethylene oxide) grafted to silicon surfaces: Grafting density and protein adsorption Macromolecules 1998, 31 (15) 5059-5070 10.1021/ma971016l
26. Saxer, S.; Portmann, C.; Tosatti, S.; Gademann, K.; Zürcher, S.; Textor, M. Surface assembly of catechol-functionalized poly(l-lysine)-graft-poly(ethylene glycol) copolymer on titanium exploiting combined electrostatically driven self-organization and biomimetic strong adhesion Macromolecules 2010, 43 (2) 1050-1060 10.1021/ma9020664
27. Tian, L.; Yam, L.; Zhou, N.; Tat, H.; Uhrich, K. E. Amphiphilic scorpion-like macromolecules: Design, synthesis, and characterization Macromolecules 2003, 37 (2) 538-543 10.1021/ma030411a
28. Cattani-Scholz, A.; Pedone, D.; Dubey, M.; Neppl, S.; Nickel, B.; Feulner, P.; Schwartz, J.; Abstreiter, G.; Tornow, M. Organophosphonate-Based PNA-Functionalization of Silicon Nanowires for Label-Free DNA Detection ACS Nano 2008, 2 (8) 1653-1660 10.1021/nn800136e
29. Zhu, B.; Eurell, T.; Gunawan, R.; Leckband, D. Chain-length dependence of the protein and cell resistance of oligo(ethylene glycol)-terminated self-assembled monolayers on gold J. Biomed. Mater. Res. 2001, 56 (3) 406-416 10.1002/1097-4636(20010905)56:3<406::AID-JBM1110>3.0.CO;2-R
30. Malisova, B.; Tosatti, S.; Textor, M.; Gademann, K.; Zürcher, S. Poly(ethylene glycol) adlayers immobilized to metal oxide substrates through catechol derivatives: Influence of assembly conditions on formation and stability Langmuir 2010, 26 (6) 4018-4026 10.1021/la903486z
31. Gnauck, M.; Jaehne, E.; Blaettler, T.; Tosatti, S.; Textor, M.; Adler, H.-J. P. Carboxy-terminated oligo(ethylene glycol)-alkane phosphate: Synthesis and self-assembly on titanium oxide surfaces Langmuir 2007, 23 (2) 377-381 10.1021/la0606648
32. Lomoschitz, C. J.; Feichtenschlager, B.; Moszner, N.; Puchberger, M.; Müller, K.; Abele, M.; Kickelbick, G. Directing Alkyl Chain Ordering of Functional Phosphorus Coupling Agents on ZrO2 Langmuir 2011, 27 (7) 3534-3540 10.1021/la104527b
33. Kenausis, G. L.; Vörös, J.; Elbert, D. L.; Huang, N.; Hofer, R.; Ruiz-Taylor, L.; Textor, M.; Hubbell, J. A.; Spencer, N. D. Poly(l-lysine)-g-Poly(ethylene glycol) Layers on Metal Oxide Surfaces: Attachment Mechanism and Effects of Polymer Architecture on Resistance to Protein Adsorption J. Phys. Chem. B 2000, 104 (14) 3298-3309 10.1021/jp993359m
34. Spori, D. M.; Venkataraman, N. V.; Tosatti, S. G.; Durmaz, F.; Spencer, N. D.; Zürcher, S. Influence of alkyl chain length on phosphate self-assembled monolayers Langmuir 2007, 23 (15) 8053-8060 10.1021/la700474v
35. Choudhary, S.; Haberstroh, K. M.; Webster, T. J. Enhanced functions of vascular cells on nanostructured Ti for improved stent applications Tissue Eng. 2007, 13 (7) 1421-1430 10.1089/ten.2006.0376
36. Zorn, G.; Gotman, I.; Gutmanas, E.; Adadi, R.; Salitra, G.; Sukenik, C. Surface modification of Ti45Nb alloy with an alkylphosphonic acid self-assembled monolayer Chem. Mater. 2005, 17 (16) 4218-4226 10.1021/cm050477f
37. Schwartz, D. K. Mechanisms and kinetics of self-assembled monolayer formation Annu. Rev. Phys. Chem. 2001, 52 (1) 107-137 10.1146/annurev.physchem.52.1.107
38. Raynor, J. E.; Capadona, J. R.; Collard, D. M.; Petrie, T. A.; García, A. J. Polymer brushes and self-assembled monolayers: Versatile platforms to control cell adhesion to biomaterials (Review) Biointerphases 2009, 4 (2) FA3-FA16 10.1116/1.3089252
39. Abizaid, A.; Costa, J. R. New Drug-Eluting Stents: An Overview on Biodegradable and Polymer-Free Next-Generation Stent Systems Circ.: Cardiovasc. Interventions 2010, 3 (4) 384-393 10.1161/CIRCINTERVENTIONS.109.891192
40. Gouzman, I.; Dubey, M.; Carolus, M. D.; Schwartz, J.; Bernasek, S. L. Monolayer vs. multilayer self-assembled alkylphosphonate films: X-ray photoelectron spectroscopy studies Surf. Sci. 2006, 600 (4) 773-781 10.1016/j.susc.2005.11.030
41. Kaufmann, C. R.; Mani, G.; Marton, D.; Johnson, D. M.; Agrawal, C. M. Long-term stability of self-assembled monolayers on 316L stainless steel Biomed. Mater. 2010, 5 (2) 025008 10.1088/1748-6041/5/2/025008
42. Mani, G.; Johnson, D. M.; Marton, D.; Dougherty, V. L.; Feldman, M. D.; Patel, D.; Ayon, A. A.; Agrawal, C. M. Stability of self-assembled monolayers on titanium and gold Langmuir 2008, 24 (13) 6774-6784 10.1021/la8003646
43. Thissen, P.; Valtiner, M.; Grundmeier, G. Stability of phosphonic acid self-assembled monolayers on amorphous and single-crystalline aluminum oxide surfaces in aqueous solution Langmuir 2009, 26 (1) 156-164 10.1021/la900935s
44. Faig, A.; Petersen, L. K.; Moghe, P. V.; Uhrich, K. E. Impact of Hydrophobic Chain Composition on Amphiphilic Macromolecule Antiatherogenic Bioactivity Biomacromolecules 2014, 15 (9) 3328-3337 10.1021/bm500809f
45. Kenagy, R. Biology of Restenosis and Targets for Intervention. In Mechanisms of Vascular Disease, 1 st ed.; Fitridge, R.; Thompson, M., Eds.; University of Adelaide Bar Smith Press: 2011; pp 115-151.
46. Ren, Y.; Yang, K.; Zhang, B. In vitro study of platelet adhesion on medical nickel-free stainless steel surface Mater. Lett. 2005, 59 (14-15) 1785-1789 10.1016/j.matlet.2005.01.067
47. Thierry, B.; Merhi, Y.; Bilodeau, L.; Trépanier, C.; Tabrizian, M. Nitinol versus stainless steel stents: acute thrombogenicity study in an ex vivo porcine model Biomaterials 2002, 23 (14) 2997-3005 10.1016/S0142-9612(02)00030-3
48. Monnink, S. H.; van Boven, A. J.; Peels, H. O.; Tigchelaar, I.; de Kam, P. J.; Crijns, H. J.; van Oeveren, W. Silicon-carbide coated coronary stents have low platelet and leukocyte adhesion during platelet activation J. Invest. Med. 1999, 47 (6) 304-310
49. Amiji, M.; Park, K. Prevention of protein adsorption and platelet adhesion on surfaces by PEO/PPO/PEO triblock copolymers Biomaterials 1992, 13 (10) 682-692 10.1016/0142-9612(92)90128-B
50. Gölander, C. G.; Herron, J.; Lim, K.; Claesson, P.; Stenius, P.; Andrade, J. D. Properties of immobilized PEG films and the interaction with proteins. In Poly(ethylene glycol) Chemistry; Harris, J. M., Ed.; Springer: New York, 1992; pp 221-245.
51. Deible, C. R.; Petrosko, P.; Johnson, P. C.; Beckman, E. J.; Russell, A. J.; Wagner, W. R. Molecular barriers to biomaterial thrombosis by modification of surface proteins with polyethylene glycol Biomaterials 1998, 19 (20) 1885-1893 10.1016/S0142-9612(98)00098-2
52. Michel, R.; Pasche, S.; Textor, M.; Castner, D. G. Influence of PEG Architecture on Protein Adsorption and Conformation Langmuir 2005, 21 (26) 12327-12332 10.1021/la051726h
53. Bozzini, S.; Petrini, P.; Tanzi, M. C.; Zürcher, S.; Tosatti, S. Poly(ethylene glycol) and Hydroxy Functionalized Alkane Phosphate Mixed Self-Assembled Monolayers to Control Nonspecific Adsorption of Proteins on Titanium Oxide Surfaces Langmuir 2010, 26 (9) 6529-6534 10.1021/la904066y
54. Chatterjee, S. Role of oxidized human plasma low density lipoproteins in atherosclerosis: Effects on smooth muscle cell proliferation Mol. Cell. Biochem. 1992, 111 (1-2) 143-147 10.1007/BF00229586