Cascading "triclick" functionalization of poly(caprolactone) thin films quantified via a quartz crystal microbalance

Biomacromolecules

Volumn 14, Issue 8, 2013, Pages 2857-2865

  Lin, Fei ^a   Zheng, Jukuan ^a   Yu, Jiayi ^a   Zhou, Jinjun ^a   Becker, Matthew L ^a,b  

^a University of Akron   (United States)

^b Austen BioInnovation Institute in Akron   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COPOLYMER COMPOSITIONS; FUNCTIONALIZATIONS; MICHAEL ADDITIONS; MULTI-FUNCTIONALIZED; POLYMER THIN FILMS; STATIC CONTACT ANGLE; SURFACE CONJUGATION; SURFACE FUNCTIONALIZATION;

ADDITION REACTIONS; CONTACT ANGLE; HYDROCARBONS; KETONES; PEPTIDES; POLYMER FILMS; QUARTZ CRYSTAL MICROBALANCES; SURFACES; THIN FILMS;

POLYMERS;

2 OXEPANE 1,5 DIONE; ACRYLIC ACID METHYL ESTER; ALKYNE; ARGINYLGLYCYLASPARTIC ACID; AZIDE; COPOLYMER; FUNCTIONAL GROUP; KETONE; OXEPANE DERIVATIVE; POLYCAPROLACTONE; UNCLASSIFIED DRUG; ARGINYL-GLYCYL-ASPARTIC ACID; BIOMATERIAL; IMMOBILIZED PROTEIN; OLIGOPEPTIDE; POLYESTER;

ARTICLE; CLICK CHEMISTRY; CONJUGATION; CONTACT ANGLE; CONTROLLED STUDY; CORRELATION ANALYSIS; CYCLOADDITION; FILM; MICHAEL ADDITION; PRIORITY JOURNAL; QUARTZ CRYSTAL MICROBALANCE; SYNTHESIS; CHEMISTRY; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SURFACE PROPERTY;

BIOCOMPATIBLE MATERIALS; CLICK CHEMISTRY; CYCLOADDITION REACTION; IMMOBILIZED PROTEINS; MAGNETIC RESONANCE SPECTROSCOPY; OLIGOPEPTIDES; POLYESTERS; QUARTZ CRYSTAL MICROBALANCE TECHNIQUES; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; SURFACE PROPERTIES;

EID: 84881594251     PISSN: 15257797     EISSN: 15264602     Source Type: Journal    
DOI: 10.1021/bm400711q     Document Type: Article

References (55)

1. Yoshimoto, H.; Shin, Y. M.; Terai, H.; Vacanti, J. P. Biomaterials 2003, 24, 2077-2082
2. Coombes, A. G. A.; Rizzi, S. C.; Williamson, M.; Barralet, J. E.; Downes, S.; Wallace, W. A. Biomaterials 2004, 25, 315-325
3. Rapoport, N. Prog. Polym. Sci. 2007, 32, 962-990
4. Lou, C.-W.; Yao, C.-H.; Chen, Y.-S.; Hsieh, T.-C.; Lin, J.-H.; Hsing, W.-H. Text. Res. J. 2008, 78, 958-965
5. Lecomte, P.; Riva, R.; Schmeits, S.; Rieger, J.; Van Butsele, K.; Jéroîme, C.; Jéroîme, R. Macromol. Symp. 2006, 240, 157-165
6. Wang, R.; Chen, W.; Meng, F.; Cheng, R.; Deng, C.; Feijen, J.; Zhong, Z. Macromolecules 2011, 44, 6009-6016
7. Riva, R.; Schmeits, S.; Stoffelbach, F.; Jerome, C.; Jerome, R.; Lecomte, P. Chem. Commun. 2005, 5334-5336
8. Taniguchi, I.; Mayes, A. M.; Chan, E. W. L.; Griffith, L. G. Macromolecules 2004, 38, 216-219
9. Tempelaar, S.; Mespouille, L.; Dubois, P.; Dove, A. P. Macromolecules 2011, 44, 2084-2091
10. Onbulak, S.; Tempelaar, S.; Pounder, R. J.; Gok, O.; Sanyal, R.; Dove, A. P.; Sanyal, A. Macromolecules 2012, 45, 1715-1722
11. Ji, S.; Bruchmann, B.; Klok, H.-A. Macromolecules 2011, 44, 5218-5226
12. Van Horn, B. A.; Wooley, K. L. Soft Matter 2007, 3, 1032-1040
13. Zhang, S.; Li, A.; Zou, J.; Lin, L. Y.; Wooley, K. L. ACS Macro Lett. 2012, 1, 328-333
14. Tseng, Y. Y.; Li, W.-H. Proc. Natl Acad. Sci. U.S.A. 2012, 109, 1170-1175
15. Christman, K. L.; Maynard, H. D. Langmuir 2005, 21, 8389-9393
16. Lempens, E. M.; Helms, B.; Merkx, M. In Bioconjugation Protocols; Mark, S. S., Ed.; Humana Press: New York, 2011; Vol. 751, pp 401-420.
17. Costa, F.; Carvalho, I. F.; Montelaro, R. C.; Gomes, P.; Martins, M. C. L. Acta Biomater. 2011, 7, 1431-1440
18. Gevrek, T. N.; Ozdeslik, R. N.; Sahin, G. S.; Yesilbag, G.; Mutlu, S.; Sanyal, A. Macromol. Chem. Phys. 2012, 213, 166-172
19. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004-2021
20. Iha, R. K.; Wooley, K. L.; Nystrom, A. M.; Burke, D. J.; Kade, M. J.; Hawker, C. J. Chem. Rev. 2009, 109, 5620-5686
21. Hoyle, C. E.; Bowman, C. N. Angew. Chem., Int. Ed. 2010, 49, 1540-1573
22. Mather, B. D.; Viswanathan, K.; Miller, K. M.; Long, T. E. Prog. Polym. Sci. 2006, 31, 487-531
23. Dirksen, A.; Hackeng, T. M.; Dawson, P. E. Angew. Chem., Int. Ed. 2006, 45, 7581-7584
24. Spruell, J. M.; Wolffs, M.; Leibfarth, F. A.; Stahl, B. C.; Heo, J.; Connal, L. A.; Hu, J.; Hawker, C. J. J. Am. Chem. Soc. 2011, 133, 16698-16706
25. Leibfarth, F. A.; Kang, M.; Ham, M.; Kim, J.; Campos, L. M.; Gupta, N.; Moon, B.; Hawker, C. J. Nat. Chem. 2010, 2, 207-212
26. Zheng, J.; Liu, K.; Reneker, D. H.; Becker, M. L. J. Am. Chem. Soc. 2012, 134, 17274-17277
27. Inglis, A. J.; Barner-Kowollik, C. Macromol. Rapid Commun. 2010, 31, 1247-1226
28. Debets, M. F.; van der Doelen, C. W. J.; Rutjes, F. P. J. T.; van Delft, F. L. ChemBioChem 2010, 11, 1168-1184
29. Sletten, E. M.; Bertozzi, C. R. Angew. Chem., Int. Ed. 2009, 48, 6974-6998
30. Baskin, J. M.; Prescher, J. A.; Laughlin, S. T.; Agard, N. J.; Chang, P. V.; Miller, I. A.; Lo, A.; Codelli, J. A.; Bertozzi, C. R. Proc. Natl Acad. Sci. U.S.A. 2007, 104, 16793-16797
31. Zheng, J.; Smith Callahan, L. A.; Hao, J.; Guo, K.; Wesdemiotis, C.; Weiss, R. A.; Becker, M. L. ACS Macro Lett. 2012, 1, 1071-1013
32. Ma, Y.; Zheng, J.; Amond, E. F.; Stafford, C. M.; Becker, M. L. Biomacromolecules 2013, 14, 665-671
33. Prime, E. L.; Hamid, Z. A. A.; Cooper-White, J. J.; Qiao, G. G. Biomacromolecules 2007, 8, 2416-2421
34. Deng, X.; Friedmann, C.; Lahann, J. Angew. Chem., Int. Ed. 2011, 50, 6522-6526
35. Parrish, B.; Breitenkamp, R. B.; Emrick, T. J. Am. Chem. Soc. 2005, 127, 7404-7410
36. Tian, D.; Dubois, P.; Jéroîme, R. Macromolecules 1997, 30, 2575-2581
37. Tian, D.; Dubois, P.; Grandfils, C.; Jéroîme, R. Macromolecules 1997, 30, 406-409
38. Latere Dwan'Isa, J.-P.; Lecomte, P.; Dubois, P.; Jéroîme, R. Macromolecules 2003, 36, 2609-2615
39. Latere, J.-P.; Lecomte, P.; Dubois, P.; Jéroîme, R. Macromolecules 2002, 35, 7857-7859
40. Dwan'Isa, J.-P. L.; Lecomte, P.; Dubois, P.; Jéroîme, R. Macromol. Chem. Phys. 2003, 204, 1191-1201
41. Grover, G. N.; Lam, J.; Nguyen, T. H.; Segura, T.; Maynard, H. D. Biomacromolecules 2012, 13, 3013-3017
42. Ossipov, D. A.; Yang, X.; Varghese, O.; Kootala, S.; Hilborn, J. Chem. Commun. 2010, 46, 8368-8370
43. Sauerbrey, G. Z. Phys. 1959, 155, 206-222
44. Pierschbacher, M. D.; Ruoslahti, E. Nature 1984, 309, 30-33
45. Gallant, N. D.; Lavery, K. A.; Amis, E. J.; Becker, M. L. Adv. Mater. 2007, 19, 965-969
46. Acharya, A. P.; Dolgova, N. V.; Moore, N. M.; Xia, C.-Q.; Clare-Salzler, M. J.; Becker, M. L.; Gallant, N. D.; Keselowsky, B. G. Biomaterials 2010, 31, 7444-7454
47. Shu, J. Y.; Panganiban, B.; Xu, T. Annu. Rev. Phys. Chem. 2013, 64, 631-657
48. Orelma, H.; Teerinen, T.; Johansson, L.-S.; Holappa, S.; Laine, J. Biomacromolecules 2012, 13, 1051-1058
49. Montañez, M. I.; Hed, Y.; Utsel, S.; Ropponen, J.; Malmström, E.; WaÌŠgberg, L.; Hult, A.; Malkoch, M. Biomacromolecules 2011, 12, 2114-2125
50. Zhang, Y.; Luo, S.; Tang, Y.; Yu, L.; Hou, K.-Y.; Cheng, J.-P.; Zeng, X.; Wang, P. G. Anal. Chem. 2006, 78, 2001-2008
51. Worrell, B. T.; Malik, J. A.; Fokin, V. V. Science 2013, 340, 457-460
52. Debets, M. F.; van Berkel, S. S.; Dommerholt, J.; Dirks, A. J.; Rutjes, F. P. J. T.; van Delft, F. L. Acc. Chem. Res. 2011, 44, 805-815
53. Elbert, D. L.; Hubbell, J. A. Biomacromolecules 2001, 2, 430-441
54. Lutolf, M. P.; Tirelli, N.; Cerritelli, S.; Cavalli, L.; Hubbell, J. A. Bioconjugate Chem. 2001, 12, 1051-1056
55. Ermakova, T.; Kuznetsova, N.; Tatarova, L.; Lopyrev, V. Russ. J. Gen. Chem. 2007, 77, 132-134