Enzymatically Degradable Polyester-Based Adhesives

ACS Biomaterials Science and Engineering

Volumn 1, Issue 10, 2015, Pages 971-977

  Shi, Yinfeng ^a   Zhou, Peiran ^a   Jérôme, Valérie ^a   Freitag, Ruth ^a   Agarwal, Seema ^a  

^a UNIVERSITY OF BAYREUTH   (Germany)

Author keywords

biodegradable adhesive; catechol; radical polymerization; ring opening polymerization

Indexed keywords

2 METHYLENE 1,3 DIOXEPANE; ALKANE DERIVATIVE; CATECHOL; COPOLYMER; CROSS LINKING REAGENT; DOPA; GLYCIDYLMETHACRYLIC ACID; METAL; OLIGO(ETHYLENE GLYCOL)METHACRYLATE; POLYCAPROLACTONE; POLYESTER; POLYMETHACRYLIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; BIOCOMPATIBILITY; BIODEGRADABILITY; BIODEGRADATION; CONTROLLED STUDY; COVALENT BOND; CROSS LINKING; NONHUMAN; PH; POLYMERIZATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RADICAL REACTION; SHEAR STRENGTH; SOFT TISSUE; SYNTHESIS; THERMOSTABILITY; ULTRAVIOLET SPECTROSCOPY;

EID: 85006218264     PISSN: None     EISSN: 23739878     Source Type: Journal    
DOI: 10.1021/acsbiomaterials.5b00217     Document Type: Article

References (45)

1. Cognard, P. Equipment for the application of adhesives and sealants: mixing, metering, coating or applying the adhesives. In Handbook of Adhesives and Sealants; Philippe, C., Ed.; Elsevier Science: Maryland Heights, MO, 2006; Vol. 2, Chapter 2, pp 51-195.
2. Waite, J. H. Adhesion à la moule Integr. Comp. Biol. 2002, 42 (6) 1172-1180 10.1093/icb/42.6.1172
3. Lipatova, T. E. Medical polymer adhesives. In Biopolymers/Non-Exclusion HPLC; Springer Berlin: Heidelberg, 1986; Vol. 79, pp 65-93.
4. Moroni, L.; Elisseeff, J. H. Biomaterials engineered for integration Mater. Today 2008, 11 (5) 44-51 10.1016/S1369-7021(08)70089-0
5. Spotnitz, W. D.; Burks, S. Hemostats, sealants, and adhesives: components of the surgical toolbox Transfusion 2008, 48 (7) 1502-1516 10.1111/j.1537-2995.2008.01703.x
6. Liu, Y.; Ai, K.; Lu, L. Polydopamine and its derivative materials: synthesis and promising applications in energy, environmental, and biomedical fields Chem. Rev. 2014, 114 (9) 5057-5115 10.1021/cr400407a
7. Cencer, M.; Murley, M.; Liu, Y.; Lee, B. P. Effect of nitro-functionalization on the cross-linking and bioadhesion of biomimetic adhesive moiety Biomacromolecules 2015, 16 (1) 404-410 10.1021/bm5016333
8. Waite, J. H.; Tanzer, M. L. Polyphenolic substance of mytilus edulis: novel adhesive containing L-Dopa and hydroxyproline Science 1981, 212 (4498) 1038-1040 10.1126/science.212.4498.1038
9. Deming, T. J. Mussel byssus and biomolecular materials Curr. Opin. Chem. Biol. 1999, 3 (1) 100-105 10.1016/S1367-5931(99)80018-0
10. Holten-Andersen, N.; Harrington, M. J.; Birkedal, H.; Lee, B. P.; Messersmith, P. B.; Lee, K. Y. C.; Waite, J. H. pH-Induced metal-ligand cross-links inspired by mussel yield self-healing polymer networks with near-covalent elastic moduli Proc. Natl. Acad. Sci. U. S. A. 2011, 108 (7) 2651-2655 10.1073/pnas.1015862108
11. Harrington, M. J.; Masic, A.; Holten-Andersen, N.; Waite, J. H.; Fratzl, P. Iron-clad fibers: a metal-based biological strategy for hard flexible coatings Science 2010, 328 (5975) 216-220 10.1126/science.1181044
12. Ryu, J. H.; Lee, Y.; Kong, W. H.; Kim, T. G.; Park, T. G.; Lee, H. Catechol-functionalized chitosan/pluronic hydrogels for tissue adhesives and hemostatic materials Biomacromolecules 2011, 12 (7) 2653-2659 10.1021/bm200464x
13. Lee, H.; Scherer, N. F.; Messersmith, P. B. Single-molecule mechanics of mussel adhesion Proc. Natl. Acad. Sci. U. S. A. 2006, 103 (35) 12999-13003 10.1073/pnas.0605552103
14. Fan, X.; Lin, L.; Dalsin, J. L.; Messersmith, P. B. Biomimetic anchor for surface-initiated polymerization from metal substrates J. Am. Chem. Soc. 2005, 127 (45) 15843-15847 10.1021/ja0532638
15. Faure, E.; Falentin-Daudré, C.; Jérôme, C.; Lyskawa, J.; Fournier, D.; Woisel, P.; Detrembleur, C. Catechols as versatile platforms in polymer chemistry Prog. Polym. Sci. 2013, 38 (1) 236-270 10.1016/j.progpolymsci.2012.06.004
16. Burke, S. A.; Ritter-Jones, M.; Lee, B. P.; Messersmith, P. B. Thermal gelation and tissue adhesion of biomimetic hydrogels Biomed. Mater. 2007, 2 (4) 203-210 10.1088/1748-6041/2/4/001
17. Chung, H.; Grubbs, R. H. Rapidly cross-linkable DOPA containing terpolymer adhesives and PEG-based cross-linkers for biomedical applications Macromolecules 2012, 45 (24) 9666-9673 10.1021/ma3017986
18. Shao, H.; Bachus, K. N.; Stewart, R. J. A water-borne adhesive modeled after the sandcastle glue of P. californica Macromol. Biosci. 2009, 9 (5) 464-471 10.1002/mabi.200800252
19. Lee, B. P.; Chao, C.-Y.; Nunalee, F. N.; Motan, E.; Shull, K. R.; Messersmith, P. B. Rapid gel formation and adhesion in photocurable and biodegradable block copolymers with high DOPA content Macromolecules 2006, 39 (5) 1740-1748 10.1021/ma0518959
20. Matos-Pérez, C. R.; White, J. D.; Wilker, J. J. Polymer composition and substrate influences on the adhesive bonding of a biomimetic, cross-linking polymer J. Am. Chem. Soc. 2012, 134 (22) 9498-9505 10.1021/ja303369p
21. Huang, K.; Lee, B. P.; Ingram, D. R.; Messersmith, P. B. Synthesis and characterization of self-assembling block copolymers containing bioadhesive end groups Biomacromolecules 2002, 3 (2) 397-406 10.1021/bm015650p
22. Yang, J.; Cohen Stuart, M. A.; Kamperman, M. Jack of all trades: versatile catechol crosslinking mechanisms Chem. Soc. Rev. 2014, 43 (24) 8271-8298 10.1039/C4CS00185K
23. Yu, M.; Deming, T. J. Synthetic polypeptide mimics of marine adhesives Macromolecules 1998, 31 (15) 4739-4745 10.1021/ma980268z
24. Zhou, J.; Defante, A. P.; Lin, F.; Xu, Y.; Yu, J.; Gao, Y.; Childers, E.; Dhinojwala, A.; Becker, M. L. Adhesion properties of catechol-based biodegradable amino acid-based poly(ester urea) copolymers inspired from mussel proteins Biomacromolecules 2015, 16 (1) 266-274 10.1021/bm501456g
25. Murphy, J. L.; Vollenweider, L.; Xu, F.; Lee, B. P. Adhesive performance of biomimetic adhesive-coated biologic scaffolds Biomacromolecules 2010, 11 (11) 2976-2984 10.1021/bm1007794
26. Brubaker, C. E.; Messersmith, P. B. Enzymatically degradable mussel-inspired adhesive hydrogel Biomacromolecules 2011, 12 (12) 4326-4334 10.1021/bm201261d
27. Jin, S.; Gonsalves, K. E. Synthesis and characterization of functionalized poly(μ-caprolactone) copolymers by free-radical polymerization Macromolecules 1998, 31 (4) 1010-1015 10.1021/ma9707289
28. Bailey, W. J.; Ni, Z.; Wu, S.-R. Synthesis of poly-iu-caprolactone via a free radical mechanism. Free radical ring-opening polymerization of 2-methylene-1,3-dioxepane J. Polym. Sci., Polym. Chem. Ed. 1982, 20 (11) 3021-3030 10.1002/pol.1982.170201101
29. Agarwal, S. Chemistry, chances and limitations of the radical ring-opening polymerization of cyclic ketene acetals for the synthesis of degradable polyesters Polym. Chem. 2010, 1 (7) 953-964 10.1039/c0py00040j
30. Agarwal, S.; Naumann, N.; Xie, X. Synthesis and microstructural characterization of ethylene carbonate-μ-caprolactone/L-lactide copolymers using one- and two-dimensional NMR spectroscopy Macromolecules 2002, 35 (20) 7713-7717 10.1021/ma020584k
31. Agarwal, S.; Ren, L. Polycaprolactone-based novel degradable ionomers by radical ring-opening polymerization of 2-methylene-1,3-dioxepane Macromolecules 2009, 42 (5) 1574-1579 10.1021/ma802615f
32. Shi, Y.; Agarwal, S. Thermally stable opticaly transparent copolymers of 2-methylene-1,3-dioxepane and N-phenyl maleimide with degradable ester linkages e-Polym. 2015, 15 (4) 217-226 10.1515/epoly-2015-0096
33. Cai, T.; Chen, Y.; Wang, Y.; Wang, H.; Liu, X.; Jin, Q.; Agarwal, S.; Ji, J. Functional 2-methylene-1,3-dioxepane terpolymer: a versatile platform to construct biodegradable polymeric prodrugs for intracellular drug delivery Polym. Chem. 2014, 5 (13) 4061-4068 10.1039/C4PY00259H
34. Undin, J.; Finne-Wistrand, A.; Albertsson, A.-C. Adjustable degradation properties and biocompatibility of amorphous and functional poly(ester-acrylate)-based materials Biomacromolecules 2014, 15 (7) 2800-2807 10.1021/bm500689g
35. van Vlerken, L.; Vyas, T.; Amiji, M. Poly(ethylene glycol)-modified nanocarriers for tumor-targeted and intracellular delivery Pharm. Res. 2007, 24 (8) 1405-1414 10.1007/s11095-007-9284-6
36. Liu, G.; Jin, Q.; Liu, X.; Lv, L.; Chen, C.; Ji, J. Biocompatible vesicles based on PEO-b-PMPC/[small alpha]-cyclodextrin inclusion complexes for drug delivery Soft Matter 2011, 7 (2) 662-669 10.1039/C0SM00708K
37. Gasteier, P.; Reska, A.; Schulte, P.; Salber, J.; Offenhäusser, A.; Moeller, M.; Groll, J. Surface grafting of PEO-based star-shaped molecules for bioanalytical and biomedical applications Macromol. Biosci. 2007, 7 (8) 1010-1023 10.1002/mabi.200700064
38. 13C NMR spectroscopy Polymer 2001, 42 (8) 3393-3397 10.1016/S0032-3861(00)00253-6
39. Nanni, E. J.; Stallings, M. D.; Sawyer, D. T. Does superoxide ion oxidize catechol,.alpha.-tocopherol, and ascorbic acid by direct electron transfer? J. Am. Chem. Soc. 1980, 102 (13) 4481-4485 10.1021/ja00533a029
40. 2 in alkaline aqueous solutions containing Mg(II) ions Spectrosc. Lett. 1998, 31 (2) 327-333 10.1080/00387019808003257
41. 1 FEBS Lett. 1998, 436 (2) 293-299 10.1016/S0014-5793(98)01113-2
42. Liu, Y.; Meng, H.; Konst, S.; Sarmiento, R.; Rajachar, R.; Lee, B. P. Injectable dopamine-modified poly(ethylene glycol) nanocomposite hydrogel with enhanced adhesive property and bioactivity ACS Appl. Mater. Interfaces 2014, 6 (19) 16982-16992 10.1021/am504566v
43. Zhang, Z.; Kuijer, R.; Bulstra, S. K.; Grijpma, D. W.; Feijen, J. The in vivo and in vitro degradation behavior of poly(trimethylene carbonate) Biomaterials 2006, 27 (9) 1741-1748 10.1016/j.biomaterials.2005.09.017
44. Sun, L. F.; Zhuo, R. X.; Liu, Z. L. Synthesis and enzymatic degradation of 2-methylene-1,3-dioxepane and methyl acrylate copolymers J. Polym. Sci., Part A: Polym. Chem. 2003, 41 (18) 2898-2904 10.1002/pola.10868
45. Strehin, I.; Nahas, Z.; Arora, K.; Nguyen, T.; Elisseeff, J. A versatile pH sensitive chondroitin sulfate-PEG tissue adhesive and hydrogel Biomaterials 2010, 31 (10) 2788-2797 10.1016/j.biomaterials.2009.12.033