Catechol Acetonide Glycidyl Ether (CAGE): A Functional Epoxide Monomer for Linear and Hyperbranched Multi-Catechol Functional Polyether Architectures

Macromolecules

Volumn 49, Issue 5, 2016, Pages 1655-1665

  Niederer, Kerstin ^a   Schüll, Christoph ^a   Leibig, Daniel ^a   Johann, Tobias ^a   Frey, Holger ^a  

^a JOHANNES GUTENBERG UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BIOCOMPATIBILITY; COPOLYMERIZATION; DENDRIMERS; ETHERS; ETHYLENE; HYDROPHILICITY; MONOMERS; NETWORK ARCHITECTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYETHYLENE GLYCOLS; POLYETHYLENE OXIDES; POLYMERS; POLYVINYL CHLORIDES;

ABA TRIBLOCK COPOLYMER; CROSS-LINKED NETWORKS; HYPERBRANCHED POLYGLYCEROL; METAL COMPLEXATION; METAL-LIGAND INTERACTIONS; MULTIPLE SURFACES; RANDOM COPOLYMERIZATION; SURFACE ATTACHMENT;

PHENOLS;

EID: 84960458485     PISSN: 00249297     EISSN: 15205835     Source Type: Journal    
DOI: 10.1021/acs.macromol.5b02441     Document Type: Article

References (55)

1. 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
2. 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
3. Yu, M. E.; Hwang, J. Y.; Deming, T. J. Role of L-3,4-dihydroxyphenylalanine in mussel adhesive proteins J. Am. Chem. Soc. 1999, 121 (24) 5825-5826 10.1021/ja990469y
4. Ye, Q.; Zhou, F.; Liu, W. Bioinspired catecholic chemistry for surface modification Chem. Soc. Rev. 2011, 40 (7) 4244-4258 10.1039/c1cs15026j
5. 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
6. Lee, H.; Dellatore, S. M.; Miller, W. M.; Messersmith, P. B. Mussel-inspired surface chemistry for multifunctional coatings Science 2007, 318 (5849) 426-430 10.1126/science.1147241
7. Lee, H.; Lee, K. D.; Pyo, K. B.; Park, S. Y.; Lee, H. Catechol-grafted poly(ethylene glycol) for PEGylation on versatile substrates Langmuir 2010, 26 (6) 3790-3793 10.1021/la904909h
8. Sedó, J.; Saiz-Poseu, J.; Busqué, F.; Ruiz-Molina, D. Catechol-Based Biomimetic Functional Materials Adv. Mater. 2013, 25 (5) 653-701 10.1002/adma.201202343
9. Madhurakkat Perikamana, S. K.; Lee, J.; Lee, Y. B.; Shin, Y. M.; Lee, E. J.; Mikos, A. G.; Shin, H. Materials from Mussel-Inspired Chemistry for Cell and Tissue Engineering Applications Biomacromolecules 2015, 16 (9) 2541-2555 10.1021/acs.biomac.5b00852
10. Patil, N.; Falentin-Daudré, C.; Jérôme, C.; Detrembleur, C. Mussel-inspired protein-repelling ambivalent block copolymers: controlled synthesis and characterization Polym. Chem. 2015, 6 (15) 2919-2933 10.1039/C5PY00127G
11. 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
12. Dang, Y.; Quan, M.; Xing, C.-M.; Wang, Y.-B.; Gong, Y.-K. Biocompatible and antifouling coating of cell membrane phosphorylcholine and mussel catechol modified multi-arm PEGs J. Mater. Chem. B 2015, 3 (11) 2350-2361 10.1039/C4TB02140A
13. Barrett, D. G.; Fullenkamp, D. E.; He, L.; Holten-Andersen, N.; Lee, K. Y.; Messersmith, P. B. pH-Based Regulation of Hydrogel Mechanical Properties Through Mussel-Inspired Chemistry and Processing Adv. Funct. Mater. 2013, 23 (9) 1111-1119 10.1002/adfm.201201922
14. Holten-Andersen, N.; Harrington, M. J.; Birkedal, H.; Lee, B. P.; Messersmith, P. B.; Lee, K. Y.; 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
15. Krogsgaard, M.; Behrens, M. A.; Pedersen, J. S.; Birkedal, H. Self-healing mussel-inspired multi-pH-responsive hydrogels Biomacromolecules 2013, 14 (2) 297-301 10.1021/bm301844u
16. Kim, B. J.; Oh, D. X.; Kim, S.; Seo, J. H.; Hwang, D. S.; Masic, A.; Han, D. K.; Cha, H. J. Mussel-mimetic protein-based adhesive hydrogel Biomacromolecules 2014, 15 (5) 1579-1585 10.1021/bm4017308
17. Lee, B. P.; Dalsin, J. L.; Messersmith, P. B. Synthesis and Gelation of DOPA-Modified Poly(ethylene glycol) Hydrogels Biomacromolecules 2002, 3 (5) 1038-1044 10.1021/bm025546n
18. 4 Nanoparticles Macromol. Rapid Commun. 2010, 31 (18) 1608-1615 10.1002/marc.201000193
19. Wilms, V. S.; Bauer, H.; Tonhauser, C.; Schilmann, A. M.; Muller, M. C.; Tremel, W.; Frey, H. Catechol-initiated polyethers: multifunctional hydrophilic ligands for PEGylation and functionalization of metal oxide nanoparticles Biomacromolecules 2013, 14 (1) 193-199 10.1021/bm3015889
20. Thomas, A.; Bauer, H.; Schilmann, A.-M.; Fischer, K.; Tremel, W.; Frey, H. The "Needle in the Haystack" Makes the Difference: Linear and Hyperbranched Polyglycerols with a Single Catechol Moiety for Metal Oxide Nanoparticle Coating Macromolecules 2014, 47 (14) 4557-4566 10.1021/ma5003672
21. Chung, H.; Glass, P.; Pothen, J. M.; Sitti, M.; Washburn, N. R. Enhanced adhesion of dopamine methacrylamide elastomers via viscoelasticity tuning Biomacromolecules 2011, 12 (2) 342-347 10.1021/bm101076e
22. White, E. M.; Seppala, J. E.; Rushworth, P. M.; Ritchie, B. W.; Sharma, S.; Locklin, J. Switching the Adhesive State of Catecholic Hydrogels using Phototitration Macromolecules 2013, 46 (22) 8882-8887 10.1021/ma401594z
23. Xu, H.; Nishida, J.; Ma, W.; Wu, H.; Kobayashi, M.; Otsuka, H.; Takahara, A. Competition between Oxidation and Coordination in Cross-Linking of Polystyrene Copolymer Containing Catechol Groups ACS Macro Lett. 2012, 1 (4) 457-460 10.1021/mz200217d
24. Black, K. C. L.; Liu, Z.; Messersmith, P. B. Catechol Redox Induced Formation of Metal Core-Polymer Shell Nanoparticles Chem. Mater. 2011, 23 (5) 1130-1135 10.1021/cm1024487
25. Preuss, C. M.; Zieger, M. M.; Rodriguez-Emmenegger, C.; Zydziak, N.; Trouillet, V.; Goldmann, A. S.; Barner-Kowollik, C. Fusing Catechol-Driven Surface Anchoring with Rapid Hetero Diels-Alder Ligation ACS Macro Lett. 2014, 3, 1169-1173 10.1021/mz5006469
26. Mattson, K. M.; Latimer, A. A.; McGrath, A. J.; Lynd, N. A.; Lundberg, P.; Hudson, Z. M.; Hawker, C. J. A facile synthesis of catechol-functionalized poly(ethylene oxide) block and random copolymers J. Polym. Sci., Part A: Polym. Chem. 2015, 53 (23) 2685-2692 10.1002/pola.27749
27. 4) Nanoparticles via Trichloro-s-triazine Chem. Mater. 2006, 18 (23) 5401-5403 10.1021/cm061793c
28. Wei, Q.; Becherer, T.; Mutihac, R. C.; Noeske, P. L.; Paulus, F.; Haag, R.; Grunwald, I. Multivalent anchoring and cross-linking of mussel-inspired antifouling surface coatings Biomacromolecules 2014, 15 (8) 3061-3071 10.1021/bm500673u
29. Wei, Q.; Becherer, T.; Noeske, P. L.; Grunwald, I.; Haag, R. A universal approach to crosslinked hierarchical polymer multilayers as stable and highly effective antifouling coatings Adv. Mater. 2014, 26 (17) 2688-2693 10.1002/adma.201304737
30. Wei, Q.; Krysiak, S.; Achazi, K.; Becherer, T.; Noeske, P. L.; Paulus, F.; Liebe, H.; Grunwald, I.; Dernedde, J.; Hartwig, A.; Hugel, T.; Haag, R. Multivalent anchored and crosslinked hyperbranched polyglycerol monolayers as antifouling coating for titanium oxide surfaces Colloids Surf., B 2014, 122, 684-692 10.1016/j.colsurfb.2014.08.001
31. Wei, Q.; Achazi, K.; Liebe, H.; Schulz, A.; Noeske, P. L.; Grunwald, I.; Haag, R. Mussel-inspired dendritic polymers as universal multifunctional coatings Angew. Chem., Int. Ed. 2014, 53 (43) 11650-11655 10.1002/anie.201407113
32. Bailey, F. E. J.; Koleske, J. V. Poly(ethylene oxide); Academic Press: 1976.
33. Herzberger, J.; Niederer, K.; Pohlit, H.; Seiwert, J.; Worm, M.; Wurm, F. R.; Frey, H. Polymerization of Ethylene Oxide, Propylene Oxide, and Other Alkylene Oxides: Synthesis, Novel Polymer Architectures, and Bioconjugation Chem. Rev. 2015, 10.1021/acs.chemrev.5b00441
34. Veronese, F. M.; Pasut, G. PEGylation, successful approach to drug delivery Drug Discovery Today 2005, 10 (21) 1451-1458 10.1016/S1359-6446(05)03575-0
35. Alconcel, S. N. S.; Baas, A. S.; Maynard, H. D. FDA-approved poly(ethylene glycol)-protein conjugate drugs Polym. Chem. 2011, 2 (7) 1442-1448 10.1039/c1py00034a
36. Thompson, M. S.; Vadala, T. P.; Vadala, M. L.; Lin, Y.; Riffle, J. S. Synthesis and applications of heterobifunctional poly(ethylene oxide) oligomers Polymer 2008, 49 (2) 345-373 10.1016/j.polymer.2007.10.029
37. Mangold, C.; Wurm, F.; Frey, H. Functional PEG-based polymers with reactive groups via anionic ROP of tailor-made epoxides Polym. Chem. 2012, 3 (7) 1714-1721 10.1039/c2py00489e
38. Obermeier, B.; Wurm, F.; Mangold, C.; Frey, H. Multifunctional Poly(ethylene glycol)s Angew. Chem., Int. Ed. 2011, 50 (35) 7988-7997 10.1002/anie.201100027
39. Podsiadlo, P.; Liu, Z.; Paterson, D.; Messersmith, P. B.; Kotov, N. A. Fusion of Seashell Nacre and Marine Bioadhesive Analogs: High-Strength Nanocomposite by Layer-by-Layer Assembly of Clay and L-3,4-Dihydroxyphenylalanine Polymer Adv. Mater. 2007, 19 (7) 949-955 10.1002/adma.200602706
40. Haller, C. M.; Buerzle, W.; Brubaker, C. E.; Messersmith, P. B.; Mazza, E.; Ochsenbein-Koelble, N.; Zimmermann, R.; Ehrbar, M. Mussel-mimetic tissue adhesive for fetal membrane repair: a standardized ex vivo evaluation using elastomeric membranes Prenatal Diagn. 2011, 31 (7) 654-660 10.1002/pd.2712
41. Kainthan, R. K.; Janzen, J.; Levin, E.; Devine, D. V.; Brooks, D. E. Biocompatibility Testing of Branched and Linear Polyglycidol Biomacromolecules 2006, 7 (3) 703-709 10.1021/bm0504882
42. Imran ul-haq, M.; Lai, B. F.; Chapanian, R.; Kizhakkedathu, J. N. Influence of architecture of high molecular weight linear and branched polyglycerols on their biocompatibility and biodistribution Biomaterials 2012, 33 (35) 9135-9147 10.1016/j.biomaterials.2012.09.007
43. Kainthan, R. K.; Hester, S. R.; Levin, E.; Devine, D. V.; Brooks, D. E. In vitro biological evaluation of high molecular weight hyperbranched polyglycerols Biomaterials 2007, 28 (31) 4581-4590 10.1016/j.biomaterials.2007.07.011
44. Lange, M.; Braune, S.; Luetzow, K.; Richau, K.; Scharnagl, N.; Weinhart, M.; Neffe, A. T.; Jung, F.; Haag, R.; Lendlein, A. Surface Functionalization of Poly(ether imide) Membranes with Linear, Methylated Oligoglycerols for Reducing Thrombogenicity Macromol. Rapid Commun. 2012, 33 (17) 1487-1492 10.1002/marc.201200426
45. First conference presentation of the CAGE structure: Niederer, K.; Schüll, C.; Johann, T.; Frey, H. at MACROMEX 2014, Nuevo Vallarta, Mexico, 2014.
46. In a recent thesis, synthesis and polymerization of the CAGE monomer has also been targeted: Shin, E.; Kim, B.-S. Mussel-inspired Polyglycerol: Synthesis and Versatile Surface Modification. Master Thesis, Ulsan National Institute of Science and Technology, 2015.
47. Mangold, C.; Dingels, C.; Obermeier, B.; Frey, H.; Wurm, F. PEG-based Multifunctional Polyethers with Highly Reactive Vinyl-Ether Side Chains for Click-Type Functionalization Macromolecules 2011, 44 (16) 6326-6334 10.1021/ma200898n
48. Tonhauser, C.; Alkan, A.; Schömer, M.; Dingels, C.; Ritz, S.; Mailänder, V.; Frey, H.; Wurm, F. R. Ferrocenyl Glycidyl Ether: A Versatile Ferrocene Monomer for Copolymerization with Ethylene Oxide to Water-Soluble, Thermoresponsive Copolymers Macromolecules 2013, 46 (3) 647-655 10.1021/ma302241w
49. Obermeier, B.; Wurm, F.; Frey, H. Amino Functional Poly(ethylene glycol) Copolymers via Protected Amino Glycidol Macromolecules 2010, 43 (5) 2244-2251 10.1021/ma902245d
50. Mangold, C.; Wurm, F.; Obermeier, B.; Frey, H. Functional Poly(ethylene glycol)": PEG-Based Random Copolymers with 1,2-Diol Side Chains and Terminal Amino Functionality Macromolecules 2010, 43 (20) 8511-8518 10.1021/ma1015352
51. Fineman, M.; Ross, S. D. Linear method for determining monomer reactivity ratios in copolymerization J. Polym. Sci. 1950, 5 (2) 259-262 10.1002/pol.1950.120050210
52. Sunder, A.; Hanselmann, R.; Frey, H.; Mülhaupt, R. Controlled Synthesis of Hyperbranched Polyglycerols by Ring-Opening Multibranching Polymerization Macromolecules 1999, 32 (13) 4240-4246 10.1021/ma990090w
53. Avdeef, A.; Sofen, S. R.; Bregante, T. L.; Raymond, K. N. Coordination chemistry of microbial iron transport compounds. 9. Stability constants for catechol models of enterobactin J. Am. Chem. Soc. 1978, 100 (17) 5362-5370 10.1021/ja00485a018
54. Wu, W.; Wu, J.; Kim, J. H.; Lee, N. Y. Instantaneous room temperature bonding of a wide range of non-silicon substrates with poly(dimethylsiloxane) (PDMS) elastomer mediated by a mercaptosilane Lab Chip 2015, 15 (13) 2819-2825 10.1039/C5LC00285K
55. Tong, W. L.; Tan, M. K.; Chin, J. K.; Ong, K. S.; Hung, Y. M. Coupled effects of hydrophobic layer and vibration on thermal efficiency of two-phase closed thermosyphons RSC Adv. 2015, 5 (14) 10332-10340 10.1039/C4RA14589E