Facile Access to Multistimuli-Responsive Self-Assembled Block Copolymers via a Catechol/Boronic Acid Ligation

Macromolecules

Volumn 49, Issue 23, 2016, Pages 8925-8932

  Coumes, Fanny ^a   Woisel, Patrice ^a   Fournier, David ^a  

^a Ecole Nationale Superieure de Chimie de Lille   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REACTIONS; FLUORESCENCE; FLUORESCENCE SPECTROSCOPY; LIVING POLYMERIZATION; MOLECULES; SELF ASSEMBLY;

AMPHIPHILIC BLOCK COPOLYMERS; CHAIN TRANSFER AGENTS; COUPLING REACTION; FLUORESCENT PROBES; HYDROPHOBIC MOLECULES; MULTIRESPONSIVENESS; RAFT POLYMERIZATION; RELEASE PROFILES;

BLOCK COPOLYMERS;

EID: 85006264008     PISSN: 00249297     EISSN: 15205835     Source Type: Journal    
DOI: 10.1021/acs.macromol.6b01889     Document Type: Article

References (53)

1. Schattling, P.; Jochum, F. D.; Theato, P. Multi-stimuli responsive polymers-the all-in-one talents Polym. Chem. 2014, 5, 25-36 10.1039/C3PY00880K
2. Smith, A. E.; Xu, X.; McCormick, C. L. Stimuli-responsive amphiphilic (co)polymers via RAFT polymerization Prog. Polym. Sci. 2010, 35, 45-93 10.1016/j.progpolymsci.2009.11.005
3. Zhuang, J.; Gordon, M. R.; Ventura, J.; Li, L.; Thayumanavan, S. Multi-stimuli responsive macromolecules and their assemblies Chem. Soc. Rev. 2013, 42, 7421-7435 10.1039/c3cs60094g
4. Bawa, P.; Pillay, V.; Choonara, Y. E.; Du Toit, L. C. Stimuli-responsive polymers and their applications in drug delivery Biomed. Mater. 2009, 4, 022001 10.1088/1748-6041/4/2/022001
5. Puoci, F.; Iemma, F.; Picci, N. Stimuli-Responsive Molecularly Imprinted Polymers for Drug Delivery: A Review Curr. Drug Delivery 2008, 5, 85-96 10.2174/156720108783954888
6. Mura, S.; Nicolas, J.; Couvreur, P. Stimuli-responsive nanocarriers for drug delivery Nat. Mater. 2013, 12, 991-1003 10.1038/nmat3776
7. Alvarez-Lorenzo, C.; Concheiro, A. Smart Materials for Drug Delivery; Royal Society of Chemistry: 2013.
8. Stuart, M. A. C.; Huck, W. T. S.; Genzer, J.; Muller, M.; Ober, C.; Stamm, M.; Sukhorukov, G. B.; Szleifer, I.; Tsukruk, V. V.; Urban, M.; Winnik, F.; Zauscher, S.; Luzinov, I.; Minko, S. Emerging applications of stimuli-responsive polymer materials Nat. Mater. 2010, 9, 101-113 10.1038/nmat2614
9. Hu, J.; Meng, H.; Li, G.; Ibekwe, S. I. A review of stimuli-responsive polymers for smart textile applications Smart Mater. Struct. 2012, 21, 053001 10.1088/0964-1726/21/5/053001
10. Bury, K.; Neugebauer, D. Novel self-assembly graft copolymers as carriers for anti-inflammatory drug delivery Int. J. Pharm. 2014, 460, 150-157 10.1016/j.ijpharm.2013.10.051
11. Trubetskoy, V. S. Polymeric micelles as carriers of diagnostic agents Adv. Drug Delivery Rev. 1999, 37, 81-88 10.1016/S0169-409X(98)00100-8
12. Blanazs, A.; Armes, S. P.; Ryan, A. J. Self-Assembled Block Copolymer Aggregates: From Micelles to Vesicles and their Biological Applications Macromol. Rapid Commun. 2009, 30, 267-277 10.1002/marc.200800713
13. Gaucher, G.; Dufresne, M.-H.; Sant, V. P.; Kang, N.; Maysinger, D.; Leroux, J.-C. Block copolymer micelles: preparation, characterization and application in drug delivery J. Controlled Release 2005, 109, 169-188 10.1016/j.jconrel.2005.09.034
14. Rösler, A.; Vandermeulen, G. W. M.; Klok, H.-A. Advanced drug delivery devices via self-assembly of amphiphilic block copolymers Adv. Drug Delivery Rev. 2001, 53, 95-108 10.1016/S0169-409X(01)00222-8
15. Gohy, J.-F.; Lohmeijer, B. G. G.; Schubert, U. S. Metallo-Supramolecular Block Copolymer Micelles Macromolecules 2002, 35, 4560-4563 10.1021/ma012042t
16. Moughton, A. O.; O'Reilly, R. K. Using Metallo-Supramolecular Block Copolymers for the Synthesis of Higher Order Nanostructured Assemblies Macromol. Rapid Commun. 2010, 31, 37-52 10.1002/marc.200900496
17. Chiper, M.; Fournier, D.; Hoogenboom, R.; Schubert, U. S. Thermosensitive and Switchable Terpyridine-Functionalized Metallo-Supramolecular Poly(N-isopropylacrylamide) Macromol. Rapid Commun. 2008, 29, 1640-1647 10.1002/marc.200800339
18. Yan, Q.; Xin, Y.; Zhou, R.; Yin, Y.; Yuan, J. Light-controlled smart nanotubes based on the orthogonal assembly of two homopolymers Chem. Commun. 2011, 47, 9594-9596 10.1039/c1cc12644j
19. Sambe, L.; Stoffelbach, F.; Poltorak, K.; Lyskawa, J.; Malfait, A.; Bria, M.; Cooke, G.; Woisel, P. Elaboration of Thermoresponsive Supramolecular Diblock Copolymers in Water from Complementary CBPQT4+ and TTF End-Functionalized Polymers Macromol. Rapid Commun. 2014, 35, 498-504 10.1002/marc.201300729
20. Zou, J.; Guan, B.; Liao, X.; Jiang, M.; Tao, F. Dual Reversible Self-Assembly of PNIPAM-Based Amphiphiles Formed by Inclusion Complexation Macromolecules 2009, 42, 7465-7473 10.1021/ma901276c
21. Montarnal, D.; Delbosc, N.; Chamignon, C.; Virolleaud, M.-A.; Luo, Y.; Hawker, C. J.; Drockenmuller, E.; Bernard, J. Highly Ordered Nanoporous Films from Supramolecular Diblock Copolymers with Hydrogen-Bonding Junctions Angew. Chem., Int. Ed. 2015, 54, 11117-11121 10.1002/anie.201504838
22. Yang, X.; Hua, F.; Yamato, K.; Ruckenstein, E.; Gong, B.; Kim, W.; Ryu, C. Y. Supramolecular AB Diblock Copolymers Angew. Chem., Int. Ed. 2004, 43, 6471-6474 10.1002/anie.200460472
23. Takae, S.; Miyata, K.; Oba, M.; Ishii, T.; Nishiyama, N.; Itaka, K.; Yamasaki, Y.; Koyama, H.; Kataoka, K. PEG-Detachable Polyplex Micelles Based on Disulfide-Linked Block Catiomers as Bioresponsive Nonviral Gene Vectors J. Am. Chem. Soc. 2008, 130, 6001-6009 10.1021/ja800336v
24. Tang, L.-Y.; Wang, Y.-C.; Li, Y.; Du, J.-Z.; Wang, J. Shell-Detachable Micelles Based on Disulfide-Linked Block Copolymer As Potential Carrier for Intracellular Drug Delivery Bioconjugate Chem. 2009, 20, 1095-1099 10.1021/bc900144m
25. Khorsand Sourkohi, B.; Schmidt, R.; Oh, J. K. New Thiol-Responsive Mono-Cleavable Block Copolymer Micelles Labeled with Single Disulfides Macromol. Rapid Commun. 2011, 32, 1652-1657 10.1002/marc.201100372
26. Ko, N. R.; Yao, K.; Tang, C.; Oh, J. K. Synthesis and thiol-responsive degradation of polylactide-based block copolymers having disulfide junctions using ATRP and ROP J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 3071-3080 10.1002/pola.26335
27. Schumers, J.-M.; Gohy, J.-F.; Fustin, C.-A. A versatile strategy for the synthesis of block copolymers bearing a photocleavable junction Polym. Chem. 2010, 1, 161-163 10.1039/B9PY00218A
28. Zhao, H.; Sterner, E. S.; Coughlin, E. B.; Theato, P. o-Nitrobenzyl Alcohol Derivatives: Opportunities in Polymer and Materials Science Macromolecules 2012, 45, 1723-1736 10.1021/ma201924h
29. Kang, M.; Moon, B. Synthesis of Photocleavable Poly(styrene-block-ethylene oxide) and Its Self-Assembly into Nanoporous Thin Films Macromolecules 2009, 42, 455-458 10.1021/ma802434g
30. Yang, H.; Jia, L.; Wang, Z.; Di-Cicco, A.; Lévy, D.; Keller, P. Novel Photolabile Diblock Copolymers Bearing Truxillic Acid Derivative Junctions Macromolecules 2011, 44, 159-165 10.1021/ma1016264
31. Liu, Y.-L.; Chuo, T.-W. Self-healing polymers based on thermally reversible Diels-Alder chemistry Polym. Chem. 2013, 4, 2194-2205 10.1039/c2py20957h
32. Zhou, J.; Guimard, N. K.; Inglis, A. J.; Namazian, M.; Lin, C. Y.; Coote, M. L.; Spyrou, E.; Hilf, S.; Schmidt, F. G.; Barner-Kowollik, C. Thermally reversible Diels-Alder-based polymerization: an experimental and theoretical assessment Polym. Chem. 2012, 3, 628-639 10.1039/C1PY00356A
33. Scarano, W.; Duong, H. T. T.; Lu, H.; De Souza, P. L.; Stenzel, M. H. Folate Conjugation to Polymeric Micelles via Boronic Acid Ester to Deliver Platinum Drugs to Ovarian Cancer Cell Lines Biomacromolecules 2013, 14, 962-975 10.1021/bm400121q
34. Guo, Z.; Shin, I.; Yoon, J. Recognition and sensing of various species using boronic acid derivatives Chem. Commun. 2012, 48, 5956-5967 10.1039/c2cc31985c
35. Nishiyabu, R.; Kubo, Y.; James, T. D.; Fossey, J. S. Boronic acid building blocks: tools for sensing and separation Chem. Commun. 2011, 47, 1106-1123 10.1039/c0cc02920c
36. Scarano, W.; Lu, H.; Stenzel, M. H. Boronic acid ester with dopamine as a tool for bioconjugation and for visualization of cell apoptosis Chem. Commun. 2014, 50, 6390-6393 10.1039/c3cc49100e
37. Yang, W.; Gao, X.; Wang, B. Boronic acid compounds as potential pharmaceutical agents Med. Res. Rev. 2003, 23, 346-368 10.1002/med.10043
38. Cambre, J. N.; Sumerlin, B. S. Biomedical applications of boronic acid polymers Polymer 2011, 52, 4631-4643 10.1016/j.polymer.2011.07.057
39. Brooks, W. L. A.; Sumerlin, B. S. Synthesis and Applications of Boronic Acid-Containing Polymers: From Materials to Medicine Chem. Rev. 2016, 116, 1375-1397 10.1021/acs.chemrev.5b00300
40. Deng, C. C.; Brooks, W. L. A.; Abboud, K. A.; Sumerlin, B. S. Boronic Acid-Based Hydrogels Undergo Self-Healing at Neutral and Acidic pH ACS Macro Lett. 2015, 4, 220-224 10.1021/acsmacrolett.5b00018
41. Yang, B.; Lv, Y.; Zhu, J.-Y.; Han, Y.-T.; Jia, H.-Z.; Chen, W.-H.; Feng, J.; Zhang, X.-Z.; Zhuo, R.-X. A pH-responsive drug nanovehicle constructed by reversible attachment of cholesterol to PEGylated poly(l-lysine) via catechol-boronic acid ester formation Acta Biomater. 2014, 10, 3686-3695 10.1016/j.actbio.2014.05.018
42. 4 Nanoparticles J. Phys. Chem. C 2011, 115, 683-691 10.1021/jp1109306
43. Shafiq, Z.; Cui, J.; Pastor-Pérez, L.; San Miguel, V.; Gropeanu, R. A.; Serrano, C.; del Campo, A. Bioinspired Underwater Bonding and Debonding on Demand Angew. Chem., Int. Ed. 2012, 51, 4332-4335 10.1002/anie.201108629
44. Sedó, J.; Saiz-Poseu, J.; Busqué, F.; Ruiz-Molina, D. Catechol-Based Biomimetic Functional Materials Adv. Mater. 2013, 25, 653-701 10.1002/adma.201202343
45. Coumes, F.; Malfait, A.; Bria, M.; Lyskawa, J.; Woisel, P.; Fournier, D. Catechol/boronic acid chemistry for the creation of block copolymers with a multi-stimuli responsive junction Polym. Chem. 2016, 7, 4682-4692 10.1039/C6PY00738D
46. De, P.; Gondi, S. R.; Roy, D.; Sumerlin, B. S. Boronic Acid-Terminated Polymers: Synthesis by RAFT and Subsequent Supramolecular and Dynamic Covalent Self-Assembly Macromolecules 2009, 42, 5614-5621 10.1021/ma900835y
47. Springsteen, G.; Wang, B. Alizarin Red S. as a general optical reporter for studying the binding of boronic acids with carbohydrates Chem. Commun. 2001, 1608-1609 10.1039/b104895n
48. Tang, T.; Castelletto, V.; Parras, P.; Hamley, I. W.; King, S. M.; Roy, D.; Perrier, S.; Hoogenboom, R.; Schubert, U. S. Thermo-responsive Poly(methyl methacrylate)-b-poly(N-isopropylacrylamide) Block Copolymers Synthesized by RAFT Polymerization: Micellization and Gelation Macromol. Chem. Phys. 2006, 207, 1718-1726 10.1002/macp.200600309
49. Bull, S. D.; Davidson, M. G.; van den Elsen, J. M. H.; Fossey, J. S.; Jenkins, A. T. A.; Jiang, Y.-B.; Kubo, Y.; Marken, F.; Sakurai, K.; Zhao, J.; James, T. D. Exploiting the Reversible Covalent Bonding of Boronic Acids: Recognition, Sensing, and Assembly Acc. Chem. Res. 2013, 46, 312-326 10.1021/ar300130w
50. He, L.; Fullenkamp, D. E.; Rivera, J. G.; Messersmith, P. B. pH responsive self-healing hydrogels formed by boronate-catechol complexation Chem. Commun. 2011, 47, 7497-7499 10.1039/c1cc11928a
51. Su, J.; Chen, F.; Cryns, V. L.; Messersmith, P. B. Catechol Polymers for pH-Responsive, Targeted Drug Delivery to Cancer Cells J. Am. Chem. Soc. 2011, 133, 11850-11853 10.1021/ja203077x
52. Li, Y.; Xiao, W.; Xiao, K.; Berti, L.; Luo, J.; Tseng, H. P.; Fung, G.; Lam, K. S. Well-Defined, Reversible Boronate Crosslinked Nanocarriers for Targeted Drug Delivery in Response to Acidic pH Values and cis-Diols Angew. Chem. 2012, 124, 2918-2923 10.1002/ange.201107144
53. Wöll, D.; Walbert, S.; Stengele, K.-P.; Albert, T. J.; Richmond, T.; Norton, J.; Singer, M.; Green, R. D.; Pfleiderer, W.; Steiner, U. E. Triplet-Sensitized Photodeprotection of Oligonucleotides in Solution and on Microarray Chips Helv. Chim. Acta 2004, 87, 28-45 10.1002/hlca.200490015