Interplay between Molecular Packing, Drug Loading, and Core Cross-Linking in Bottlebrush Copolymer Micelles

Macromolecules

Volumn 50, Issue 4, 2017, Pages 1342-1352

  Unsal, Hande ^a,b   Onbulak, Sebla ^a   Calik, Filiz ^c   Er Rafik, Meriem ^d   Schmutz, Marc ^d   Sanyal, Amitav ^c   Rzayev, Javid ^a  

^a UNIVERSITY AT BUFFALO   (United States)

^b HACETTEPE UNIVERSITY   (Turkey)

^c BOGAZICI UNIVERSITY   (Turkey)

^d UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BLOCK COPOLYMERS; CHAINS; CROSSLINKING; EFFICIENCY; ETHYLENE; GRAFTING (CHEMICAL); HYDROPHILICITY; MATERIALS PROPERTIES; MICELLES; POLYETHYLENE OXIDES;

AMPHIPHILIC CO-POLYMERS; COPOLYMER MICELLES; GRAFTING FROM METHOD; HYDROPHILIC HEADGROUPS; LOADING EFFICIENCY; MOLECULAR PACKINGS; POLYMER ARCHITECTURE; STRUCTURAL REARRANGEMENT;

LOADING;

EID: 85014085887     PISSN: 00249297     EISSN: 15205835     Source Type: Journal    
DOI: 10.1021/acs.macromol.6b02182     Document Type: Article

References (61)

1. Forster, S.; Antonietti, M. Amphiphilic block copolymers in structure-controlled nanomaterial hybrids Adv. Mater. 1998, 10, 195 10.1002/(SICI)1521-4095(199802)10:3<195::AID-ADMA195>3.0.CO;2-V
2. Lindman, B.; Alexandridis, P. Amphiphilic Block Copolymers: Self-Assembly and Applications, 1st ed.; Elsevier: Amsterdam, 2000; p 435.
3. Riess, G. Micellization of block copolymers Prog. Polym. Sci. 2003, 28, 1107-1170 10.1016/S0079-6700(03)00015-7
4. Gomez-Escudero, A.; Azagarsamy, M. A.; Theddu, N.; Vachet, R. W.; Thayumanavan, S. Selective peptide binding using facially amphiphilic dendrimers J. Am. Chem. Soc. 2008, 130, 11156-11163 10.1021/ja803082v
5. Gu, D.; Ladewig, K.; Klimak, M.; Haylock, D.; McLean, K. M.; O’Connor, A. J.; Qiao, G. G. Amphiphilic core cross-linked star polymers as water-soluble, biocompatible and biodegradable unimolecular carriers for hydrophobic drugs Polym. Chem. 2015, 6, 6475-6487 10.1039/C5PY00655D
6. Li, Y.; Zou, J.; Das, B. P.; Tsianou, M.; Cheng, C. Well-Defined Amphiphilic Double-Brush Copolymers and Their Performance as Emulsion Surfactants Macromolecules 2012, 45, 4623-4629 10.1021/ma300565j
7. Pang, X.; Zhao, L.; Akinc, M.; Kim, J. K.; Lin, Z. Novel Amphiphilic Multi-Arm, Star-Like Block Copolymers as Unimolecular Micelles Macromolecules 2011, 44, 3746-3752 10.1021/ma200594j
8. Percec, V.; Dulcey, A. E.; Balagurusamy, V. S. K.; Miura, Y.; Smidrkal, J.; Peterca, M.; Nummelin, S.; Edlund, U.; Hudson, S. D.; Heiney, P. A.; Duan, H.; Magonov, S. N.; Vinogradov, S. A. Self-assembly of amphiphilic dendritic dipeptides into helical pores Nature 2004, 430, 764-768 10.1038/nature02770
9. Sunder, A.; Kramer, M.; Hanselmann, R.; Mulhaupt, R.; Frey, H. Molecular nanocapsules based on amphiphilic hyperbranched polyglycerols Angew. Chem., Int. Ed. 1999, 38, 3552-3555 10.1002/(SICI)1521-3773(19991203)38:23<3552::AID-ANIE3552>3.3.CO;2-7
10. Yesilyurt, V.; Ramireddy, R.; Thayumanavan, S. Photoregulated Release of Noncovalent Guests from Dendritic Amphiphilic Nanocontainers Angew. Chem., Int. Ed. 2011, 50, 3038-3042 10.1002/anie.201006193
11. Luo, H.; Raciti, D.; Wang, C.; Herrera-Alonso, M. Macromolecular Brushes as Stabilizers of Hydrophobic Solute Nanoparticles Mol. Pharmaceutics 2016, 13, 1855-1865 10.1021/acs.molpharmaceut.6b00019
12. Luo, H.; Santos, J. L.; Herrera-Alonso, M. Toroidal structures from brush amphiphiles Chem. Commun. 2014, 50, 536-538 10.1039/C3CC46834H
13. Garofalo, C.; Capuano, G.; Sottile, R.; Tallerico, R.; Adami, R.; Reverchon, E.; Carbone, E.; Izzo, L.; Pappalardo, D. Different Insight into Amphiphilic PEG-PLA Copolymers: Influence of Macromolecular Architecture on the Micelle Formation and Cellular Uptake Biomacromolecules 2014, 15, 403-415 10.1021/bm401812r
14. Aguilar-Castillo, B. A.; Santos, J. L.; Luo, H.; Aguirre-Chagala, Y. E.; Palacios-Hernandez, T.; Herrera-Alonso, M. Nanoparticle stability in biologically relevant media: influence of polymer architecture Soft Matter 2015, 11, 7296-7307 10.1039/C5SM01455G
15. Sant, S.; Poulin, S.; Hildgen, P. Effect of polymer architecture on surface properties, plasma protein adsorption, and cellular interactions of pegylated nanoparticles J. Biomed. Mater. Res., Part A 2008, 87A, 885-895 10.1002/jbm.a.31800
16. 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
17. Adams, M. L.; Lavasanifar, A.; Kwon, G. S. Amphiphilic block copolymers for drug delivery J. Pharm. Sci. 2003, 92, 1343-1355 10.1002/jps.10397
18. Duncan, R.; Ringsdorf, H.; Satchi-Fainaro, R. Polymer therapeutics: Polymers as drugs, drug and protein conjugates and gene delivery systems: Past, present and future opportunities. In Polymer Therapeutics I: Polymers as Drugs, Conjugates and Gene Delivery Systems, 2006; Vol. 192, pp 1-8.
19. Torchilin, V. P. Micellar nanocarriers: Pharmaceutical perspectives Pharm. Res. 2006, 24, 1-16 10.1007/s11095-006-9132-0
20. Nicolas, J.; Mura, S.; Brambilla, D.; Mackiewicz, N.; Couvreur, P. Design, functionalization strategies and biomedical applications of targeted biodegradable/biocompatible polymer-based nanocarriers for drug delivery Chem. Soc. Rev. 2013, 42, 1147-1235 10.1039/C2CS35265F
21. 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
22. Xiao, R. Z.; Zeng, Z. W.; Zhou, G. L.; Wang, J. J.; Li, F. Z.; Wang, A. M. Recent advances in PEG-PLA block copolymer nanoparticles Int. J. Nanomed. 2010, 5, 1057-1065 10.2147/IJN.S14912
23. Saffer, E. M.; Tew, G. N.; Bhatia, S. R. Poly(lactic acid)-poly(ethylene oxide) Block Copolymers: New Directions in Self-Assembly and Biomedical Applications Curr. Med. Chem. 2011, 18, 5676-5686 10.2174/092986711798347324
24. Cohn, D.; Younes, H. Biodegradable PEO/PLA block copolymers J. Biomed. Mater. Res. 1988, 22, 993-1009 10.1002/jbm.820221104
25. Liggins, R. T.; Burt, H. M. Polyether-polyester diblock copolymers for the preparation of paclitaxel loaded polymeric micelle formulations Adv. Drug Delivery Rev. 2002, 54, 191-202 10.1016/S0169-409X(02)00016-9
26. Ma, P.; Mumper, R. J. Paclitaxel Nano-Delivery Systems: A Comprehensive Review J. Nanomed. Nanotechnol. 2013, 4, 1000164 10.4172/2157-7439.1000164
27. Owen, S. C.; Chan, D. P. Y.; Shoichet, M. S. Polymeric micelle stability Nano Today 2012, 7, 53-65 10.1016/j.nantod.2012.01.002
28. Eetezadi, S.; Ekdawi, S. N.; Allen, C. The challenges facing block copolymer micelles for cancer therapy: In vivo barriers and clinical translation Adv. Drug Delivery Rev. 2015, 91, 7-22 10.1016/j.addr.2014.10.001
29. Kim, S.; Shi, Y.; Kim, J. Y.; Park, K.; Cheng, J.-X. Overcoming the barriers in micellar drug delivery: loading efficiency, in vivo stability, and micelle-cell interaction Expert Opin. Drug Delivery 2010, 7, 49-62 10.1517/17425240903380446
30. Fenyves, R.; Schmutz, M.; Horner, I. J.; Bright, F. V.; Rzayev, J. Aqueous Self-Assembly of Giant Bottlebrush Block Copolymer Surfactants as Shape-Tunable Building Blocks J. Am. Chem. Soc. 2014, 136, 7762-7770 10.1021/ja503283r
31. Verduzco, R.; Li, X.; Pesek, S. L.; Stein, G. E. Structure, function, self-assembly, and applications of bottlebrush copolymers Chem. Soc. Rev. 2015, 44, 2405-2420 10.1039/C4CS00329B
32. Sheiko, S. S.; Sumerlin, B. S.; Matyjaszewski, K. Cylindrical molecular brushes: Synthesis, characterization, and properties Prog. Polym. Sci. 2008, 33, 759-785 10.1016/j.progpolymsci.2008.05.001
33. Wintermantel, M.; Gerle, M.; Fischer, K.; Schmidt, M.; Wataoka, I.; Urakawa, H.; Kajiwara, K.; Tsukahara, Y. Molecular bottlebrushes Macromolecules 1996, 29, 978-983 10.1021/ma950227s
34. Rathgeber, S.; Pakula, T.; Wilk, A.; Matyjaszewski, K.; Beers, K. L. On the shape of bottle-brush macromolecules: Systematic variation of architectural parameters J. Chem. Phys. 2005, 122, 124904 10.1063/1.1860531
35. Rathgeber, S.; Pakula, T.; Wilk, A.; Matyjaszewski, K.; Lee, H. I.; Beers, K. L. Bottle-brush macromolecules in solution: Comparison between results obtained from scattering experiments and computer simulations Polymer 2006, 47, 7318-7327 10.1016/j.polymer.2006.06.010
36. Zhang, B.; Grohn, F.; Pedersen, J. S.; Fischer, K.; Schmidt, M. Conformation of cylindrical brushes in solution: Effect of side chain length Macromolecules 2006, 39, 8440-8450 10.1021/ma0613178
37. Huang, K.; Canterbury, D. P.; Rzayev, J. Organosoluble polypyrrole nanotubes from core-shell bottlebrush copolymers Chem. Commun. 2010, 46, 6326-6328 10.1039/c002447c
38. Huang, K.; Jacobs, A.; Rzayev, J. De Novo Synthesis and Cellular Uptake of Organic Nanocapsules with Tunable Surface Chemistry Biomacromolecules 2011, 12, 2327-2334 10.1021/bm200394t
39. Huang, K.; Rzayev, J. Charge and Size Selective Molecular Transport by Amphiphilic Organic Nanotubes J. Am. Chem. Soc. 2011, 133, 16726 10.1021/ja204296v
40. Kose, M. M.; Onbulak, S.; Yilmaz, I. I.; Sanyal, A. Orthogonally “Clickable” Biodegradable Dendrons Macromolecules 2011, 44, 2707-2714 10.1021/ma200593r
41. He, J.; Zhao, Y.; Zhao, Y. Photoinduced bending of a coumarin-containing supramolecular polymer Soft Matter 2009, 5, 308-310 10.1039/B814278E
42. Bates, C. M.; Chang, A. B.; Momčilović, N.; Jones, S. C.; Grubbs, R. H. ABA Triblock Brush Polymers: Synthesis, Self-Assembly, Conductivity, and Rheological Properties Macromolecules 2015, 48, 4967-4973 10.1021/acs.macromol.5b00880
43. Runge, M. B.; Bowden, N. B. Synthesis of High Molecular Weight Comb Block Copolymers and Their Assembly into Ordered Morphologies in the Solid State J. Am. Chem. Soc. 2007, 129, 10551-10560 10.1021/ja072929q
44. Xia, Y.; Kornfield, J. A.; Grubbs, R. H. Efficient Synthesis of Narrowly Dispersed Brush Polymers via Living Ring-Opening Metathesis Polymerization of Macromonomers Macromolecules 2009, 42, 3761-3766 10.1021/ma900280c
45. Jha, S.; Dutta, S.; Bowden, N. B. Synthesis of ultralarge molecular weight bottlebrush polymers using Grubbs’ catalysts Macromolecules 2004, 37, 4365-4374 10.1021/ma049647k
46. Li, Z.; Zhang, K.; Ma, J.; Cheng, C.; Wooley, K. L. Facile syntheses of cylindrical molecular brushes by a sequential RAFT and ROMP “grafting-through” methodology J. Polym. Sci., Part A: Polym. Chem. 2009, 47, 5557-5563 10.1002/pola.23626
47. Teo, Y. C.; Xia, Y. Importance of Macromonomer Quality in the Ring-Opening Metathesis Polymerization of Macromonomers Macromolecules 2015, 48, 5656-5662 10.1021/acs.macromol.5b01176
48. Lohmeijer, B. G. G.; Pratt, R. C.; Leibfarth, F.; Logan, J. W.; Long, D. A.; Dove, A. P.; Nederberg, F.; Choi, J.; Wade, C.; Waymouth, R. M.; Hedrick, J. L. Guanidine and amidine organocatalysts for ring-opening polymerization of cyclic esters Macromolecules 2006, 39, 8574-8583 10.1021/ma0619381
49. Matyjaszewski, K.; Xia, J. H. Atom transfer radical polymerization Chem. Rev. 2001, 101, 2921-2990 10.1021/cr940534g
50. Beers, K. L.; Gaynor, S. G.; Matyjaszewski, K.; Sheiko, S. S.; Möller, M. The synthesis of densely grafted copolymers by atom transfer radical polymerization Macromolecules 1998, 31, 9413-9415 10.1021/ma981402i
51. Sumerlin, B. S.; Neugebauer, D.; Matyjaszewski, K. Initiation efficiency in the synthesis of molecular brushes by grafting from via atom transfer radical polymerization Macromolecules 2005, 38, 702-708 10.1021/ma048351b
52. He, G.; Ma, L. L.; Pan, J.; Venkatraman, S. ABA and BAB type triblock copolymers of PEG and PLA: A comparative study of drug release properties and “stealth” particle characteristics Int. J. Pharm. 2007, 334, 48-55 10.1016/j.ijpharm.2006.10.020
53. Huh, K. M.; Lee, S. C.; Cho, Y. W.; Lee, J.; Jeong, J. H.; Park, K. Hydrotropic polymer micelle system for delivery of paclitaxel J. Controlled Release 2005, 101, 59-68 10.1016/j.jconrel.2004.07.003
54. Jie, P.; Venkatraman, S. S.; Min, F.; Freddy, B. Y. C.; Huat, G. L. Micelle-like nanoparticles of star-branched PEO-PLA copolymers as chemotherapeutic carrier J. Controlled Release 2005, 110, 20-33 10.1016/j.jconrel.2005.09.011
55. Xiao, L.; Xiong, X.; Sun, X.; Zhu, Y.; Yang, H.; Chen, H.; Gan, L.; Xu, H.; Yang, X. Role of cellular uptake in the reversal of multidrug resistance by PEG-b-PLA polymeric micelles Biomaterials 2011, 32, 5148-5157 10.1016/j.biomaterials.2011.03.071
56. Kim, S. C.; Kim, D. W.; Shim, Y. H.; Bang, J. S.; Oh, H. S.; Kim, S. W.; Seo, M. H. In vivo evaluation of polymeric micellar paclitaxel formulation: toxicity and efficacy J. Controlled Release 2001, 72, 191-202 10.1016/S0168-3659(01)00275-9
57. Burt, H. M.; Zhang, X.; Toleikis, P.; Embree, L.; Hunter, W. L. Development of copolymers of poly(d,l-lactide) and methoxypolyethylene glycol as micellar carriers of paclitaxel Colloids Surf., B 1999, 16, 161-171 10.1016/S0927-7765(99)00067-3
58. Kim, J.-H.; Emoto, K.; Iijima, M.; Nagasaki, Y.; Aoyagi, T.; Okano, T.; Sakurai, Y.; Kataoka, K. Core-stabilized polymeric micelle as potential drug carrier: increased solubilization of taxol Polym. Adv. Technol. 1999, 10, 647-654 10.1002/(SICI)1099-1581(199911)10:11<647::AID-PAT918>3.0.CO;2-Y
59. Trenor, S. R.; Shultz, A. R.; Love, B. J.; Long, T. E. Coumarins in polymers: From light harvesting to photo-cross-linkable tissue scaffolds Chem. Rev. 2004, 104, 3059-3077 10.1021/cr030037c
60. Ling, J.; Rong, M. Z.; Zhang, M. Q. Coumarin imparts repeated photochemical remendability to polyurethane J. Mater. Chem. 2011, 21, 18373-18380 10.1039/c1jm13467a
61. Onbulak, S.; Rzayev, J. Cylindrical Nanocapsules from Photo-Cross-Linkable Core-Shell Bottlebrush Copolymers Polym. Chem. 2015, 6, 764-771 10.1039/C4PY01215A