Functionalization of Cellulose Nanocrystals with PEG-Metal-Chelating Block Copolymers via Controlled Conjugation in Aqueous Media

ACS Omega

Volumn 1, Issue 1, 2016, Pages 93-107

  Guo, Melinda ^a   Her, Sohyoung ^a   Keunen, Rachel ^a   Zhang, Shengmiao ^a,b   Allen, Christine ^a   Winnik, Mitchell A ^a  

^a UNIVERSITY OF TORONTO   (Canada)

^b EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85021643955     PISSN: None     EISSN: 24701343     Source Type: Journal    
DOI: 10.1021/acsomega.6b00055     Document Type: Article

References (61)

1. Caldorera-Moore, M.; Guimard, N.; Shi, L.; Roy, K. Designer Nanoparticles: Incorporating Size, Shape and Triggered Release into Nanoscale Drug Carriers Expert Opin. Drug Delivery 2010, 7, 479-495 10.1517/17425240903579971
2. Lazarovits, J.; Chen, Y. Y.; Sykes, E. A.; Chan, W. C. W. Nanoparticle-Blood Interactions: The Implications on Solid Tumour Targeting Chem. Commun. 2015, 51, 2756-2767 10.1039/C4CC07644C
3. Hu, X.; Hu, J.; Tian, J.; Ge, Z.; Zhang, G.; Luo, K.; Liu, S. Polyprodrug Amphiphiles: Hierarchical Assemblies for Shape-Regulated Cellular Internalization, Trafficking, and Drug Delivery J. Am. Chem. Soc. 2013, 135, 17617-17629 10.1021/ja409686x
4. Albanese, A.; Tang, P. S.; Chan, W. C. W. The Effect of Nanoparticle Size, Shape, and Surface Chemistry on Biological Systems Annu. Rev. Biomed. Eng. 2012, 14, 1-16 10.1146/annurev-bioeng-071811-150124
5. Geng, Y.; Dalhaimer, P.; Cai, S.; Tsai, R.; Tewari, M.; Minko, T.; Discher, D. E. Shape Effects of Filaments versus Spherical Particles in Flow and Drug Delivery Nat. Nanotechnol. 2007, 2, 249-255 10.1038/nnano.2007.70
6. Chithrani, B. D.; Ghazani, A. A.; Chan, W. C. W. Determining the Size and Shape Dependence of Gold Nanoparticle Uptake into Mammalian Cells Nano Lett. 2006, 6, 662-668 10.1021/nl052396o
7. Patil, V. R. S.; Campbell, C. J.; Yun, Y. H. et al. Particle Diameter Influences Adhesion under Flow Biophys. J. 2001, 80, 1733-1743 10.1016/S0006-3495(01)76144-9
8. Stolnik, S.; Illum, L.; Davis, S. S. Long Circulating Microparticulate Drug Carriers Adv. Drug Delivery Rev. 1995, 16, 195-214 10.1016/0169-409X(95)00025-3
9. Moghimi, S. M.; Hunter, A. C.; Murray, J. C. Long-Circulating and Target-Specific Nanoparticles: Theory to Practice Pharmacol. Rev. 2001, 53, 283-318
10. Chauhan, V. P.; Popović, Z.; Chen, O.; Cui, J.; Fukumura, D.; Bawendi, M. G.; Jain, R. K. Fluorescent Nanorods and Nanospheres for Real-Time In Vivo Probing of Nanoparticle Shape-Dependent Tumor Penetration Angew. Chem., Int. Ed. 2011, 50, 11417-11420 10.1002/anie.201104449
11. Habibi, Y.; Lucia, L. A.; Rojas, O. J. Cellulose Nanocrystals: Chemistry, Self-Assembly, and Applications Chem. Rev. 2010, 110, 3479-3500 10.1021/cr900339w
12. Lam, E.; Male, K. B.; Chong, J. H.; Leung, A. C. W.; Luong, J. H. T. Applications of Functionalized and Nanoparticle-Modified Nanocrystalline Cellulose Trends Biotechnol. 2012, 30, 283-290 10.1016/j.tibtech.2012.02.001
13. Hosseinidoust, Z.; Alam, M. N.; Sim, G.; Tufenkji, N.; van de Ven, T. G. M. Cellulose Nanocrystals with Tunable Surface Charge for Nanomedicine Nanoscale 2015, 7, 16647-16657 10.1039/C5NR02506K
14. De France, K. J.; Chan, K. J. W.; Cranston, E. D.; Hoare, T. Enhanced Mechanical Properties in Cellulose Nanocrystal-Poly(oligoethylene Glycol Methacrylate) Injectable Nanocomposite Hydrogels through Control of Physical and Chemical Cross-Linking Biomacromolecules 2016, 17, 649-660 10.1021/acs.biomac.5b01598
15. Kim, H. J.; Park, S.; Kim, S. H.; Kim, J. H.; Yu, H.; Kim, H. J.; Yang, Y.-H.; Kan, E.; Kim, Y. H.; Lee, S. H. Biocompatible Cellulose Nanocrystals as Supports to Immobilize Lipase J. Mol. Catal. B: Enzym. 2015, 122, 170-178 10.1016/j.molcatb.2015.09.007
16. Dugan, J. M.; Gough, J. E.; Eichhorn, S. J. Bacterial Cellulose Scaffolds and Cellulose Nanowhiskers for Tissue Engineering Nanomedicine 2013, 8, 287-298 10.2217/nnm.12.211
17. Akhlaghi, S. P.; Berry, R. C.; Tam, K. C. Surface Modification of Cellulose Nanocrystal with Chitosan Oligosaccharide for Drug Delivery Applications Cellulose 2013, 20, 1747-1764 10.1007/s10570-013-9954-y
18. Habibi, Y. Key Advances in the Chemical Modification of Nanocellulose Chem. Soc. Rev. 2014, 43, 1519-1542 10.1039/C3CS60204D
19. Eyley, S.; Thielemans, W. Surface Modification of Cellulose Nanocrystals Nanoscale 2014, 6, 7764-7779 10.1039/C4NR01756K
20. Dong, S.; Hirani, A. A.; Colacino, K. R.; Lee, Y. W.; Roman, M. Cytotoxicity and Cellular Uptake of Cellulose Nanocrystals Nano Life 2012, 2, 1241006 10.1142/S1793984412410061
21. Araki, J.; Wada, M.; Kuga, S. Steric Stabilization of Cellulose Microcrystal Suspension by Poly(ethylene Glycol) Grafting Langmuir 2001, 17, 21-27 10.1021/la001070m
22. Sassi, J.-F.; Chanzy, H. Ultrastructural Aspects of the Acetylation of Cellulose Cellulose 1995, 2, 111-127 10.1007/BF00816384
23. Siqueira, G.; Bras, J.; Dufresne, A. New Process of Chemical Grafting of Cellulose Nanoparticles with a Long Chain Isocyanate Langmuir 2010, 26, 402-411 10.1021/la9028595
24. Ljungberg, N.; Bonini, C.; Bortolussi, F.; Boisson, C.; Heux, L.; Cavaille, J.-Y. New Nanocomposite Materials Reinforced with Cellulose Whiskers in Atactic Polypropylene: Effects of Surface and Dispersion Characteristics Biomacromolecules 2005, 6, 2732-2739 10.1021/bm050222v
25. Mangalam, A. P.; Simonsen, J.; Benight, A. S. Cellulose/DNA Hybrid Nanomaterials Biomacromolecules 2009, 10, 497-504 10.1021/bm800925x
26. Kan, K. H. M.; Li, J.; Wijesekera, K.; Cranston, E. D. Polymer-Grafted Cellulose Nanocrystals as pH-Responsive Reversible Flocculants Biomacromolecules 2013, 14, 3130-3139 10.1021/bm400752k
27. Schwartz, D. A. Biomolecule/Polymer Conjugates. U.S. Patent 6,911,535, June 28, 2005.
28. Schwartz, D. A. Hydrazine-Based and Carbonyl-Based Bifunctional Crosslinking Reagents. U.S. Patent 6,800,728, October 5, 2004.
29. Solulink Bioconjugation Primer, 2013. http://www.solulink.com/white-papers/Why-Solulink.pdf.
30. Grotzky, A.; Manaka, Y.; Kojima, T.; Walde, P. Preparation of Catalytically Active, Covalent α-Polylysine-Enzyme Conjugates via UV/Vis-Quantifiable Bis-Aryl Hydrazone Bond Formation Biomacromolecules 2011, 12, 134-144 10.1021/bm101074s
31. Grotzky, A.; Nauser, T.; Erdogan, H.; Schlüter, A. D.; Walde, P. A Fluorescently Labeled Dendronized Polymer-Enzyme Conjugate Carrying Multiple Copies of Two Different Types of Active Enzymes J. Am. Chem. Soc. 2012, 134, 11392-11395 10.1021/ja304837f
32. Knop, K.; Hoogenboom, R.; Fischer, D.; Schubert, U. S. Poly(ethylene Glycol) in Drug Delivery: Pros and Cons as Well as Potential Alternatives Angew. Chem., Int. Ed. 2010, 49, 6288-6308 10.1002/anie.200902672
33. Liu, P.; Boyle, A. J.; Lu, Y.; Adams, J.; Chi, Y.; Reilly, R. M.; Winnik, M. A. Metal-Chelating Polymers (MCPs) with Zwitterionic Pendant Groups Complexed to Trastuzumab Exhibit Decreased Liver Accumulation Compared to Polyanionic MCP Immunoconjugates Biomacromolecules 2015, 16, 3613-3623 10.1021/acs.biomac.5b01066
34. Yook, S.; Cai, Z.; Lu, Y.; Winnik, M. A.; Pignol, J.-P.; Reilly, R. M. Intratumorally Injected 177Lu-Labeled Gold Nanoparticles: Gold Nanoseed Brachytherapy with Application for Neoadjuvant Treatment of Locally Advanced Breast Cancer J. Nucl. Med. 2016, 57, 936-942 10.2967/jnumed.115.168906
35. Liu, T.; Li, X.; Qian, Y.; Hu, X.; Liu, S. Multifunctional pH-Disintegrable Micellar Nanoparticles of Asymmetrically Functionalized β-Cyclodextrin-Based Star Copolymer Covalently Conjugated with Doxorubicin and DOTA-Gd Moieties Biomaterials 2012, 33, 2521-2531 10.1016/j.biomaterials.2011.12.013
36. Hu, X.; Liu, G.; Li, Y.; Wang, X.; Liu, S. Cell-Penetrating Hyperbranched Polyprodrug Amphiphiles for Synergistic Reductive Milieu-Triggered Drug Release and Enhanced Magnetic Resonance Signals J. Am. Chem. Soc. 2015, 137, 362-368 10.1021/ja5105848
37. Kloser, E.; Gray, D. G. Surface Grafting of Cellulose Nanocrystals with Poly(Ethylene Oxide) in Aqueous Media Langmuir 2010, 26, 13450-13456 10.1021/la101795s
38. Wang, H.; He, J.; Zhang, M.; Tam, K. C.; Ni, P. A New Pathway towards Polymer Modified Cellulose Nanocrystals via a "grafting Onto" Process for Drug Delivery Polym. Chem. 2015, 6, 4206-4209 10.1039/C5PY00466G
39. Liu, Y. N.; Yu, H. Y.; Qin, Z. Y.; Chen, L. Enhanced Heat Conduction in Cellulose Nanocrystals Grafting Polyethylene Glycol as Solid-Solid Phase Change Materials Adv. Mater. Res. 2012, 557-559, 563-566 10.4028/www.scientific.net/AMR.557-559.563
40. Thérien-Aubin, H.; Lukach, A.; Pitch, N.; Kumacheva, E. Structure and Properties of Composite Films Formed by Cellulose Nanocrystals and Charged Latex Nanoparticles Nanoscale 2015, 7, 6612 10.1039/c5nr00660k
41. Dong, S.; Roman, M. Fluorescently Labeled Cellulose Nanocrystals for Bioimaging Applications J. Am. Chem. Soc. 2007, 129, 13810-13811 10.1021/ja076196l
42. Ganster, J.; Fink, H.-P. Physical Constants of Cellulose. In Polymer Handbook; Brandrup, J.; Immergut, E. H.; Grulke, E. A., Eds.; John Wiley & Sons: New York, 1999; pp V/135-V/157.
43. Khan, M. K.; Giese, M.; Yu, M.; Kelly, J. A.; Hamad, W. Y.; MacLachlan, M. J. Flexible Mesoporous Photonic Resins with Tunable Chiral Nematic Structures Angew. Chem., Int. Ed. 2013, 52, 8921-8924 10.1002/anie.201303829
44. Lu, Y.; Mbong, G. N. N.; Liu, P.; Chan, C.; Cai, Z.; Weinrich, D.; Boyle, A. J.; Reilly, R. M.; Winnik, M. A. Synthesis of Polyglutamide-Based Metal-Chelating Polymers and Their Site-Specific Conjugation to Trastuzumab for Auger Electron Radioimmunotherapy Biomacromolecules 2014, 15, 2027-2037 10.1021/bm500174p
45. Majonis, D.; Herrera, I.; Ornatsky, O.; Schulze, M.; Lou, X.; Soleimani, M.; Nitz, M.; Winnik, M. A. Synthesis of a Functional Metal-Chelating Polymer and Steps toward Quantitative Mass Cytometry Bioassays Anal. Chem. 2010, 82, 8961-8969 10.1021/ac101901x
46. Tehrani, S. M.; Lu, Y.; Guerin, G.; Soleimani, M.; Pichugin, D.; Winnik, M. A. Temperature-Invariant Aqueous Microgels as Hosts for Biomacromolecules Biomacromolecules 2015, 16, 3134-3144 10.1021/acs.biomac.5b00768
47. Mahmoud, K. A.; Mena, J. A.; Male, K. B.; Hrapovic, S.; Kamen, A.; Luong, J. H. T. Effect of Surface Charge on the Cellular Uptake and Cytotoxicity of Fluorescent Labeled Cellulose Nanocrystals ACS Appl. Mater. Interfaces 2010, 2, 2924-2932 10.1021/am1006222
48. Johnston, D. C. Stretched Exponential Relaxation Arising from a Continuous Sum of Exponential Decays Phys. Rev. B 2006, 74, 184430 10.1103/physrevb.77.179901
49. Dirksen, A.; Dawson, P. E. Rapid Oxime and Hydrazone Ligations with Aromatic Aldehydes for Biomolecular Labeling Bioconjugate Chem. 2008, 19, 2543-2548 10.1021/bc800310p
50. Ando, T.; Yamamoto, T.; Kobayashi, N.; Munekata, E. Synthesis of a Highly Luminescent Terbium Chelate and Its Application to Actin Biochim. Biophys. Acta, Bioenerg. 1992, 1102, 186-194 10.1016/0005-2728(92)90099-N
51. Minchinton, A. I.; Tannock, I. F. Drug Penetration in Solid Tumours Nat. Rev. Cancer 2006, 6, 583-592 10.1038/nrc1893
52. Chauhan, V. P.; Stylianopoulos, T.; Boucher, Y.; Jain, R. K. Delivery of Molecular and Nanoscale Medicine to Tumors: Transport Barriers and Strategies Annu. Rev. Chem. Biomol. Eng. 2011, 2, 281-298 10.1146/annurev-chembioeng-061010-114300
53. Ekdawi, S. N.; Stewart, J. M. P.; Dunne, M.; Stapleton, S.; Mitsakakis, N.; Dou, Y. N.; Jaffray, D. A.; Allen, C. Spatial and Temporal Mapping of Heterogeneity in Liposome Uptake and Microvascular Distribution in an Orthotopic Tumor Xenograft Model J. Controlled Release 2015, 207, 101-111 10.1016/j.jconrel.2015.04.006
54. Lee, H.; Hoang, B.; Fonge, H.; Reilly, R. M.; Allen, C. In Vivo Distribution of Polymeric Nanoparticles at the Whole-Body, Tumor, and Cellular Levels Pharm. Res. 2010, 27, 2343-2355 10.1007/s11095-010-0068-z
55. Hoang, B.; Ekdawi, S. N.; Reilly, R. M.; Allen, C. Active Targeting of Block Copolymer Micelles with Trastuzumab Fab Fragments and Nuclear Localization Signal Leads to Increased Tumor Uptake and Nuclear Localization in HER2-Overexpressing Xenografts Mol. Pharmaceutics 2013, 10, 4229-4241 10.1021/mp400315p
56. Cabral, H.; Matsumoto, Y.; Mizuno, K.; Chen, Q.; Murakami, M.; Kimura, M.; Terada, Y.; Kano, M. R.; Miyazono, K.; Uesaka, M. et al. Accumulation of Sub-100 nm Polymeric Micelles in Poorly Permeable Tumours Depends on Size Nat. Nanotechnol. 2011, 6, 815-823 10.1038/nnano.2011.166
57. Mikhail, A. S.; Eetezadi, S.; Ekdawi, S. N.; Stewart, J.; Allen, C. Image-Based Analysis of the Size- and Time-Dependent Penetration of Polymeric Micelles in Multicellular Tumor Spheroids and Tumor Xenografts Int. J. Pharm. 2014, 464, 168-177 10.1016/j.ijpharm.2014.01.010
58. Friedrich, J.; Ebner, R.; Kunz-Schughart, L. A. Experimental Anti-Tumor Therapy in 3-D: Spheroids-Old Hat or New Challenge? Int. J. Radiat. Biol. 2007, 83, 849-871 10.1080/09553000701727531
59. Hirschhaeuser, F.; Menne, H.; Dittfeld, C.; West, J.; Mueller-Klieser, W.; Kunz-Schughart, L. A. Multicellular Tumor Spheroids: An Underestimated Tool Is Catching up Again J. Biotechnol. 2010, 148, 3-15 10.1016/j.jbiotec.2010.01.012
60. Kunz-Schughart, L. A. Multicellular Tumor Spheroids: Intermediates between Monolayer Culture and in Vivo Tumor Cell Biol. Int. 1999, 23, 157-161 10.1006/cbir.1999.0384
61. Eetezadi, S.; De Souza, R.; Vythilingam, M.; Cataldi, R. L.; Allen, C. Effects of Doxorubicin Delivery Systems and Mild Hyperthermia on Tissue Penetration in 3D Cell Culture Models of Ovarian Cancer Residual Disease Mol. Pharmaceutics 2015, 12, 3973-3985 10.1021/acs.molpharmaceut.5b00426