Amphiphilic and Hydrophilic Block Copolymers from Aliphatic N-Substituted 8-Membered Cyclic Carbonates: A Versatile Macromolecular Platform for Biomedical Applications

Biomacromolecules

Volumn 18, Issue 1, 2017, Pages 178-188

  Venkataraman, Shrinivas ^a   Tan, Jeremy P K ^a   Ng, Victor W L ^a   Tan, Eddy W P ^a   Hedrick, James L ^b   Yang, Yi Yan ^a  

^a INSTITUTE OF BIOENGINEERING AND NANOTECHNOLOGY   (Singapore)

^b IBM ALMADEN RESEARCH CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOCOMPATIBILITY; BIODEGRADABLE POLYMERS; BIOLOGICAL MATERIALS; BLOCK COPOLYMERS; CARBONATES; GENE TRANSFER; MEDICAL APPLICATIONS; POLYETHYLENE GLYCOLS; POLYMERS; SUBSTITUTION REACTIONS;

BIOLOGICAL INTERACTIONS; BIOMEDICAL APPLICATIONS; DEGRADABLE BLOCK COPOLYMER; DICLOFENAC SODIUM SALTS; DRUG DELIVERY VEHICLES; HYDROPHILIC COMPONENTS; HYDROPHILIC POLYMERS; HYDROPHILIC RESIDUES;

HYDROPHILICITY;

ALIPHATIC COMPOUND; AMPHOLYTE; AMPHOPHILE; COPOLYMER; DICLOFENAC; DIETHANOLAMINE; DOXORUBICIN; POLYCARBONATE; TERTIARY AMINE; ANTINEOPLASTIC ANTIBIOTIC; BIOMATERIAL; CARBONIC ACID DERIVATIVE; MACROGOL DERIVATIVE; MACROMOLECULE; NONSTEROID ANTIINFLAMMATORY AGENT; POLYMER;

ARTICLE; DEPROTECTION REACTION; DRUG DELIVERY SYSTEM; HYDROPHILICITY; MACROMOLECULE; MICELLE; PH; POLYMERIZATION; PRIORITY JOURNAL; SYNTHESIS; CHEMICAL PHENOMENA; CHEMISTRY; HUMAN; METABOLISM;

ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; ANTIBIOTICS, ANTINEOPLASTIC; BIOCOMPATIBLE MATERIALS; CARBONATES; DICLOFENAC; DOXORUBICIN; DRUG DELIVERY SYSTEMS; HUMANS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; MACROMOLECULAR SUBSTANCES; POLYETHYLENE GLYCOLS; POLYMERS;

EID: 85016307787     PISSN: 15257797     EISSN: 15264602     Source Type: Journal    
DOI: 10.1021/acs.biomac.6b01463     Document Type: Article

References (67)

1. 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 ( 1-3 ) 169-188 10.1016/j.jconrel.2005.09.034
2. Wiradharma, N.; Zhang, Y.; Venkataraman, S.; Hedrick, J. L.; Yang, Y. Y. Self-assembled polymer nanostructures for delivery of anticancer therapeutics Nano Today 2009, 4 ( 4 ) 302-317 10.1016/j.nantod.2009.06.001
3. 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 ( 4-5 ) 267-277 10.1002/marc.200800713
4. Lee, A. L.; Venkataraman, S.; Sirat, S. B.; Gao, S.; Hedrick, J. L.; Yang, Y. Y. The use of cholesterol-containing biodegradable block copolymers to exploit hydrophobic interactions for the delivery of anticancer drugs Biomaterials 2012, 33 ( 6 ) 1921-1928 10.1016/j.biomaterials.2011.11.032
5. Lee, Y.; Ishii, T.; Cabral, H.; Kim, H. J.; Seo, J.-H.; Nishiyama, N.; Oshima, H.; Osada, K.; Kataoka, K. Charge-Conversional Polyionic Complex Micelles-Efficient Nanocarriers for Protein Delivery into Cytoplasm Angew. Chem. 2009, 121 ( 29 ) 5413-5416 10.1002/ange.200900064
6. Samadi, N.; van Steenbergen, M. J.; van den Dikkenberg, J. B.; Vermonden, T.; van Nostrum, C. F.; Amidi, M.; Hennink, W. E. Nanoparticles Based on a Hydrophilic Polyester with a Sheddable PEG Coating for Protein Delivery Pharm. Res. 2014, 31 ( 10 ) 2593-2604 10.1007/s11095-014-1355-x
7. Venkataraman, S.; Hedrick, J. L.; Ong, Z. Y.; Yang, C.; Ee, P. L. R.; Hammond, P. T.; Yang, Y. Y. The effects of polymeric nanostructure shape on drug delivery Adv. Drug Delivery Rev. 2011, 63 ( 14 ) 1228-1246 10.1016/j.addr.2011.06.016
8. Aggarwal, P.; Hall, J. B.; McLeland, C. B.; Dobrovolskaia, M. A.; McNeil, S. E. Nanoparticle interaction with plasma proteins as it relates to particle biodistribution, biocompatibility and therapeutic efficacy Adv. Drug Delivery Rev. 2009, 61 ( 6 ) 428-437 10.1016/j.addr.2009.03.009
9. Venkataraman, S. Rational Design of Multifunctional Nanoscale Self-Assembled Soft Materials for Biomedical Delivery Application; Springer: Berlin, Heidelberg, 2014; pp 1-19.
10. Iha, R. K.; Wooley, K. L.; Nyström, A. M.; Burke, D. J.; Kade, M. J.; Hawker, C. J. Applications of orthogonal “click” chemistries in the synthesis of functional soft materials Chem. Rev. 2009, 109 ( 11 ) 5620-5686 10.1021/cr900138t
11. Tian, H.; Tang, Z.; Zhuang, X.; Chen, X.; Jing, X. Biodegradable synthetic polymers: Preparation, functionalization and biomedical application Prog. Polym. Sci. 2012, 37 ( 2 ) 237-280 10.1016/j.progpolymsci.2011.06.004
12. Kiesewetter, M. K.; Shin, E. J.; Hedrick, J. L.; Waymouth, R. M. Organocatalysis: Opportunities and Challenges for Polymer Synthesis Macromolecules 2010, 43, 2093-2107 10.1021/ma9025948
13. Ottou, W. N.; Sardon, H.; Mecerreyes, D.; Vignolle, J.; Taton, D. Update and challenges in organo-mediated polymerization reactions Prog. Polym. Sci. 2016, 56, 64-115 10.1016/j.progpolymsci.2015.12.001
14. Nuyken, O.; Pask, S. D. Ring-Opening Polymerization-An Introductory Review Polymers 2013, 5, 361-403 10.3390/polym5020361
15. Feng, J.; Zhuo, R.-X.; Zhang, X.-Z. Construction of functional aliphatic polycarbonates for biomedical applications Prog. Polym. Sci. 2012, 37 ( 2 ) 211-236 10.1016/j.progpolymsci.2011.07.008
16. Wang, Y.-C.; Yuan, Y.-Y.; Du, J.-Z.; Yang, X.-Z.; Wang, J. Recent Progress in Polyphosphoesters: From Controlled Synthesis to Biomedical Applications Macromol. Biosci. 2009, 9 ( 12 ) 1154-1164 10.1002/mabi.200900253
17. Seyednejad, H.; Ghassemi, A. H.; van Nostrum, C. F.; Vermonden, T.; Hennink, W. E. Functional aliphatic polyesters for biomedical and pharmaceutical applications J. Controlled Release 2011, 152 ( 1 ) 168-176 10.1016/j.jconrel.2010.12.016
18. Cheng, J.; Deming, T. Synthesis of Polypeptides by Ring-Opening Polymerization of α-Amino Acid N-Carboxyanhydrides. In Peptide-Based Materials; Deming, T., Ed.; Springer: Berlin, Heidelberg, 2012; Vol. 310, pp 1-26.
19. Zhang, H.; Lin, X.; Chin, S.; Grinstaff, M. W. Synthesis and Characterization of Poly(glyceric Acid Carbonate): A Degradable Analogue of Poly(acrylic Acid) J. Am. Chem. Soc. 2015, 137 ( 39 ) 12660-12666 10.1021/jacs.5b07911
20. Mikami, K.; Lonnecker, A. T.; Gustafson, T. P.; Zinnel, N. F.; Pai, P.-J.; Russell, D. H.; Wooley, K. L. Polycarbonates Derived from Glucose via an Organocatalytic Approach J. Am. Chem. Soc. 2013, 135 ( 18 ) 6826-6829 10.1021/ja402319m
21. Tempelaar, S.; Mespouille, L.; Dubois, P.; Dove, A. P. Organocatalytic synthesis and postpolymerization functionalization of allyl-functional poly(carbonate)s Macromolecules 2011, 44, 2084-2091 10.1021/ma102882v
22. Tempelaar, S.; Barker, I. A.; Truong, V. X.; Hall, D. J.; Mespouille, L.; Dubois, P.; Dove, A. P. Organocatalytic synthesis and post-polymerization functionalization of propargyl-functional poly(carbonate)s Polym. Chem. 2013, 4, 174-183 10.1039/C2PY20718D
23. Chen, W.; Yang, H.; Wang, R.; Cheng, R.; Meng, F.; Wei, W.; Zhong, Z. Versatile synthesis of functional biodegradable polymers by combining ring-opening polymerization and postpolymerization modification via michael-type addition reaction Macromolecules 2010, 43, 201-207 10.1021/ma901897y
24. Wang, R.; Chen, W.; Meng, F.; Cheng, R.; Deng, C.; Feijen, J.; Zhong, Z. Unprecedented Access to Functional Biodegradable Polymers and Coatings Macromolecules 2011, 44, 6009-6016 10.1021/ma200824k
25. Zhang, X.; Zhong, Z.; Zhuo, R. Preparation of Azido Polycarbonates and Their Functionalization via Click Chemistry Macromolecules 2011, 44, 1755-1759 10.1021/ma200137a
26. Xu, J.; Prifti, F.; Song, J. A Versatile Monomer for Preparing Well-Defined Functional Polycarbonates and Poly(ester-carbonates) Macromolecules 2011, 44, 2660-2667 10.1021/ma200021m
27. Al-Azemi, T. F.; Bisht, K. S. Novel Functional Polycarbonate by Lipase-Catalyzed Ring-Opening Polymerization of 5-Methyl-5-benzyloxycarbonyl-1,3-dioxan-2-one Macromolecules 1999, 32, 6536-6540 10.1021/ma990639r
28. Kühling, S.; Keul, H.; Höcker, H. Copolymerization of 2,2-dimethyltrimethylene carbonate with 2-allyloxymethyl-2-ethyltrimethylene carbonate and with ε-caprolactone using initiators on the basis of Li, Al, Zn and Sn Makromol. Chem. 1992, 193, 1207-1217 10.1002/macp.1992.021930517
29. Shen, Y.; Chen, X.; Gross, R. A. Polycarbonates from Sugars: Ring-Opening Polymerization of 1,2-O-Isopropylidene-D-Xylofuranose-3,5-Cyclic Carbonate (IPXTC) Macromolecules 1999, 32, 2799-2802 10.1021/ma981791g
30. Sanda, F.; Kamatani, J.; Endo, T. Synthesis and Anionic Ring-Opening Polymerization Behavior of Amino Acid-Derived Cyclic Carbonates Macromolecules 2001, 34, 1564-1569 10.1021/ma0013307
31. Venkataraman, S.; Lee, A. L.; Maune, H. T.; Hedrick, J. L.; Prabhu, V. M.; Yang, Y. Y. Formation of disk-and stacked-disk-like self-assembled morphologies from cholesterol-functionalized amphiphilic polycarbonate diblock copolymers Macromolecules 2013, 46 ( 12 ) 4839-4846 10.1021/ma400423b
32. Venkataraman, S.; Hedrick, J. L.; Yang, Y. Y. Fluorene-functionalized aliphatic polycarbonates: design, synthesis and aqueous self-assembly of amphiphilic block copolymers Polym. Chem. 2014, 5 ( 6 ) 2035-2040 10.1039/C3PY01207G
33. Tempelaar, S.; Mespouille, L.; Coulembier, O.; Dubois, P.; Dove, A. P. Synthesis and post-polymerisation modifications of aliphatic poly(carbonate)s prepared by ring-opening polymerisation Chem. Soc. Rev. 2013, 42, 1312-1336 10.1039/C2CS35268K
34. Engler, A. C.; Chan, J. M. W.; Coady, D. J.; O’Brien, J. M.; Sardon, H.; Nelson, A.; Sanders, D. P.; Yang, Y. Y.; Hedrick, J. L. Accessing New Materials through Polymerization and Modification of a Polycarbonate with a Pendant Activated Ester Macromolecules 2013, 46 ( 4 ) 1283-1290 10.1021/ma4001258
35. Chan, J. M. W.; Ke, X.; Sardon, H.; Engler, A. C.; Yang, Y. Y.; Hedrick, J. L. Chemically modifiable N-heterocycle-functionalized polycarbonates as a platform for diverse smart biomimetic nanomaterials Chem. Sci. 2014, 5 ( 8 ) 3294-3300 10.1039/c4sc00789a
36. Ono, R. J.; Liu, S. Q.; Venkataraman, S.; Chin, W.; Yang, Y. Y.; Hedrick, J. L. Benzyl Chloride-Functionalized Polycarbonates: A Versatile Platform for the Synthesis of Functional Biodegradable Polycarbonates Macromolecules 2014, 47 ( 22 ) 7725-7731 10.1021/ma501734y
37. Engler, A. C.; Ke, X.; Gao, S.; Chan, J. M. W.; Coady, D. J.; Ono, R. J.; Lubbers, R.; Nelson, A.; Yang, Y. Y.; Hedrick, J. L. Hydrophilic Polycarbonates: Promising Degradable Alternatives to Poly(ethylene glycol)-Based Stealth Materials Macromolecules 2015, 48 ( 6 ) 1673-1678 10.1021/acs.macromol.5b00156
38. Olsén, P.; Odelius, K.; Albertsson, A.-C. Ring-Closing Depolymerization: A Powerful Tool for Synthesizing the Allyloxy-Functionalized Six-Membered Aliphatic Carbonate Monomer 2-Allyloxymethyl-2-ethyltrimethylene Carbonate Macromolecules 2014, 47 ( 18 ) 6189-6195 10.1021/ma5012304
39. Onbulak, S.; Tempelaar, S.; Pounder, R. J.; Gok, O.; Sanyal, R.; Dove, A. P.; Sanyal, A. Synthesis and Functionalization of Thiol-Reactive Biodegradable Polymers Macromolecules 2012, 45 ( 3 ) 1715-1722 10.1021/ma2019528
40. Pratt, R.; Nederberg, F.; Waymouth, R. M.; Hedrick, J. L. Tagging alcohols with cyclic carbonate: A versatile equivalent of (meth)acrylate for ring-opening polymerization Chem. Commun. 2008, 114-116 10.1039/B713925J
41. Venkataraman, S.; Veronica, N.; Voo, Z. X.; Hedrick, J. L.; Yang, Y. Y. 2-Amino-1,3-propane diols: a versatile platform for the synthesis of aliphatic cyclic carbonate monomers Polym. Chem. 2013, 4, 2945-2948 10.1039/c3py00318c
42. Venkataraman, S.; Ng, V. W.; Coady, D. J.; Horn, H. W.; Jones, G. O.; Fung, T. S.; Sardon, H.; Waymouth, R. M.; Hedrick, J. L.; Yang, Y. Y. A Simple and Facile Approach to Aliphatic N-Substituted Functional Eight-Membered Cyclic Carbonates and Their Organocatalytic Polymerization J. Am. Chem. Soc. 2015, 137 ( 43 ) 13851-13860 10.1021/jacs.5b06355
43. Mindemark, J.; Bowden, T. Diversity in cyclic carbonates: Synthesis of triazole-functional monomers using click chemistry Polym. Chem. 2012, 3, 1399-1401 10.1039/c2py20152f
44. Olsson, J. V.; Hult, D.; Cai, Y.; Garcia-Gallego, S.; Malkoch, M. Reactive imidazole intermediates: simplified synthetic approach to functional aliphatic cyclic carbonates Polym. Chem. 2014, 5, 6651-6655 10.1039/C4PY00911H
45. Pascual, A.; Tan, J. P. K.; Yuen, A.; Chan, J. M. W.; Coady, D. J.; Mecerreyes, D.; Hedrick, J. L.; Yang, Y. Y.; Sardon, H. Broad-Spectrum Antimicrobial Polycarbonate Hydrogels with Fast Degradability Biomacromolecules 2015, 16 ( 4 ) 1169-1178 10.1021/bm501836z
46. Nederberg, F.; Zhang, Y.; Tan, J. P. K.; Xu, K.; Wang, H.; Yang, C.; Gao, S.; Guo, X. D.; Fukushima, K.; Li, L.; Hedrick, J. L.; Yang, Y.-Y. Biodegradable nanostructures with selective lysis of microbial membranes Nat. Chem. 2011, 3 ( 5 ) 409-414 10.1038/nchem.1012
47. Yang, C.; Ong, Z. Y.; Yang, Y.-Y.; Ee, P. L. R.; Hedrick, J. L. Novel Biodegradable Block Copolymers of Poly(ethylene glycol) (PEG) and Cationic Polycarbonate: Effects of PEG Configuration on Gene Delivery Macromol. Rapid Commun. 2011, 32 ( 22 ) 1826-1833 10.1002/marc.201100350
48. Wang, H.-F.; Su, W.; Zhang, C.; Luo, X.-h.; Feng, J. Biocatalytic Fabrication of Fast-Degradable, Water-Soluble Polycarbonate Functionalized with Tertiary Amine Groups in Backbone Biomacromolecules 2010, 11 ( 10 ) 2550-2557 10.1021/bm1001476
49. Engler, A. C.; Tan, J. P. K.; Ong, Z. Y.; Coady, D. J.; Ng, V. W. L.; Yang, Y. Y.; Hedrick, J. L. Antimicrobial Polycarbonates: Investigating the Impact of Balancing Charge and Hydrophobicity Using a Same-Centered Polymer Approach Biomacromolecules 2013, 14 ( 12 ) 4331-4339 10.1021/bm401248t
50. Yoshida, T.; Lai, T. C.; Kwon, G. S.; Sako, K. pH-and ion-sensitive polymers for drug delivery Expert Opin. Drug Delivery 2013, 10 ( 11 ) 1497-1513 10.1517/17425247.2013.821978
51. Schlenoff, J. B. Zwitteration: Coating Surfaces with Zwitterionic Functionality to Reduce Nonspecific Adsorption Langmuir 2014, 30 ( 32 ) 9625-9636 10.1021/la500057j
52. Yang, C.; Ebrahim Attia, A. B.; Tan, J. P. K.; Ke, X.; Gao, S.; Hedrick, J. L.; Yang, Y.-Y. The role of non-covalent interactions in anticancer drug loading and kinetic stability of polymeric micelles Biomaterials 2012, 33 ( 10 ) 2971-2979 10.1016/j.biomaterials.2011.11.035
53. Ebrahim Attia, A. B.; Ong, Z. Y.; Hedrick, J. L.; Lee, P. P.; Ee, P. L. R.; Hammond, P. T.; Yang, Y.-Y. Mixed micelles self-assembled from block copolymers for drug delivery Curr. Opin. Colloid Interface Sci. 2011, 16 ( 3 ) 182-194 10.1016/j.cocis.2010.10.003
54. Ebrahim Attia, A. B.; Yang, C.; Tan, J. P. K.; Gao, S.; Williams, D. F.; Hedrick, J. L.; Yang, Y.-Y. The effect of kinetic stability on biodistribution and anti-tumor efficacy of drug-loaded biodegradable polymeric micelles Biomaterials 2013, 34 ( 12 ) 3132-3140 10.1016/j.biomaterials.2013.01.042
55. Venkataraman, S.; Ong, W. L.; Ong, Z. Y.; Joachim Loo, S. C.; Rachel Ee, P. L.; Yang, Y. Y. The role of PEG architecture and molecular weight in the gene transfection performance of PEGylated poly(dimethylaminoethyl methacrylate) based cationic polymers Biomaterials 2011, 32 ( 9 ) 2369-2378 10.1016/j.biomaterials.2010.11.070
56. Hoffman, A. S. The origins and evolution of “controlled” drug delivery systems J. Controlled Release 2008, 132 ( 3 ) 153-163 10.1016/j.jconrel.2008.08.012
57. Li, S.-D.; Huang, L. Stealth nanoparticles: High density but sheddable PEG is a key for tumor targeting J. Controlled Release 2010, 145 ( 3 ) 178-181 10.1016/j.jconrel.2010.03.016
58. O’Reilly, R. K.; Hawker, C. J.; Wooley, K. L. Cross-linked block copolymer micelles: functional nanostructures of great potential and versatility Chem. Soc. Rev. 2006, 35 ( 11 ) 1068-1083 10.1039/b514858h
59. Halperin, A. Polymeric vs. Monomeric Amphiphiles: Design Parameters J. Macromol. Sci., Polym. Rev. 2006, 46 ( 2 ) 173-214 10.1080/15321790600724369
60. Prabhu, V. M.; Venkataraman, S.; Yang, Y. Y.; Hedrick, J. L. Star-Like Structure of Oligocarbonate-Fluorene End-Functionalized Poly(ethylene glycol) ABA Triblock Copolymers Below the Gel Point Macromol. Symp. 2015, 358 ( 1 ) 157-169 10.1002/masy.201500076
61. Prabhu, V. M.; Venkataraman, S.; Yang, Y. Y.; Hedrick, J. L. Equilibrium Self-Assembly, Structure, and Dynamics of Clusters of Star-Like Micelles ACS Macro Lett. 2015, 4 ( 10 ) 1128-1133 10.1021/acsmacrolett.5b00507
62. Lee, A. L. Z.; Venkataraman, S.; Fox, C. H.; Coady, D. J.; Frank, C. W.; Hedrick, J. L.; Yang, Y. Y. Modular composite hydrogels from cholesterol-functionalized polycarbonates for antimicrobial applications J. Mater. Chem. B 2015, 3 ( 34 ) 6953-6963 10.1039/C5TB00811E
63. Li, X.; Zhang, Z.; Li, J.; Sun, S.; Weng, Y.; Chen, H. Diclofenac/biodegradable polymer micelles for ocular applications Nanoscale 2012, 4 ( 15 ) 4667-4673 10.1039/c2nr30924f
64. Jiang, S.; Cao, Z. Ultralow-Fouling, Functionalizable, and Hydrolyzable Zwitterionic Materials and Their Derivatives for Biological Applications Adv. Mater. 2010, 22 ( 9 ) 920-932 10.1002/adma.200901407
65. 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 ( 36 ) 6288-6308 10.1002/anie.200902672
66. Tew, G. N.; Sanabria-DeLong, N.; Agrawal, S. K.; Bhatia, S. R. New properties from PLA-PEO-PLA hydrogels Soft Matter 2005, 1 ( 4 ) 253-258 10.1039/b509800a
67. Yu, L.; Ding, J. Injectable hydrogels as unique biomedical materials Chem. Soc. Rev. 2008, 37 ( 8 ) 1473-1481 10.1039/b713009k