Poly(d-glucose carbonate) block copolymers: A platform for natural product-based nanomaterials with solvothermatic characteristics

Biomacromolecules

Volumn 14, Issue 9, 2013, Pages 3346-3353

  Gustafson, Tiffany P ^a   Lonnecker, Alexander T ^a   Heo, Gyu Seong ^a   Zhang, Shiyi ^a   Dove, Andrew P ^b   Wooley, Karen L ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

^b UNIVERSITY OF WARWICK   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1 ,5 ,7-TRIAZABICYCLO[4.4.0]DEC-5-ENE; AMPHIPHILIC POLYMERS; ASSEMBLY-DISASSEMBLY; CORE-SHELL MORPHOLOGIES; CORE-SHELL NANOSTRUCTURES; FUNCTIONAL ARCHITECTURE; LOWER CRITICAL SOLUTION TEMPERATURE; RENEWABLE MATERIALS;

BLOCK COPOLYMERS; CARBONATION;

BYPRODUCTS;

AMPHOPHILE; BICYCLO COMPOUND; CARBONIC ACID DERIVATIVE; COPOLYMER; ESTER DERIVATIVE; GLUCOSE DERIVATIVE; NANOMATERIAL; NATURAL PRODUCT; POLY(DEXTRO GLUCOSE CARBONATE) BLOCK COPOLYMER; THIOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL PARAMETERS; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CONTROLLED STUDY; HYDROPHOBICITY; MICELLIZATION; NANOCATALYST; NANOCHEMISTRY; POLYMERIZATION; PRIORITY JOURNAL; RING OPENING; SOLUTION AND SOLUBILITY; SYNTHESIS; TEMPERATURE;

BIOCOMPATIBLE MATERIALS; CATALYSIS; CLICK CHEMISTRY; GLUCOSE; HYDROLYSIS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; KINETICS; MICELLES; NANOSTRUCTURES; ORGANOPHOSPHATES; POLYESTERS; POLYMERIZATION; SONICATION; SURFACE-ACTIVE AGENTS;

EID: 84883780541     PISSN: 15257797     EISSN: 15264602     Source Type: Journal    
DOI: 10.1021/bm4010832     Document Type: Article

References (36)

1. Elsabahy, M.; Wooley, K. L. Design of polymeric nanoparticles for biomedical delivery applications Chem. Soc. Rev. 2012, 41 (7) 2545-2561
2. Kamaly, N.; Xiao, Z.; Valencia, P. M.; Radovic-Moreno, A. F.; Farokhzad, O. C. Targeted polymeric therapeutic nanoparticles: design, development and clinical translation Chem. Soc. Rev. 2012, 41 (7) 2971-3010
3. Lee, D.-E.; Heebeom, K.; Sun, I.-C.; Ryu, J. H.; Kwangmeyung, K.; Kwon, I. C. Multifunctional nanoparticles for multimodal imaging and theragnosis Chem. Soc. Rev. 2012, 41, 2656-2672
4. Langer, R. Perspectives and challenges in tissue engineering and regenerative medicine Adv. Mater. 2009, 21, 3235-3236
5. Vert, M. Degradable and bioresorbable polymers in surgery and in pharmacology: beliefs and facts J. Mater. Sci.: Mater. Med. 2009, 20 (2) 437-446
6. Balasundaram, G.; Webster, T. An overview of nano-polymers for orthopedic applications Macromol. Biosci. 2007, 7, 635-642
7. Mecking, S. Nature or petrochemistry? Biologically degradable materials Angew. Chem., Int. Ed. 2004, 43, 1078-1085
8. Galbis, J. A.; Garcia-Martin, M. G. Sugars as monomers. In Monomers, Polymers and Composites from Renewable Resources; Gandini, M. N. B. a. A., Ed.; Elsevier: Oxford, U.K., 2008; pp 89-114.
9. Robert, C.; de Montigny, F.; Thomas, C. M., Tandem synthesis of alternating polyesters from renewable resources. Nat. Commun. 2011, 2.
10. Wilbon, P. A.; Chu, F.; Tang, C. Progress in renewable polymers from natural terpenes, terpenoids, and rosin Macromol. Rapid Commun. 2013, 34, 8-37
11. Chen, X.; Gross, R. A. Versatile copolymers from l -lactide and d -xylofuranose Macromolecules 1998, 32 (2) 308-314
12. 2 Macromolecules 2005, 38, 3562-3563
13. 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 (8) 2799-2802
14. Azechi, M.; Matsumoto, K.; Endo, T. Anionic ring-opening polymerization of a five-membered cyclic carbonate having a glucopyranoside structure J. Polym. Sci., Part A: Polym. Chem. 2013, 7, 1651-1655
15. Shin, J.; Lee, Y.; Tolman, W. B.; Hillmyer, M. A. Thermoplastic elastomers derived from menthide and tulipalin A Biomacromolecules 2012, 13 (11) 3833-3840
16. Zhang, D.; Hillmyer, M. A.; Tolman, W. B. Catalytic polymerization of a cyclic ester derived from a "cool" natural precursor Biomacromolecules 2005, 6, 2091-2095
17. 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
18. Zhang, S.; Li, A.; Zou, J.; Lin, L. Y.; Wooley, K. L. Facile synthesis of clickable, water-soluble and degradable polyphosphoesters ACS Macro Lett. 2012, 1 (2) 328-333
19. Zhang, S.; Zou, J.; Zhang, F.; Elsabahy, M.; Felder, S. E.; Zhu, J.; Pochan, D. J.; Wooley, K. L. Rapid and versatile construction of diverse and functional nanostructures derived from a polyphosphoester-based biomimetic block copolymer system J. Am. Chem. Soc. 2012, 134 (44) 18467-18474
20. 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
21. Miura, Y. Design and synthesis of well-defined glycopolymers for the control of biological functionalities Polym. J. 2012, 44, 679-689
22. Kumar, J.; McDowall, L.; Chen, G.; Stenzel, M. H. Synthesis of thermoresponsive glycopolymers via copper catalysed azide-alkyne "click" chemistry for inhibition of ricin: the effect of spacer between polymer backbone and galactose Polym. Chem. 2011, 2, 1879-1886
23. Suriano, F.; Pratt, R.; Tan, J. P. K.; Wiradharma, N.; Nelson, A.; Yang, Y. Y.; Dubois, P.; Hedrick, J. L. Synthesis of a family of amphiphilic glycopolymers via controlled ring-opening polymerization of functionalized cyclic carbonates and their application in drug delivery Biomaterials 2010, 31, 2637-2645
24. Zhang, S.; Li, A.; Zou, J.; Lin, L. Y.; Wooley, K. L. Facile synthesis of clickable, water-soluble and degradable polyphosphoesters ACS Macro Lett. 2012, 1 (2) 328-333
25. 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. 2012, 41, 1312-1336
26. Nederberg, F.; Lohmeijer, B. G.; Leibfarth, F.; Pratt, R. C.; Choi, J.; Dove, A. P.; Waymouth, R. M.; Hedrick, J. L. Organocatalytic ring opening polymerization of trimethylene carbonate Biomacromolecules 2007, 8 (1) 153-160
27. 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
28. Heskins, M.; Guillet, J. E. Solution properties of poly(N -isopropylacrylamide) J. Macromol. Sci., Part A: Pure Appl. Chem. 1968, 2, 1441-1455
29. Gibson, M. I.; O'Reilly, R. K. To aggregate or not to aggregate? Considerations in the design and application of polymeric thermally-responsive nanoparticles Chem. Soc. Rev. 2013, 42, 7204-7213
30. Takahashi, M.; Shimazaki, M.; Yamamoto, J. Thermoreversible gelation and phase separation in aqueous methyl cellulose solutions J. Polym. Sci., Part B: Polym. Phys. 2001, 39, 91-100
31. Wang, Y. C.; Li, Y.; Yang, X. Z.; Yuan, Y. Y.; Yan, L. F.; Wang, J. Tunable thermosensitivity of biodegradable polymer micelles of poly(ε-caprolactone) and polyphosphoester block copolymers Macromolecules 2009, 42, 3026-3032
32. Zhai, X.; Huang, W.; Liu, J.; Pang, Y.; Zhu, X.; Zhou, Y.; Yan, D. Micelles from amphiphilic block copolyphosphates for drug delivery Macromol. Biosci. 2011, 11, 1603-1610
33. Kim, S. H.; Tan, J. P.; Fukushima, K.; Nederberg, F.; Yang, Y. Y.; Waymouth, R. M.; Hedrick, J. L. Thermoresponsive nanostructured polycarbonate block copolymers as biodegradable therapeutic delivery carriers Biomaterials 2011, 32 (23) 5505-5514
34. Zhang, N.; Salzinger, S.; Rieger, B. Poly(vinylphosphonate)s with widely tunable LCST: a promising alternative to conventional thermoresponsive polymers Macromolecules 2013, 45 (24) 9751-9758
35. Kim, Y.-H.; Kwon, I. C.; Bae, Y. H.; Kim, S. W. Saccharide effects on the lower critical solution temperature of thermosensitive polymers Macromolecules 1995, 28, 929-944
36. Kotsuchibashi, Y.; Agustin, R. V. C. A.; Lu, J. Y.; Hall, D. G.; Narain, R. Temperature, pH, and glucose responsive gels via simple mixing of boroxole- and glyco-based polymers ACS Macro Lett. 2013, 2, 260-264