Synthesis and Biomedical Applications of Functional Poly(α-hydroxy acids) via Ring-Opening Polymerization of O-Carboxyanhydrides

Accounts of Chemical Research

Volumn 48, Issue 7, 2015, Pages 1777-1787

  Yin, Qian ^a   Yin, Lichen ^b   Wang, Hua ^a   Cheng, Jianjun ^a  

^a United States of America   (United States)

^b SOOCHOW UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ANHYDRIDE; BIOMATERIAL; HYDROXYACID; POLYMER;

CHEMISTRY; CONFORMATION; DRUG DELIVERY SYSTEM; PARTICLE SIZE; POLYMERIZATION; PROCEDURES; SURFACE PROPERTY; SYNTHESIS;

ACETIC ANHYDRIDES; BIOCOMPATIBLE MATERIALS; DRUG DELIVERY SYSTEMS; HYDROXY ACIDS; MOLECULAR CONFORMATION; PARTICLE SIZE; POLYMERIZATION; POLYMERS; SURFACE PROPERTIES;

EID: 84937401439     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar500455z     Document Type: Article

References (48)

1. Albertsson, A. C.; Varma, I. K. Aliphatic polyesters: Synthesis, properties and applications Adv. Polym. Sci. 2002, 157, 1-40
2. Gilding, D. K.; Reed, A. M. Biodegradable Polymers for Use in Surgery-Polyglycolic/Poly(actic acid) Homo- and Copolymers: 1 Polymer 1979, 20, 1459-1464
3. Yamamoto, H.; Kuno, Y.; Sugimoto, S.; Takeuchi, H.; Kawashima, Y. Surface-modified PLGA nanosphere with chitosan improved pulmonary delivery of calcitonin by mucoadhesion and opening of the intercellular tight junctions J. Controlled Release 2005, 102, 373-381
4. Miller, R. A.; Brady, J. M.; Cutright, D. E. Degradation Rates of Oral Resorbable Implants (Polylactates and Polyglycolates)-Rate Modification with Changes in PLA-PGA Copolymer Ratios J. Biomed. Mater. Res. 1977, 11, 711-719
5. Bala, I.; Hariharan, S.; Kumar, M. PLGA nanoparticles in drug delivery: The state of the art Crit. Rev. Ther. Drug Carrier Syst. 2004, 21, 387-422
6. Silvers, A. L.; Chang, C. C.; Emrick, T. Functional aliphatic polyesters and nanoparticles prepared by organocatalysis and orthogonal grafting chemistry J. Polym. Sci., Part A: Polym. Chem. 2012, 50, 3517-3529
7. Leemhuis, M.; van Nostrum, C. F.; Kruijtzer, J. A. W.; Zhong, Z. Y.; ten Breteler, M. R.; Dijkstra, P. J.; Feijen, J.; Hennink, W. E. Functionalized poly(α-hydroxy acid)s via ring-opening polymerization: Toward hydrophilic polyesters with pendant hydroxyl groups Macromolecules 2006, 39, 3500-3508
8. Theryo, G.; Jing, F.; Pitet, L. M.; Hillmyer, M. A. Tough Polylactide Graft Copolymers Macromolecules 2010, 43, 7394-7397
9. Cohen-Arazi, N.; Domb, A. J.; Katzhendler, J. New biocompatible polyesters derived from α-amino acids: Hydrolytic degradation behavior Polymers 2010, 2, 418-439
10. Dechy-Cabaret, O.; Martin-Vaca, B.; Bourissou, D. Controlled ring-opening polymerization of lactide and glycolide Chem. Rev. 2004, 104, 6147-6176
11. Li, Y.; Wang, X. L.; Yang, K. K.; Wang, Y. Z. A rapid synthesis of poly(p -dioxanone) by ring-opening polymerization under microwave irradiation Polym. Bull. 2006, 57, 873-880
12. Hori, M.; Kamitakahara, H.; Nakatsubo, F. Substituent effects of the orthoester group on ring-opening polymerization of α- d -glucopyranose 1,2,4-orthoester derivatives Macromolecules 1997, 30, 2891-2896
13. Pounder, R. J.; Dove, A. P. Towards poly(ester) nanoparticles: Recent advances in the synthesis of functional poly(ester)s by ring-opening polymerization Polym. Chem. 2010, 1, 260-271
14. Seyednejad, H.; Ghassemi, A. H.; van Nostnum, C. F.; Vermonden, T.; Hennink, W. E. Functional aliphatic polyesters for biomedical and pharmaceutical applications J. Controlled Release 2011, 152, 168-176
15. Jéroîme, C.; Lecomte, P. Recent advances in the synthesis of aliphatic polyesters by ring-opening polymerization Adv. Drug Delivery Rev. 2008, 60, 1056-1076
16. Choi, Y. R.; Bae, Y. H.; Kim, S. W. Star-shaped poly(ether-ester) block copolymers: Synthesis, characterization, and their physical properties Macromolecules 1998, 31, 8766-8774
17. Kricheldorf, H. R.; Eggerstedt, S. Macrocycles, 5. Ring expansion of macrocyclic tin alkoxides with cyclic anhydrides Macromol. Chem. Phys. 1999, 200, 587-593
18. Ryner, M.; Finne, A.; Albertsson, A. C.; Kricheldorf, H. R. L-Lactide macromonomer synthesis initiated by new cyclic tin alkoxides functionalized for brushlike structures Macromolecules 2001, 34, 7281-7287
19. Freichels, H.; Pourcelle, V.; Auzély-Velty, R.; Marchand-Brynaert, J.; Jéroîme, C. Synthesis of Poly(lactide- co -glycolide- co -ε-caprolactone)- graft -mannosylated Poly(ethylene oxide) Copolymers by Combination of "Clip" and "Click" Chemistries Biomacromolecules 2012, 13, 760-768
20. Jing, F.; Hillmyer, M. A. A bifunctional monomer derived from lactide for toughening polylactide J. Am. Chem. Soc. 2008, 130, 13826-13827
21. Jiang, X.; Smith, M. R.; Baker, G. L. Water-soluble thermoresponsive polylactides Macromolecules 2008, 41, 318-324
22. Kricheldorf, H. R.; Jonte, J. M. New Polymer Syntheses. 8. Synthesis and Polymerization of l -Lactic Acid O -Carboxyanhydride (5-Methyl-Dioxolan-2,4-dione) Polym. Bull. 1983, 9, 276-283
23. du Boullay, O. T.; Marchal, E.; Martin-Vaca, B.; Cossio, F. P.; Bourissou, D. An activated equivalent of lactide toward organocatalytic ring-opening polymerization J. Am. Chem. Soc. 2006, 128, 16442-16443
24. Bonduelle, C.; Martin-Vaca, B.; Cossio, F. P.; Bourissou, D. Monomer versus Alcohol Activation in the 4-Dimethylaminopyridine-Catalyzed Ring-Opening Polymerization of Lactide and Lactic O -Carboxylic Anhydride Chem.-Eur. J. 2008, 14, 5304-5312
25. du Boullay, O. T.; Bonduelle, C.; Martin-Vaca, B.; Bourissou, D. Functionalized polyesters from organocatalyzed ROP of gluOCA, the O -carboxyanhydride derived from glutamic acid Chem. Commun. 2008, 1786-1788
26. du Boullay, O. T.; Saffon, N.; Diehl, J. P.; Martin-Vaca, B.; Bourissou, D. Organo-Catalyzed Ring Opening Polymerization of a 1,4-Dioxane-2,5-dione Deriving from Glutamic Acid Biomacromolecules 2010, 11, 1921-1929
27. Pounder, R. J.; Dove, A. P. Synthesis and Organocatalytic Ring-Opening Polymerization of Cyclic Esters Derived from l -Malic Acid Biomacromolecules 2010, 11, 1930-1939
28. Pounder, R. J.; Fox, D. J.; Barker, I. A.; Bennison, M. J.; Dove, A. P. Ring-opening polymerization of an O -carboxyanhydride monomer derived from l -malic acid Polym. Chem. 2011, 2, 2204-2212
29. Lu, Y. B.; Yin, L. C.; Zhang, Y. F.; Zhang, Z. H.; Xu, Y. X.; Tong, R.; Cheng, J. J. Synthesis of Water-Soluble Poly(α-hydroxy acids) from Living Ring-Opening Polymerization of O -Benzyl- l -serine Carboxyanhydrides ACS Macro Lett. 2012, 1, 441-444
30. Bonduelle, C.; Martin-Vaca, B.; Bourissou, D. Lipase-Catalyzed Ring-Opening Polymerization of the O -Carboxylic Anhydride Derived from Lactic Acid Biomacromolecules 2009, 10, 3069-3073
31. Zhang, Z.; Yin, L.; Xu, Y.; Ren, J.; Cheng, J. Facile Functionalization of Polyesters through Thiol-Yne Chemistry for the Design of Degradable, Cell-Penetrating and Gene Delivery Dual-Functional Agents Biomacromolecules 2012, 13, 3456-3462
32. Rieth, L. R.; Moore, D. R.; Lobkovsky, E. B.; Coates, G. W. Single-site β-diiminate zinc catalysts for the ring-opening polymerization of β-butyrolactone and β-valerolactone to poly(3-hydroxyalkanoates) J. Am. Chem. Soc. 2002, 124, 15239-15248
33. Chamberlain, B. M.; Cheng, M.; Moore, D. R.; Ovitt, T. M.; Lobkovsky, E. B.; Coates, G. W. Polymerization of lactide with zinc and magnesium β-diiminate complexes: Stereocontrol and mechanism J. Am. Chem. Soc. 2001, 123, 3229-3238
34. Davis, M. E.; Chen, Z.; Shin, D. M. Nanoparticle therapeutics: An emerging treatment modality for cancer Nat. Rev. Drug Discovery 2008, 7, 771-782
35. Duncan, R. The dawning era of polymer therapeutics Nat. Rev. Drug Discovery 2003, 2, 347-360
36. Tong, R.; Yala, L.; Fan, T. M.; Cheng, J. The formulation of aptamer-coated paclitaxel-polylactide nanoconjugates and their targeting to cancer cells Biomaterials 2010, 31, 3043-3053
37. Tong, R.; Cheng, J. Paclitaxel-initiated, controlled polymerization of lactide for the formulation of polymeric nanoparticulate delivery vehicles Angew. Chem., Int. Ed. 2008, 47, 4830-4834
38. Tong, R.; Cheng, J. Ring-Opening Polymerization-Mediated Controlled Formulation of Polylactide-Drug Nanoparticles J. Am. Chem. Soc. 2009, 131, 4744-4754
39. Yin, Q.; Tong, R.; Xu, Y. X.; Baek, K.; Dobrucki, L. W.; Fan, T. M.; Cheng, J. J. Drug-Initiated Ring-Opening Polymerization of O -Carboxyanhydrides for the Preparation of Anticancer Drug-Poly(O -carboxyanhydride) Nanoconjugates Biomacromolecules 2013, 14, 920-929
40. Binauld, S.; Scarano, W.; Stenzel, M. H. pH-Triggered Release of Platinum Drugs Conjugated to Micelles via an Acid-Cleavable Linker Macromolecules 2012, 45, 6989-6999
41. Sugihara, S.; Ito, S.; Irie, S.; Ikeda, I. Synthesis of Thermoresponsive Shell Cross-Linked Micelles via Living Cationic Polymerization and UV Irradiation Macromolecules 2010, 43, 1753-1760
42. Tao, Y.; Han, J.; Ye, C.; Thomas, T.; Dou, H. Reduction-responsive gold-nanoparticle-conjugated Pluronic micelles: An effective anti-cancer drug delivery system J. Mater. Chem. 2012, 22, 18864-18871
43. Ge, Z.; Liu, S. Functional block copolymer assemblies responsive to tumor and intracellular microenvironments for site-specific drug delivery and enhanced imaging performance Chem. Soc. Rev. 2013, 42, 7289-7325
44. Wang, H.; Tang, L.; Tu, C. L.; Song, Z. Y.; Yin, Q.; Yin, L. C.; Zhang, Z. H.; Cheng, J. J. Redox-Responsive, Core-Cross-Linked Micelles Capable of On-Demand, Concurrent Drug Release and Structure Disassembly Biomacromolecules 2013, 14, 3706-3712
45. Zhang, Z.; Yin, L.; Tu, C.; Song, Z.; Zhang, Y.; Xu, Y.; Tong, R.; Zhou, Q.; Ren, J.; Cheng, J. Redox-Responsive, Core Cross-Linked Polyester Micelles ACS Macro Lett. 2012, 2, 40-44
46. Lim, Y. B.; Kim, C. H.; Kim, K.; Kim, S. W.; Park, J. S. Development of a safe gene delivery system using biodegradable polymer, poly[α-(4-aminobutyl)- l -glycolic acid] J. Am. Chem. Soc. 2000, 122, 6524-6525
47. Gabrielson, N. P.; Cheng, J. J. Multiplexed supramolecular self-assembly for non-viral gene delivery Biomaterials 2010, 31, 9117-9127
48. Duchardt, F.; Fotin-Mleczek, M.; Schwarz, H.; Fischer, R.; Brock, R. A comprehensive model for the cellular uptake of cationic cell-penetrating peptides Traffic 2007, 8, 848-866