Polyacetals

Natural and Synthetic Biomedical Polymers

Volumn , Issue , 2014, Pages 219-233

  Carmali, Sheiliza ^a   Brocchini, Steve ^a  

^a UNIVERSITY OF LONDON   (United Kingdom)

Author keywords

Acid labile degradation; Nonacidic by products; Polyacetal; Polyketal

Indexed keywords

EID: 84902912195     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1016/B978-0-12-396983-5.00014-4     Document Type: Chapter

References (136)

1. Tannock I., Rotin D. Acid pH in tumors and its potential for therapeutic exploitation perspectives. Cancer Res. 1989, 49:4373-4384.
2. Akinc A., Langer R. Measuring the pH environment of DNA delivered using nonviral vectors: implications for lysosomal trafficking. Biotechnol. Bioeng. 2002, 78:503-508.
3. Asokan A., Cho M. Exploitation of intracellular pH gradients in the cellular delivery of macromolecules. J. Pharm. Sci. 2002, 91:903-913.
4. Ulery B., Nair L., Laurencin C. Biomedical applications of biodegradable polymers. J. Polym. Sci. B Polym. Phys. 2011, 49:832-864.
5. Esser-Kahn A., Odom S., Sottos N., White S., Moore J. Triggered release from polymer capsules. Macromolecules 2011, 44:5539-5553.
6. Roy D., Cambre J., Sumerlin B. Future perspectives and recent advances in stimuli-responsive materials. Prog. Polym. Sci. 2010, 35:278-301.
7. Gil E., Hudson S. Stimuli-responsive polymers and their bioconjugates. Prog. Polym. Sci. 2004, 29:1173-1222.
8. Schacht E., Toncheva V., Vandertaelen K., Heller J. Polyacetal and poly(ortho ester)-poly(ethylene glycol) graft copolymer thermogels: preparation, hydrolysis and FITC-BSA release studies. J. Control. Release 2006, 116:219-225.
9. Binauld S., Stenzel M. Acid-degradable polymers for drug delivery: a decade of innovation. Chem. Commun. (Camb.) 2013, 49:2082-2102.
10. Deshayes S., Kasko A. Polymeric biomaterials with engineered degradation. J. Polym. Sci. A Polym. Chem. 2013, 51:3531-3566.
11. Heller J., Barr J., Ng S., Abdellauoi K., Gurny R. Poly(ortho esters): synthesis, characterization, properties and uses. Adv. Drug Deliv. Rev. 2002, 54:1015-1039.
12. Erbacher P., Bettinger T., Belguise-Valladier P., Zou S., Coll J., Behr J., Remy J. Transfection and physical properties of various saccharide, poly(ethylene glycol), and antibody-derivatized polyethylenimines (PEI). J. Gene Med. 1999, 1:210-222.
13. Knorr V., Ogris M., Wagner E. An acid sensitive ketal-based polyethylene glycol-oligoethylenimine copolymer mediates improved transfection efficiency at reduced toxicity. Pharm. Res. 2008, 25:2937-2945.
14. Knorr V., Russ V., Allmendinger L., Ogris M., Wagner E. Acetal linked oligoethylenimines for use as pH-sensitive gene carriers. Bioconjug. Chem. 2008, 19:1625-1634.
15. Yoo H., Lee E., Park T. Doxorubicin-conjugated biodegradable polymeric micelles having acid-cleavable linkages. J. Control. Release 2002, 82:17-27.
16. Bae Y., Fukushima S., Harada A., Kataoka K. Design of environment-sensitive supramolecular assemblies for intracellular drug delivery: polymeric micelles that are responsive to intracellular pH change. Angew. Chem. Int. Ed. Engl. 2003, 42:4640-4643.
17. DuBois Clochard M., Rankin S., Brocchini S. Synthesis of soluble polymers for medicine that degrade by intramolecular acid catalysis. Macromol. Rapid Commun. 2000, 21:853-859.
18. Paramonov S., Bachelder E., Beaudette T., Standley S., Lee C., Dashe J., Fréchet J. Fully acid-degradable biocompatible polyacetal microparticles for drug delivery. Bioconjug. Chem. 2008, 19:911-919.
19. Goh S., Murthy N., Xu M., Fréchet J. Cross-linked microparticles as carriers for the delivery of plasmid DNA for vaccine development. Bioconjug. Chem. 2004, 15:467-474.
20. Broaders K., Pastine S., Grandhe S., Fréchet J. Acid-degradable solid-walled microcapsules for pH-responsive burst-release drug delivery. Chem. Commun. 2011, 47:665-667.
21. Gillies E., Fréchet J. pH-Responsive copolymer assemblies for controlled release of doxorubicin. Bioconjug. Chem. 2005, 16:361-368.
22. Kwon Y., Standley S., Goodwin A., Gillies E., Fréchet J. Directed antigen presentation using polymeric microparticulate carriers degradable at lysosomal pH for controlled immune responses. Mol. Pharm. 2005, 2:83-91.
23. Vicent M., Tomlinson R., Brocchini S., Duncan R. Polyacetal-diethylstilboestrol: a polymeric drug designed for pH-triggered activation. J. Drug Target. 2004, 12:491-501.
24. Melton G., Peters E., Arisman R. Engineering Thermoplastics. Applied Plastics Engineering Handbook 2011, 9-10. Elsevier, Waltham MA, USA. M. Kutz (Ed.).
25. Teoh S., Tang Z., Hastings G. Thermoplastics in biomedical applications: structures, properties and processing. Handbook of Biomaterial Properties 1998, 270-302. Chapman and Hall, London/UK. J. Black, G.W. Hastings (Eds.).
26. Schweitzer C., MacDonald R., Punderson J. Thermally stable high molecular weight polyoxymethylenes. J. Appl. Polym. Sci. 1959, 1(2):158-163.
27. Wang Y., Morinaga H., Sudo A., Endo T. Synthesis of amphiphilic polyacetal by polycondensation of aldehyde and polyethylene glycol as an acid-labile polymer for controlled release of aldehyde. J. Polym. Sci. A Polym. Chem. 2011, 49:596-602.
28. Heffernan M., Murthy N. Polyketal nanoparticles: a new pH-sensitive biodegradable drug delivery vehicle. Bioconjug. Chem. 2005, 16:1340-1342.
29. Heller J., Penhale D., Helwing R. Preparation of polyacetals by the reaction of divinyl ethers and polyols. J. Polym. Sci. Polym. Lett. Ed. 1980, 18:293-297.
30. Mathias L., Canterberry J. Polyacetal formation of the monovinyl ether of tetraethylene glycol. J. Polym. Sci. Polym. Chem. Ed. 1982, 20:2731-2734.
31. Tomlinson R., Klee M., Garrett S., Heller J., Duncan R., Brocchini S. Pendent chain functionalized polyacetals that display pH-dependent degradation: a platform for the development of novel polymer therapeutics. Macromolecules 2002, 35:473-480.
32. England R., Masiá E., Giménez V., Lucas R., Vicent M. Polyacetal-stilbene conjugates-the first examples of polymer therapeutics for the inhibition of HIF-1 in the treatment of solid tumours. J. Control. Release 2012, 164:314-322.
33. Ruckenstein E., Zhang H. Novel copolymer networks via the combination of polyaddition and anionic polymerization. J. Polym. Sci. A Polym. Chem. 2001, 39:117-126.
34. Tomlinson R., Heller J., Brocchini S., Duncan R. Polyacetal-doxorubicin conjugates designed for pH-dependent degradation. Bioconjug. Chem. 2003, 14:1096-1106.
35. Duncan R., Vicent M. Polymer therapeutics-prospects for 21st century: the end of the beginning. Adv. Drug Deliv. Rev. 2013, 65:60-70.
36. Duncan R., Gaspar R. Nanomedicine(s) under the microscope. Mol. Pharm. 2011, 8:2101-2141.
37. Duncan R. Drug-polymer conjugates: potential for improved chemotherapy. Anticancer Drugs 1992, 3:175-210.
38. Nucci M., Shorr R. The therapeutic value of poly(ethylene glycol)-modified proteins. Adv. Drug Deliv. Rev. 1991, 6:133-151.
39. Pasut G., Veronese F. State of the art in PEGylation: the great versatility achieved after forty years of research. J. Control. Release 2011, 161:461-472.
40. Goddard P., Williamson I., Brown J., Hutchinson L., Nicholls J., Petrak K. Soluble polymeric carriers for drug delivery-Part 4: tissue autoradiography and whole-body tissue distribution in mice, of N-(2-hydroxypropyl)methacrylamide copolymers following intravenous administration. J. Bioact. Compat. Polym. 1991, 6:4-24.
41. Seymour L., Duncan R. Effect of molecular weight of N-(2- hydroxypropyl)methacrylamide copolymers on body distribution and rate of excretion after subcutaneous, intraperitoneal and intravenous administration to rats. J. Biomed. Mater. Res. 1987, 21:1341-1358.
42. Barz M., Luxenhofer R., Zentel R., Vicent M. Overcoming the PEG-addiction: well-defined alternatives to PEG, from structure-property relationships to better defined therapeutics. Polym. Chem. 2011, 2:1900-1918.
43. Paz-Ares L., et al. Phase III trial comparing paclitaxel poliglumex vs docetaxel in the second-line treatment of non-small-cell lung cancer. Br. J. Cancer 2008, 98:1608-1613.
44. Albain K.S., Belani C.P., Bonomi P., O'Byrne K.J., Schiller J.H., Socinski M. PIONEER: a phase III randomized trial of paclitaxel poliglumex versus paclitaxel in chemotherapy-naive women with advanced-stage non-small-cell lung cancer and performance status of 2. Clin. Lung Cancer 2006, 7:417-419.
45. Singer J., Bhatt R., Tulinsky J., Buhler K., Heasley E., Klein P., de Vries P. Water-soluble poly-(L-glutamic acid)-gly-camptothecin conjugates enhance camptothecin stability and efficacy in vivo. J. Control. Release 2001, 74:243-247.
46. Yokoyama M., Inoue S. Preparation of adriamycin-conjugated poly(ethy1ene glycol)-poly(aspartic acid) block copolymer. A new type of polymeric anticancer agent. Makromol. Chem. Rapid Commun. 1987, 435:431-435.
47. Yokoyama M., Miyauchi M., Yamada N., Okano T. Polymer micelles as novel drug carrier: adriamycin-conjugated poly (ethylene glycol)-poly (aspartic acid) block copolymer. J. Control. Release 1990, 11:269-278.
48. Yokoyama M., Miyauchi M., Yamada N., Okano T., Sakurai Y., Kataoka K., Inoue S. Characterization and anticancer activity of the micelle-forming polymeric anticancer drug adriamycin-conjugated poly(ethylene glycol)-poly(aspartic acid) block copolymer. Cancer Res. 1990, 50:1693-1700.
49. Sedlačík T., Studenovská H., Rypáček F. Enzymatic degradation of the hydrogels based on synthetic poly(α-amino acid)s. J. Mater. Sci. Mater. Med. 2011, 22:781-788.
50. Petros R., DeSimone J. Strategies in the design of nanoparticles for therapeutic applications. Nat. Rev. Drug Discov. 2010, 9:615-627.
51. Maeda H., Wu J., Sawa T., Matsumura Y., Hori K. Tumor vascular permeability and the EPR effect in macromolecular therapeutics: a review. J. Control. Release 2000, 65:271-284.
52. Matsumura Y., Maeda H. A new concept for macromolecular therapeutics in cancer chemotherapy: mechanism of tumoritropic accumulation of proteins and the antitumor agent smancs. Cancer Res. 1986, 46:6387-6392.
53. Sinha R., Kim G., Nie S., Shin D. Nanotechnology in cancer therapeutics: bioconjugated nanoparticles for drug delivery. Mol. Cancer Ther. 2006, 5:1909-1917.
54. Graham M.L. PEGaspargase: a review of clinical studies. Adv. Drug Deliv. Rev. 2003, 55:1293-1302.
55. Reddy R., Modi M., Pedder S. Use of PEGinterferon alfa-2a (40 KD) (PEGasys) for the treatment of hepatitis C. Adv. Drug Deliv. Rev. 2002, 54:571-586.
56. Molineux G. PEGfilgrastim: using PEGylation technology to improve neutropenia support in cancer patients. Anticancer Drugs 2003, 14:259-264.
57. Fang J., Sawa T., Akaike T., Maeda H. Tumor-targeted delivery of polyethylene glycol-conjugated d-amino acid Oxidase for antitumor therapy via enzymatic generation of hydrogen peroxide. Cancer Res. 2002, 62:3138-3143.
58. Wang Y.-S., Youngster S., Grace M., Bausch J., Bordens R., Wyss D. Structural and biological characterization of PEGylated recombinant interferon alpha-2b and its therapeutic implications. Adv. Drug Deliv. Rev. 2002, 54:547-570.
59. Bissett D., Cassidy J., de Bono J., Muirhead F., Main M., Robson L., Fraier D., Magnè M., Pellizzoni C., Porro M., Spinelli R., Speed W., Twelves C. Phase I and pharmacokinetic (PK) study of MAG-CPT (PNU 166148): a polymeric derivative of camptothecin (CPT). Br. J. Cancer 2004, 91:50-55.
60. Seymour L., Ferry D., Anderson D., Hesslewood S., Julyan P., Poyner R., Doran J., Young A., Burtles S., Kerr D. Hepatic drug targeting: phase I evaluation of polymer-bound doxorubicin. J. Clin. Oncol. 2002, 20:1668-1676.
61. Vasey P., Kaye S., Morrison R., Twelves C., Wilson P., Duncan R., Thomson A., Murray L., Hilditch T., Murray T., Burtles S., Fraier D., Frigerio E. Phase I clinical and pharmacokinetic study of PK1 N -(2-hydroxypropyl) methacrylamide copolymer doxorubicin: first member of a new class of chemotherapeutic agents-drug-polymer conjugates. Clin. Cancer Res. 1999, 5:83-94.
62. Li C., Wallace S. Polymer-drug conjugates: recent development in clinical oncology. Adv. Drug Deliv. Rev. 2008, 60:886-898.
63. Pasut G., Veronese F. Polymer-drug conjugation, recent achievements and general strategies. Prog. Polym. Sci. 2007, 32:933-961.
64. Khandare J., Minko T. Polymer-drug conjugates: progress in polymeric prodrugs. Prog. Polym. Sci. 2006, 31:359-397.
65. Ducry L., Stump B. Antibody-drug conjugates: linking cytotoxic payloads to monoclonal antibodies. Bioconjug. Chem. 2010, 21:5-13.
66. Doronina S., Mendelsohn B., Bovee T., Cerveny C., Alley S., Meyer D., Oflazoglu E., Toki B., Sanderson R., Zabinski R., Wahl A., Senter P. Enhanced activity of monomethylauristatin F through monoclonal antibody delivery: effects of linker technology on efficacy and toxicity. Bioconjug. Chem. 2006, 17:114-124.
67. Flygare J., Pillow T., Aristoff P. Antibody-drug conjugates for the treatment of cancer. Chem. Biol. Drug Des. 2013, 81:113-121.
68. Alley S., Okeley N., Senter P. Antibody-drug conjugates: targeted drug delivery for cancer. Curr. Opin. Chem. Biol. 2010, 14:529-537.
69. Rickerby J., Prabhakar R., Ali M., Knowles J., Brocchini S. Water-soluble polyacetals derived from diphenols. J. Mater. Chem. 2005, 15:1849-1856.
70. Bourke S., Kohn J. Polymer derived from the amino acid L-tyrosine: polycarbonates, polyarylates and copolymers with poly(ethylene glycol). Adv. Drug Deliv. Rev. 2003, 55:447-466.
71. Gimenez V., James C., Arminan A., Schweins R., Paul A., Vicent M. Demonstrating the importance of polymer-conjugate conformation in solution on its therapeutic output: diethylstilbestrol (DES)-polyacetals as prostate cancer treatment. J. Control. Release 2012, 159:290-301.
72. Yurkovetskiy A., Fram R. XMT-1001, a novel polymeric camptothecin pro-drug in clinical development for patients with advanced cancer. Adv. Drug Deliv. Rev. 2009, 61:1193-1202.
73. Papisov M., Hiller A., Yurkovetskiy A., Yin M., Barzana M., Hillier S., Fischman A. Semisynthetic hydrophilic polyals. Biomacromolecules 2005, 6:2659-2670.
74. Yurkovetskiy V., Hiller A., Syed S., Yin M., Lu X., Fischman J., Papisov M. Synthesis of a macromolecular camptothecin conjugate with dual phase drug release. Mol. Pharm. 2004, 1:375-382.
75. Li Q.-Y., Zu Y.-G., Shi R.-Z., Yao L.-P. Review camptothecin: current perspectives. Curr. Med. Chem. 2006, 13:2021-2039.
76. Yu D., Peng P., Dharap S., Wang Y., Mehlig M., Chandna P., Zhao H., Filpula D., Yang K., Borowski V., Borchard G., Zhang Z., Minko T. Antitumor activity of poly(ethylene glycol)-camptothecin conjugate: the inhibition of tumor growth in vivo. J. Control. Release 2005, 110:90-102.
77. Cheng J., Khin K., Davis M. Antitumor activity of beta-cyclodextrin polymer-camptothecin conjugates. Mol. Pharm. 2004, 1:1831-1893.
78. Walsh M., Hanna S., Sen J., Rawal S., Cabral C., Yurkovetskiy A., Fram R., Lowinger T., Zamboni W. Pharmacokinetics and antitumor efficacy of XMT-1001, a novel, polymeric topoisomerase I inhibitor, in mice bearing HT-29 human colon carcinoma xenografts. Clin. Cancer Res. 2012, 18:2591-2602.
79. Conover C., Greenwald R., Pendri A., Gilbert C., Shum K. Camptothecin delivery systems: enhanced efficacy and tumor accumulation of camptothecin following its conjugation to polyethylene glycol via a glycine linker. Cancer Chemother. Pharmacol. 1998, 42:407-414.
80. Murthy N., Thng Y., Schuck S., Xu M., Fréchet J. A novel strategy for encapsulation and release of proteins: hydrogels and microgels with acid-labile acetal cross-linkers. J. Am. Chem. Soc. 2002, 124:12398-12399.
81. Murthy N., Xu M., Schuck S., Kunisawa J., Shastri N., Fréchet J. A macromolecular delivery vehicle for protein-based vaccines: acid-degradable protein-loaded microgels. Proc. Natl. Acad. Sci. U. S. A. 2003, 100:4995-5000.
82. Yang S., Bhide M., Crispe I., Pierce R., Murphy N. Polyketal copolymers: a new acid sensitive delivery vehicle for treating acute inflammatory diseases. Bioconjug. Chem. 2009, 19:1164-1169.
83. Sy J., Seshadri G., Yang S., Brown M., Oh T., Dikalov S., Murthy N., Davis M. Sustained release of a p38 inhibitor from non-inflammatory microspheres inhibits cardiac dysfunction. Nat. Mater. 2008, 7:863-868.
84. Gray W., Che P., Brown M., Ning X., Murthy N., Davis M. N-acetylglucosamine conjugated to nanoparticles enhances myocyte uptake and improves delivery of a small molecule p38 inhibitor for post-infarct healing. J. Cardiovasc. Transl. Res. 2011, 4:631-643.
85. Khaja S., Lee S., Murthy N. Acid-degradable protein delivery vehicles based on metathesis chemistry. Biomacromolecules 2007, 8:1391-1395.
86. Jain R., Standley S., Frechet J. Synthesis and degradation of pH-sensitive linear poly (amidoamine)s. Macromolecules 2007, 40:452-457.
87. Satoh K., Poelma J., Campos L., Stahl B., Hawker C. A facile synthesis of clickable and acid-cleavable PEO for acid-degradable block copolymers. Polym. Chem. 2012, 3:1890.
88. Bachelder E., Beaudette T., Broaders K., Paramonov S., Dashe J., Frechet J. Acid-degradable polyurethane particles for protein-based vaccines: biological evaluation and in vitro analysis of particle degradation products. Mol. Pharm. 2008, 25:876-884.
89. Chatterjee S., Ramakrishnan S. Hyperbranched polyacetals with tunable degradation rates. Macromolecules 2011, 44:4658-4664.
90. Ferruti P., Marchisio M., Duncan R. Poly(amido-amine)s: biomedical applications. Macromol. Rapid Commun. 2002, 23:332-355.
91. Akinc A., Lynn D., Anderson D., Langer R. Parallel synthesis and biophysical characterization of a degradable polymer library for gene delivery. J. Am. Chem. Soc. 2003, 125:5316-5323.
92. Akinc A., Anderson D., Lynn D., Langer R. Synthesis of poly(beta-amino ester)s optimized for highly effective gene delivery. Bioconjug. Chem. 2003, 14:979-988.
93. Standley S., Kwon Y., Murthy N., Kunisawa J., Shastri N., Guillaudeu S., Lau L., Fréchet J. Acid-degradable particles for protein-based vaccines: enhanced survival rate for tumor-challenged mice using ovalbumin model. Bioconjug. Chem. 2004, 15:1281-1288.
94. Cohen J., Almutairi A., Cohen J., Bernstein M., Brody S., Schuster D., Fréchet J. Enhanced cell penetration of acid-degradable particles functionalized with cell-penetrating peptides. Bioconjug. Chem. 2008, 19:876-881.
95. Reid B., Tzeng S., Warren A., Kozielski K., Elisseeff J. Development of a PEG derivative containing hydrolytically degradable hemiacetals. Macromolecules 2010, 43:9588-9590.
96. Dingels C., Müller S., Steinbach T., Tonhauser C., Frey H. Universal concept for the implementation of a single cleavable unit at tunable position in functional poly(ethylene glycol)s. Biomacromolecules 2013, 14:448-459.
97. Li R., Broyer R., Maynard H. Well-defined polymers with acetal side chains as reactive scaffolds synthesized by atom transfer radical polymerization. J. Polym. Sci. A Polym. Chem. 2006, 44:5004-5013.
98. Christman K., Maynard H. Protein micropatterns using a pH-responsive polymer and light. Langmuir 2005, 21:8389-8393.
99. Fletcher J., Godwin A., Pedone E., Jahangeer B., Buckton G., Brocchini S. The use of precursor polymers to prepare new excipients. J. Drug Deliv. Sci. Technol. 2005, 15:295-299.
100. Godwin A., Hartenstein M., Muller A., Brocchini S. Narrow molecular weight distribution precursor polymers. Angew. Chem. Int. Ed. Engl. 2001, 40:594-597.
101. Pedone E., Li X., Koseva N., Alpar O., Brocchini S. An information rich biomedical polymer library. J. Mater. Chem. 2003, 13:2825-2837.
102. Wich P., Fréchet J. Degradable dextran particles for gene delivery applications. Aust. J. Chem. 2012, 65:15.
103. Bachelder E., Beaudette T., Broaders K., Dashe J., Fréchet J. Acetal-derivatized dextran: an acid-responsive biodegradable material for therapeutic applications. J. Am. Chem. Soc. 2008, 130:10494-10495.
104. Cohen J., Beaudette T., Cohen J., Broaders K., Bachelder E., Fréchet J. Acetal-modified dextran microparticles with controlled degradation kinetics and surface functionality for gene delivery in phagocytic and non-phagocytic cells. Adv. Mater. 2010, 22:3593-3597.
105. Chen W., Meng F., Cheng R., Zhong Z. pH-Sensitive degradable polymersomes for triggered release of anticancer drugs: a comparative study with micelles. J. Control. Release 2010, 142:40-46.
106. Ornelas-Megiatto C., Shah P., Wich P., Cohen J., Tagaev J., Smolen J., Wright B., Panzner M., Youngs W., Fréchet J., Cannon C. Aerosolized antimicrobial agents based on degradable dextran nanoparticles loaded with silver carbene complexes. Mol. Pharm. 2012, 9:3012-3022.
107. Kauffman K., Do C., Sharma S., Gallovic M., Bachelder E., Ainslie K. Synthesis and characterization of acetalated dextran polymer and microparticles with ethanol as a degradation product. Appl. Mater. Interface 2012, 4:4149-4155.
108. Chikhacheva I., Zubov V., Puolokainen M. Polymer-analog reactions of polyvinyl alcohol under the action of microwave radiation. Russ. J. Gen. Chem. 2011, 81:545-549.
109. Scholz C., Wagner E. Therapeutic plasmid DNA versus siRNA delivery: common and different tasks for synthetic carriers. J. Control. Release 2012, 161:554-565.
110. Chollet P., Favrot M.C., Hurbin A., Coll J.-L. Side-effects of a systemic injection of linear polyethylenimine-DNA complexes. J. Gene Med. 2002, 4:84-91.
111. Ogris M., Brunner S., Schüller S., Kircheis R., Wagner E. PEGylated DNA/transferrin-PEI complexes: reduced interaction with blood components, extended circulation in blood and potential for systemic gene delivery. Gene Ther. 1999, 6:595-605.
112. Murthy N., Campbell J., Fausto N., Hoffman A., Stayton P. Design and synthesis of pH-responsive polymeric carriers that target uptake and enhance the intracellular delivery of oligonucleotides. J. Control. Release 2003, 89:365-374.
113. Shim M., Kwon Y. Acid-responsive linear polyethylenimine for efficient, specific, and biocompatible siRNA delivery. Bioconjug. Chem. 2009, 20:488-499.
114. Shim M., Kwon Y. Controlled delivery of plasmid DNA and siRNA to intracellular targets using ketalized polyethylenimine. Biomacromolecules 2008, 9:444-455.
115. Kwon Y. Before and after endosomal escapes: roles of stimuli-converting siRNA/polymer interactions in determining gene silencing efficiency. Acc. Chem. Res. 2012, 45:1077-1088.
116. Ko I., Ziady A., Lu S., Kwon Y. Acid-degradable cationic methacrylamide polymerized in the presence of plasmid DNA as tunable non-viral gene carrier. Biomaterials 2008, 29:3872-3881.
117. Shim M., Kwon Y. Acid-transforming polypeptide micelles for targeted nonviral gene delivery. Biomaterials 2010, 31:3404-3413.
118. Kulkarni A., DeFrees K., Hyun S.-H., Thompson D. Pendant polymer:amino-β-cyclodextrin: siRNA guest:host nanoparticles as efficient vectors for gene silencing. J. Am. Chem. Soc. 2012, 134:7596-7599.
119. Kulkarni A., Deng W., Hyun S.-H., Thompson D. Development of a low toxicity, effective pDNA vector based on noncovalent assembly of bioresponsive amino-β-cyclodextrin:adamantane-poly(vinyl alcohol)-poly(ethylene glycol) transfection complexes. Bioconjug. Chem. 2012, 23:933-940.
120. Hoffman A. Hydrogels for biomedical applications. Adv. Drug Deliv. Rev. 2012, 64:18-23.
121. Eccleston G. Wound dressings. Pharmaceutics: The Design and Manufacture of Medicines, 2007, 598-605. Elsevier, Churchill Livingstone. M.E. Aulton (Ed.).
122. Lee K., Mooney D. Hydrogels for tissue engineering. Chem. Rev. 2001, 101:1869-1880.
123. Compañ V., Andrio A., López-Alemany A., Riande E., Refojo M. Oxygen permeability of hydrogel contact lenses with organosilicon moieties. Biomaterials 2002, 23:2767-2772.
124. Peppas N., Bures P., Leobandung W., Ichikawa H. Hydrogels in pharmaceutical formulations. Eur. J. Pharm. Biopharm. 2000, 50:27-46.
125. Falco E., Patel M., Fisher J. Recent developments in cyclic acetal biomaterials for tissue engineering applications. Pharm. Res. 2008, 25:2348-2356.
126. Sui X.-C., Shi Y., Fu Z.-F. Novel degradable polymer networks containing acetal components and well-defined backbones. Aust. J. Chem. 2010, 63:1497.
127. Larmi T., Karkola P. Shrinkage and degradation of the Delrin occluder in tilting-disc valve prosthesis. J. Thorac. Cardiovasc. Surg. 1974, 68:66-69.
128. Thompson M., Northmore-Ball M., Tanner K. Tensile mechanical properties of polyacetal after one and six months' immersion in Ringer ' s solution. J. Mater. Sci. Mater. Med. 2001, 12:883-887.
129. Strazar K., Cör A., Antolic V. Biological impact of polyacetal particles on loosening of isoelastic stems. Biomacromolecules 2006, 7:2507-2511.
130. Kurtz S., Muhlstein C., Edidin A. Surface morphology and wear mechanisms of four clinically relevant biomaterials after hip simulator testing. J. Biomed. Mater. Res. 2000, 52:447-459.
131. Lee K., Choi M. Phase velocity and normalized broadband ultrasonic attenuation in polyacetal cuboid bone-mimicking phantoms. J. Acoust. Soc. Am. 2007, 121:EL263-EL269.
132. Kaihara S., Matsumura S., Fisher J. Synthesis and properties of poly [poly(ethylene glycol)-co-cyclic acetal] based hydrogels. Macromolecules 2007, 40:7625-7632.
133. Patel M., Patel K., Caccamese J., Coletti D., Sauk J., Fisher J. Characterization of cyclic acetal hydroxyapatite nanocomposites for craniofacial tissue engineering. J. Biomed. Mater. Res. A 2010, 94:408-418.
134. Betz M., Caccamese J., Coletti D., Sauk J., Fisher J. Tissue response and orbital floor regeneration using cyclic acetal hydrogels. J. Biomed. Mater. Res. A 2009, 90:819-829.
135. Wang K., Lu J., Yin R., Chen L., Du S., Jiang Y., Yu Q. Preparation and properties of cyclic acetal based biodegradable gel by thiol-ene photopolymerization. Mater. Sci. Eng. 2013, C33:1261-1266.
136. Lundberg P., Lee B., Van Den Berg S., Pressly E., Lee A., Hawker C., Lynd N. Poly[(ethylene oxide)-co-(methylene ethylene oxide)]: a hydrolytically-degradable poly(ethylene oxide) platform. MacroLetters 2012, 1:1240-1243.