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You are here: Home > Journals > CH > CH16144
REVIEW
Contents Vol 69(11)

Polyanhydrides: Synthesis, Properties, and Applications

Katie L. Poetz A and Devon A. Shipp A B
+ Author Affiliations
- Author Affiliations

A Department of Chemistry and Biomolecular Science, and Center for Advanced Material Processing, Clarkson University, Potsdam, NY 13699-5810, USA.

B Corresponding author. Email: dshipp@clarkson.edu




Dr Katie L. Poetz received her B.Sc. in chemistry from Lewis University in Romeoville, Illinois, in 2010 and her Ph.D. in chemistry at Clarkson University, Potsdam, New York, in 2015. Her research interests are in the general areas of biomaterials, including hydrogels, nanoparticles, colloids, degradable polymers, and peptides/polypeptides. She has published several peer-reviewed papers and attended and presented at a number of international conferences. She was awarded an NSF-EAPSI Fellowship to conduct research at the Monash Institute of Pharmaceutical Sciences in Melbourne, Australia, working with Professor Sebastien Perrier. After successfully defending her Ph.D., she began work at the research laboratories of Bausch and Lomb, Rochester, New York.


Professor Devon A. Shipp completed a B.Sc. (Hons) in chemistry (1993), and then a Ph.D. (1998) at the University of Melbourne (Australia) working with Professor David H. Solomon, Dr Graeme Moad, and Dr Trevor A. Smith. He then accepted the Bayer Postdoctoral Research Fellowship at Carnegie Mellon University (Pittsburgh, Pennsylvania) with Professor Kris Matyjaszewski. In 1999, he began his independent research career at Clarkson University in northern New York State where he is currently Professor and Chair of the Department of Chemistry and Biomolecular Science. His research group focusses on new polymer chemistries, particularly radical polymerizations, nanocomposites, and degradable polymers for bio-related applications. He is an Associate Editor of the Australian Journal of Chemistry, and was a Fulbright Scholar in Slovenia in 2015, hosted by the Slovenian National Institute of Chemistry and the Faculty of Chemistry and Chemical Technology at the University of Ljubljana. His website URL is: www.clarkson.edu/~dshipp.

Australian Journal of Chemistry 69(11) 1223-1239 https://doi.org/10.1071/CH16144
Submitted: 9 March 2016  Accepted: 28 April 2016   Published: 1 June 2016

Abstract

This review focusses on polyanhydrides, a fascinating class of degradable polymers that have been used in and investigated for many bio-related applications because of their degradability and capacity to undergo surface erosion. This latter phenomenon is driven by hydrolysis of the anhydride moieties at the surface and high hydrophobicity of the polymer such that degradation and mass loss (erosion) occur before water can penetrate deep within the bulk of the polymer. As such, when surface-eroding polymers are used as therapeutic delivery vehicles, the rate of delivery is often controlled by the rate of polymer erosion, providing predictable and controlled release rates that are often zero-order. These desirable attributes are heavily influenced by polymer composition and morphology, and therefore also monomer structure and polymerization method. This review examines approaches for polyanhydride synthesis, discusses their general thermomechanical properties, surveys their hydrolysis and degradation processes along with their biocompatibility, and looks at recent developments and uses of polyanhydrides in drug delivery, stimuli-responsive materials, and novel nanotechnologies.


References

[1]  M. S. Lesniak, H. Brem, Nat. Rev. Drug Discov. 2004, 3, 499.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXksVaqsro%3D&md5=46d0838f3558717637d7398136e6dae7CAS | 15173839PubMed |

[2]  H. Brem, S. Piantadosi, P. C. Burger, M. Walker, R. Selker, N. A. Vick, K. Black, M. Sisti, S. Brem, G. Mohr, P. Muller, R. Morawetz, S. C. Schold, Lancet 1995, 345, 1008.
         | Crossref | GoogleScholarGoogle Scholar | 1:STN:280:DyaK2M3ktVansw%3D%3D&md5=cf56dbef67b1e40ffda497dddbc3ce7bCAS | 7723496PubMed |

[3]  J. Kohn, S. Abramson, R. Langer, Biomaterials Science: An Introduction to Materials in Medicine (2nd edn) 2004 (Elsevier: London).

[4]  J. E. Bucher, W. C. Slade, J. Am. Chem. Soc. 1909, 31, 1319.
         | Crossref | GoogleScholarGoogle Scholar |

[5]  J. W. Hill, J. Am. Chem. Soc. 1930, 52, 4110.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaA3cXltlSltQ%3D%3D&md5=d7aa0c5d9fcf9db78c4039b5d92c8e5aCAS |

[6]  J. W. Hill, W. H. Carothers, J. Am. Chem. Soc. 1932, 54, 1569.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaA38XisFyktw%3D%3D&md5=fe42ce2141034c8f8843f23f4d0d6edcCAS |

[7]  W. H. Carothers, J. W. Hill, J. Am. Chem. Soc. 1932, 54, 1579.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaA38XisFyktA%3D%3D&md5=ca18325e249207ec557ba92af7aa1156CAS |

[8]  A. Conix, J. Polym. Sci., Polym. Phys. Ed. 1958, 29, 343.
         | 1:CAS:528:DyaF3cXhtVKlsb8%3D&md5=8774467f7ed054e8d839522a2a960a89CAS |

[9]  N. Yoda, Makromol. Chem. 1959, 32, 1.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaF3cXmvFWn&md5=246e1c88270c7e106bea9975c0ff270eCAS |

[10]  N. Yoda, Makromol. Chem. 1962, 56, 36.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaF2cXptFejsQ%3D%3D&md5=f9e821a25c81a78a1d017e94235f7adcCAS |

[11]  N. Yoda, Makromol. Chem. 1962, 55, 174.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaF38Xks1amurs%3D&md5=145193e0df5d4a6b0395610bf2752fa1CAS |

[12]  N. Yoda, Makromol. Chem. 1962, 56, 10.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaF2cXptFejsA%3D%3D&md5=62716b4f99fbf19b31009e12c0108c10CAS |

[13]  A. Göpferich, J. Tessmar, Adv. Drug Deliv. Rev. 2002, 54, 911.
         | Crossref | GoogleScholarGoogle Scholar | 12384315PubMed |

[14]  Y. Ikada, in Handbook of Biodegradable Polymers: Synthesis, Characterization and Applications (Eds A. Lendlein, A. Sisson) 2011, pp. 341–362 (Wiley-VCH: Weinheim).

[15]  D. Rickert, B. Hiebl, R. Fuhrmann, F. Jung, A. Lendlein, R.-P. Franke, in Handbook of Biodegradable Polymers: Synthesis, Characterization and Applications (Eds A. Lendlein, A. Sisson) 2011, pp. 309–340 (Wiley-VCH: Weinheim).

[16]  K. W. Leong, B. C. Brott, R. Langer, J. Biomed. Mater. Res. 1985, 19, 941.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL28XhtlGqsbg%3D&md5=946552e707157c26328ecc41471e459fCAS | 3880353PubMed |

[17]  A. Domb, J. P. Jain, N. Kumar, in Handbook of Biodegradable Polymers: Synthesis, Characterization and Applications (Eds A. Lendlein, A. Sisson) 2011, pp. 45–75 (Wiley-VCH: Weinheim).

[18]  A. J. Domb, E. Ron, R. Langer, Macromolecules 1988, 21, 1925.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL1cXktlygt7s%3D&md5=cdda2bfdb83a8beb74412d286616dc40CAS |

[19]  K. W. Leong, V. Simonte, R. Langer, Macromolecules 1987, 20, 705.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL2sXhtlyrsLw%3D&md5=072f134ddb7c37ee3153b099ef6cf3eeCAS |

[20]  R. Subramanyam, A. G. Pinkus, J. Macromol. Sci., Chem. 1985, 22, 23.
         | Crossref | GoogleScholarGoogle Scholar |

[21]  A. Staubli, E. Ron, R. Langer, J. Am. Chem. Soc. 1990, 112, 4419.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3cXitFOlsbY%3D&md5=ec251ffe89a084e492d477c4efd858d2CAS |

[22]  K. S. Anseth, V. R. Shastri, R. Langer, Nat. Biotechnol. 1999, 17, 156.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXpslyqsg%3D%3D&md5=713790f1106487debb01129fc6e2ce4aCAS | 10052351PubMed |

[23]  P. J. Tarcha, L. Su, T. Baker, D. Langridge, V. Shastri, R. Langer, J. Polym. Sci. Part A: Polym. Chem. 2001, 39, 4189.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXptVamu7s%3D&md5=3bbb1f13f2b05b05a48704d4059af163CAS |

[24]  A. J. Domb, R. Langer, Macromolecules 1989, 22, 2117.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL1MXitFersL0%3D&md5=41d693ed477f2a91d5cfcdf1697bf015CAS |

[25]  C. D. Hurd, M. F. Dull, J. Am. Chem. Soc. 1932, 54, 3427.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaA38Xks1ChsA%3D%3D&md5=9259054634344dd7ac9b111df4496315CAS |

[26]  M. I. Lawton, K. R. Tillman, H. S. Mohammed, W. Kuang, D. A. Shipp, P. T. Mather, ACS Macro Lett. 2016, 5, 203.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC28XhtVKrsLo%3D&md5=5ac9763ec9aefdc2a89ec298fdcf8832CAS |

[27]  A. A. Weiner, D. M. Shuck, J. R. Bush, V. P. Shastri, Biomaterials 2007, 28, 5259.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhtFGrtrjI&md5=fc202cd17a312b151e3039480abfe460CAS | 17825904PubMed |

[28]  A. A. Weiner, E. A. Bock, M. E. Gipson, V. P. Shastri, Biomaterials 2008, 29, 2400.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXjtlSitrY%3D&md5=8f8f30edc04ecf2f760199c38dcd4419CAS | 18299148PubMed |

[29]  D. A. Shipp, C. W. McQuinn, B. G. Rutherglen, R. A. McBath, Chem. Commun. 2009, 6415.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXht1yisrbJ&md5=86ae6e670d0708a83b599255cc204068CAS |

[30]  K. L. Poetz, H. S. Mohammed, D. A. Shipp, Biomacromolecules 2015, 16, 1650.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2MXmtlalurw%3D&md5=9024fbe57ed5441c60b7cedce3a38b7fCAS | 25867183PubMed |

[31]  A. J. Domb, M. Maniar, J. Polym. Sci. Part A: Polym. Chem. 1993, 31, 1275.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3sXltVeju7k%3D&md5=559afd1f9e3ba34f5e778f0a6d3b7a4fCAS |

[32]  D. Teomim, A. Nyska, A. J. Domb, J. Biomed. Mater. Res. 1999, 45, 258.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXisVequr8%3D&md5=b708af7b6e80ac2a004d06d37a070112CAS | 10397984PubMed |

[33]  L. Shieh, J. Tamada, I. Chen, J. Pang, A. Domb, R. Langer, J. Biomed. Mater. Res. 1994, 28, 1465.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2MXitlOiu74%3D&md5=2a4f736741e5ba0facbbfed4e2c4f74bCAS | 7876286PubMed |

[34]  D. Teomim, A. J. Domb, Biomacromolecules 2001, 2, 37.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXoslGqtrw%3D&md5=03d3d50c408471e916dd3d4795fee2bfCAS | 11749153PubMed |

[35]  J. Natarajan, S. Rattan, U. Singh, G. Madras, K. Chatterjee, Ind. Eng. Chem. Res. 2014, 53, 7891.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXmtVOhtLo%3D&md5=a04c84375aebd0fb3f70a2c050018422CAS |

[36]  O. Türünc, M. A. R. Meier, Green Chem. 2011, 13, 314.
         | Crossref | GoogleScholarGoogle Scholar |

[37]  C. Lluch, G. Lligadas, J. C. Ronda, M. Galia, V. Cadiz, Macromol. Rapid Commun. 2011, 32, 1343.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXntVGksbk%3D&md5=eb6ffcd6e9c1b0333e0a0167f97a7948CAS | 21648006PubMed |

[38]  A. J. Domb, Macromolecules 1992, 25, 12.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK38Xisl2hsA%3D%3D&md5=2147357c240d05d25fa08ad46cd6cf22CAS |

[39]  E. Mathiowitz, E. Ron, G. Mathiowitz, C. Amato, R. Langer, Macromolecules 1990, 23, 3212.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3cXktVOhsrw%3D&md5=eaa5caa2a6e35885bc81eab233a3fe83CAS |

[40]  R. J. Cottler, M. Matzner, Chem. Weekbl. 1967, 63, 113.

[41]  G. Cheng, M. A. Aponte, C. A. Ramírez, Polymer 2004, 45, 3157.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXjt1altLY%3D&md5=318fc993ff827e57e8e0fe6032ac3852CAS |

[42]  A. J. Domb, E. Mathiowitz, E. Ron, S. Giannos, R. Langer, J. Polym. Sci. Part A: Polym. Chem. 1991, 29, 571.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3MXhvVKhs7k%3D&md5=8479903d1b60ae1eed604a99541dbf2aCAS |

[43]  B. G. Rutherglen, R. A. McBath, Y. L. Huang, D. A. Shipp, Macromolecules 2010, 43, 10297.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhsFaktL7N&md5=e4158fa8336a89529b843940348979b1CAS |

[44]  C. E. Hoyle, A. B. Lowe, C. N. Bowman, Chem. Soc. Rev. 2010, 39, 1355.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXjs1Ggu74%3D&md5=e59108689ec0fc426287d347213eb865CAS | 20309491PubMed |

[45]  M. Y. Krasko, A. Shikanov, A. Ezra, A. J. Domb, J. Polym. Sci. Part A: Polym. Chem. 2003, 41, 1059.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXisVKrt70%3D&md5=c6eb35cf8b0c846d78616cc38ec50cadCAS |

[46]  A. Shikanov, B. Vaisman, M. Y. Krasko, A. Nyska, A. J. Domb, J. Biomed. Mater. Res. Part A 2004, 69A, 47.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXisFGhtrw%3D&md5=3f95d486f622775ee9868f89eacd3790CAS |

[47]  N. D. Stebbins, J. J. Faig, W. Yu, R. Guliyev, K. E. Uhrich, Biomater. Sci. 2015, 3, 1171.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2MXpsVWqsLo%3D&md5=4d38830f00803849439f37624ee275e7CAS | 26222033PubMed |

[48]  L. Erdmann, K. E. Uhrich, Biomaterials 2000, 21, 1941.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXkvVyrsLc%3D&md5=26a9a20543594065940830ee8da1cc7fCAS | 10941915PubMed |

[49]  Y. Q. Liang, L. Xiao, Y. L. Zhai, C. P. Xie, L. D. Deng, A. J. Dong, J. Appl. Polym. Sci. 2013, 127, 3948.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XnsVGkurs%3D&md5=74f2c757b4d793c4cf97828ca30a4897CAS |

[50]  Z. Li, M. Y. Gao, M. L. Yuan, J. Y. Hao, X. M. Deng, J. Polym. Sci. Part A: Polym. Chem. 2003, 41, 1511.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXjt1Gnurc%3D&md5=7ee6ca07e8a174c9cd6dcabdafb10efaCAS |

[51]  A. O. Helminen, H. Korhonen, J. V. Seppälä, J. Polym. Sci. Part A: Polym. Chem. 2003, 41, 3788.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXptFGgu7Y%3D&md5=8773ce5cb6b5c49a3cd38180f06ea1b9CAS |

[52]  A. Göpferich, R. Langer, Macromolecules 1993, 26, 4105.
         | Crossref | GoogleScholarGoogle Scholar |

[53]  J. A. Tamada, R. Langer, Proc. Natl. Acad. Sci. USA 1993, 90, 552.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3sXotFGrug%3D%3D&md5=70291ff8e39710245fc3b8933216a126CAS | 8421690PubMed |

[54]  J. L. Koenig, M. C. Agboatwalla, J. Macromol. Sci. Part B: Phys. 1968, 2, 391.
         | Crossref | GoogleScholarGoogle Scholar |

[55]  R. Langer, Acc. Chem. Res. 1993, 26, 537.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3sXlvVynsbc%3D&md5=7fa9e49480002d31d09cd94e981326ebCAS |

[56]  R. Langer, Acc. Chem. Res. 2000, 33, 94.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXotFw%3D&md5=8b33cb6d15e399fbd7965eff6df17346CAS | 10673317PubMed |

[57]  M. P. Wu, J. A. Tamada, H. Brem, R. Langer, J. Biomed. Mater. Res. 1994, 28, 387.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2cXit1Kksr0%3D&md5=23b40db55195ea362c22dd5308ebcd3fCAS | 8077254PubMed |

[58]  A. Göpferich, Biomaterials 1996, 17, 103.
         | Crossref | GoogleScholarGoogle Scholar | 8624387PubMed |

[59]  A. Göpferich, Macromolecules 1997, 30, 2598.
         | Crossref | GoogleScholarGoogle Scholar |

[60]  A. Göpferich, Biomaterials 1997, 18, 397.
         | Crossref | GoogleScholarGoogle Scholar | 9061180PubMed |

[61]  F. von Burkersroda, L. Schedl, A. Gopferich, Biomaterials 2002, 23, 4221.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XlvVeltbs%3D&md5=8595ff2ac14de081d811e68afd3f95fdCAS | 12194525PubMed |

[62]  S. N. Rothstein, W. J. Federspiel, S. R. Little, Biomaterials 2009, 30, 1657.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXpsFyisA%3D%3D&md5=662f57ca1b611bfa550ac297abdb2bffCAS | 19101031PubMed |

[63]  D. Larobina, G. Mensitieri, M. J. Kipper, B. Narasimhan, AIChE J. 2002, 48, 2960.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XpslWks7k%3D&md5=b190c070ec63caae77849712934b5b29CAS |

[64]  M. J. Kipper, B. Narasimhan, Macromolecules 2005, 38, 1989.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXnvVentg%3D%3D&md5=30295f3277dbf2a832fcc4b5cd7a5d39CAS |

[65]  S. Domanskyi, K. L. Poetz, D. A. Shipp, V. Privman, Phys. Chem. Chem. Phys. 2015, 17, 13215.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2MXjs1Knu78%3D&md5=63e19c5c9adaed2d00a730448949b234CAS | 25766671PubMed |

[66]  J. P. Jain, S. Modi, A. J. Domb, N. Kumar, J. Control. Release 2005, 103, 541.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXivFKhtbo%3D&md5=71ada8e2c64ef59758bcf7b9f32adec9CAS | 15820403PubMed |

[67]  J. P. Jain, D. Chitkara, N. Kumar, Expert Opin. Drug Deliv. 2008, 5, 889.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXpvFynuro%3D&md5=62bef5587462c01a22996c7bd577f4caCAS | 18712998PubMed |

[68]  J. Griffin, R. Delgado-Rivera, S. Meiner, K. E. Uhrich, J. Biomed. Mater. Res. Part A 2011, 97A, 230.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXkvVWmt70%3D&md5=67e3bd9e215070b017d4f2d8ccea137aCAS |

[69]  Y. S. Lee, J. Griffin, S. N. Masand, D. I. Shreiber, K. E. Uhrich, J. Biomed. Mater. Res. Part A 2016, 104, 975.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC28Xps12htw%3D%3D&md5=c31283c13ccc237ede5a7cc0fb63764eCAS |

[70]  M. A. Rogers, Y. F. Yan, K. Ben-Elazer, Y. Lan, J. Faig, K. Smith, Biomacromolecules 2014, 15, 3406.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXht1CltrzN&md5=ca518aa3d283100ea457486be366624cCAS | 25082798PubMed |

[71]  R. C. Schmeltzer, K. E. Uhrich, Polym. Bull. 2006, 57, 281.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28Xmt1Giu7o%3D&md5=b267a86fb1f4e95a4280da50afe66b12CAS |

[72]  K. Wada, W. Yu, M. Elazizi, S. Barakat, M. A. Ouimet, R. Rosario-Melendez, J. P. Fiorellini, D. T. Graves, K. E. Uhrich, J. Control. Release 2013, 171, 33.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXht1OiurzM&md5=d6350af6212b63e2437d5dd6fc33f4d1CAS | 23827476PubMed |

[73]  A. Prudencio, N. D. Stebbins, M. Johnson, M. Song, B. A. Langowski, K. E. Uhrich, J. Bioact. Compat. Polym. 2014, 29, 208.
         | Crossref | GoogleScholarGoogle Scholar |

[74]  M. L. Johnson, K. E. Uhrich, J. Biomed. Mater. Res. Part A 2009, 91A, 671.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhtlSltrbF&md5=d72bd08012cf2adcedaad7fc903f8c68CAS |

[75]  A. L. Carbone-Howell, N. D. Stebbins, K. E. Uhrich, Biomacromolecules 2014, 15, 1889.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXls1Skt7g%3D&md5=1ef04042adc3fd4611d2237ccc30b4a6CAS | 24702678PubMed |

[76]  M. A. Ouimet, J. Griffin, A. L. Carbone-Howell, W. H. Wu, N. D. Stebbins, K. E. Uhrich, Biomacromolecules 2013, 14, 854.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXpsVahsQ%3D%3D&md5=d62d394cdfc0c50d377673356edd1e0eCAS | 23327626PubMed |

[77]  M. A. Ouimet, N. D. Stebbins, K. E. Uhrich, Macromol. Rapid Commun. 2013, 34, 1231.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhtVKqsL%2FN&md5=c86fc6dd7736e94df04f2a985f07a7ceCAS | 23836606PubMed |

[78]  A. Prudencio, A. L. Carbone, J. Griffin, K. E. Uhrich, Macromol. Rapid Commun. 2009, 30, 1101.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXosVGksbc%3D&md5=1b17af5587154983376471aef158f518CAS | 21706573PubMed |

[79]  R. Rosario-Melendez, C. L. Harris, R. Delgado-Rivera, L. Yu, K. E. Uhrich, J. Control. Release 2012, 162, 538.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhtlOnt7%2FK&md5=83e27d8cf3a4893b3a6ca9854412a7aeCAS | 22877734PubMed |

[80]  Y. Chandorkar, R. K. Bhagat, G. Madras, B. Basu, Biomacromolecules 2014, 15, 863.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXitFKntLs%3D&md5=9de36f853361f6ac929bd4ebb45b5bc3CAS | 24517727PubMed |

[81]  Y. Chandorkar, N. Bhaskar, G. Madras, B. Basu, Biomacromolecules 2015, 16, 636.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2MXktFSmtQ%3D%3D&md5=5455026c21682becf4c565ad369db895CAS | 25559641PubMed |

[82]  Q. X. Cai, K. J. Zhu, D. Chen, L. P. Gao, Eur. J. Pharm. Biopharm. 2003, 55, 203.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXhvFaju7c%3D&md5=2500fdd6453bcacc404a5d868d4298efCAS | 12637098PubMed |

[83]  Y. Tian, L. Li, X. Gao, J. Deng, D. Stephens, D. Robinson, H. Chang, Drug Dev. Ind. Pharm. 2002, 28, 897.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XnslGntrk%3D&md5=e3d2eb5300b014f62e4b1b670a2cd559CAS | 12378959PubMed |

[84]  D. Teomim, I. Fishbien, G. Golomb, L. Orloff, M. Mayberg, A. J. Domb, J. Control. Release 1999, 60, 129.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXjslKjtLc%3D&md5=ece815d19e956c801edd6e20b2f25172CAS | 10370177PubMed |

[85]  D. B. Masters, C. B. Berde, S. Dutta, T. Turek, R. Langer, Pharm. Res. 1993, 10, 1527.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2cXhsVOntw%3D%3D&md5=3f145d07bccc96131bca9ace554feb76CAS | 8272418PubMed |

[86]  F. Jia, X. P. Liu, L. H. Li, S. Mallapragada, B. Narasimhan, Q. Wang, J. Control. Release 2013, 172, 1020.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhvFOisL%2FL&md5=4c9dbee51276dcb21954c105481a05dcCAS | 24140748PubMed |

[87]  S. Bagherifam, G. W. Griffiths, G. M. Maelandsmo, B. Nystron, V. Hasirci, N. Hasirci, J. Microencapsul. 2015, 32, 166.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2MXpvV2qtL8%3D&md5=b08454686762aafc6b834703d25842e2CAS | 25323326PubMed |

[88]  L. K. Petersen, Y. Phanse, A. E. Ramer-Tait, M. J. Wannemuehler, B. Narasimhan, Mol. Pharm. 2012, 9, 874.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XjtFWhs7o%3D&md5=32b50a025457184fbfb2c34869c8f018CAS | 22380593PubMed |

[89]  K. A. Ross, H. Loyd, W. W. Wu, L. Huntimer, M. J. Wannemuehler, S. Carpenter, B. Narasimhan, J. Biomed. Mater. Res. Part A 2014, 102, 4161.
         | Crossref | GoogleScholarGoogle Scholar |

[90]  V. B. Joshi, S. M. Geary, B. R. Carrillo-Conde, B. Narasimhan, A. K. Salem, Acta Biomater. 2013, 9, 5583.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhvVSlsLfP&md5=df7eb89a2059975feb954f749e958568CAS | 23153760PubMed |

[91]  M. P. Torres, J. H. Wilson-Welder, S. K. Lopac, Y. Phanse, B. R. Carrillo-Conde, A. E. Ramer-Tait, B. H. Bellaire, M. J. Wannemuehler, B. Narasimhan, Acta Biomater. 2011, 7, 2857.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXmslKnsLw%3D&md5=a0b292c9fe16b5bfb9c343229eccb1c3CAS | 21439412PubMed |

[92]  D. J. Quick, K. K. Macdonald, K. S. Anseth, J. Control. Release 2004, 97, 333.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXkslKmur8%3D&md5=3aee2faea44e15b4a3fa60a300653762CAS | 15196760PubMed |

[93]  B. R. Carrillo-Conde, R. J. Darling, S. J. Seiler, A. E. Ramer-Tait, M. J. Wannemuehler, B. Narasimhan, Chem. Eng. Sci. 2015, 125, 98.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXhsVeqtbvL&md5=f29941e2eb79e600c039e89c52bc2f55CAS |

[94]  S. L. Haughney, L. K. Petersen, A. D. Schoofs, A. E. Ramer-Tait, J. D. King, D. E. Briles, M. J. Wannemuehler, B. Narasimhan, Acta Biomater. 2013, 9, 8262.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhtVOjurrM&md5=a8019f70e0febbe75fab8c85d27a237eCAS | 23774257PubMed |

[95]  D. S. Katti, S. Lakshmi, R. Langer, C. T. Laurencin, Adv. Drug Deliv. Rev. 2002, 54, 933.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XnvVKiur0%3D&md5=4432eb375c3524df0726c5d343aac267CAS | 12384316PubMed |

[96]  K. W. Leong, P. D’Amore, M. Marletta, R. Langer, J. Biomed. Mater. Res. 1986, 20, 51.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL28XitFejurk%3D&md5=4c9185077fdd1c36f6a1f3d47db193c2CAS | 3949823PubMed |

[97]  C. Laurencin, A. J. Domb, C. Morris, V. Brown, M. Chasin, R. McConnell, N. Lange, R. Langer, J. Biomed. Mater. Res. 1990, 24, 1463.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3MXhslGgsA%3D%3D&md5=608e94cc4edc88efbe7a3ce50b072a38CAS | 2279981PubMed |

[98]  M. A. Attawia, K. M. Herbert, K. E. Uhrich, R. Langer, C. T. Laurencin, J. Biomed. Mater. Res. 1999, 48, 322.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXjsFynurc%3D&md5=b7c3fa3cfde304708bc1a70f017ae4eeCAS | 10398037PubMed |

[99]  M. A. Attawia, K. E. Uhrich, E. Botchwey, M. Fan, R. Langer, C. T. Laurencin, J. Biomed. Mater. Res. 1995, 29, 1233.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2MXotlKhurw%3D&md5=1297686e73cc80659f793726096476a9CAS | 8557725PubMed |

[100]  M. A. Attawia, K. E. Uhrich, E. Botchwey, R. Langer, C. T. Laurencin, J. Orthop. Res. 1996, 14, 445.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK28Xks1Sgurk%3D&md5=b03d8607c3a82239de7e1c335e139764CAS | 8676258PubMed |

[101]  S. E. M. Ibim, K. E. Uhrich, M. A. Attawia, V. R. Shastri, S. F. El-Amin, R. Bronson, R. Langer, C. T. Laurencin, J. Biomed. Mater. Res. 1998, 43, 374.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXnvVGrurg%3D&md5=1b93186ebc6a7def6f057f1d435b14d4CAS |

[102]  S. M. Ibim, K. E. Uhrich, R. Bronson, S. F. El-Amin, R. Langer, C. T. Laurencin, Biomaterials 1998, 19, 941.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXktlais7Y%3D&md5=eef17d7fe25e4eb81157790ac2297822CAS | 9690836PubMed |

[103]  M. P. Torres, B. M. Vogel, B. Narasimhan, S. K. Mallapragada, J. Biomed. Mater. Res. Part A 2006, 76A, 102.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XhsVehtg%3D%3D&md5=76c6ded6eac4921cf1686819f849c08eCAS |

[104]  M. P. Torres, A. S. Determan, G. L. Anderson, S. K. Mallapragada, B. Narasimhan, Biomaterials 2007, 28, 108.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XhtVWku7jP&md5=28d337356301b8b348537d3512cd5e15CAS | 16965812PubMed |

[105]  L. Huntimer, A. E. Ramer-Tait, L. K. Petersen, K. A. Ross, K. A. Walz, C. Wang, J. Hostetter, B. Narasimhan, M. J. Wannemuehler, Adv. Healthc. Mater. 2013, 2, 369.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXit1Whsbk%3D&md5=8baef110d012c7d4c4aa66528452306bCAS | 23184561PubMed |

[106]  V. P. Shastri, R. F. Padera, P. Tarcha, R. Langer, Biomaterials 2004, 25, 715.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXosFOrt7w%3D&md5=34a7a9ee74fb6c2a27df825b93935132CAS | 14607510PubMed |

[107]  A. K. Burkoth, J. Burdick, K. S. Anseth, J. Biomed. Mater. Res. 2000, 51, 352.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXkslagtrs%3D&md5=66e4a8bb8ae63aded83baefc624ed7c2CAS | 10880076PubMed |

[108]  H. S. Mohammed, B. L. Snyder, D. S. K. Samways, D. A. Shipp, J. Biomed. Mater. Res. Part A 2016,
         | Crossref | GoogleScholarGoogle Scholar |

[109]  K. L. Poetz, H. S. Mohammed, B. L. Snyder, G. Liddil, D. S. K. Samways, D. A. Shipp, Biomacromolecules 2014, 15, 2573.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXot1yhs70%3D&md5=d5e5e79991d0fedd9665674cf8630d22CAS | 24848134PubMed |

[110]  E. Mathiowitz, R. Langer, J. Control. Release 1987, 5, 13.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL2sXkvVersbw%3D&md5=00c8f15f08e359b32379aebb5838eedaCAS |

[111]  D. E. Chickering, J. S. Jacob, T. A. Desai, M. Harrison, W. P. Harris, C. N. Morrell, P. Chaturvedi, E. Mathiowitz, J. Control. Release 1997, 48, 35.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXkslSlt74%3D&md5=6287a9faacc911dcb3e93c5e8507e2d1CAS |

[112]  S. Furtado, D. Abramson, R. Burrill, G. Olivier, C. Gourd, E. Bubbers, E. Mathiowitz, Int. J. Pharm. 2008, 347, 149.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhtlOjsrjL&md5=c534ab8270ef6c24d0f7a98efa6fe794CAS | 17707601PubMed |

[113]  K. P. Leach, E. Mathiowitz, Biomaterials 1998, 19, 1973.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXotVSis7Y%3D&md5=cce5ee5a6391cde261206a53f16396b6CAS |

[114]  K. P. Leach, S. Takahashi, E. Mathiowitz, Biomaterials 1998, 19, 1981.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXotVSis7c%3D&md5=d29614c088ec4b2d9b598c60f94f64c2CAS |

[115]  E. Mathiowitz, J. S. Jacob, Y. S. Jong, G. P. Carino, D. E. Chickering, P. Chaturvedi, C. A. Santos, K. Vijayaraghavan, S. Montgomery, M. Bassett, C. Morrell, Nature 1997, 386, 410.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXit1Wrt7s%3D&md5=998a26da9557a3814404167813b2572dCAS | 9121559PubMed |

[116]  K. J. Pekarek, J. S. Jacob, E. Mathiowitz, Nature 1994, 367, 258.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2cXhsVeqtb0%3D&md5=f824f5baa440176f8f956cc36163401eCAS | 8121490PubMed |

[117]  C. A. Santos, B. D. Freedman, S. Ghosn, J. S. Jacob, M. Scarpulla, E. Mathiowitz, Biomaterials 2003, 24, 3571.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXktlOgtLk%3D&md5=b6df1f41a8aa53f8cfd093d510049f4dCAS | 12809786PubMed |

[118]  C. G. Thanos, Z. Liu, M. Goddard, J. Reineke, N. Bailey, M. Cross, R. Burrill, E. Mathiowitz, J. Pharm. Sci. 2003, 92, 1677.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXmtFektrY%3D&md5=659d256df4f112b550420235b67997ecCAS | 12884254PubMed |

[119]  A. S. Determan, B. G. Trewyn, V. S.-Y. Lin, M. Nilsen-Hamilton, B. Narasimhan, J. Control. Release 2004, 100, 97.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXosFSktbk%3D&md5=53eebd827bf60daf8b7fb06080e59fc9CAS | 15491814PubMed |

[120]  M. J. Kipper, E. Shen, A. Determan, B. Narasimhan, Biomaterials 2002, 23, 4405.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XmtVSrs7Y%3D&md5=3cdba02e328c447fa2024e1863916892CAS | 12219831PubMed |

[121]  S. K. Lopac, M. P. Torres, J. H. Wilson-Welder, M. J. Wannemuehler, B. Narasimhan, J. Biomed. Mater. Res. Part B 2009, 91B, 938.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXht1agsb3P&md5=6ec01986e7c771ae9dd38130c7fadbfaCAS |

[122]  R. Delgado-Rivera, R. Rosario-Melendez, W. Yu, K. E. Uhrich, J. Biomed. Mater. Res. Part A 2014, 102, 2736.
         | Crossref | GoogleScholarGoogle Scholar |

[123]  Y. Yu, T. L. Lu, W. Zhao, W. G. Sun, T. Chen, J. Appl. Polym. Sci. 2011, 121, 352.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXktFyjtbc%3D&md5=9251ebef2405614a7a42b81475ead61eCAS |

[124]  K. L. Poetz, O. Z. Durham, D. A. Shipp, Polym. Chem. 2015, 6, 5464.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2MXhtFSksrzI&md5=d2694bb60bd93eeb742b62c687600a06CAS |

[125]  S. Acharya, S. K. Sahoo, Adv. Drug Deliv. Rev. 2011, 63, 170.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXktF2juro%3D&md5=b69c671eeb1f044f269339da463e4a29CAS | 20965219PubMed |

[126]  J. Panyam, V. Labhasetwar, Adv. Drug Deliv. Rev. 2003, 55, 329.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXhs1Cgurw%3D&md5=857f90d6fe39f623b3276c9c33e249aaCAS | 12628320PubMed |

[127]  C. Deng, Y. J. Jiang, R. Cheng, F. H. Meng, Z. Y. Zhong, Nano Today 2012, 7, 467.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhsFCqs7rF&md5=3033179481da43a27b5cc19de565b200CAS |

[128]  Y. Sun, X. L. Yan, T. M. Yuan, J. Liang, Y. J. Fan, Z. W. Gu, X. D. Zhang, Biomaterials 2010, 31, 7124.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXosF2msL0%3D&md5=b746862cc707b9f9af91e64bea6a4b8fCAS | 20580429PubMed |

[129]  X. Guo, C. L. Shi, J. Wang, S. B. Di, S. B. Zhou, Biomaterials 2013, 34, 4544.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXktFamt7o%3D&md5=b772b9f1d1c8e27ddfdc4c4908bad735CAS | 23510854PubMed |

[130]  P. L. Lai, C. C. Hsu, T. H. Liu, D. W. Hong, L. H. Chen, W. J. Chen, I. M. Chu, React. Funct. Polym. 2012, 72, 846.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhtlKis77E&md5=95388819d60ec8d26433eca8fe3d975aCAS |

[131]  J. Wang, G. Yang, X. Guo, Z. Tang, Z. Zhong, S. Zhou, Biomaterials 2014, 35, 3080.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXis1KhtA%3D%3D&md5=1b9f2a89a8dfd29c5e0f5c31e944954bCAS | 24388799PubMed |

[132]  M. Behl, M. Y. Razzaq, A. Lendlein, Adv. Mater. 2010, 22, 3388.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhtVSisL7F&md5=a1d707a3ed660553ef796c3bdb33559aCAS | 20574951PubMed |

[133]  C. Liu, H. Qin, P. T. Mather, J. Mater. Chem. 2007, 17, 1543.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXjvF2qu7c%3D&md5=5dee41d387bfd8c06959ce0188f76077CAS |

[134]  C. M. Yakacki, Polym. Rev. 2013, 53, 1.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhvFyhsLc%3D&md5=2f9e15a5e8be80737bef72b9224ebc2dCAS |