Synlett 2016; 27(16): 2285-2292
DOI: 10.1055/s-0035-1562505
synpacts
© Georg Thieme Verlag Stuttgart · New York

Progress towards the Synthesis of Amino Polyesters via Ring-Opening Polymerization (ROP) of Functional Lactones

Jing Hao
a   Department of Chemistry, George Fox University, Newberg, OR 97132, USA
,
Sussana Elkassih
b   Simmons Comprehensive Cancer Center, Department of Biochemistry, The University of Texas Southwestern Medical Center, Dallas, TX 75390, USA   Email: daniel.siegwart@utsouthwestern.edu
,
Daniel J. Siegwart*
b   Simmons Comprehensive Cancer Center, Department of Biochemistry, The University of Texas Southwestern Medical Center, Dallas, TX 75390, USA   Email: daniel.siegwart@utsouthwestern.edu
› Author Affiliations
Further Information

Publication History

Received: 15 April 2016

Accepted after revision: 30 May 2016

Publication Date:
07 July 2016 (online)


Abstract

Amine-functionalized polyesters are an important class of materials for biomedical applications due to their utility in gene and drug delivery, bioconjugation reactions, hydrogels, and controlled release systems. The synthesis of amino polyesters by ring-opening polymerization (ROP) is an ongoing challenge that is being aided by advances in reaction development. For the benefit of this important research area, this article highlights the related works of synthesizing amino polyesters by ROP as well as our recent synthesis of a new library of amino polyesters from amine-functionalized lactone monomers.

1 Polymerization of Lactone Monomers with Unprotected Amine Functionalities

2 Synthesis of Amino-Functionalized Polyesters via Postpolymerization Modification of Functionalized Monomers

3 Design of Novel Amino-Functionalized Lactone Monomers and Direct Synthesis of Amino Polyesters

 
  • References

  • 1 Albertsson A.-C, Varma IK. Biomacromolecules 2003; 4: 1466
  • 2 Lecomte P, Riva R, Schmeits S, Rieger J, van Butsele K, Jerome C, Jerome R. Macromol. Symp. 2006; 240: 157
  • 3 Jerôme C, Lecomte P. Adv. Drug Delivery Rev. 2008; 60: 1056
  • 4 Pounder R, Dove A. Polym. Chem. 2010; 1: 260
  • 5 Seyednejad H, Ghassemi AH, van Nostrum CF, Vermonden T, Hennink WE. J. Controlled Release 2011; 152: 168
  • 6 Tian H, Tang Z, Zhuang X, Chen X, Jing X. Prog. Polym. Sci. 2012; 37: 237
  • 7 Hao J, Rainbolt EA, Washington K, Biewer MC, Stefan MC. Curr. Org. Chem. 2013; 17: 930
  • 8 Pack DW, Hoffman AS, Pun S, Stayton PS. Nat. Rev. Drug Discovery 2005; 4: 581
  • 9 Kanasty R, Dorkin JR, Vegas A, Anderson D. Nat. Mater. 2013; 12: 967
  • 10 Uhrich KE, Cannizzaro SM, Langer RS, Shakesheff KM. Chem. Rev. 1999; 99: 3181
  • 11 Lü J.-M, Wang X, Marin-Muller C, Wang H, Lin PH, Yao Q, Chen C. Expert Rev. Mol. Diagn. 2009; 9: 325
  • 12 Ulery BD, Nair LS, Laurencin CT. J. Polym. Sci., Part B: Polym. Phys. 2011; 49: 832
  • 13 Anselmo AC, Mitragotri S. J. Controlled Release 2014; 190: 15
  • 14 Cheng CJ, Tietjen GT, Saucier-Sawyer JK, Saltzman WM. Nat. Rev. Drug Discovery 2015; 14: 239
  • 15 Kamaly N, Yameen B, Wu J, Farokhzad OC. Chem. Rev. 2016; 116: 2602
  • 16 El Ali B, Alper H. Synlett 2000; 161
  • 17 Hao J, Kos P, Zhou K, Miller JB, Xue L, Yan Y, Xiong H, Elkassih S, Siegwart DJ. J. Am. Chem. Soc. 2015; 137: 9206
  • 18 Fietier I, Le Borgne A, Spassky N. Polym. Bull. 1990; 24: 349
  • 19 Blanquer S, Tailhades J, Darcos V, Amblard M, Martinez J, Nottelet B, Coudane J. J. Polym. Sci., Part A: Polym. Chem. 2010; 48: 5891
  • 20 Nottelet B, Patterer M, François B, Schott M.-A, Domurado M, Garric X, Domurado D, Coudane J. Biomacromolecules 2012; 13: 1544
  • 21 Yan J, Zhang Y, Xiao Y, Zhang Y, Lang M. React. Funct. Polym. 2010; 70: 400
  • 22 Yan J, Ye Z, Luo H, Chen M, Zhou Y, Tan W, Xiao Y, Zhang Y, Lang M. Polym. Chem. 2011; 2: 1331
  • 23 El Habnouni S, Blanquer S, Darcos V, Coudane J. J. Polym. Sci., Part A: Polym. Chem. 2009; 47: 6104
  • 24 Xiong X.-B, Uludağ H, Lavasanifar A. Biomaterials 2009; 30: 242
  • 25 Riva R, Schmeits S, Stoffelbach F, Jerôme C, Jerôme R, Lecomte P. Chem. Commun. 2005; 5334
  • 26 Detrembleur C, Mazza M, Lou X, Halleux O, Lecomte P, Mecerreyes D, Hedrick JL, Jérôme R. Macromolecules 2000; 33: 7751
  • 27 Detrembleur C, Mazza M, Halleux O, Lecomte P, Mecerreyes D, Hedrick JL, Jérôme R. Macromolecules 2000; 33: 14
  • 28 Lenoir S, Riva R, Lou X, Detrembleur C, Jérôme R, Lecomte P. Macromolecules 2004; 37: 4055
  • 29 Riva R, Chafaqi L, Jerôme R, Lecomte P. ARKIVOC 2007; (x): 292
  • 30 van der Ende A, Kravitz E, Harth E. J. Am. Chem. Soc. 2008; 130: 8706
  • 31 Darcos V, Antoniacomi S, Paniagua C, Coudane J. Polym. Chem. 2012; 3: 362
  • 32 Mecerreyes D, Miller RD, Hedrick JL, Detrembleur C, Jerôme R. J. Polym. Sci., Part A: Polym. Chem. 2000; 38: 870
  • 33 Mecerreyes D, Humes J, Miller RD, Hedrick JL, Detrembleur C, Lecomte P, Jerôme R, San Roman J. Macromol. Rapid Commun. 2000; 21: 779
  • 34 Lou X, Detrembleur C, Lecomte P, Jerôme R. Macromolecules 2001; 34: 5806
  • 35 Lou X, Detrembleur C, Lecomte P, Jerôme R. J. Polym. Sci., Part A: Polym. Chem. 2002; 40: 2286
  • 36 Li H, Jerôme R, Lecomte P. Polymer 2006; 47: 8406
  • 37 Lynn DM, Langer R. J. Am. Chem. Soc. 2000; 122: 10761
  • 38 Green J, Langer R, Anderson D. Acc. Chem. Res. 2008; 41: 749
  • 39 Tian HY, Tang ZH, Zhuang XL, Chen XS, Jing XB. Prog. Polym. Sci. 2012; 37: 237
  • 40 Gokhale S, Xu Y, Joy A. Biomacromolecules 2013; 14: 2489
  • 41 Yan Y, Siegwart DJ. Polym. Chem. 2014; 5: 1362
  • 42 Yan YF, Xue L, Miller JB, Zhou KJ, Kos P, Elkassih S, Liu L, Nagai A, Xiong H, Siegwart DJ. Polymer 2015; 72: 271
  • 43 Nederberg F, Zhang Y, Tan JP. K, Xu KJ, Wang HY, Yang C, Gao SJ, Guo XD, Fukushima K, Li LJ, Hedrick JL, Yang YY. Nat. Chem. 2011; 3: 409
  • 44 Geihe EI, Cooley CB, Simon JR, Kiesewetter MK, Edward JA, Hickerson RP, Kaspar RL, Hedrick JL, Waymouth RM, Wender PA. Proc. Natl. Acad. Sci. U.S.A. 2012; 109: 13171
  • 45 Zhang XJ, Cai MM, Zhong ZL, Zhuo RX. Macromol. Rapid Commun. 2012; 33: 693
  • 46 Blake TR, Waymouth RM. J. Am. Chem. Soc. 2014; 136: 9252
  • 47 Zhang ZH, Yin LC, Xu YX, Tong R, Lu YB, Ren J, Cheng JJ. Biomacromolecules 2012; 13: 3456
  • 48 Jones CH, Chen CK, Jiang M, Fang L, Cheng C, Pfeifer BA. Mol. Pharmaceutics 2013; 10: 1138
  • 49 Kim H, Olsson JV, Hedrick JL, Waymouth RM. ACS Macro Lett. 2012; 1: 845
  • 50 Winkler M, Raupp YS, Kohl LA. M, Wagner HE, Meier MA. R. Macromolecules 2014; 47: 2842
  • 51 Li XW, Li H, Zhao YY, Tang XY, Ma SF, Gong B, Li MF. Polym. Chem. 2015; 6: 6452
  • 52 Jayaraman M, Ansell SM, Mui BL, Tam YK, Chen JX, Du XY, Butler D, Eltepu L, Matsuda S, Narayanannair JK, Rajeev KG, Hafez IM, Akinc A, Maier MA, Tracy MA, Cullis PR, Madden TD, Manoharan M, Hope MJ. Angew. Chem. Int. Ed. 2012; 51: 8529
  • 53 Wittrup A, Ai A, Liu X, Hamar P, Trifonova R, Charisse K, Manoharan M, Kirchhausen T, Lieberman J. Nat. Biotechnol. 2015; 33: 870
  • 54 Zhou K, Nguyen LH, Miller JB, Yan Y, Kos P, Xiong H, Li L, Hao J, Minnig JT, Zhu H, Siegwart DJ. Proc. Natl. Acad. Sci. U.S.A. 2016; 113: 520