Crystallization-driven assembly of fully degradable, natural product-based poly(L-lactide)-block-poly(α-D-glucose carbonate)s in aqueous solution

Polymer

Volumn 122, Issue , 2017, Pages 270-279

  Song, Yue ^a   Chen, Yingchao ^a   Su, Lu ^a   Li, Richen ^a   Letteri, Rachel A ^a   Wooley, Karen L ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

Amphiphilic block copolymer; Crystallization driven self assembly (CDSA); Cylindrical micelles; Degradable; Natural product based polymers

Indexed keywords

AMINO ACIDS; ASSEMBLY; ATOMIC FORCE MICROSCOPY; BLOCK COPOLYMERS; CARBONATION; DEGRADATION; DRUG DELIVERY; ELECTROSPRAY IONIZATION; GLUCOSE; HIGH RESOLUTION TRANSMISSION ELECTRON MICROSCOPY; MASS SPECTROMETRY; MICELLES; NANOSTRUCTURES; NATURAL POLYMERS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SELF ASSEMBLY; SOLUTIONS; TRANSMISSION ELECTRON MICROSCOPY;

AMPHIPHILIC BLOCK COPOLYMERS; AMPHIPHILIC DIBLOCK COPOLYMERS; CYLINDRICAL MICELLES; DEGRADABLE; DEGRADATION OF THE MATERIAL; ELECTROSPRAY IONIZATION (ESI); MATRIX ASSISTED LASER DESORPTION; NATURAL PRODUCTS;

RING OPENING POLYMERIZATION;

EID: 85021654160     PISSN: 00323861     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.polymer.2017.06.065     Document Type: Article

References (59)

1. Jain, S., Bates, F.S., On the origins of morphological complexity in block copolymer surfactants. Science 300:5618 (2003), 460–464.
2. Holder, S.J., Sommerdijk, N.A.J.M., New micellar morphologies from amphiphilic block copolymers: disks, toroids and bicontinuous micelles. Polym. Chem. 2:5 (2011), 1018–1028.
3. Blanazs, A., Madsen, J., Battaglia, G., Ryan, A.J., Armes, S.P., Mechanistic insights for block copolymer morphologies: how do worms form vesicles?. J. Am. Chem. Soc. 133:41 (2011), 16581–16587.
4. Qiu, H., Hudson, Z.M., Winnik, M.A., Manners, I., Multidimensional hierarchical self-assembly of amphiphilic cylindrical block comicelles. Science 347:6228 (2015), 1329–1332.
5. Mai, Y., Eisenberg, A., Self-assembly of block copolymers. Chem. Soc. Rev. 41:18 (2012), 5969–5985.
6. Zhang, F., Zhang, S., Pollack, S.F., Li, R., Gonzalez, A.M., Fan, J., Zou, J., Leininger, S.E., Pavia-Sanders, A., Johnson, R., Nelson, L.D., Raymond, J.E., Elsabahy, M., Hughes, D.M., Lenox, M.W., Gustafson, T.P., Wooley, K.L., Improving paclitaxel delivery: in vitro and in vivo characterization of PEGylated polyphosphoester-based nanocarriers. J. Am. Chem. Soc. 137:5 (2015), 2056–2066.
7. Chai, J., Buriak, J.M., Using cylindrical domains of block copolymers to self-assemble and align metallic nanowires. ACS Nano 2:3 (2008), 489–501.
8. Sun, L., Pitto-Barry, A., Thomas, A.W., Inam, M., Doncom, K., Dove, A.P., O'Reilly, R.K., Core functionalization of semi-crystalline polymeric cylindrical nanoparticles using photo-initiated thiol-ene radical reactions. Polym. Chem. 7:13 (2016), 2337–2341.
9. Zhang, M., Müller, A.H.E., Cylindrical polymer brushes. J. Polym. Sci. Part A Polym. Chem. 43:16 (2005), 3461–3481.
10. Petzetakis, N., Walker, D., Dove, A.P., O'Reilly, R.K., Crystallization-driven sphere-to-rod transition of poly(lactide)-b-poly(acrylic acid) diblock copolymers: mechanism and kinetics. Soft Matter 8:28 (2012), 7408–7414.
11. Petzetakis, N., Dove, A.P., O'Reilly, R.K., Cylindrical micelles from the living crystallization-driven self-assembly of poly (lactide)-containing block copolymers. Chem. Sci. 2:5 (2011), 955–960.
12. Wang, X., Guerin, G., Wang, H., Wang, Y., Manners, I., Winnik, M.A., Cylindrical block copolymer micelles and Co-Micelles of controlled length and architecture. Science 317:5838 (2007), 644–647.
13. Gilroy, J.B., Gädt, T., Whittell, G.R., Chabanne, L., Mitchels, J.M., Richardson, R.M., Winnik, M.A., Manners, I., Monodisperse cylindrical micelles by crystallization-driven living self-assembly. Nat. Chem. 2:7 (2010), 566–570.
14. Müllner, M., Müller, A.H., Cylindrical polymer brushes–anisotropic building blocks, unimolecular templates and particulate nanocarriers. Polymer 98 (2016), 389–401.
15. Yuan, J., Müller, A.H., One-dimensional organic–inorganic hybrid nanomaterials. Polymer 51:18 (2010), 4015–4036.
16. Löbling, T.I., Borisov, O., Haataja, J.S., Ikkala, O., Gröschel, A.H., Müller, A.H.E., Rational design of ABC triblock terpolymer solution nanostructures with controlled patch morphology. Nat. Commun., 7, 2016, 12097.
17. Groschel, A.H., Walther, A., Lobling, T.I., Schacher, F.H., Schmalz, H., Muller, A.H.E., Guided hierarchical co-assembly of soft patchy nanoparticles. Nature 503:7475 (2013), 247–251.
18. Gröschel, A.H., Schacher, F.H., Schmalz, H., Borisov, O.V., Zhulina, E.B., Walther, A., Müller, A.H.E., Precise hierarchical self-assembly of multicompartment micelles. Nat. Commun., 3, 2012, 710.
19. Geng, Y., Dalhaimer, P., Cai, S., Tsai, R., Tewari, M., Minko, T., Discher, D.E., Shape effects of filaments versus spherical particles in flow and drug delivery. Nat. Nanotechnol. 2:4 (2007), 249–255.
20. Zhang, K., Fang, H., Chen, Z., Taylor, J.-S.A., Wooley, K.L., Shape effects of nanoparticles conjugated with cell-penetrating peptides (HIV tat PTD) on CHO cell uptake. Bioconjugate Chem. 19:9 (2008), 1880–1887.
21. Harada, A., Kataoka, K., Supramolecular assemblies of block copolymers in aqueous media as nanocontainers relevant to biological applications. Progr. Polym. Sci. 31:11 (2006), 949–982.
22. Hinde, E., Thammasiraphop, K., Duong, H.T., Yeow, J., Karagoz, B., Boyer, C., Gooding, J.J., Gaus, K., Pair correlation microscopy reveals the role of nanoparticle shape in intracellular transport and site of drug release. Nat. Nanotechnol. 12:1 (2017), 81–89.
23. Lee, N.S., Lin, L.Y., Neumann, W.L., Freskos, J.N., Karwa, A., Shieh, J.J., Dorshow, R.B., Wooley, K.L., Influence of nanostructure morphology on host capacity and kinetics of guest release. Small 7:14 (2011), 1998–2003.
24. Massey, J.A., Temple, K., Cao, L., Rharbi, Y., Raez, J., Winnik, M.A., Manners, I., Self-assembly of organometallic block copolymers: the role of crystallinity of the core-forming polyferrocene block in the micellar morphologies formed by poly(ferrocenylsilane-b-dimethylsiloxane) in n-alkane solvents. J. Am. Chem. Soc. 122:47 (2000), 11577–11584.
25. Cambridge, G., Gonzalez-Alvarez, M.J., Guerin, G., Manners, I., Winnik, M.A., Solution self-assembly of blends of crystalline-coil polyferrocenylsilane-block-polyisoprene with crystallizable polyferrocenylsilane homopolymer. Macromolecules 48:3 (2015), 707–716.
26. Crassous, J.J., Schurtenberger, P., Ballauff, M., Mihut, A.M., Design of block copolymer micelles via crystallization. Polymer 62 (2015), A1–A13.
27. Sun, L., Petzetakis, N., Pitto-Barry, A., Schiller, T.L., Kirby, N., Keddie, D.J., Boyd, B.J., O'Reilly, R.K., Dove, A.P., Tuning the size of cylindrical micelles from poly(l-lactide)-b-poly(acrylic acid) diblock copolymers based on crystallization-driven self-assembly. Macromolecules 46:22 (2013), 9074–9082.
28. Pitto-Barry, A., Kirby, N., Dove, A.P., O'Reilly, R.K., Expanding the scope of the crystallization-driven self-assembly of polylactide-containing polymers. Polym. Chem. 5:4 (2014), 1427–1436.
29. Sun, L., Pitto-Barry, A., Kirby, N., Schiller, T.L., Sanchez, A.M., Dyson, M.A., Sloan, J., Wilson, N.R., O'Reilly, R.K., Dove, A.P., Structural reorganization of cylindrical nanoparticles triggered by polylactide stereocomplexation. Nat. Commun., 5, 2014, 5746.
30. Inam, M., Cambridge, G., Pitto-Barry, A., Laker, Z.P.L., Wilson, N.R., Mathers, R.T., Dove, A.P., O'Reilly, R.K., 1D vs. 2D shape selectivity in the crystallization-driven self-assembly of polylactide block copolymers. Chem. Sci. 8 (2017), 4223–4230.
31. Wang, J., Zhu, W., Peng, B., Chen, Y., A facile way to prepare crystalline platelets of block copolymers by crystallization-driven self-assembly. Polymer 54:25 (2013), 6760–6767.
32. Shearouse, W.C., Lillie, L.M., Reineke, T.M., Tolman, W.B., Sustainable polyesters derived from glucose and Castor oil: building block structure impacts properties. ACS Macro Lett. 4:3 (2015), 284–288.
33. Hillmyer, M.A., Tolman, W.B., Aliphatic polyester block polymers: renewable, degradable, and sustainable. Acc. Chem. Res. 47:8 (2014), 2390–2396.
34. Miller, S.A., Sustainable polymers: opportunities for the next decade. ACS Macro Lett. 2:6 (2013), 550–554.
35. Gustafson, T.P., Lonnecker, A.T., Heo, G.S., Zhang, S., Dove, A.P., Wooley, K.L., Poly(d-glucose carbonate) block copolymers: a platform for natural product-based nanomaterials with solvothermatic characteristics. Biomacromolecules 14:9 (2013), 3346–3353.
36. Su, L., Khan, S., Fan, J.W., Lin, Y.N., Wang, H., Gustafson, T.P., Zhang, F.W., Wooley, K.L., Functional sugar-based polymers and nanostructures comprised of degradable poly(D-glucose carbonate)s. Polym. Chem. 8:10 (2017), 1699–1707.
37. 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. 135:18 (2013), 6826–6829.
38. 2 and glucoside. Macromolecules 50:4 (2017), 1362–1370.
39. Pratt, R.C., Lohmeijer, B.G., Long, D.A., Waymouth, R.M., Hedrick, J.L., Triazabicyclodecene: a simple bifunctional organocatalyst for acyl transfer and ring-opening polymerization of cyclic esters. J. Am. Chem. Soc. 128:14 (2006), 4556–4557.
40. Kiesewetter, M.K., Shin, E.J., Hedrick, J.L., Waymouth, R.M., Organocatalysis: opportunities and challenges for polymer synthesis. Macromolecules 43:5 (2010), 2093–2107.
41. Liang, L., Astruc, D., The copper (I)-catalyzed alkyne-azide cycloaddition (CuAAC)“click” reaction and its applications. An overview. Coord. Chem. Rev. 255:23 (2011), 2933–2945.
42. Hoyle, C.E., Bowman, C.N., Thiol–ene click chemistry. Angew. Chem. Int. Ed. 49:9 (2010), 1540–1573.
43. Lowe, A.B., Hoyle, C.E., Bowman, C.N., Thiol-yne click chemistry: a powerful and versatile methodology for materials synthesis. J. Mater. Chem. 20:23 (2010), 4745–4750.
44. Halbes-Letinois, U., Weibel, J.-M., Pale, P., The organic chemistry of silver acetylides. Chem. Soc. Rev. 36:5 (2007), 759–769.
45. Kikkawa, Y., Abe, H., Iwata, T., Inoue, Y., Doi, Y., Crystallization, stability, and enzymatic degradation of poly(l-lactide) thin film. Biomacromolecules 3:2 (2002), 350–356.
46. Kiesewetter, M.K., Scholten, M.D., Kirn, N., Weber, R.L., Hedrick, J.L., Waymouth, R.M., Cyclic guanidine organic catalysts: what is magic about triazabicyclodecene?. J. Org. Chem. 74:24 (2009), 9490–9496.
47. Tsao, Y.-Y.T., Wooley, K.L., Synthetic, functional thymidine-derived polydeoxyribonucleotide analogues from a six-membered cyclic phosphoester. J. Am. Chem. Soc. 139:15 (2017), 5467–5473.
48. Zhang, S., Wang, H., Shen, Y., Zhang, F., Seetho, K., Zou, J., Taylor, J.S., Dove, A.P., Wooley, K.L., A simple and efficient synthesis of an acid-labile polyphosphoramidate by organobase-catalyzed ring-opening polymerization and transformation to polyphosphoester ionomers by acid treatment. Macromolecules 46:13 (2013), 5141–5149.
49. Appel, E.A., Lee, V.Y., Nguyen, T.T., McNeil, M., Nederberg, F., Hedrick, J.L., Swope, W.C., Rice, J.E., Miller, R.D., Sly, J., Toward biodegradable nanogel star polymers via organocatalytic ROP. Chem. Commun. 48:49 (2012), 6163–6165.
50. Jaffredo, C.G., Carpentier, J.-F., Guillaume, S.M., Organocatalyzed controlled ROP of [small beta]-lactones towards poly(hydroxyalkanoate)s: from [small beta]-butyrolactone to benzyl [small beta]-malolactone polymers. Polym. Chem. 4:13 (2013), 3837–3850.
51. Lowe, A.B., McCormick, C.L., Synthesis and solution properties of zwitterionic polymers. Chem. Rev. 102:11 (2002), 4177–4190.
52. 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. 134:44 (2012), 18467–18474.
53. Lim, Y.H., Heo, G.S., Cho, S., Wooley, K.L., Construction of a reactive diblock copolymer, polyphosphoester–poly(L-lactide), as a versatile framework for functional materials that are capable of full degradation and nanoscopic assembly formation. ACS Macro Lett. 2:9 (2013), 785–789.
54. Wang, W., Qi, H., Zhou, T., Mei, S., Han, L., Higuchi, T., Jinnai, H., Li, C.Y., Highly robust crystalsome via directed polymer crystallization at curved liquid/liquid interface. Nat. Commun., 7, 2016, 10599.
55. Tokiwa, Y., Calabia, B.P., Ugwu, C.U., Aiba, S., Biodegradability of plastics. Int. J. Mol. Sci. 10:9 (2009), 3722–3742.
56. Garlotta, D., A literature review of poly(lactic acid). J. Polym. Environ. 9:2 (2001), 63–84.
57. Lim, Y.H., Tiemann, K.M., Heo, G.S., Wagers, P.O., Rezenom, Y.H., Zhang, S., Zhang, F., Youngs, W.J., Hunstad, D.A., Wooley, K.L., Preparation and in vitro antimicrobial activity of silver-bearing degradable polymeric nanoparticles of polyphosphoester-block-poly(l-lactide). ACS Nano 9:2 (2015), 1995–2008.
58. Wang, H., Su, L., Li, R., Zhang, S., Fan, J., Zhang, F., Nguyen, T.P., Wooley, K.L., Polyphosphoramidates that undergo acid-triggered backbone degradation. ACS Macro Lett. 6:3 (2017), 219–223.
59. Akbulut, H., Yamada, S., Endo, T., Preparation of a zwitterionic polymer based on l-cysteine for recovery application of precious metals. RSC Adv. 6:110 (2016), 108689–108696.