Interfacial assembly of dendritic microcapsules with host-guest chemistry

Nature Communications

Volumn 5, Issue , 2014, Pages

  Zheng, Yu ^a   Yu, Ziyi ^a   Parker, Richard M ^a   Wu, Yuchao ^a   Abell, Chris ^a   Scherman, Oren A ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CHLOROFORM; POLYMER; WATER;

FLUIDIZATION; HIERARCHICAL SYSTEM; INTERFACE; MOLECULAR ANALYSIS; POLYMER;

ARTICLE; BINDING AFFINITY; CELL COMPARTMENTALIZATION; COMPLEX FORMATION; CONTROLLED STUDY; HYDROPHILICITY; HYDROPHOBICITY; MICROCAPSULE; MICROENCAPSULATION; MICROFLUIDICS; MOLECULAR WEIGHT; POLYMERIZATION; SUPRAMOLECULAR CHEMISTRY;

EID: 84922672973     PISSN: None     EISSN: 20411723     Source Type: Journal    
DOI: 10.1038/ncomms6772     Document Type: Article

References (51)

1. Huang, X. et al. Interfacial assembly of protein-polymer nano-conjugates into stimulus-responsive biomimetic protocells. Nat. Commun. 4, 2239 (2013).
2. Groschel, A. H. et al. Guided hierarchical co-assembly of soft patchy nanoparticles. Nature 503, 247-251 (2013).
3. Bain, C. D. et al. Formation of monolayer films by the spontaneous assembly of organic thiols from solution onto gold. J. Am. Chem. Soc. 111, 321-335 (1989).
4. Lin, Y. et al. Ultrathin cross-linked nanoparticle membranes. J. Am. Chem. Soc. 125, 12690-12691 (2003).
5. Genzer, J. & Kirill, E. Creating long-lived superhydrophobic polymer surfaces through mechanically assembled monolayers. Science 290, 2130-2133 (2000).
6. Zhao, B. & Brittain, W. J. Polymer brushes: surface-immobilized macromolecules. Prog. Polym. Sci. 25, 677-710 (2000).
7. Skaff, H. et al. Crosslinked capsules of quantum dots by interfacial assembly and ligand crosslinking. Adv. Mater. 17, 2082-2086 (2005).
8. Lin, Y., Skaff, H., Emrick, T., Dinsmore, A. D. & Russell, T. P. Nanoparticle assembly and transport at liquid-liquid interfaces. Science 299, 226-229 (2003).
9. Russell, J. T. et al. Self-assembly and cross-linking of bionanoparticles at liquid-liquid interfaces. Angew. Chem. Int. Ed. 44, 2420-2426 (2005).
10. Theberge, A. B. et al. Microdroplets in microfluidics: an evolving platform for discoveries in chemistry and biology. Angew. Chem. Int. Ed. 49, 5846-5868 (2010).
11. Tumarkin, E. & Kumacheva, E. Microfluidic generation of microgels from synthetic and natural polymers. Chem. Soc. Rev. 38, 2161-2168 (2009).
12. Stephenson, G. et al. Supramolecular colloidosomes: fabrication, characterisation and triggered release of cargo. Chem. Commun. 50, 7048-7051 (2014).
13. Zhou, S. et al. Thermally switched release from nanoparticle colloidosomes. Adv. Funct. Mater. 23, 5925-5929 (2013).
14. Abbaspourrad, A., Carroll, N. J., Kim, S.-H. & Weitz, D. A. Polymer microcapsules with programmable active release. J. Am. Chem. Soc. 135, 7744-7750 (2013).
15. Kim, S.-H., Park, J.-G., Choi, T. M., Manoharan, V. N. & Weitz, D. A. Osmotic-pressure-controlled concentration of colloidal particles in thin-shelled capsules. Nat. Commun. 5, 3068 (2014).
16. Jiao, D. et al. Supramolecular peptide amphiphile vesicles through host-guest complexation. Angew. Chem. Int. Ed. 51, 9633-9637 (2012).
17. Kim, E. et al. Facile, template-free synthesis of stimuli-responsive polymer nanocapsules for targeted drug delivery. Angew. Chem. Int. Ed. 49, 4405-4408 (2010).
18. Li, H. et al. Mesoporous titania spheres with tunable chamber stucture and enhanced photocatalytic activity. J. Am. Chem. Soc. 129, 8406-8407 (2007).
19. Amstad, E., Kim, S.-H. & Weitz, D. A. Photo-and thermoresponsive polymersomes for triggered release. Angew. Chem. Int. Ed. 51, 12499-12503 (2012).
20. Peyratout, C. S. & Dahne, L. Tailor-made polyelectrolyte microcapsules: from multilayers to smart containers. Angew. Chem. Int. Ed. 43, 3762-3783 (2004).
21. Becker, A. L., Johnston, A. P. R. & Caruso, F. Layer-by-layer-assembled capsules and films for therapeutic delivery. Small 6, 1836-1852 (2010).
22. De Cock, L. J. et al. Polymeric multilayer capsules in drug delivery. Angew. Chem. Int. Ed. 49, 6954-6973 (2010).
23. Utada, A. S. et al. Monodisperse double emulsions generated from a microcapillary device. Science 308, 537-541 (2005).
24. Gao, F., Su, Z.-G., Wang, P. & Ma, G.-H. Double emulsion templated microcapsules with single hollow cavities and thickness-controllable shells. Langmuir 25, 3832-3838 (2009).
25. Hermanson, K., Huemmerich, D., Scheibel, T. & Bausch, A. R. Engineered microcapsules fabricated from reconstituted spider silk. Adv. Mater. 19, 1810-1815 (2007).
26. Thompson, K. L. et al. Covalently cross-linked colloidosomes. Macromolecules 43, 10466-10474 (2010).
27. Duan, H. et al. Magnetic colloidosomes derived from nanoparticle interfacial self-assembly. Nano Lett. 5, 949-952 (2005).
28. Wang, W. et al. Hole-shell microparticles from controllably evolved double emulsions. Angew. Chem. Int. Ed. 52, 8084-8087 (2013).
29. Abbaspourrad, A., Carroll, N. J., Kim, S. H. & Weitz, D. A. Polymer microcapsules with programmable active release. J. Am. Chem. Soc. 135, 7744-7750 (2013).
30. Tsuda, N., Ohtsubo, T. & Fuji, M. Preparation of self-bursting microcapsules by interfacial polymerization. Adv. Powder Tech. 23, 724-730 (2012).
31. Kobaslija, M. & McQuade, D. T. Polyurea microcapsules from oil-in-oil emulsions via interfacial polymerization. Macromolecules 39, 6371-6375 (2006).
32. Levy, M. C. & Andry, M. C. Microcapsules prepared through interfacial crosslinking of starch derivatives. Int. J. Pharm. 62, 27-35 (1990).
33. del Barrio, J. et al. Photocontrol over cucurbit[8]uril complexes: stoichiometry and supramolecular polymers. J. Am. Chem. Soc. 135, 11760-11763 (2013).
34. Liu, Y., Yu, Y., Gao, J., Wang, Z. & Zhang, X. Water-soluble supramolecular polymerization driven by multiple host-stabilized charge-transfer interactions. Angew. Chem. Int. Ed. 122, 6726-6729 (2010).
35. Rauwald, U. & Scherman, O. A. Supramolecular block copolymers with cucurbit[8]uril in water. Angew. Chem. Int. Ed. 47, 3950-3953 (2008).
36. Appel, E. A. et al. Supramolecular cross-linked networks via host-guest complexation with cucurbit[8]uril. J. Am. Chem. Soc. 132, 14251-14260 (2010).
37. Appel, E. A. et al. Ultrahigh-water-content supramolecular hydrogels exhibiting multistimuli responsiveness. J. Am. Chem. Soc. 134, 11767-11773 (2012).
38. Lan, Y., Wu, Y., Karas, A. & Scherman, O. A. Photoresponsive hybrid raspberry-like colloids based on cucurbit[8]uril host-guest interactions. Angew. Chem. Int. Ed. 126, 2166-2169 (2014).
39. Zhang, J. et al. One-step fabrication of supramolecular microcapsules from microfluidic droplets. Science 335, 690-694 (2012).
40. Ko, Y. H., Kim, E., Hwang, I. & Kim, K. Supramolecular assemblies built with host-stabilized charge-transfer interactions. Chem. Commun. 13, 1305-1315 (2007).
41. Isaacs, L. Cucurbit[n]urils: from mechanism to structure and function. Chem. Commun. 6, 619-629 (2009).
42. Hecht, S. & Frechet, J. M. J. Dendritic encapsulation of function: applying nature's site isolation principle from biomimetics to materials science. Angew. Chem. Int. Ed. 40, 74-91 (2001).
43. Patri, A. K., Majoros, I. J. & Baker, J. R. Dendritic polymer macromolecular carriers for drug delivery. Curr. Opin. Chem. Biol. 6, 466-471 (2002).
44. Geng, J., Jiao, D., Rauwald, U. & Scherman, O. A. An aqueous supramolecular side-chain polymer designed for molecular loading. Aust. J. Chem. 63, 627-630 (2010).
45. Loh, X. J., del Barrio, J., Lee, T.-C. & Scherman, O. A. Supramolecular polymeric peptide amphiphile vesicles for the encapsulation of basic fibroblast growth factor. Chem. Commun. 50, 3033-3035 (2014).
46. Rauwald, U., Biedermann, F., Deroo, S., Robinson, C. V. & Scherman, O. A. Correlating solution binding and ESI-MS stabilities by incorporating solvation effects in a confined cucurbit[8]uril system. J. Phys. Chem. B 114, 8606-8615 (2010).
47. Zheng, Y. et al. 3D single cyclized polymer chain structure from controlled polymerization of multi-vinyl monomers: beyond Flory-Stockmayer theory. J. Am. Chem. Soc. 133, 13130-13137 (2011).
48. Zhao, T., Zheng, Y., Poly, J. & Wang, W. Controlled multi-vinyl monomer homopolymerization through vinyl oligomer combination as a universal approach to hyperbranched architectures. Nat. Commun. 4, 1873 (2013).
49. Tian, F., Jiao, D., Biedermann, F. & Scherman, O. A. Orthogonal switching of a single supramolecular complex. Nat. Commun. 3, 1207 (2012).
50. Appel, E. A., Koutsioubas, A., Forster, R. A., Toprakcioglu, C. & Scherman, O. A. Activation energies control macroscopic properties of physically crosslinked materials. Angew. Chem. Int. Ed. 38, 10038-10043 (2014).
51. Yang, H., Yuan, B., Zhang, X. & Scherman, O. A. Supramolecular chemistry at interfaces: host-guest interactions for fabricating multifunctional biointerfaces. Acc. Chem. Res. 47, 2106-2115 (2014).