Small-molecule/polymer recognition triggers aqueous-phase assembly and encapsulation

Langmuir

Volumn 29, Issue 1, 2013, Pages 144-150

  Zhou, Zhun ^a   Bong, Dennis ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5-FLUOROURACIL; 5-FLUOROURACIL (5-FU); BINDING INTERACTION; BINDING SIGNATURES; CYANURIC ACIDS; HETEROCYCLES; HYDROGEN BONDING INTERACTIONS; HYDROPHOBIC BLOCKS; SMALL MOLECULES; X RAY CRYSTAL STRUCTURES;

ALKYLATION; BINDING ENERGY; HYDROGEN BONDS; MACROMOLECULES;

POLYMERS;

CYANURIC ACID; FLUOROURACIL; MELAMINE; NANOPARTICLE; POLYMER; TRIAZINE DERIVATIVE; WATER;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; HYDROGEN BOND; MICROCAPSULE; X RAY CRYSTALLOGRAPHY;

CAPSULES; CRYSTALLOGRAPHY, X-RAY; FLUOROURACIL; HYDROGEN BONDING; MODELS, MOLECULAR; NANOPARTICLES; POLYMERS; TRIAZINES; WATER;

EID: 84872100031     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la304457y     Document Type: Article

References (71)

1. Stenzel, M. H. RAFT polymerization: an avenue to functional polymeric mimcelles for drug delivery Chem. Commun. 2008, 2008, 3486-3503
2. Kataoka, K.; Harada, A.; Nagasaki, Y. Block copolymer micelles for drug delivery: design, characterization and biological significance Adv. Drug Delivery Rev. 2001, 47, 113-131
3. Kim, S.; Park, K. Polymer micelles for drug delivery. In Targeted Delivery of Small and Macromolecular Drugs; Narang, A. S.; Mahato, R. I., Eds.; CRC Press: Boca Raton, FL, 2010; pp 513-551.
4. Mai, Y.; Eisenberg, A. Self-assembly of block copolymers Chem. Soc. Rev. 2012, 41, 5969-5985
5. Lee, S.-M.; Chen, H.; Dettmer, C. M.; O'Halloran, T. V.; Nguyen, S. T. Polymer-caged liposomes: a pH-responsive delivery system with high stability J. Am. Chem. Soc. 2007, 129, 15096-15097
6. Bronich, T. K.; Keifer, P. A.; Shlyakhtenko, L. S.; Kabanov, A. V. Polymer micelle with cross-linked ionic core J. Am. Chem. Soc. 2005, 127, 8236-7
7. Christian, D. A.; Tian, A. W.; Ellenbroek, W. G.; Levental, I.; Rajagopal, K.; Janmey, P. A.; Liu, A. J.; Baumgart, T.; Discher, D. E. Spotted vesicles, striped micelles and Janus assemblies induced by ligand binding Nat. Mater. 2009, 8, 843-849
8. Discher, D. E.; Eisenberg, A. Polymer vesicles Science 2002, 297, 967-73
9. Ishihara, Y.; Bazzi, H. S.; Toader, V.; Godin, F.; Sleiman, H. F. Molecule-responsive block copolymer micelles Chem.-Eur. J. 2007, 13, 4560-4570
10. Lo, P. K.; Sleiman, H. F. Nucleobase-templated polymerization: copying the chain length and polydispersity of living polymers into conjugated polymers J. Am. Chem. Soc. 2009, 131, 4182-4183
11. McHale, R.; Patterson, J. P.; Zetterlund, P. B.; O'Reilly, R. K. Biomimetic radical polymerization via cooperative assembly of segregating templates Nat. Chem. 2012, 4, 491-7
12. McHale, R.; O'Reilly, R. K. Nucleobase containing synthetic polymers: advancing biomimicry via controlled synthesis and self-assembly Macromolecules 2012, 45, 7665-7675
13. Bayer, F. M.; Tang, M.; Michels, R.; Schmidt, C.; Huber, K. Molecular recognition with 2,4-diaminotriazine-functionalized colloids Langmuir 2011, 27, 12851-12858
14. Bong, D. T.; Clark, T. D.; Granja, J. R.; Ghadiri, M. R. Self-assembling organic nanotubes Angew. Chem., Int. Ed. 2001, 40, 988-1011
15. De Greef, T. F. A.; Smulders, M. M. J.; Wolffs, M.; Schenning, A.; Sijbesma, R. P.; Meijer, E. W. Supramolecular polymerization Chem. Rev. 2009, 109, 5687-5754
16. Brunsveld, L.; Folmer, B. J. B.; Meijer, E. W.; Sijbesma, R. P. Supramolecular polymers Chem. Rev. 2001, 101, 4071-4098
17. Aida, T.; Meijer, E. W.; Stupp, S. I. Functional supramolecular polymers Science 2012, 335, 813-817
18. Korevaar, P. A.; George, S. J.; Markvoort, A. J.; Smulders, M. M.; Hilbers, P. A.; Schenning, A. P.; De Greef, T. F.; Meijer, E. W. Pathway complexity in supramolecular polymerization Nature 2012, 481, 492-6
19. Kawasaki, T.; Tokuhiro, M.; Kimizuka, N.; Kunitake, T. Hierarchical self-assembly of chiral complementary hydrogen-bond networks in water: reconstitution of supramolecular membranes J. Am. Chem. Soc. 2001, 123, 6792-800
20. Appel, E. A.; del Barrio, J.; Loh, X. J.; Scherman, O. A. Supramolecular polymeric hydrogels Chem. Soc. Rev. 2012, 41, 6195-6214
21. Tan, S. W.; Wang, H. J.; Tu, K. H.; Jiang, H. L.; Wang, L. Q. Ibuprofen induced drug loaded polymeric micelles Chin. Chem. Lett. 2011, 22, 1123-1126
22. Ma, M.; Gong, Y.; Bong, D. Lipid membrane adhesion and fusion driven by designed, minimally multivalent hydrogen-bonding lipids J. Am. Chem. Soc. 2009, 131, 16919-26
23. Ma, M.; Paredes, A.; Bong, D. Intra- and intermembrane pairwise molecular recognition between synthetic hydrogen-bonding phospholipids J. Am. Chem. Soc. 2008, 130, 14456-8
24. Ariga, K.; Kunitake, T. Molecular recognition at air-water and related interfaces: complementary hydrogen bonding and multisite interaction Acc. Chem. Res. 1998, 31, 371-378
25. Kimizuka, N.; Kawasaki, T.; Hirata, K.; Kunitake, T. Supramolecular membranes. Spontaneous assembly of aqueous bilayer membrane via formation of hydrogen bonded pairs of melamine and cyanuric acid derivatives J. Am. Chem. Soc. 1998, 120, 4094-4104
26. LaManna, C. M.; Lusic, H.; Camplo, M.; McIntosh, T. J.; Barthélémy, P.; Grinstaff, M. W. Charge-reversal lipids, peptide-based lipids, and nucleoside-based lipids for gene delivery Acc. Chem. Res. 2012, 45, 1026-1038
27. Moreau, L.; Barthélémy, P.; El Maataoui, M.; Grinstaff, M. W. Supramolecular assemblies of nucleoside phosphocholine amphiphiles J. Am. Chem. Soc. 2004, 126, 7533-7539
28. Ma, M.; Bong, D. Determinants of cyanuric acid and melamine assembly in water Langmuir 2011, 27, 8841-8853
29. Ma, M.; Bong, D. Directed peptide assembly at the lipid-water interface cooperatively enhances membrane binding and activity Langmuir 2011, 27, 1480-1486
30. Mittapalli, G. K.; Osornio, Y. M.; Guerrero, M. A.; Reddy, K. R.; Krishnamurthy, R.; Eschenmoser, A. Mapping the landscape of potentially primordial informational oligomers: oligodipeptides tagged with 2,4-disubstituted 5-aminopyrimidines as recognition elements Angew. Chem., Int. Ed. 2007, 46, 2478-84
31. Mittapalli, G. K.; Reddy, K. R.; Xiong, H.; Munoz, O.; Han, B.; De Riccardis, F.; Krishnamurthy, R.; Eschenmoser, A. Mapping the landscape of potentially primordial informational oligomers: oligodipeptides and oligodipeptoids tagged with triazines as recognition elements Angew. Chem., Int. Ed. 2007, 46, 2470-7
32. Fenniri, H.; Packiarajan, M.; Vidale, K. L.; Sherman, D. M.; Hallenga, K.; Wood, K. V.; Stowell, J. G. Helical rosette nanotubes: design, self-assembly, and characterization J. Am. Chem. Soc. 2001, 123, 3854-3855
33. Nowick, J. S.; Cao, T.; Noronha, G. Molecular recognition between uncharged molecules in aqueous micelles J. Am. Chem. Soc. 1994, 116, 3285-3289
34. Nowick, J. S.; Chen, J. S. Molecular recognition in aqueous micellar solution: adenine-thymine base-pairing in SDS micelles J. Am. Chem. Soc. 1992, 114, 1107-1108
35. Zeng, Y.; Pratumyot, Y.; Piao, X.; Bong, D. Discrete assembly of synthetic peptide-DNA triplex structures from polyvalent melamine-thymine bifacial recognition J. Am. Chem. Soc. 2012, 134, 832-5
36. Ma, M.; Bong, D. Protein assembly directed by synthetic molecular recognition motifs Org. Biomol. Chem. 2011, 9, 7296-9
37. Ma, M.; Bong, D. Directed peptide assembly at the lipid-water interface cooperatively enhances membrane binding and activity Langmuir 2011, 27, 1480-6
38. Ma, M.; Bong, D. Determinants of cyanuric acid and melamine assembly in water Langmuir 2011, 27, 8841-53
39. Ma, M.; Gong, Y.; Bong, D. Lipid membrane adhesion and fusion driven by designed, minimally multivalent hydrogen-bonding lipids J. Am. Chem. Soc. 2009, 131, 16919-16926
40. ten Cate, M. G. J.; Huskens, J.; Crego-Calama, M.; Reinhoudt, D. N. Thermodynamic stability of hydrogen-bonded nanostructures: a calorimetric study Chem.-Eur. J. 2004, 10, 3632-3639
41. Damodaran, K.; Sanjayan, G. J.; Rajamohanan, P. R.; Ganapathy, S.; Ganesh, K. N. Solid state NMR of a molecular self-assembly: multinuclear approach to the cyanuric acid-melamine system Org. Lett. 2001, 3, 1921-1924
42. Prins, L. J.; Reinhoudt, D. N.; Timmerman, P. Noncovalent synthesis using hydrogen bonding Angew. Chem., Int. Ed. 2001, 40, 2382-2426
43. Krische, M. J.; Lehn, J. M. The utilization of persistent H-bonding motifs in the self-assembly of supramolecular architectures. In Molecular Self-Assembly; Springer-Verlag: Berlin, Germany, 2000; Vol. 96, pp 3-29.
44. Seto, C. T.; Whitesides, G. M. Molecular self-assembly through hydrogen bonding: supramolecular aggregates based on the cyanuric acid-melamine lattice J. Am. Chem. Soc. 1993, 115, 905-16
45. Zerkowski, J. A.; Seto, C. T.; Whitesides, G. M. Solid-state structures of rosette and crinkled tape motifs derived from the cyanuric acid melamine lattice J. Am. Chem. Soc. 1992, 114, 5473-5475
46. Seto, C. T.; Whitesides, G. M. Self-assembly based on the cyanuric acid-melamine lattice J. Am. Chem. Soc. 1990, 112, 6409-11
47. Longley, D. B.; Harkin, D. P.; Johnston, P. G. 5-Fluorouracil: mechanisms of action and clinical strategies Nat. Rev. Cancer 2003, 3, 330-338
48. Huang, Z.; Jaafari, M. R.; Szoka, F. C., Jr. Disterolphospholipids: nonexchangeable lipids and their application to liposomal drug delivery Angew. Chem., Int. Ed. 2009, 48, 4146-9
49. Huang, Z.; Szoka, F. C., Jr. Sterol-modified phospholipids: cholesterol and phospholipid chimeras with improved biomembrane properties J. Am. Chem. Soc. 2008, 130, 15702-12
50. Ranganathan, A.; Pedireddi, V. R.; Rao, C. N. R. Hydrothermal synthesis of organic channel structures: 1: 1 hydrogen-bonded adducts of melamine with cyanuric and trithiocyanuric acids J. Am. Chem. Soc. 1999, 121, 1752-1753
51. Wang, Y.; Wei, B.; Wang, Q. Crystal structure of melamine cyanuric acid complex (1:1) trihydrochloride, MCA·3HCl J. Chem. Crystallogr. 1990, 20, 79-84
52. Lange, R. F. M.; Beijer, F. H.; Sijbesma, R. P.; Hooft, R. W. W.; Kooijman, H.; Spek, A. L.; Kroon, J.; Meijer, E. W. Crystal engineering of melamine-imide complexes; tuning the stoichiometry by steric hindrance of the imide carbonyl groups Angew. Chem., Int. Ed. Engl. 1997, 36, 969-971
53. Thomas, R.; Kulkarni, G. U. A hydrogen-bonded channel structure formed by a complex of uracil and melamine Beilstein J. Org. Chem. 2007, 3, 17
54. Bartels, J. W.; Cauet, S. I.; Billings, P. L.; Lin, L. Y.; Zhu, J.; Fidge, C.; Pochan, D. J.; Wooley, K. L. Evaluation of isoprene chain extension from PEO macromolecular chain transfer agents for the preparation of dual, invertible block copolymer nanoassemblies Macromolecules 2010, 43, 7128-7138
55. Keddie, D. J.; Moad, G.; Rizzardo, E.; Thang, S. H. RAFT agent design and synthesis Macromolecules 2012, 45, 5321-5342
56. Linegar, K.; Adeniran, A.; Kostko, A.; Anisimov, M. Hydrodynamic radius of polyethylene glycol in solution obtained by dynamic light scattering Colloid J. 2010, 72, 279-281
57. Lazzara, G.; Milioto, S.; Gradzielski, M. The solubilisation behaviour of some dichloroalkanes in aqueous solutions of PEO-PPO-PEO triblock copolymers: a dynamic light scattering, fluorescence spectroscopy, and SANS study Phys. Chem. Chem. Phys. 2006, 8, 2299-2312
58. Lejeune, E.; Drechsler, M.; Jestin, J.; Müller, A. H. E.; Chassenieux, C.; Colombani, O. Amphiphilic diblock copolymers with a moderately hydrophobic block: toward dynamic micelles Macromolecules 2010, 43, 2667-2671
59. Nicolai, T.; Colombani, O.; Chassenieux, C. Dynamic polymeric micelles versus frozen nanoparticles formed by block copolymers Soft Matter 2010, 6, 3111-3118
60. Lejeune, E.; Chassenieux, C.; Colombani, O. pH Induced desaggregation of highly hydrophilic amphiphilic diblock copolymers Prog. Colloid Polym. Sci. 2011, 138, 7-16
61. Jin, Q.; Mitschang, F.; Agarwal, S. Biocompatible drug delivery system for photo-triggered controlled release of 5-fluorouracil Biomacromolecules 2011, 12, 3684-3691
62. Venditto, V. J.; Simanek, E. E. Cancer therapies utilizing the camptothecins: a review of the in vivo literature Mol. Pharmaceutics 2010, 7, 307-349
63. Fox, M. E.; Szoka, F. C.; Frechet, J. M. Soluble polymer carriers for the treatment of cancer: the importance of molecular architecture Acc. Chem. Res. 2009, 42, 1141-1151
64. Li, X.; Xu, Y.; Chen, G.; Wei, P.; Ping, Q. PLGA nanoparticles for the oral delivery of 5-fluorouracil using high pressure homogenization- emulsification as the preparation method and in vitro/in vivo studies Drug Dev. Ind. Pharm. 2008, 34, 107-115
65. Yassin, A. E.; Anwer, M. K.; Mowafy, H. A.; El-Bagory, I. M.; Bayomi, M. A.; Alsarra, I. A. Optimization of 5-flurouracil solid-lipid nanoparticles: a preliminary study to treat colon cancer Int. J. Med. Sci. 2010, 7, 398-408
66. TIglI AydIn, R. S.; Pulat, M. 5-Fluorouracil encapsulated chitosan nanoparticles for pH-stimulated drug delivery: evaluation of controlled release kinetics J. Nanomater. 2012, 2012, 1-10
67. O'Shea, E. K.; Klemm, J. D.; Kim, P. S.; Alber, T. X-ray structure of the GCN4 leucine zipper, a two-stranded, parallel coiled coil Science 1991, 254, 539-44
68. Paumet, F.; Rahimian, V.; Rothman, J. E. The specificity of SNARE-dependent fusion is encoded in the SNARE motif Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 3376-3380
69. Fasshauer, D.; Sutton, R. B.; Brunger, A. T.; Jahn, R. Conserved structural features of the synaptic fusion complex: SNARE proteins reclassified as Q- and R-SNAREs Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 15781-15786
70. Galmarini, C. M.; Mackey, J. R.; Dumontet, C. Nucleoside analogues: mechanisms of drug resistance and reversal strategies Leukemia 2001, 15, 875-90
71. Tao, Y.; Yang, Y.; Shi, D.; Chen, M.; Yang, C.; Liu, X. Micelles formation of polystyrene-co-poly (N-acryloylthymine) and its aggregation behavior induced by triple hydrogen bonding Polymer 2012, 53, 1551-1557