Synthesis and applications of biomedical and pharmaceutical polymers via click chemistry methodologies

Bioconjugate Chemistry

Volumn 20, Issue 11, 2009, Pages 2001-2016

  Van Dijk, Maarten ^a   Rijkers, Dirk T S ^a   Liskamp, Rob M J ^a   Van Nostrum, Cornelus F ^a   Hennink, Wim E ^a  

^a UTRECHT UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER COMPOUNDS; FUNCTIONAL POLYMERS;

BIOMEDICAL APPLICATIONS; BLOCK AND GRAFT COPOLYMERS; CLICK CHEMISTRY; CLICK REACTION; CYCLOADDITIONS; NEW APPROACHES; PHARMACEUTICAL APPLICATIONS; SELECTED EXAMPLES; SYNTHESISED; THIOL-ENE REACTIONS;

MEDICAL APPLICATIONS;

ALKYNE; AZIDE; BIOMATERIAL; COPOLYMER; COPPER; DENDRIMER; NANOPARTICLE; POLYMER; POLYPEPTIDE; THIOL;

AMINO ACID SEQUENCE; BIOMEDICAL ENGINEERING; CHEMICAL REACTION; CONJUGATION; CYCLOADDITION; DRUG DELIVERY SYSTEM; DRUG SYNTHESIS; HYDROGEL; NONVIRAL GENE DELIVERY SYSTEM; PARTICLE SIZE; POLYMERIZATION; REACTION ANALYSIS; REVIEW; ROOM TEMPERATURE;

EID: 71249129936     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc900087a     Document Type: Review

References (137)

1. Deming, T. J. (1997) Polypeptide materials: New synthetic methods and applications. Adv. Mater. 9, 299-311. (Pubitemid 127527620)
2. Kolb, H. C., Finn, M. G., and Sharpless, K. B. (2001) Click chemistry: diverse chemical function from a few good reactions. Angew. Chem., Int. Ed. 40, 2004-2021
3. Gacal, B., Durmaz, H., Tasdeln, M. A., Hizal, G., Tunca, U., Yagci, Y., and Demirel, A. L. (2006) Anthracene-maleimide-based Diels-Alder "click chemistry" as a novel route to graft copolymers. Macromolecules 39, 5330-5336
4. Posner, T. (1905) Beiträge zur Kenntniss der ungesättigten Verbindungen. II. Ueber die Addition von Mercaptanen an ungesättigte Kohlenwasserstoffe. Chem. Ber. 38, 646-657
5. Saxon, E., Armstrong, J. I., and Bertozzi, C. R. (2000) A "traceless" Staudinger ligation for the chemoselective synthesis of amide bonds. Org. Lett. 2, 2141-2143
6. Nilsson, B. L., Kiessling, L. L., and Raines, R. T. (2000) Staudinger ligation: A peptide from a thioester and azide. Org. Lett. 2, 1939-1941
7. Saxon, E., and Bertozzi, C. R. (2000) Cell surface engineering by a modified Staudinger reaction. Science 287, 2007-2010 (Pubitemid 30158675)
8. Dawson, P. E., Muir, T. W., Clark-Lewis, I., and Kent, S. B. H. (1994) Synthesis of proteins by native chemical ligation. Science 266, 776-779 (Pubitemid 24359280)
9. Ruttekolk, I. R., Duchardt, F., Fischer, R., Wiesmuller, K. H., Rademann, J., and Brock, R. (2008) HPMA as a scaffold for the modular assembly of functional peptide polymers by native chemical ligation. Bioconjugate Chem. 19, 2081-2087
10. Shangguan, N., Katukojvala, S., Greenburg, R., and Williams, L. J. (2003) The reaction of thio acids with azides: A new mechanism and new synthetic applications. J. Am. Chem. Soc. 125, 7754-7755 (Pubitemid 36789754)
11. Merkx, R., Brouwer, A. J., Rijkers, D. T. S., and Liskamp, R. M. J. (2005) Highly efficient coupling of beta-substituted aminoethane sulfonyl azides with thio acids, toward a new chemical ligation reaction. Org. Lett. 7, 1125-1128 (Pubitemid 40626917)
12. Kolakowski, R. V., Shangguan, N., Sauers, R. R., and Williams, L. J. (2006) Mechanism of thio acid/azide amidation. J. Am. Chem. Soc. 128, 5695-5702
13. Barlett, K. N., Kolakowski, R. V., Katukojvala, S., and Williams, L. J. (2006) Thio acid/azide amidation: An improved route to N-acyl sulfonamides. Org. Lett. 8, 823-826
14. Merkx, R., van Haren, M. J., Rijkers, D. T. S., and Liskamp, R. M. (2007) Resin-bound sulfonyl azides: efficient loading and activation strategy for the preparation of the N-acyl sulfonamide linker. J. Org. Chem. 72, 4574-4577 (Pubitemid 46903339)
15. Zhang, X., Li, F., Lu, X. W., and Liu, C. F. (2009) Protein C-terminal modification through thioacid/azide amidation. Bioconjugate Chem. 20, 197-200.
16. th American Peptide Symposium; Lebl, M., and Houghten, R. A. Eds.; American Peptide Society and Kluwer Academic Publishers: San Diego, 263-264
17. Tornøe, C. W., Christensen, C., and Meldal, M. (2002) Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides. J. Org. Chem. 67, 3057-3064 (Pubitemid 34457265)
18. Rostovtsev, V. V., Green, L. G., Fokin, V. V., and Sharpless, K. B. (2002) A stepwise Huisgen cycloaddition process: Copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes. Angew. Chem., Int. Ed. 41, 2596-2599
19. Binder, W. H., and Sachsenhofer, R. (2007) 'Click' chemistry in polymer and materials science. Macromol. Rapid Commun. 28, 15-54. (Pubitemid 46192085)
20. Binder, W. H., and Sachsenhofer, R. (2008) 'Click' chemistry in polymer and material science: An update. Macromol. Rapid Commun. 29, 952-981
21. Meldal, M. (2008) Polymer "Clicking" by CuAAC reactions. Macromol. Rapid Commun. 29, 1016-1051
22. Nandivada, H., Jiang, X. W., and Lahann, J. (2007) Click chemistry: Versatility and control in the hands of materials scientists. Adv. Mater. 19, 2197-2208 (Pubitemid 47409277)
23. Lutz, J. F. (2007) 1,3-dipolar cycloadditions of azides and alkynes: A universal ligation tool in polymer and materials science. Angew. Chem., Int. Ed. 46, 1018-1025
24. Johnson, J. A., Finn, M. G., Koberstein, J. T., and Turro, N. J. (2008) Construction of linear polymers, dendrimers, networks, and other polymeric architectures by copper-catalyzed azide-alkyne cycloaddition "Click" chemistry. Macromol. Rapid Commun. 29, 1052-1072
25. Angell, Y. L., and Burgess, K. (2007) Peptidomimetics via copper-catalyzed azide-alkyne cycloadditions. Chem. Soc. Rev. 36, 1674-1689
26. Pieters, R. J., Rijkers, D. T. S., and Liskamp, R. M. J. (2007) Application of the 1,3-dipolar cycloaddition reaction in chemical biology: Approaches toward multivalent carbohydrates and peptides and peptide-based polymers. QSAR Comb. Sci. 26, 1181-1190
27. Dirks, A. J., Cornelissen, J. J. L. M., van Delft, F. L., van Hest, J. C. M., Nolte, R. J. M., Rowan, A. E., and Rutjes, F. P. J. T. (2007) From (bio)molecules to biohybrid materials with the click chemistry approach. QSAR Comb. Sci. 26, 1200-1210
28. Le Droumaguet, B., and Velonia, K. (2008) Click chemistry: A powerful tool to create polymer-based macromolecular chimeras. Macromol. Rapid Commun. 29, 1073-1089
29. Lutz, J. F., and Zarafshani, Z. (2008) Efficient construction of therapeutics, bioconjugates, biomaterials and bioactive surfaces using azide-alkyne "click" chemistry. Adv. Drug Delivery Rev. 60, 958-970
30. Fournier, D., Hoogenboom, R., and Schubert, U. S. (2007) Clicking polymers: a straightforward approach to novel macromolecular architectures. Chem. Soc. Rev. 36, 1369-1380
31. Read, E. S., and Armes, S. P. (2007) Recent advances in shell cross-linked micelles. Chem. Commun. 3021-3035
32. Lecomte, P., Riva, R., Jerome, C., and Jerome, R. (2008) Macromolecular engineering of biodegradable polyesters by ring-opening polymerization and 'Click' chemistry. Macromol. Rapid Commun. 29, 982-997
33. Lutz, J. F. (2008) Copper-free azide-alkyne cycloadditions: New insights and perspectives. Angew. Chem., Int. Ed. 47, 2182-2184
34. Meldal, M., and Tornøe, C. W. (2008) Cu-catalyzed azide-alkyne cycloaddition. Chem. Rev. 108, 2952-3015.
35. Bock, V. D., Hiemstra, H., and van Maarseveen, J. H. (2005) Cu(I)-catalyzed alkyne-azide "click" cycloadditions from a mechanistic and synthetic perspective. Eur. J. Org. Chem. 51-68.
36. Moses, J. E., and Moorhouse, A. D. (2007) The growing applications of click chemistry. Chem. Soc. Rev. 36, 1249-1262
37. Moorhouse, A. D., and Moses, J. E. (2008) Click chemistry and medicinal chemistry: a case of "cyclo-addiction". ChemMedChem 3, 715-723
38. Huisgen, R. (1968) Cycloadditions - definition, classification, and characterization. Angew. Chem., Int. Ed. Engl. 7, 321-328
39. Huisgen, R., Szeimies, G., and Mobius, L. (1967) 1.3-Dipolare Cycloadditionen, XXXII. Kinetik der Additionen organischer Azide an CC-Mehrfachbindungen. Chem. Ber. 100, 2494-2507
40. Horne, W. S., Yadav, M. K., Stout, C. D., and Ghadiri, M. R. (2004) Heterocyclic peptide backbone modifications in an alpha-helical coiled coil. J. Am. Chem. Soc. 126, 15366-15367
41. Angelo, N. G., and Arora, P. S. (2005) Nonpeptidic foldamers from amino acids: Synthesis and characterization of 1,3-substituted triazole oligomers. J. Am. Chem. Soc. 127, 17134-17135
42. van Maarseveen, J. H., Horne, W. S., and Ghadiri, M. R. (2005) Efficient route to C2 symmetric heterocyclic backbone modified cyclic peptides. Org. Lett. 7, 4503-4506
43. Wittig, G., and Krebs, A. (1961) Zur Existenz niedergliedriger Cycloalkine, I. Chem. Ber. 94, 3260-3275
44. Agard, N. J., Prescher, J. A., and Bertozzi, C. R. (2004) A strain-promoted [3 + 2] azide-alkyne cycloaddition for covalent modification of biomolecules in living systems. J. Am. Chem. Soc. 126, 15046-15047
45. Ning, X. H., Guo, J., Wolfert, M. A., and Boons, G. J. (2008) Visualizing metabolically labeled glycoconjugates of living cells by copper-free and fast Huisgen cycloadditions. Angew. Chem., Int. Ed. 47, 2253-2255
46. Codelli, J. A., Baskin, J. M., Agard, N. J., and Bertozzi, C. R. (2008) Second-generation difluorinated cyclooctynes for copper-free click chemistry. J. Am. Chem. Soc. 130, 11486-11493
47. Sletten, E. M., and Bertozzi, C. R. (2008) A hydrophilic azacyclooctyne for Cu-free click chemistry. Org. Lett. 10, 3097-3099
48. Baskin, J. M., Prescher, J. A., Laughlin, S. T., Agard, N. J., Chang, P. V., Miller, I. A., Lo, A., Codelli, J. A., and Bertozzi, C. R. (2007) Copper-free click chemistry for dynamic in vivo imaging. Proc. Natl. Acad. Sci. U.S.A. 104, 16793-16797 (Pubitemid 350210944)
49. van Berkel, S. S., Dirks, A. T., Debets, M. F., van Delft, F. L., Cornelissen, J. J. L. M., Nolte, R. J. M., and Rutjes, F. P. J. T. (2007) Metal-free triazole formation as a tool for bioconjugation. ChemBioChem 8, 1504-1508
50. Mocharla, V. P., Colasson, B., Lee, L. V., Roper, S., Sharpless, K. B., Wong, C. H., and Kolb, H. C. (2004) In situ click chemistry: enzyme-generated inhibitors of carbonic anhydrase II. Angew. Chem., Int. Ed. 44, 116-120
51. Zhang, L., Chen, X. G., Xue, P., Sun, H. H. Y., Williams, I. D., Sharpless, K. B., Fokin, V. V., and Jia, G. C. (2005) Ruthenium-catalyzed cycloaddition of alkynes and organic azides. J. Am. Chem. Soc. 127, 15998-15999 (Pubitemid 41689208)
52. Majireck, M. M., and Weinreb, S. M. (2006) A study of the scope and regioselectivity of the ruthenium-catalyzed [3 + 2]-cycloaddition of azides with internal alkynes. J. Org. Chem. 71, 8680-8683
53. Rasmussen, L. K., Boren, B. C., and Fokin, V. V. (2007) Ruthenium-catalyzed cycloaddition of aryl azides and alkynes. Org. Lett. 9, 5337-5339
54. Boren, B. C., Narayan, S., Rasmussen, L. K., Zhang, L., Zhao, H. T., Lin, Z. Y., Jia, G. C., and Fokin, V. V. (2008) Ruthenium-catalyzed azide-alkyne cycloaddition: Scope and mechanism. J. Am. Chem. Soc. 130, 8923-30 (correction: J. Am. Chem. Soc., 14900).
55. Jemal, M., and Hawthorne, D. J. (1997) Quantitative determination of BMS186716, a thiol compound, in dog plasma by high-performance liquid chromatography-positive ion electrospray mass spectrometry after formation of the methyl acrylate adduct. J. Chromatogr., B: Biomed. Sci. Appl. 693, 109-116 (Pubitemid 27229622)
56. Romanowska, A., Meunier, S. J., Tropper, F. D., Laferriere, C. A., and Roy, R. (1994) Michael additions for syntheses of neoglycoproteins. Methods Enzymol. 242, 90-101.
57. Masri, M. S., and Friedman, M. (1988) Protein reactions with methyl and ethyl vinyl sulfones. J. Protein Chem. 7, 49-54.
58. Morpurgo, M., Veronese, F. M., Kachensky, D., and Harris, J. M. (1996) Preparation of characterization of poly(ethylene glycol) vinyl sulfone. Bioconjugate Chem. 7, 363-368 (Pubitemid 126639671)
59. Pounder, R. J., Stanford, M. J., Brooks, P., Richards, S. P., and Dove, A. P. (2008) Metal free thiol-maleimide 'Click' reaction as a mild functionalisation strategy for degradable polymers. Chem. Commun. 5158-5160
60. Gress, A., Volkel, A., and Schlaad, H. (2007) Thio-click modification of poly[2-(3-butenyl)-2-oxazoline]. Macromolecules 40, 7928-7933
61. Dondoni, A. (2008) The emergence of thiol-ene coupling as a click process for materials and bioorganic chemistry. Angew. Chem., Int. Ed. 47, 8995-8997
62. Geng, Y., Discher, D. E., Justynska, J., and Schlaad, H. (2006) Grafting short peptides onto polybutadiene-block-poly(ethylene oxide): A platform for self-assembling hybrid amphiphiles. Angew. Chem., Int. Ed. 45, 7578-7581 (Pubitemid 44851687)
63. Hordyjewicz-Baran, Z., You, L. C., Smarsly, B., Sigel, R., and Schlaad, H. (2007) Bioinspired polymer vesicles based on hydrophilically modified polybutadienes. Macromolecules 40, 3901-3903 (Pubitemid 46953830)
64. Justynska, J., Hordyjewicz, Z., and Schlaad, H. (2005) Toward a toolbox of functional block copolymers via free-radical addition of mercaptans. Polymer 46, 12057-12064 (Pubitemid 41815250)
65. Woghiren, C., Sharma, B., and Stein, S. (1993) Protected thiol-polyethylene glycol: a new activated polymer for reversible protein modification. Bioconjugate Chem. 4, 314-318
66. Goessl, A., Tirelli, N., and Hubbell, J. A. (2004) A hydrogel system for stimulus-responsive, oxygen-sensitive in situ gelation. J. Biomater. Sci. Polym. Ed. 15, 895-904. (Pubitemid 39076867)
67. Hoyle, C. E., Lee, T. Y., and Roper, T. (2004) Thiol-enes: Chemistry of the past with promise for the future. J. Polym. Sci., Part A: Polym. Chem. 42, 5301-5338
68. Morgan, C. R., Magnotta, F., and Ketley, A. D. (1977) Thiol/ene photocurable polymers. J. Polym. Sci., Polym. Chem. Ed. 15, 627-645
69. van Hest, J. C. M., and Tirrell, D. A. (2001) Protein-based materials, toward a new level of structural control. Chem. Commun. 1897-1904
70. Kricheldorf, H. R. (1987) Alpha-Aminoacid-N-Carboxyanhydrides and Related Heterocycles, Springer, Berlin.
71. Chiu, H. C., Kopeckova, P., Deshmane, S. S., and Kopecek, J. (1997) Lysosomal degradability of poly(alpha-amino acids). J. Biomed. Mater. Res. 34, 381-392
72. Metzke, M., O'Connor, N., Maiti, S., Nelson, E., and Guan, Z. B. (2005) Saccharide-peptide hybrid copolymers as biomaterials. Angew. Chem., Int. Ed. 44, 6529-6533
73. Haider, M., Megeed, Z., and Ghandehari, H. (2004) Genetically engineered polymers: status and prospects for controlled release. J. Controlled Release 95, 1-26. (Pubitemid 38173016)
74. Kent, S. B. H. (2009) Total chemical synthesis of proteins. Chem. Soc. Rev. 38, 338-351
75. Zhang, Z. S., and Fan, E. (2006) Solid phase synthesis of peptidotriazoles with multiple cycles of triazole formation. Tetrahedron Lett. 47, 665-669 (Pubitemid 43014789)
76. Aucagne, V., and Leigh, D. A. (2006) Chemoselective formation of successive triazole linkages in one pot: " Click-click" chemistry. Org. Lett. 8, 4505-4507
77. Orsini, A., Viterisi, A., Bodlenner, A., Weibel, J.-M., and Pale, P. (2005) A chemoselective deprotection of trimethylsilyl acetylenes catalyzed by silver salts. Tetrahedron Lett. 46, 2259-2262 (Pubitemid 40332225)
78. Carpita, A., Mannocci, L., and, and Rossi, R. (2005) Silver(I)-catalysed protiodesilylation of 1-(trimethylsilyl)-1-alkynes. Eur. J. Org. Chem. 1859-1864
79. van Dijk, M., Mustafa, K., Dechesne, A. C., van Nostrum, C. F., Hennink, W. E., Rijkers, D. T. S., and Liskamp, R. M. J. (2007) Synthesis of peptide-based polymers by microwave-assisted cycloaddition backbone polymerization. Biomacromolecules 8, 327-330 (Pubitemid 46323243)
80. van Dijk, M., Nollet, M. L., Weijers, P., Dechesne, A. C., van Nostrum, C. F., Hennink, W. E., Rijkers, D. T. S., and Liskamp, R. M. J. (2008) Synthesis and characterization of biodegradable peptide-based polymers prepared by microwave-assisted click chemistry. Biomacromolecules 9, 2834-2843
81. Yu, T.-B., Bai, J. Z., and Guan, Z. (2009) Cycloaddition-promoted self-assembly of a polymer into well-defined β sheets and hierarchical nanofibrils. Angew. Chem., Int. Ed. 48, 1097-1101
82. Agut, W., Agnaou, R., Lecommandoux, S., and Taton, D. (2008) Synthesis of block copolypeptides by click chemistry. Macromol. Rapid Commun. 29, 1147-1155
83. Parrish, B., Breitenkamp, R. B., and Emrick, T. (2005) PEG- and peptide-grafted aliphatic polyesters by click chemistry. J. Am. Chem. Soc. 127, 7404-7410 (Pubitemid 40746025)
84. Tirrell, D. A. (2004) Chemical biology - Hitting the sweet spot. Nature 430, 837.
85. Dwek, R. A. (1996) Glycobiology: Toward understanding the function of sugars. Chem. Rev. 96, 683-720.
86. Kiessling, L. L., and Cairo, C. W. (2002) Hitting the sweet spot. Nat. Biotechnol. 20, 234-235
87. Ambrosi, M., Cameron, N. R., and Davis, B. G. (2005) Lectins: tools for the molecular understanding of the glycocode. Org. Biomol. Chem. 3, 1593-1608
88. Lundquist, J. J., and Toone, E. J. (2002) The cluster glycoside effect. Chem. Rev. 102, 555-578
89. Srinivasachari, S., Liu, Y. M., Zhang, G. D., Prevette, L., and Reineke, T. M. (2006) Trehalose click polymers inhibit nanoparticle aggregation and promote pDNA delivery in serum. J. Am. Chem. Soc. 128, 8176-8184 (Pubitemid 43967762)
90. Srinivasachari, S., Liu, Y. M., Prevette, L. E., and Reineke, T. M. (2007) Effects of trehalose click polymer length on pDNA complex stability and delivery efficacy. Biomaterials 28, 2885-2898 (Pubitemid 46482656)
91. Ladmiral, V., Mantovani, G., Clarkson, G. J., Cauet, S., Irwin, J. L., and Haddleton, D. M. (2006) Synthesis of neoglycopolymers by a combination of "click chemistry" and living radical polymerization. J. Am. Chem. Soc. 128, 4823-4830
92. Geng, J., Mantovani, G., Tao, L., Nicolas, J., Chen, G., Wallis, R., Mitchell, D. A., Johnson, B. R., Evans, S. D., and Haddleton, D. M. (2007) Site-directed conjugation of "clicked" glycopolymers to form glycoprotein mimics: binding to mammalian lectin and induction of immunological function. J. Am. Chem. Soc. 129, 15156-15163 (Pubitemid 350247799)
93. Chen, G. J., Amajjahe, S., and Stenzel, M. H. (2009) Synthesis of thiol-linked neoglycopolymers and thermo-responsive glycomicelles as potential drug carrier. Chem. Commun. 1198-1200
94. Diehl, C., and Schlaad, H. (2009) Thermo-responsive polyoxazolines with widely tuneable LCST. Macromol. Biosci. 9, 157-161
95. Nurmi, L., Lindqvist, J., Randev, R., Syrett, J., and Haddleton, D. M. (2009) Glycopolymers via ctalytic chain transfer polymerisation (CCTP), huisgens cycloaddition and thiol-ene double click reactions. Chem. Commun. 2727-2729
96. El-Aneed, A. (2004) Current strategies in cancer gene therapy. Eur. J. Pharmacol. 498, 1-8. (Pubitemid 39213940)
97. Zhou, H. S., Liu, D. P., and Liang, C. C. (2004) Challenges and strategies: the immune responses in gene therapy. Med. Res. Rev. 24, 748-761 (Pubitemid 39362482)
98. Mintzer, M. A., and Simanek, E. E. (2009) Nonviral vectors for gene delivery. Chem. Rev. 109, 259-302.
99. White, S., Szewczyk, J. W., Turner, J. M., Baird, E. E., and Dervan, P. B. (1998) Recognition of the four Watson-Crick base pairs in the DNA minor groove by synthetic ligands. Nature 391, 468-471 (Pubitemid 28086542)
100. Petersen, H., Merdan, T., Kunath, K., Fischer, D., and Kissel, T. (2002) Poly(ethylenimine-co-L-lactamide-co-succinamide): a biodegradable polyethylenimine derivative with an advantageous pH-dependent hydrolytic degradation for gene delivery. Bioconjugate Chem. 13, 812-821 (Pubitemid 34801124)
101. Luten, J., van Nostrum, C. F., De Smedt, S. C., and Hennink, W. E. (2008) Biodegradable polymers as non-viral carriers for plasmid DNA delivery. J. Controlled Release 126, 97-110.
102. Jiang, X., Lok, M. C., and Hennink, W. E. (2007) Degradable-brushed pHEMA-pDMAEMA synthesized via ATRP and click chemistry for gene delivery. Bioconjugate Chem. 18, 2077-2084 (Pubitemid 350220011)
103. Varki, A. (1993) Biological roles of oligosaccharides: all of the theories are correct. Glycobiology 3, 97-130.
104. Kramer, R. H., and Karpen, J. W. (1998) Spanning binding sites on allosteric proteins with polymer-linked ligand dimers. Nature 395, 710-713
105. Mammen, M., Choi, S.-K., and Whitesides, G. M. (1998) Polyvalent interactions in biological systems: implications for design and use of multivalent ligands and inhibitors. Angew. Chem., Int. Ed. 37, 2754-2794 (Pubitemid 29008561)
106. Joosten, J. A. F., Tholen, N. T. H., El Maate, F. A., Brouwer, A. J., van Esse, G. W., Rijkers, D. T. S., Liskamp, R. M. J., and Pieters, R. J. (2005) High-yielding microwave-assisted synthesis of triazole-linked glycodendrimers by copper-catalyzed [3 + 2] cycloaddition. Eur. J. Org. Chem. 3182-3185
107. Rijkers, D. T. S., van Esse, G. W., Merkx, R., Brouwer, A. J., Jacobs, H. J. J., Pieters, R. J., and Liskamp, R. M. J. (2005) Efficient microwave-assisted synthesis of multivalent dendrimeric peptides using cycloaddition reaction (click) chemistry. Chem. Commun. 4581-4583 (Pubitemid 41428453)
108. Dijkgraaf, I., Rijnders, A. Y., Soede, A., Dechesne, A. C., van Esse, G. W., Brouwer, A. J., Corstens, F. H., Boerman, O. C., Rijkers, D. T. S., and Liskamp, R. M. J. (2007) Synthesis of DOTA-conjugated multivalent cyclic-RGD peptide dendrimers via 1,3-dipolar cycloaddition and their biological evaluation: implications for tumor targeting and tumor imaging purposes. Org. Biomol. Chem. 5, 935-944 (Pubitemid 46375649)
109. Killops, K. L., Campos, L. M., and Hawker, C. J. (2008) Robust, efficient, and orthogonal synthesis of dendrimers via thiol-ene "click" chemistry. J. Am. Chem. Soc. 130, 5062-5064
110. Jonkheijm, P., Weinrich, D., Kohn, M., Engelkamp, H., Christianen, P. C., Kuhlmann, J., Maan, J. C., Nusse, D., Schroeder, H., Wacker, R., Breinbauer, R., Niemeyer, C. M., and Waldmann, H. (2008) Photochemical surface patterning by the thiol-ene reaction. Angew. Chem., Int. Ed. 47, 4421-4424
111. Xia, Y. N. (2008) Nanomaterials at work in biomedical research. Nat. Mater. 7, 758-760
112. Schiffelers, R. M., Ansari, A., Xu, J., Zhou, Q., Tang, Q., Storm, G., Molema, G., Lu, P. Y., Scaria, P. V., and Woodle, M. C. (2004) Cancer siRNA therapy by tumor selective delivery with ligand-targeted sterically stabilized nanoparticle. Nucleic Acids Res. 32, e149.
113. Panyam, J., and Labhasetwar, V. (2003) Biodegradable nanoparticles for drug and gene delivery to cells and tissue. Adv. Drug Delivery Rev. 55, 329-347 (Pubitemid 36297053)
114. Opsteen, J. A., Brinkhuis, R. P., Teeuwen, R. L. M., Löwik, D. W. P. M., and van Hest, J. C. M. (2007) "Clickable" polymersomes. Chem. Commun. 3136-3138
115. Such, G. K., Quinn, J. F., Quinn, A., Tjipto, E., and Caruso, F. (2006) Assembly of ultrathin polymer multilayer films by click chemistry. J. Am. Chem. Soc. 128, 9318-9319 (Pubitemid 44117076)
116. Such, G. K., Tjipto, E., Postma, A., Johnston, A. P., and Caruso, F. (2007) Ultrathin, responsive polymer click capsules. Nano Lett. 7, 1706-1710 (Pubitemid 47140449)
117. De Geest, B. G., Van Camp, W., Du Prez, F. E., De Smedt, S. C., Demeester, J., and Hennink, W. E. (2008) Degradable multilayer films and hollow capsules via a 'click' strategy. Macromol. Rapid Commun. 29, 1111-1118
118. De Geest, B. G., Van Camp, W., Du Prez, F. E., De Smedt, S. C., Demeester, J., and Hennink, W. E. (2008) Biodegradable microcapsules designed via 'click' chemistry. Chem. Commun. 190-192
119. Connal, L. A., Kinnane, C. R., Zelikin, A. N., and Caruso, F. (2009) Stabilization and functionalization of polymer multilayers and capsules via thiol-ene click chemistry. Chem. Mater. 21, 576-578
120. Sousa-Herves, A., Fernandez-Megia, E., and Riguera, R. (2008) Synthesis and supramolecular assembly of clicked anionic dendritic polymers into polyion complex micelles. Chem. Commun. 3136-3138 (Pubitemid 351915389)
121. Breed, D. R., Thibault, R., Xie, F., Wang, Q., Hawker, C. J., and Pine, D. J. (2009) Functionalization of polymer microspheres using click chemistry. Langmuir 25, 4370-4376
122. Peppas, N. A., Bures, P., Leobandung, W., and Ichikawa, H. (2000) Hydrogels in pharmaceutical formulations. Eur. J. Pharm. Biopharm. 50, 27-46.
123. Ossipov, D. A., and Hilborn, J. (2006) Poly(vinyl alcohol)-based hydrogels formed by "click chemistry". Macromolecules 39, 1709-1718
124. Malkoch, M., Vestberg, R., Gupta, N., Mespouille, L., Dubois, P., Mason, A. F., Hedrick, J. L., Liao, Q., Frank, C. W., Kingsbury, K., and Hawker, C. J. (2006) Synthesis of well-defined hydrogel networks using Click chemistry. Chem. Commun. 2774-2776 (Pubitemid 43962813)
125. Crescenzi, V., Cornelio, L., Di Meo, C., Nardecchia, S., and Lamanna, R. (2007) Novel hydrogels via click chemistry: Synthesis and potential biomedical applications. Biomacromolecules 8, 1844-1850 (Pubitemid 47009962)
126. Polizzotti, B. D., Fairbanks, B. D., and Anseth, K. S. (2008) Three-dimensional biochemical patterning of click-based composite hydrogels via thiolene photopolymerization. Biomacromolecules 9, 1084-1087
127. Mespouille, L., Coulembier, O., Paneva, D., Degée, E., Rashkov, I., and Dubois, P. (2008) Synthesis of adaptative and amphiphilic polymer model conetworks by versatile combination of ATRP, ROP and "click chemistry". J. Polym. Sci., Part A: Polym. Chem. 46, 4997-5013.
128. Johnson, J. A., Finn, M. G., Koberstein, J. T., and Turro, N. J. (2007) Synthesis of photocleavable linear macromonomers by ATRP and star macromonomers by a tandem ATRP-click reaction: precursors to photodegradable model networks. Macromolecules 40, 3589-3598
129. Johnson, J. A., Baskin, J. M., Bertozzi, C. R., Koberstein, J. T., and Turro, N. J. (2008) Copper-free click chemistry for the in situ crosslinking of photodegradable star polymers. Chem. Commun. 3064-3066
130. Xu, X., Chen, C., Wang, Z., Wang, G., Cheng, S., Zhang, X., and Zhou, R. (2008) "Click" chemistry for in situ formation of thermoresponsive p(NIPAAm-co-HEMA)-based hydrogels. J. Polym. Sci., Part A: Polym. Chem. 46, 5263-77.
131. Lui, S. Q., Ee, P. L. R., Ke, C. Y., Hendrick, J. L., and Yang, Y. Y. (2009) Biodegradable poly(ethylene glycol)-peptide hydrogels with well-defined structure and properties for cell delivery. Biomaterials 30, 1453-1461
132. Qiu, B., Stefanos, S., Ma, J., Lalloo, A., Perry, B. A., Leibowitz, M. J., Sinko, P. J., and Stein, S. (2003) A hydrogel prepared by in situ cross-linking of a thiol-containing poly(ethylene glycol)-based copolymer: a new biomaterial for protein drug delivery. Biomaterials 24, 11-18 (Pubitemid 35300198)
133. Metters, A., and Hubbell, J. (2005) Network formation and degradation behavior of hydrogels formed by Michael-type addition reactions. Biomacromolecules 6, 290-301. (Pubitemid 40277026)
134. Schoenmakers, R. G., van de Wetering, P., Elbert, D. L., and Hubbell, J. A. (2004) The effect of the linker on the hydrolysis rate of drug-linked ester bonds. J. Controlled Release 95, 291-300.
135. Hiemstra, C., Zhong, Z., Van Tomme, S. R., van Steenbergen, M. J., Jacobs, J. J. L., Den Otter, W., Hennink, W. E., and Feijen, J. (2007) In vitro and in vivo protein delivery from in situ forming poly(ethylene glycol)-poly(lactide) hydrogels. J. Controlled Release 119, 320-327 (Pubitemid 46770885)
136. Hiemstra, C., van der Aa, L. J., Zhong, Z. Y., Dijkstra, P. J., and Feijen, J. (2007) Novel in situ forming, degradable dextran hydrogels by Michael addition chemistry: Synthesis, rheology, and degradation. Macromolecules 40, 1165-1173 (Pubitemid 46383771)
137. Tae, G., Kim, Y. J., Choi, W. I., Kim, M., Stayton, P. S., and Hoffman, A. S. (2007) Formation of a novel heparin-based hydrogel in the presence of heparin-binding biomolecules. Biomacromolecules 8, 1979-1986 (Pubitemid 47009979)