Click chemistry, a powerful tool for pharmaceutical sciences

Pharmaceutical Research

Volumn 25, Issue 10, 2008, Pages 2216-2230

  Hein, Christopher D ^a   Liu, Xin Ming ^a   Wang, Dong ^a,b  

^a UNIVERSITY OF NEBRASKA MEDICAL CENTER   (United States)

^b UNIVERSITY OF NEBRASKA MEDICAL CENTER   (United States)

Author keywords

Bioconjugation; Click chemistry; Drug delivery; Nanomedicine; Polymer

Indexed keywords

ALKYNE; AZIDE; CUPROUS ION; NANOPARTICLE; POLYMER;

CHEMICAL REACTION; CHEMISTRY; CLICK CHEMISTRY; CYCLOADDITION; DRUG CONJUGATION; NANOPHARMACEUTICS; POLYMER PRODUCTION; PRIORITY JOURNAL; REVIEW;

ALKYNES; AZIDES; CATALYSIS; CHEMISTRY, PHARMACEUTICAL; COPPER; CYCLIZATION; DRUG CARRIERS; LIPOSOMES; METAL NANOPARTICLES; MICELLES; MODELS, CHEMICAL; MOLECULAR PROBES; POLYMERS; TECHNOLOGY, PHARMACEUTICAL;

EID: 51649102031     PISSN: 07248741     EISSN: 1573904X     Source Type: Journal    
DOI: 10.1007/s11095-008-9616-1     Document Type: Review

References (139)

1. H. C. Kolb M. G. Finn K. B. Sharpless 2001 Click chemistry: diverse chemical function from a few good reactions Angew. Chem. Int. Ed. Engl 40 2004 2021
2. H. C. Kolb K. B. Sharpless 2003 The growing impact of click chemistry on drug discovery Drug Discov. Today 8 1128 1137
3. I- Catalyzed alkyne-azide "click" cycloadditions from a mechanistic and synthetic perspective. Eur. J. Org. Chem. 2006:51-68 (2006).
4. R. Huisgen 1963 1,3-Dipolar cycloadditions Angew. Chem 75 604 637
5. I-catalyzed azide-alkyne cycloaddition reaction Angew. Chem., Int. Ed. Engl 44 2210 2215
6. V. V. Rostovtsev L. G. Green V. V. Fokin K. B. Sharpless 2002 A stepwise huisgen cycloaddition process: copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes Angew. Chem., Int. Ed. Engl 41 2596 2599
7. F. Himo T. Lovell R. Hilgraf V. V. Rostovtsev L. Noodleman K. B. Sharpless V. V. Fokin 2005 Copper(I)-catalyzed synthesis of azoles. DFT study predicts unprecedented reactivity intermediates J. Am. Chem. Soc 127 210 216
8. S. Brase C. Gil K. Knepper V. Zimmermann 2005 Organic azides: an exploding diversity of a unique class of compounds Angew. Chem., Int. Ed., Engl 44 5518 5240
9. W. H. Zhan H. N. Barnhill K. Sivakumar H. Tian Q. Wang 2005 Synthesis of hemicyanine dyes for 'click' bioconjugation Tetrahedron Lett 46 1691 1695
10. B. M. Mykhalichko O. N. Temkin M. G. Mys'kiv 2000 Polynuclear complexes of copper(I) halides: coordination chemistry and catalytic transformations of alkynes Russ. Chem. Rev 69 957 984
11. R. Chinchilla C. Najera 2007 The sonogashira reaction: a booming methodology in synthetic organic chemistry Chem. Rev 107 874 922
12. W. S. Horne C. D. Stout M. R. Ghadiri 2003 A heterocyclic polymer nanotube J. Am. Chem. Soc 125 9372 9376
13. P. L. Golas N. V. Tsarevsky B. S. Sumerlin K. Matyjaszewski 2006 Catalyst performance in "click" coupling reactions of polymers prepared by ARTP: ligand and metal effects Macromolecules 39 6451 6457
14. H. A. Orgueria D. Fokas Y. Isome P. C.-M. Chane C. M. Baldino 2005 Regioselective synthesis of [1,2,3]-triazoles catalyzes by Cu(I) generated in situ from Cu(0) nanosize activated powder and amine hydrochloride salts Tetrahedron Lett 46 2911 2914
15. I-zeolites: the huisgen [3 + 2]-cycloaddition Org. Lett 9 883 886
16. K. Klier 1988 Transition-metal ions in zeolites: the perfect surface sites Langmuir 4 13 25
17. B. K. Marcus W. E. Cormier 1999 Going green with zeolites Chem. Eng. Prog 95 47 53
18. Wittingham, S. Synthesis and characterization of the zeolite ZSM-5: a size and shape selective catalyst for xylene isomerization. http://imr.chem. binghamton.edu/labs/zeolite/zeolite.html, part of Binghamton University's Institute for Materials Research website. http://imr.chem.binghamton.edu. Accessed August 9, 2007.
19. M. A. Bennett 1962 Olefin and acetylene complexes of transition metals Chem. Rev 62 611 652
20. F. R. Hartley 1973 Thermodynamic data for olefin and acetylene complexes of transition metals Chem. Rev 73 163 190
21. L. L. Zhang X. Chen P. Xue H. H. Y. Sun I. D. Williams K. B. Sharpless V. V. Fokin G. Jia 2005 Ruthenium-catalyzed cycloaddition of alkynes and organic azides J. Am. Chem. Soc 127 15998 15999
22. G. C. Tron T. Pirali R. A. Billington P. L. Canonico G. Sorba A. A. Genazzani 2007 Click chemistry reactions in medicinal chemistry: applications of the 1,3-dipolar cycloaddition between azides and alkynes Med. Res. Rev 28 278 308
23. Z. Li T. S. Seo J. Ju 2004 1,3-Dipolar cycloaddition of azides with electron-deficient alkynes under mild condition in water Tetrahedron Lett 45 3143 3146
24. N. J. Agard J. A. Prescher C. B. Bertozzi 2004 A strain-promoted [3+2] azide-alkyne cycloaddition for covalent modification of biomolecules in living systems J. Am. Chem. Soc 126 15046 15047
25. G. Wittig A. Krebs 1961 On the existence of low-membered cycloalkynes. I Chem. Ber 94 3260 3275
26. J. M. Baskin J. A. Prescher S. T. Laughlin N. J. Agard P. V. Chang I. A. Miller A. Lo J. A. Codelli C. R. Bertozzi 2007 Copper-free click chemistry for dynamic in vivo imaging Proc. Natl. Acad. Sci. U.S.A 104 16793 16797
27. L. Weber 2004 In vitro combinatorial chemistry to create drug candidates Drug Discov. Today: Tech 1 261 267
28. K. B. Sharpless R. Manetsch 2006 In situ click chemistry: a powerful means for lead discovery Exp. Opin. Drug Discov 1 525 538
29. S. Roper H. C. Kolb 2006 Click chemistry for drug discovery Meth. Princpl. Med. Chem 34 313 339
30. R. Duncan 2003 The dawning era of polymer therapeutics Nat. Rev. Drug Discov 2 347 360
31. Y. Matsumura H. Maeda 1986 A new concept for macromolecular therapeutics in cancer chemotherapy: mechanism of tumoritropic accumulation of proteins and the antitumor agent smancs Cancer Res 46 6387 6392
32. D. Wang S. C. Miller X. M. Liu B. Anderson X. S. Wang S. R. Goldring 2007 Novel dexamethasone-HPMA copolymer conjugate and its potential application in treatment of rheumatoid arthritis Arthritis Res. Ther 9 R2
33. J. Kopeček P. Kopečková T. Minko Z. R. Lu C. M. Peterson 2001 Water soluble polymers in tumor targeted delivery J. Controlled Release 74 147 158
34. T. G. Park J. H. Jeong S. W. Kim 2006 Current status of polymeric gene delivery systems Adv. Drug Delivery Rev 58 467 486
35. M. J. Roberts M. D. Bentley J. M. Harris 2002 Chemistry for peptide and protein PEGylation Adv. Drug Delivery Rev 54 459 476
36. F. M. Veronese J. M. Harris 2008 Peptide and protein PEGylation III: advances in chemistry and clinical applications Adv. Drug Delivery Rev 60 1 2
37. Y. Kakizawa K. Kataoka 2002 Block copolymer micelles for delivery of gene and related compounds Adv. Drug Delivery Rev 54 203 222
38. R. K. O'Reilly C. J. Hawker K. L. Wooley 2006 Cross-linked block copolymer micelles: functional nanostructures of great potential and versatility Chem. Soc. Rev 35 1068 1083
39. K. Letchford H. Burt 2007 A review of the formation and classification of amphiphilic block copolymer nanoparticulate structures: micelles, nanospheres, nanocapsules and polymersomes Eur. J. Pharm. Biopharm 65 259 269
40. O. W. Webster 1991 Living polymerization methods Science (Wash. D.C.) 251 887 893
41. E. Franta P. F. Rempp 1996 The block copolymer bag of tricks Chemtech 26 24 28
42. W. Van Camp V. Germonpre L. Mespouille P. Dubois E. J. Goethals F. E. Du Prez 2007 New poly(acrylic acid) containing segmented copolymer structures by combination of "click" chemistry and atom transfer radical polymerization React. Functl. Polym 67 1168 1180
43. J. A. Opsteen J. C. M. Van Hest 2007 Modular synthesis of ABC type block copolymers by "click" chemistry J. Polym. Sci., Part A: Polym. Chem 45 2913 2924
44. D. Quemener T. P. Davis C. Barner-Kowollik M. H. Stenzel 2006 RAFT and click chemistry: a versatile approach to well-defined block copolymers Chem. Commun 48 5051 5053
45. S. R. S. Ting A. M. Granville D. Quemener T. P. Davis M. H. Stenzel C. Barner-Kowollik 2007 RAFT chemistry and Huisgen 1,3-dipolar cycloaddition: a route to block copolymers of vinyl acetate and 6-O-methacryloyl mannose Aust. J. Chem 60 405 409
46. W. Agut D. Taton S. Lecommandoux 2007 A versatile synthetic approach to polypeptide based rod-coil block copolymers by click chemistry Macromolecules 40 5653 5661
47. G. Deng D. Ma Z. Xu 2007 Synthesis of ABC-type miktoarm star polymers by "click" chemistry, ATRP and ROP Eur. Polym. J 43 1179 1187
48. O. Altintas G. Hizal U. Tunca 2006 ABC-type hetero-arm star terpolymers through "Click" chemistry J. Polym. Sci., Part A: Polym. Chem 44 5699 5707
49. S. Fleischmann H. Komber D. Appelhans B. I. Voit 2007 Synthesis of functionalized NMP initiators for click chemistry: a versatile method for the preparation of functionalized polymers and block copolymers Macromol. Chem. Phys 208 1050 1060
50. K. Kataoka A. Harada Y. Nagasaki 2001 Block copolymer micelles for drug delivery: design, characterization and biological significance Adv. Drug Delivery. Rev 47 113 131
51. A. Mitra A. Nan B. R. Line H. Ghandehari 2006 Nanocarriers for nuclear imaging and radiotherapy of cancer Curr. Pharm. Des 12 4729 4749
52. V. P. Torchilin 2007 Micellar nanocarriers: pharmaceutical perspectives Pharm. Res 24 1 16
53. F. Henselwood G. Liu 1997 Water-soluble nanospheres of poly(2-cinnamoylethyl methacrylate)-block-poly(acrylic acid) Macromolecules 30 488 493
54. B. Loppinet R. Sigel A. Larsen G. Fytas D. Vlassopoulos G. Liu 2000 Structure and dynamics in dense suspensions of micellar nanocolloids Langmuir 16 6480 6484
55. R. K. O'Reilly M. J. Joralemon C. J. Hawker K. L. Wooley 2007 Preparation of orthogonally-functionalized core click cross-linked nanoparticles New J. Chem 31 718 724
56. R. K. O'Reilly M. J. Joralemon K. L. Wooley C. J. Hawker 2005 Functionalization of micelles and shell cross-linked nanoparticles using click chemistry Chem. Mater 17 5976 5988
57. F. Kratz K. Abu Ajaj A. Warnecke 2007 Anticancer carrier-linked prodrugs in clinical trials Expert. Opin. Investig. Drugs 16 1037 1058
58. R. Duncan 2007 Designing polymer conjugates as lysosomotropic nanomedicines Biochem. Soc. Trans 35 56 60
59. K. S. Albain C. P. Belani P. Bonomi K. J. O'Byrne J. H. Schiller M. Socinski 2006 PIONEER: a phase III randomized trial of paclitaxel poliglumex versus paclitaxel in chemotherapy-naive women with advanced-stage non-small-cell lung cancer and performance status of 2 Clin. Lung. Cancer 7 417 419
60. S. A. Shaffer C. Baker-Lee J. Kennedy M. S. Lai P. de Vries K. Buhler J. W. Singer 2007 In vitro and in vivo metabolism of paclitaxel poliglumex: identification of metabolites and active proteases Cancer Chemother. Pharmacol 59 537 548
61. M. J. Roberts M. D. Bentley J. M. Harris 2002 Chemistry for peptide and protein PEGylation Adv. Drug Deliv. Rev 54 459 476
62. R. B. Greenwald Y. H. Choe J. McGuire C. D. Conover 2003 Effective drug delivery by PEGylated drug conjugates Adv. Drug Deliv. Rev 55 217 250
63. A. Nathan S. Zalipsky S. I. Ertel S. N. Agathos M. L. Yarmush J. Kohn 1993 Copolymers of lysine and polyethylene glycol: a new family of functionalized drug carriers Bioconjug. Chem 4 54 62
64. M. Pechar K. Ulbrich V. Subr L. W. Seymour E. H. Schacht 2000 Poly(ethylene glycol) multiblock copolymer as a carrier of anti-cancer drug doxorubicin Bioconjug. Chem 11 131 139
65. J. Cheng K. T. Khin G. S. Jensen A. Liu M. E. Davis 2003 Synthesis of linear, beta-cyclodextrin-based polymers and their camptothecin conjugates Bioconjug. Chem 14 1007 1017
66. Wang A. Dong H. Tang E. A. Van Kirk P. A. Johnson W. J. Murdoch M. Radosz Y. Shen 2007 Synthesis of degradable functional poly(ethylene glycol) analogs as versatile drug delivery carriers Macromol. Biosci 7 1187 1198
67. X. M. Liu A. Thakur D. Wang 2007 Efficient synthesis of linear multifunctional poly(ethylene glycol) by copper(I)-catalyzed Huisgen 1,3-dipolar cycloaddition Biomacromolecules 8 2653 2658
68. S. Svenson D. A. Tomalia 2005 Dendrimers in biomedical applications-reflections on the field Adv. Drug Delivery Rev 57 2106 2129
69. L. Y. Qiu Y. H. Bae 2006 Polymer architecture and drug delivery Pharm. Res 23 1 30
70. A. Gopin S. Ebner B. Attali D. Shabat 2006 Enzymatic activation of second-generation dendritic prodrugs: conjugation of self-immolative dendrimers with poly(ethylene glycol) via click chemistry Bioconjugate Chem 17 1432 1440
71. Y. Qiu K. Park 2001 Environment-sensitive hydrogels for drug delivery Adv. Drug Delivery Rev 53 321 339
72. J. K. Tessmar A. M. Gopferich 2007 Matrices and scaffolds for protein delivery in tissue engineering Adv. Drug Delivery Rev 59 274 291
73. V. Crescenzi L. Cornelio C. Di Meo S. Nardecchia R. Lamanna 2007 Novel hydrogels via click chemistry: synthesis and potential biomedical applications Biomacromolecules 8 1844 1850
74. M. Malkoch R. Vestberg N. Gupta L. Mespouille P. Dubois A. F. Mason J. L. Hedrick Q. Liao C. W. Frank K. Kingsbury C. J. Hawker 2006 Synthesis of well-defined hydrogel networks using click chemistry Chem. Commun 2006 2774 2776
75. D. A. Ossipov J. Hilborn 2006 Poly(vinyl alcohol)-based hydrogels formed by "click chemistry." Macromolecules 39 1709 1718
76. B. Sieczkowska M. Millaruelo M. Messerschmidt B. Voit 2007 New photolabile functional polymers for patterning onto gold obtained by click chemistry Macromolecules 40 2361 2370
77. B. Voit S. Fleischmann H. Komber A. Scheel K. Stumpe 2007 Cycloaddition reactions and dendritic polymer architectures-a perfect match Macromol. Symp 254 16 24
78. J. Panyam V. Labhasetwar 2003 Biodegradable nanoparticles for drug and gene delivery to cells and tissue Adv. Drug Delivery Rev 55 329 347
79. E. Katz I. Willner 2004 Integrated nanoparticle-biomolecule hybrid systems: synthesis, properties, and applications Angew. Chem., Int. Ed. Engl 43 6042 6108
80. P. Couvreur G. Barratt E. Fattal P. Legrand C. Vauthier 2002 Nanocapsule technology: a review Crit. Rev. Ther. Drug Carrier Syst 19 99 134
81. J. L. West N. J. Halas 2003 Engineered nanomaterials for biophotonics applications: improving, sensing, imaging, and therapeutics Annu. Rev. Biomed. Eng 5 285 292
82. P. W. Faulk M. G. Taylor 1971 Immunocolloid method for the electron microscope Immunochem 8 1081 1083
83. B.-S. Tan X.-H. Cao Z.-H. Mo 2003 Gold nanoparticles preparation and their application in DNA detection Chongqing Daxue Xuebao, Ziran Kexueban 26 58 62
84. X. Huang, I. H. E.-Sayed, and M. A. E.-Sayed. The use of surface enhanced absorption, scattering and catalytic properties of gold nanoparticles in some bio-and biomedical applications. Proc. SPIE-Int. Soc. Opt. Eng. 5929 (2005).
85. G. Han P. Ghosh M. De V. M. Rotello 2007 Drug and gene delivery using gold nanoparticles NanoBiotech 3 40 45
86. J. L. Brennan N. S. Hatzakis R. T. Tshikhudo N. Dirvianskyte V. Razumas S. Patkar J. Vind A. Svendsen R. J. M. Nolte A. E. Rowan M. Brust 2006 Bionanoconjugation via click chemistry: the creation of functional hybrids of lipases and gold nanoparticles Bioconjugate Chem 17 1373 1375
87. D. A. Fleming C. J. Thode M. E. Williams 2006 Triazole cycloaddition as a general route for functionalization of Au nanoparticles Chem. Mater 18 2327 2334
88. A. Ito M. Shinkai H. Honda T. Kobayashi 2005 Medical application of functionalized magnetic nanoparticles J. Biosci. Bioeng 100 1 11
89. A. H. Lu E. L. Salabas F. Schüth 2007 Magnetic nanoparticles: synthesis, protection, functionalization, and application Angew. Chem., Int. Ed. Engl 46 1222 1244
90. P.-C. Lin S.-H. Ueng S.-C. Yu M.-D. Jan A. K. Adak C.-C. Yu C.-C. Lin 2007 Surface modification of magnetic nanoparticle via Cu(I)-catalyzed alkyne-azide [2+3] cycloaddition Org. Lett 9 2131 2134
91. M. A. White J. A. Johnson J. T. Koberstein N. J. Turro 2006 Toward the syntheses of universal ligands for metal oxide surfaces: controlling surface functionality through click chemistry J. Am. Chem. Soc 128 11356 11357
92. A. D. Bangham D. H. Heard R. Flemans G. V. Seaman 1958 An apparatus for microelectrophoresis of small particles Nature (London) 182 642 644
93. T. M. Allen P. R. Cullis 2004 Drug delivery systems: entering the mainstream Science (Washington, D.C.) 303 1818 1822
94. M. L. Immordino F. Dosio L. Cattel 2006 Stealth lipsomes: review of the basic science, rationale, and clinical applications, existing and potential Int. J. Nanomed 1 297 315
95. X. Guo F. C. Szoka Jr. 2003 Chemical approaches to triggerable lipid vesicles for drug and gene delivery Acc. Chem. Res 36 335 341
96. L. Nobs F. Buchegger R. Gurny E. Allemann 2004 Current methods for attaching targeting ligands to liposomes and nanoparticles J. Pharm. Sci 93 1980 1992
97. O. Ishida K. Maruyama H. Tanahashi M. Iwatsuru K. Sasaki M. Eriguchi H. Yanagie 2001 Liposomes bearing polyethyleneglycol-coupled transferrin with intracellular targeting property to the solid tumors in vivo Pharm. Res 18 1042 1048
98. J. T. Derksen G. L. Scherphof 1985 An improved method for the covalent coupling of proteins to liposomes Biochim. Biophys. Acta 814 151 155
99. L. Bourel-Bonnet E. I. Pecheur C. Grandjean A. Blanpain T. Baust O. Melnyk B. Hoflack H. Gras-Masse 2005 Anchorage of synthetic peptides onto liposomes via hydrazone and alpha-oxo hydrazone bonds. Preliminary functional investigations Bioconjugate Chem 16 450 457
100. S. F. Hassane B. Frisch F. Schuber 2006 Targeted liposomes: convenient coupling of ligands to preformed vesicles using "click chemistry" Bioconjugate Chem 17 849 854
101. M. J. Copland M. A. Baird T. Rades J. L. McKenzie B. Becker F. Reck P. C. Tyler N. M. Davies 2003 Liposomal delivery of antigen to human dendritic cells Vaccine 21 883 890
102. S. Gal I. Pinchuk D. Lichtenberg 2003 Peroxidation of liposomal palmitoyllinoleoylphosphatidylcholine (PLPC), effects of surface charge on the oxidizability and on the potency of antioxidants Chem. Phys. Lipids 126 95 110
103. S. Cavalli A. R. Tipton M. Overhand A. Kros 2006 The chemical modification of liposome surfaces via a copper-mediated [3+2] azide-alkyne cycloaddition monitored by a colorimetric assay Chem. Commun 2006 3193 3195
104. A. H. Dent. Optimizing bioconjugation processes. Pharm. Tech. Eur. 19:39-40, 43-46 (2007).
105. R. B. Silverman. Drug Discovery, Design, and Development. The Organic Chemistry of Drug Design and Drug Action, 2nd edn. Elsevier Scientific, San Diego, CA, 2004.
106. K. A. Stephenson J. Zubieta S. R. Banerjee M. K. Levadala L. Taggart L. Ryan N. McFarlane D. R. Boreham K. P. Maresca J. W. Babich J. F. Valliant 2004 A new strategy for the preparation of peptide-targeted radiopharmaceuticals based on an Fmoc-lysine-derived single amino acid chelate (SAAC). Automated solid-phase synthesis, NMR characterization, and in vitro screening of fMLF(SAAC)G and fMLF[(SAAC-Re(CO)3)+]G Bioconjugate Chem 15 128 136
107. 99mTc labeling of highly potent small peptides Bioconjugate Chem 8 621 636
108. P. Bouziotis M. Fani S. C. Archimandritis G. Loundos M. Paravatou R. Bicknell A. L. Harris S. Xanthopoulos N. Stratis A. D. Varvarigou 2003 Samarium-153 and technetium-99m-labeled monoclonal antibodies in angiogenesis for tumor visualization and inhibition Anticancer Res 23 2167 2171
109. M. P. White A. Mann D. M. Cross G. V. Heller 1998 Evaluation of technetium-99m red blood cell labeling efficiency in adults receiving chemotherapy and the clinical impact on pediatric oncology patients J. Nucl. Med. Tech 26 265 268
110. R. Alberto R. Schibli A. Egli A. P. Schubiger U. Abram T. A. Kaden 1998 A novel organometallic aqua complex of technetium for the labeling of biomolecules: synthesis of [99mTc(OH2)3(CO)3] + from [99mTcO4]- in aqueous solution and its reaction with a bifunctional ligand J. Am. Chem. Soc 120 7987 7988
111. T. L. Mindt H. Struthers L. Brans T. Anguelov C. Schweinsberg V. Maes D. Tourwe R. Schibli 2006 "Click to chelate": synthesis and installation of metal chelates into biomolecules in a single step J. Am. Chem. Soc 128 15096 15097
112. W. Chen G. Georgiou 2002 Cell-surface display of heterologous proteins: from high-throughput screening to environmental applications Biotechnol. Bioeng 79 496 503
113. J. A. Link D. A. Tirrell 2003 Cell surface labeling of Escherichia coli via copper(I)-catalyzed [3 + 2] cycloaddition J. Am. Chem. Soc 125 11164 11165
114. K. L. Kiick E. Saxon D. A. Tirrell C. R. Bertozzi 2002 Incorporation of azides into recombinant proteins for chemoselective modification by the Staudinger ligation Proc. Natl. Acad. Sci. U.S.A 99 19 24
115. A. Basle G. Rummel P. Storici J. P. Rosenbusch T. Schirmer 2006 Crystal structure of osmoporin OmpC from E. coli at 2.0 ANG J. Mol. Bio 362 933 942
116. Q. Wang T. R. Chan R. Hilgraf V. V. Fokin K. B. Sharpless M. G. Finn 2003 Bioconjugation by copper(I)-catalyzed azide-alkyne [3+2] cycloaddition J. Am. Chem. Soc 125 3192 3193
117. Q. Wang E. Kaltgrad T. Lin J. E. Johnson M. G. Finn 2002 Natural supramolecular building blocks: wild-type cowpea mosaic virus Chem. Bio 9 805 811
118. Q. Wang T. Lin L. Tang J. E. Johnson M. G. Finn 2002 Icosahedral virus particles as addressable nanoscale building blocks Angew. Chem., Int. Ed. Engl 41 459 462
119. Q. Wang K. S. Raja K. D. Janda T. Lin M. G. Finn 2003 Blue fluorescent antibodies as reporters of steric accessibility in virus conjugates Bioconjugate Chem 14 38 43
120. M. H. Caruthers 1985 Gene synthesis machines: DNA chemistry and its uses Science (Washington, D.C.) 230 281 285
121. H. K. Tewary P. L. Iversen 1997 Qualitative and quantitative measurements of oligonucleotides in gene therapy: part II in vivo models J. Pharm. Biomed. Anal 15 1127 1135
122. A. M. Gewirtz 1998 Antisense oligonucleotide therapeutics for human leukemia Curr. Opin. Hemat 5 59 71
123. M. Schena D. Shalon R. W. Davis P. O. Brown 1995 Quantitative monitoring of gene expression patterns with a complementary DNA microarray Science (Wash. D.C.) 270 467 470
124. T. S. Seo Z. Li H. Ruparel J. Ju 2003 Click chemistry to construct fluorescent oligonucleotides for DNA sequencing J. Org. Chem 68 609 612
125. F. Seela V. R. Sirivolu P. Chittepu 2008 Modification of DNA with octadiynyl side chains: synthesis, base pairing, and formation of fluorescent coumarin dye conjugates of four nucleobases by the alkyne-azide "click reaction" Bioconjugate Chem 19 211 224
126. G. M. Cooper. The Cell Surface. The Cell: A Molecular Approach, 2nd edn. Sinauer, Sunderland, MA, 2000.
127. D. B. Werz P. H. Seeberger 2005 Carbohydrates as the next frontier in pharmaceutical research Chem. Eur. J 11 3194 3026
128. T. Liebert C. Hänsch T. Heinze 2006 Macromol. Rapid Commun 27 208 213
129. J. Hafrén W. Zou A. Córdova 2006 Macromol. Rapid Commun 27 1362 1366
130. C. Glaser 1869 Beiträge zur kenntniss des acetenylbenzols Ber. Dtsch. Chem. Ges 2 422 424
131. F. Straus 1905 Acetylene bonding Justus Liebig Ann. Chem 342 190 265
132. G. Eglinton A. R. Galbraith 1956 Cyclic diynes Chem. Ind. (London) 1956 737 738
133. P. Siemsen R. C. Livingston F. Diederich 2000 Acetylenic coupling: a powerful tool in molecular construction Angew. Chem., Int. Ed. Engl 39 2632 2657
134. M. D. Cameron G. E. Bennett 1957 Use of amines in the glaser coupling reaction J. Org. Chem 22 557 558
135. F. Bohlmann H. Schonowsky E. Inhoffen G. Grau 1964 Polyacetylenic compounds. LII. The mechanism of oxidative dimerization of acetylene compounds Chem. Ber 97 794 800
136. E. H. Ryu Y. Zhao 2005 Efficient synthesis of water-soluble calixarenes using click chemistry Org. Lett 7 1035 1037
137. T. Wang Z. Guo 2006 Copper in medicine: homeostasis, chelation therapy and antitumor drug design Curr. Med. Chem 13 525 537
138. K. D. Held C. F. Sylvester K. L. Hopcia J. E. Biaglow 1996 Role of Fenton chemistry in thiol-induced toxicity and apoptosis Radiat. Res 145 542 553
139. J. E. Macdonald J. A. Kelly J. G. C. Veinot 2007 Iron/iron oxide nanoparticle sequestration of catalytic metal impurities from aqueous media and organic reaction products Langmuir 23 9543 9545