Carbohydrate CuAAC click chemistry for therapy and diagnosis

Carbohydrate Research

Volumn 429, Issue , 2016, Pages 1-22

  He, Xiao Peng ^a   Zeng, Ya Li ^a   Zang, Yi ^b   Li, Jia ^b   Field, Robert A ^c   Chen, Guo Rong ^a  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

^c JOHN INNES CENTRE   (United Kingdom)

Author keywords

Carbohydrate; Click chemistry; CuAAC; Diagnosis; Therapy

Indexed keywords

CARBOHYDRATES; DIAGNOSIS; SYNTHESIS (CHEMICAL);

1 ,3-DIPOLARCYCLOADDITION; BIOACTIVE COMPOUNDS; CARBOHYDRATE DERIVATIVES; CELLULAR RECOGNITION; CLICK CHEMISTRY; CUAAC; SIGNALING MOLECULES; THERAPY;

CYCLOADDITION;

ANTINEOPLASTIC AGENT; CARBOHYDRATE DERIVATIVE; CARBONATE DEHYDRATASE; GLYCOGEN PHOSPHORYLASE; GLYCOSIDASE INHIBITOR; GLYCOSYLTRANSFERASE INHIBITOR; IMINOSUGAR; LECTIN; LECTIN RECEPTOR; PROTEIN TYROSINE PHOSPHATASE; SIALIDASE; ALKYNE; ANTIINFECTIVE AGENT; AZIDE; CARBOHYDRATE; TRIAZOLE DERIVATIVE;

ANTIMICROBIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; ANTIVIRAL ACTIVITY; BACTERIUM ADHERENCE; CLICK CHEMISTRY; CYCLOADDITION; DIAGNOSIS; GLYCOSYLATION; HUMAN; MEDICINAL CHEMISTRY; MINIMUM INHIBITORY CONCENTRATION; MOLECULAR LIBRARY; NONHUMAN; PRIORITY JOURNAL; REVIEW; CATALYSIS; CHEMISTRY; METABOLISM; NEOPLASMS; PROCEDURES; SIGNAL TRANSDUCTION; SYNTHESIS; TRENDS;

ALKYNES; ANTI-INFECTIVE AGENTS; ANTINEOPLASTIC AGENTS; AZIDES; CARBOHYDRATES; CATALYSIS; CHEMISTRY, PHARMACEUTICAL; CLICK CHEMISTRY; CYCLOADDITION REACTION; GLYCOSYLATION; HUMANS; IMINO SUGARS; NEOPLASMS; SIGNAL TRANSDUCTION; TRIAZOLES;

EID: 84964319872     PISSN: 00086215     EISSN: 1873426X     Source Type: Journal    
DOI: 10.1016/j.carres.2016.03.022     Document Type: Review

References (280)

1. A. Varki Glycobiology 3 1993 97 130
2. C.R. Bertozzi, and L.L. Kiessling Science 291 2001 2357 2364
3. J.C. Paulson, O. Blixt, and B.E. Collins Nat Chem Biol 2 2006 238 248
4. G.W. Hart, and R.J. Copeland Cell 143 2010 672 676
5. A. Metha, H. Herrera, and T. Block Adv Cancer Res 126 2015 257 279
6. Liu F.-T., and G.A. Rabinovich Nat Rev Cancer 5 2005 29 41
7. Shi Y., Zhang W., Wang F., Qi J., Wu Y., Song H., and et al. Science 342 2013 243 247
8. B. Ernst, and J.L. Magnani Nat Drug Discov 8 2009 661 667
9. S. Abrecht, P. Harrington, H. Iding, M. Karpf, R. Trussardi, B. Wirz, and et al. Chimia (Aarau) 58 2004 621 629
10. T. Feizi, F. Fazio, Chai W., and C.-H. Wong Curr Opin Struct Biol 13 2003 637 645
11. T. Feizi, and Chai W. Nat Rev Mol Cell Biol 5 2004 582 588
12. S. Park, J.C. Gildersleeve, O. Blixt, and I. Shin Chem Soc Rev 42 2013 4310 4326
13. I. Shin, and K.S. Kim Chem Soc Rev 42 2013 4267 4269
14. Yu B., and Sun J. Chem Commun 46 2010 4668 4679
15. Yu B., Sun J., and Yang X. Acc Chem Res 45 2012 1227 1236
16. H.C. Kolb, M.G. Finn, and K.B. Sharpless Angew Chem Int Ed 40 2001 2004 2021
17. V.V. Rostovtsev, K.G. Green, V.V. Fokin, and K.B. Sharpless Angew Chem Int Ed 41 2002 2596 2599
18. C.W. Tornøe, C. Christensen, and M. Meldal J Org Chem 67 2002 3057 3064
19. M. Meldal, and C.W. Tornøe Chem Rev 108 2008 2952 3015
20. P. Thirumurugan, D. Matosiuk, and K. Jozwiak Chem Rev 113 2013 4905 4979
21. A. Dondoni, and A. Marra Chem Soc Rev 41 2012 573 586
22. A. Dondoni Chem Asian J 2 2007 700 708
23. S. Dedola, S.A. Nepogodiev, and R.A. Field Org Biomol Chem 5 2007 1006 1017
24. V. Aragão-Leoneti, V.L. Campo, A.S. Gomes, R.A. Field, and I. Carvalho Tetrahedron 66 2010 9475 9492
25. Z.J. Witczak, and R. Bielski Click chemistry in glycoscience: new developments and strategies 2013 978-1-118-27533-7
26. C.T. Supuran Nat Rev Drug Discov 7 2008 168 181
27. B.P. Mahon, A.M. Hendon, J.M. Driscoll, G.M. Rankin, S.-A. Poulsen, C.T. Supuran, and et al. Bioorg Med Chem 23 2015 849 854
28. J.C. Morris, J. Chiche, C. Grellier, M. Lopez, L.F. Bornaghi, A. Maresca, and et al. J Med Chem 54 2011 6905 6918
29. R.P. Tanpure, Ren B., T.S. Peat, L.F. Bornaghi, D. Vullo, C.T. Supuran, and et al. J Med Chem 58 2015 1494 1501
30. D. Hanahan, and R.A. Weinberg Cell 100 2000 57 70
31. L.B. Peterson, and B.S.J. Blagg Bioorg Med Chem Lett 20 2010 3957 3960
32. N.K. Tonks Nat Rev Mol Cell Biol 7 2006 833 846
33. L. Lessard, M. Stuible, and M.L. Tremblay Biochim Biophys Acta 1804 2010 613 619
34. He X.-P., Xie J., Tang Y., Li J., and Chen G.-R. Curr Med Chem 19 2012 2399 2405
35. Cui L., He X.-P., Gao L.-X., Li J., and Chen G.-R. J Heterocyclic Chem 50 2013 684 688
36. He X.-P., Deng Q., Gao L.-X., Li C., Zhang W., Zhou Y.-B., and et al. Bioorg Med Chem 19 2011 3892 3900
37. He X.-P., Li C., Wang Z.-Z., Gao L.-X., Shi X.-X., Tang Y., and et al. Glycoconj J 28 2011 493 497
38. Yang J.-W., He X.-P., Li C., Gao L.-X., Sheng L., Xie J., and et al. Bioorg Med Chem Lett 21 2011 1092 1096
39. He X.-P., Li C., Jin X.-P., Song Z., Zhang H.-L., Zhu C.-J., and et al. New J Chem 35 2011 622 631
40. Deng Q., Zheng R.-R., Ding N.-N., He X.-P., and Chen G.-R. Bull Korean Chem Soc 31 2010 1055 1057
41. Wang J., He X., Gao L., Sheng L., Shi X., Li J., and et al. Chin J Chem 29 2011 1227 1232
42. Li C., He X.-P., Zhang Y.-J., Li Z., Gao L.-X., Shi X.-X., and et al. Eur J Med Chem 46 2011 4212 4218
43. Yang J.-W., Li C., He X.-P., Zhao H., Gao L.-X., Zhang W., and et al. Bull Korean Chem Soc 31 2010 3359 3365
44. Tang Y.-H., Hu M., He X.-P., S. Fahnbulleh, Li C., Gao L.-X., and et al. Bull Korean Chem Soc 32 2011 1000 1006
45. Song Z., He X.-P., Li C., Gao L.-X., Wang Z.-X., Tang Y., and et al. Carbohydr Res 346 2011 140 145
46. Song Z., He X.-P., Jin X.-P., Gao L.-X., Sheng L., Zhou Y.-B., and et al. Tetrahedron Lett 52 2011 894 898
47. Zhang Y.-J., He X.-P., Li C., Li Z., Shi D.-T., Gao L.-X., and et al. Chem Lett 39 2010 1261 1263
48. Luo L., He X.-P., Shen Q., Li J.-Y., Shi X.-X., Xie J., and et al. Chem Biodivers 8 2011 2035 2044
49. Cheng C.-Y., Feng Y.-Y., Zang Y., Li J., He X.-P., and Chen G.-R. Carbohydr Res 394 2014 39 42
50. P.K. Parida, A. Sau, T. Ghosh, K. Jana, K. Biswas, S. Raha, and et al. Bioorg Med Chem Lett 24 2014 3865 3868
51. J.R. Hwu, C.-I. Hsu, M.-H. Hsu, Liang Y.-C., Huang R.C.C., and Y.C. Lee Bioorg Med Chem Lett 21 2011 380 382
52. L. Hradilová, M. Poláková, B. Dvořáková, M. Hajdúch, and L. Peruš Carbohydr Res 361 2012 1 6
53. Song S.-X., Zhang H.-L., C.-K. Kim, Sheng L., He X.-P., Long Y.-T., and et al. Tetrahedron 66 2010 9974 9980
54. Zhang H.-L., He X.-P., Sheng L., Yao Y., Zhang W., Shi X.-X., and et al. Mol Divers 15 2011 889 900
55. Zhang Q., He P., Zhou G., Gu Y., Fu T., Xue D., and et al. Carbohydr Res 382 2013 65 70
56. E.D. Oldham, S. Seelam, C. Lema, R.J. Aguilera, J. Fiegel, S.E. Rankin, and et al. Carbohydr Res 379 2013 68 77
57. M. Tyagi, and K.P.R. Kartha Carbohydr Res 413 2015 85 92
58. A.G. Dal Bó, V. Soldi, F.C. Giacomelli, C. Travelet, R. Borsali, and S. Fort Carbohydr Res 397 2014 31 36
59. B.H. Fraser, S. Hamilton, A.M. Krause-Heuer, P.J. Wright, I. Greguric, S.P. Tucker, and et al. Med Chem Commun 4 2013 383 386
60. S. Tollas, I. Bereczki, A. Borbás, G. Batta, E. Vanderlinden, L. Naesens, and et al. Bioorg Med Chem Lett 24 2014 2420 2423
61. I. Papp, C. Sieben, A.L. Sisson, J. Kostka, C. Böttcher, K. Ludwig, and et al. Chembiochem 12 2011 887 895
62. P. Guillon, L. Dirr, I.M. El-Deeb, M. Winger, B. Bailly, T. Haselhorst, and et al. Nat Commun 5 2014 5268
63. H. Kai, H. Hinou, and S.-I. Nishimura Bioorg Med Chem 20 2012 2739 2746
64. Zou Y., A. Albohy, M. Sandbhor, and C.W. Cairo Bioorg Med Chem Lett 20 2010 7529 7533
65. M.S. Sandbhor, N. Soya, A. Albohy, Zheng R.B., J. Cartmell, D.R. Bundle, and et al. Biochemistry 50 2011 6753 6762
66. J.D. Howe, N. Smith, M.J.-R. Lee, N. Ardes-Guisot, B. Vauzeilles, J. Désiré, and et al. Bioorg Med Chem 21 2013 4831 4838
67. J. Bouckaert, Li Z., C. Xavier, M. Almant, V. Caveliers, T. Lahoutte, and et al. Chem Eur J 19 2013 7847 7855
68. A. Barras, F.A. Martin, O. Bande, J.-S. Baumann, J.-M. Ghigo, R. Boukherroub, and et al. Nanoscale 5 2013 2307 2316
69. M. Khanal, F. Larsonneur, V. Raks, A. Barras, J.-S. Baumann, F.A. Martin, and et al. Nanoscale 7 2015 2325 2335
70. V.L. Campo, R. Sesti-Costa, Z.A. Carneiro, J.S. Silva, S. Schenkman, and I. Carvalho Bioorg Med Chem 20 2012 145 156
71. V.L. Campo, I. Ivanova, I. Carvalho, C. Duque Lopes, S. Schenkman, Z.A. Carneiro, and et al. Tetrahedron 71 2015 7344 7353
72. V.L. Campo, I. Carvalho, C.H.T.P. Da Silva, S. Schenkman, L. Hill, S.A. Nepogodiev, and et al. Chem Sci 1 2010 507 514
73. E. Galante, C. Geraci, V.L. Campo, R. Sesti-Costa, P.M.M. Guedes, J.S. Silva, and et al. Tetrahedron 67 2011 2901 2912
74. I. Carvalho, P. Andrade, V.L. Campo, P.M.M. Guedes, R. Sesti-Costa, J.S. Silva, and et al. Bioorg Med Chem 18 2010 2412 2427
75. M.L. Conte, A. Marra, A. Chambery, S.S. Gurcha, G.S. Besra, and A. Dondoni J Org Chem 75 2010 6326 6336
76. K.K. Kumar, S.P. Seenivasan, V. Kumar, and T.M. Das Carbohydr Res 346 2011 2084 2090
77. B. Westermann, S. Dörner, S. Brauch, A. Schaks, R. Heinke, S. Stark, and et al. Carbohydr Res 371 2013 61 67
78. S.K. Jana, M. Löppenberg, C.G. Daniliuc, and R. Holl Tetrahedron 70 2014 6569 6577
79. L. Moni, A. Marra, J.S. Skotnicki, F.E. Koehn, M. Abou-Gharbia, and A. Dondoni Carbohydr Res 54 2013 6999 7003
80. S. Bera, G.G. Zhanel, and F. Schweizer Bioorg Med Chem Lett 20 2010 3031 3035
81. I.M. Herzog, M. Feldman, A. Eldar-Boock, R. Satchi-Fainaro, and M. Fridman Med Chem Commun 4 2013 120 124
82. Hu X.-L., Li D., Shao L., Dong X., He X.-P., Chen G.-R., and et al. ACS Med Chem Lett 6 2015 793 797
83. N. Adres-Guisot, D.S. Alonzi, G. Reinkensmeier, T.D. Butters, C. Norez, F. Becq, and et al. Org Biomol Chem 9 2011 5373 5388
84. J.D. Diot, I.G. Moreno, G. Twigg, C.O. Mellet, K. Haupt, T.D. Butters, and et al. J Org Chem 76 2011 7757 7768
85. L. Díaz, J. Bujons, J. Casas, A. Llebaria, and A. Delgado J Med Chem 53 2010 5248 5255
86. L. Díaz, J. Casas, J. Bujons, A. Llebaria, and A. Delgado J Med Chem 54 2011 2069 2079
87. R. Périon, V. Ferrières, I. García-Moreno, C.O. Mellet, R. Duval, G. Fernández, and et al. Tetrahedron 38 2005 9118 9128
88. D.R. da Rocha, W.C. Santos, E.S. Lima, and V.F. Ferreira Carbohydr Res 350 2012 14 19
89. K.R. Ajish, N. Joseph, M.P. Rani, K.G. Raghu, V.P. Vineetha, and K.V. Radhakrishnan Tetrahedron Lett 54 2013 5682 5685
90. R.K. Thakur, A. Mishra, K.K.G. Ramakrishna, R. Mahar, S.K. Shukla, A.K. Srivastava, and et al. Tetrahedron 70 2014 8462 8473
91. C. Decroocq, F. Stauffert, O. Pamlard, F. Oulaïdi, E. Gallienne, O.R. Martin, and et al. Bioorg Med Chem Lett 25 2015 830 833
92. S. Dedola, D.L. Hughes, S.A. Nepogodiev, M. Rejzek, and R.A. Field Carbohydr Res 345 2010 1123 1134
93. A. Marra, R. Zelli, D. D'Orazio, B. La Ferla, and A. Dondoni Tetrahedron 70 2014 9387 9393
94. M. Poláková, R. Stanton, I.B.H. Wilson, I. Holková, S. Šesták, E. Machová, and et al. Carbohydr Res 406 2015 34 40
95. Wang S., J.A. Cuesta-Seijo, D. Lafont, M.M. Palcic, and S. Vidal Chem Eur J 19 2013 15346 15357
96. Wang S., Shen D.L., D. Lafont, A.-S. Vercoutter-Edouart, M. Mortuaire, Shi Y., and et al. Med Chem Commun 5 2014 1172 1178
97. Li T., Guo L., Zhang Y., Wang J., Li Z., Lin L., and et al. Carbohydr Res 346 2011 1083 1092
98. R. Kumar, R. Nasi, M.B. Bhasin, N.H. Khieu, M. Hsieh, M. Gilbert, and et al. Carbohydr Res 378 2013 45 55
99. Yu C.-C., T. Hill, D.H. Kwan, Chen H.-M., Lin C.-C., W. Wakarchuk, and et al. Anal Biochem 444 2014 67 74
100. K. Seelhorst, T. Piernitzki, N. Lunau, C. Meier, and U. Hahn Bioorg Med Chem 22 2014 6430 6437
101. M. Poláková, M. Beláňpvá, K. Mikušová, E. Lattová, and H. Perreault Bioconj Chem 22 2011 289 298
102. É. Bokor, T. Docsa, P. Gergely, and L. Somsák Bioorg Med Chem 18 2010 1171 1180
103. S. Kun, G.Z. Nagy, M. Tóth, L. Czecze, A.N. Van Nhien, T. Docsa, and et al. Carbohydr Res 346 2011 1427 1438
104. D. Goyard, J.-P. Praly, and S. Vidal Carbohydr Res 362 2012 79 83
105. D. Goyard, M. Baron, P.V. Skourti, A.S. Chajistamatiou, T. Docsa, P. Gergely, and et al. Carbohydr Res 364 2012 28 40
106. I. Chlubnová, B. Sylla, C. Nugier-Chauvin, R. Daniellou, L. Legentil, B. Kralová, and et al. Nat Prod Rep 28 2011 937 952
107. L. Van Kaer Nat Rev Immunol 5 2005 31 42
108. D.I. Godfrey, S. Stankovic, and A.G. Baxter Nat Immunol 11 2010 197 206
109. M. Morita, K. Motoki, K. Akimoto, T. Natori, T. Sakai, E. Sawa, and et al. J Med Chem 38 1995 2176 2187
110. T. Lee, M. Cho, S.-Y. Ko, H.-J. Youn, D.J. Baek, W.-J. Cho, and et al. J Med Chem 50 2007 585 589
111. T. Tashiro, Y. Ishii, T. Shigeura, R. Nakagawa, H. Watarai, M. Taniguchi, and et al. Med Chem Commun 2 2011 620 625
112. A.W. McDonagh, and P.V. Murphy Tetrahedron 70 2014 3191 3196
113. P.J. Jervis, L.M. Graham, E.L. Foster, L.R. Cox, S.A. Porcelli, and G.S. Besra Bioorg Med Chem Lett 22 2012 4348 4352
114. N. Pauwels, S. Aspeslagh, D. Elewaut, and S. Van Calenbergh Bioorg Med Chem 20 2012 7149 7154
115. P.J. Jervis, M. Moulis, J.-P. Jukes, H. Ghadbane, L.R. Cox, V. Cerundolo, and et al. Carbohydr Res 356 2012 152 162
116. J.A. Morales-Serna, O. Boutureira, A. Serra, M.I. Matheu, Y. Díaz, and S. Castillón Eur J Org Chem 2010 2657 2660
117. P.J. Jervis, P. Polzella, J. Wojno, J.-P. Jukes, H. Ghadbane, Y.R.G. Diaz, and et al. Bioconj Chem 24 2013 586 594
118. G. Sureshkumar, and S. Hotha Glycoconj J 29 2012 221 230
119. J. Cartmell, E. Paszkiewicz, S. Dziadek, P.-H. Tam, T. Luu, S. Sarkar, and et al. Carbohydr Res 403 2015 123 134
120. Wu Z.L., Huang X., A.J. Burton, and K.A.D. Swift Carbohydr Res 412 2015 1 6
121. Cai H., Sun Z.-Y., Chen M.-S., Zhao Y.-F., H. Kunz, and Li Y.-M. Angew Chem Int Ed 53 2014 1699 1703
122. Yin Z., M. Comellas-Aragones, S. Chowdhury, P. Bentley, K. Kaczanowska, L. BenMohamed, and et al. ACS Chem Biol 8 2013 1253 1262
123. Tang S., Wang Q., and Guo Z. Chem Eur J 16 2010 1319 1325
124. Wang Q., Zhou Z., Tang S., and Guo Z. ACS Chem Biol 7 2012 235 240
125. S. Lamandé-Langle, C. Collet, R. Hensienne, C. Vala, F. Chrétien, Y. Chapleur, and et al. Bioorg Med Chem 22 2014 6672 6683
126. M. Fernández-González, O. Boutureira, G.J.L. Bernardes, J.M. Chalker, M.A. Young, J.C. Errey, and et al. Chem Sci 1 2010 709 715
127. W. Kowalczyk, A. Mascaraque, M. Sánchez-Navarro, J. Rojo, and D. Andreu Eur J Org Chem 2012 4563 4573
128. S. Cecioni, A. Imberty, and S. Vidal Chem Rev 115 2015 525 561
129. K. Matsuoka, H. Yamaguchi, T. Kohzu, J.-I. Sakamoto, T. Koyama, K. Hatano, and et al. Tetrahedron Lett 53 2012 6793 6796
130. Wang G.-N., S. André, H.-J. Gabius, and P.V. Murphy Org Biomol Chem 10 2012 6893 6907
131. R. Sharma, K. Naresh, Y.M. Chabre, R. Rej, N.K. Saadeh, and R. Roy Polym Chem 5 2014 4321 4331
132. Y.M. Chabre, D. Giguère, B. Blanchard, J. Rodrigue, S. Rocheleau, M. Neault, and et al. Chem Eur J 17 2011 6545 6562
133. P.A. Ledin, F. Friscourt, Guo J., and G.-K. Boons Chem Eur J 17 2011 839 846
134. D. Kushwaha, and V.K. Tiwari J Org Chem 78 2013 8184 8190
135. S. André, D.V. Jarikote, Yan D., L. Vincenz, Wang G.-N., H. Kaltner, and et al. Bioorg Med Chem Lett 22 2012 313 318
136. S. André, Wang G.-N., H.-J. Gabius, and P.V. Murphy Carbohydr Res 389 2014 25 38
137. M. Tyagi, N. Taxak, P.V. Bharatam, H. Nandanwar, and K.P.R. Kartha Carbohydr Res 407 2015 137 147
138. G.C. Daskhan, N. Berthet, B. Thomas, M. Fiore, and O. Renaudet Carbohydr Res 405 2015 13 22
139. T.K. Lindhorst, and M. Dubber Carbohydr Res 403 2015 90 97
140. A.K. Adak, Li B.-Y., and Lin C.-C. Carbohydr Res 391 2014 22 28
141. Wang S., N. Galanos, A. Rousset, K. Buffet, S. Cecioni, D. Lafont, and et al. Carbohydr Res 395 2014 15 18
142. J.P. Chinta, and Rao C.P. Carbohydr Res 369 2013 58 62
143. S. Cecioni, S.E. Matthews, H. Blanchard, J.-P. Praly, A. Imberty, and S. Vidal Carbohydr Res 356 2012 132 141
144. J. Garcia-Hartjes, S. Bernardi, C.A.G.M. Weijers, T. Wennekes, M. Gilbert, F. Sansone, and et al. Org Biomol Chem 11 2013 4340 4349
145. S. Cecioni, S. Faure, U. Darbost, I. Bonnamour, H. Parrot-Lopez, O. Roy, and et al. Chem Eur J 17 2011 2146 2159
146. S. Cecioni, J.-P. Praly, S.E. Matthews, M. Wimmerová, A. Amberty, and S. Vidal Chem Eur J 18 2012 6250 6263
147. Wang K.-R., Wang Y.-Q., Li J., An H.-W., Zhang L.-P., Zhang J.-C., and et al. Bioorg Med Chem Lett 23 2013 480 483
148. Liu J., Zhang W., S.-J. Richards, M.I. Gibson, and Chen G. Polym Chem 5 2014 2326 2332
149. Zhang Q., A. Anastasaki, Li G.-Z., A.J. Haddleton, P. Wilson, and D.M. Haddleton Polym Chem 5 2014 3876 3883
150. J. Kumar, L. McDowall, Chen G., and M.H. Stenzel Polym Chem 2 2011 1879 1886
151. L.L. Kiessling, and J.C. Grim Chem Soc Rev 42 2013 4476 4491
152. Xiao C., Zhao C., He P., Tang Z., Chen X., and Jing X. Macromol Rapid Commun 31 2010 991 997
153. S. Das, D. Pati, N. Tiwari, A. Nisal, and S.S. Gupta Biomacromolecules 13 2012 3695 3702
154. A.Y. Shaikh, S. Das, D. Pati, V. Dhaware, S.S. Gupta, and S. Hotha Biomacromolecules 15 2014 3679 3686
155. V. Dhaware, A.Y. Shaikh, M. Kar, S. Hotha, and S.S. Gupta Langmuir 29 2013 5659 5667
156. A. Siriwardena, K.K. Pulukuri, P.S. Kandiyal, S. Roy, O. Bande, S. Ghosh, and et al. Angew Chem Int Ed 52 2013 10221 10226
157. Zhang H.-L., Zang Y., Xie J., Li J., Chen G.-R., He X.-P., and et al. Sci Rep 4 2014 5513
158. Tian X., J. Pai, K.-H. Baek, S.-K. Ko, and I. Shin Chem Asian J 6 2011 2107 2113
159. R.-S. Lee, and Peng K.-Y. React Funct Polym 72 2012 564 573
160. M. François-Heude, A. Méndez-Ardoy, V. Cendret, P. Lafite, R. Daniellou, C.O. Mellet, and et al. Chem Eur J 21 2015 1978 1991
161. A.J. Cagnoni, O. Varela, M.L. Uhrig, and J. Kovensky Eur J Org Chem 2013 972 983
162. M.L. Gening, D.V. Titov, S. Cecioni, A. Audfray, A.G. Gerbst, Y.E. Tsvetkov, and et al. Chem Eur J 19 2013 9272 9285
163. Zhang Q., Su L., J. Collins, Chen G., R. Wallis, D.A. Mitchell, and et al. J Am Chem Soc 136 2014 4325 4332
164. K. Izawa, K. Akiyama, H. Abe, Y. Togashi, and T. Hasegawa Bioorg Med Chem 21 2013 2895 2902
165. F. Pertici, N.J. de Mol, J. Kemmink, and R.J. Pieters Chem Eur J 19 2013 16923 16927
166. F. Pertici, and R.J. Pieters Chem Commun 48 2012 4008 4010
167. P.R. Crocker, J.C. Paulson, and A. Varki Nat Rev Immunol 7 2007 255 266
168. C.D. Rillahan, E. Schiwartz, R. McBride, V.V. Fokin, and J.C. Paulson Angew Chem Int Ed 51 2012 11014 11018
169. C.D. Rillahan, E. Schwartz, C. Rademacher, R. McBride, J. Rangarajan, V.V. Fokin, and et al. ACS Chem Biol 8 2013 1417 1422
170. C.D. Rillahan, M.S. Macauley, E. Schwartz, He Y., R. McBride, B.M. Arlian, and et al. Chem Sci 5 2014 2398 2406
171. J. Egger, C. Weckerle, B. Cutting, O. Schwardt, S. Rabbani, K. Lemme, and et al. J Am Chem Soc 135 2013 9820 9828
172. S. André, D. Giguère, T.K. Dam, F. Brewer, H.-J. Gabius, and R. Roy New J Chem 34 2010 2229 2240
173. S.R. Rauthu, T.C. Shiao, S. André, M.C. Miller, É. Madej, K.H. Mayo, and et al. Chembiochem 16 2015 126 139
174. V.K. Rajput, H. Leffler, U.J. Nilsson, and B. Mukhopadhyay Bioorg Med Chem Lett 24 2014 3516 3520
175. D.J. Leaver, R.M. Dawson, J.M. White, A. Polyzos, and A.B. Hughes Org Biomol Chem 9 2011 8465 8474
176. R. Maheshwari, E.A. Levenson, and K.L. Kiick Macromol Biosci 10 2010 68 81
177. S.K. Mamidyala, S. Dutta, B.A. Chrunyk, C. Préville, Wang H., J.M. Withka, and et al. J Am Chem Soc 134 2012 1978 1981
178. I. Azcune, E. Balentová, M. Sagartzazu-Aizpurua, J.I. Santos, J.I. Miranda, R.M. Fratila, and et al. Eur J Org Chem 2013 2434 2444
179. Liu L., Li C., S. Cochran, S. Jimmink, and V. Ferro ChemMedChem 7 2012 1267 1275
180. For a recent themed issue, see: Chang C., T. Gunnlaugsson, and T.D. James Chem Soc Rev 44 2015 4176 4178
181. Zhang H.-L., Wei X.-L., Zang Y., Cao J.-Y., Liu S., He X.-P., and et al. Adv Mater 25 2013 4097 4101
182. K. Jain, P. Kesharwani, U. Gupta, and N.K. Jain Biomaterials 33 2012 4166 4186
183. For a recent review of this subject, see: He X.-P., Zang Y., T.D. James, Li J., and Chen G.-R. Chem Soc Rev 44 2015 4239 4248
184. E. Morales-Narváez, and A. Merkoçi Adv Mater 24 2012 3298 3308
185. Feng L., Wu L., and Qu X. Adv Mater 25 2013 168 186
186. He X.-P., Deng Q., Cai L., Wang C.-Z., Zang Y., Li J., and et al. ACS Appl Mater Interfaces 6 2014 5379 5382
187. Sun X., Zhu B., Ji D.-L., Chen Q., He X.-P., Chen G.-R., and et al. ACS Appl Mater Interfaces 6 2014 10078 10082
188. He X.-P., and Tian H. Small 12 2016 144 160
189. Ji D.-K., Chen G.-R., He X.-P., and Tian H. Adv Funct Mater 25 2015 3483 3487
190. Ji D.-K., Zhang Y., He X.-P., and Chen G.-R. J Mater Chem B 3 2015 6656 6661
191. Ji D.-K., Zhang Y., Zang Y., Liu W., Zhang X., Li J., and et al. J Mater Chem B 3 2015 9182 9185
192. Wang L., Pu K.-Y., Li J., Qi X., Li H., Zhang H., and et al. Adv Mater 23 2011 4386 4391
193. Chen Y., H. Vedala, G.P. Kotchey, A. Audfray, S. Cecioni, A. Imberty, and et al. ACS Nano 6 2012 760 770
194. M. Namvari, and H. Namazi Carbohydr Res 396 2014 1 8
195. He X.-P., Li R.-H., S. Maisonneuve, Ruan Y., Chen G.-R., and Xie J. Chem Commun 50 2014 14141 14144
196. Luo J., Xie Z., W.Y. Lam, Cheng L., Chen H., Qiu C., and et al. Chem Commun 2001 1740 1741
197. R.T.K. Kwok, C.W.T. Leung, J.W.Y. Lam, and Tang B.Z. Chem Soc Rev 44 2015 4228 4238
198. Liang J., Tang B.Z., and Liu B. Chem Soc Rev 44 2015 2798 2811
199. Hu R., N.L.C. Leung, and Tang B.Z. Chem Soc Rev 43 2014 4494 4562
200. Hong Y., J.W.Y. Lam, and Tang B.Z. Chem Soc Rev 40 2011 5361 5388
201. Hang Y., He X.-P., Yang L., and Hua J. Biosens Bioelectron 65 2015 420 426
202. S.A. Ingale, and F. Seela Tetrahedron 70 2014 380 391
203. R. Daly, G. Vaz, A.M. Davies, M.O. Senge, and E.M. Scanlan Chem Eur J 18 2012 14671 14679
204. B. Trastoy, M.E. Pérez-Ojeda, R. Sastre, and J.L. Chiara Chem Eur J 16 2010 3833 3841
205. M.E. Pérez-Ojeda, B. Trastoy, Á. Rol, M.D. Chiara, I. García-Moreno, and J.L. Chiara Chem Eur J 19 2013 6630 6640
206. Wu D., S. Cheung, R. Daly, H. Burke, E.M. Scanlan, and D.F. O'Shea Eur J Org Chem 2014 6841 6845
207. Pu S., Liu H., Liu G., Chen B., and Tong Z. Tetrahedron 70 2014 852 858
208. Y.H. Lau, P.J. Rutledge, M. Watkinson, and M.H. Todd Chem Soc Rev 40 2011 2848 2866
209. B. Schulze, and U.S. Schubert Chem Soc Rev 43 2014 2522 2571
210. Deng Q., Shi H.-W., Ding N.-N., Chen B.-Q., He X.-P., Liu G., and et al. Corros Sci 57 2012 220 227
211. Deng Q., Ding N.-N., Wei X.-L., Cai L., He X.-P., Long Y.-T., and et al. Corros Sci 64 2012 64 73
212. Deng Q., He X.-P., Shi H.-W., Chen B.-Q., Liu G., Tang Y., and et al. Ind Eng Chem Res 51 2012 7160 7169
213. Shi D.-T., Zhang B., Yang Y.-X., Guan C.-C., He X.-P., Li Y.-C., and et al. Analyst 138 2013 2808 2811
214. J.A. Cotruvo, A.T. Aron, K.M. Ramos-Torres, and Chang C.J. Chem Soc Rev 44 2015 4400 4414
215. Zhang Y.-J., He X.-P., Hu M., Li Z., Shi X.-X., and Chen G.-R. Dyes Pigments 88 2011 391 395
216. Chen X., T. Pradhan, Wang F., J.S. Kim, and J. Yoon Chem Rev 112 2012 1910 1956
217. Li K.-B., Wei X.-L., Zang Y., He X.-P., Chen G.-R., Li J., and et al. Analyst 138 2013 7087 7089
218. Li K.-B., Zhang H.-L., Zhu B., He X.-P., Xie J., and Chen G.-R. Dyes Pigments 102 2014 273 277
219. Ruan Y.-B., Yi H., and Xie J. Photochem Photobiol Sci 12 2013 1103 1109
220. Li K.-B., Zang Y., Wang H., Li J., Chen G.-R., and T.D. James Chem Commun 50 2014 11735 11737
221. Li K.-B., Wang H., Zang Y., He X.-P., Li J., Chen G.-R., and et al. ACS Appl Mater Interfaces 6 2014 19600 19605
222. Dong L., Zang Y., Zhou D., He X.-P., Chen G.-R., T.D. James, and et al. Chem Commun 51 2015 11852 11855
223. Shi D.-T., Zhou D., Zang Y., Li J., Chen G.-R., T.D. James, and et al. Chem Commun 51 2015 3653 3655
224. Li K.-B., Zhou D., He X.-P., and Chen G.-R. Dyes Pigments 116 2015 52 57
225. S. Hoogendoorn, K.L. Habets, S. Passemard, J. Kuiper, G.A. van der Marel, B.I. Florea, and et al. Chem Commun 47 2011 9363 9365
226. A.K. Yadav, Shen D.L., Shan X., He X., A.R. Kermode, and D.J. Vocadlo J Am Chem Soc 137 2015 1181 1189
227. F. Bellot, R. Hardré, G. Pelosi, M. Thérisod, and C. Policar Chem Commun 41 2005 5414 5416
228. L. Garcia, S. Maisonneuve, Xie J., R. Guillot, P. Dorlet, E. Rivière, and et al. Inorg Chem 49 2010 7282 7288
229. L. Garcia, S. Maisonneuve, J.O.-S. Marcu, R. Guillot, F. Lambert, Xie J., and et al. Inorg Chem 50 2011 11353 11362
230. L. Garcia, M. Lazzaretti, A. Diguet, F. Mussi, F. Biscegile, Xie J., and et al. New J Chem 37 2013 3030 3034
231. He X.-P., Song Z., Wang Z.-Z., Shi X.-X., Chen K., and Chen G.-R. Tetrahedron 67 2011 3343 3347
232. Xue J.-L., He X.-P., Yang J.-W., Shi D.-T., Cheng C.-Y., Xie J., and et al. Carbohydr Res 363 2012 38 42
233. Shi D.-T., Wei X.-L., Sheng Y., Zang Y., He X.-P., Xie J., and et al. Sci Rep 4 2014 4252
234. Tang Y.-H., Qu Y., Song Z., He X.-P., Xie J., Hua J., and et al. Org Biomol Chem 10 2012 555 560
235. He X., Xie J., Chen G., and Chen K. Chin J Chem 30 2012 2874 2878
236. A. Allam, L. Dupont, J.-B. Behr, and R. Plantier-Royon Eur J Org Chem 2012 817 823
237. A.A. Salman, M. Tabandeh, T. Heidelberg, and R.S.D. Hussen Carbohydr Res 406 2015 41 45
238. Yu Y., N. Bogliotti, Tang J., and Xie J. Eur J Org Chem 2013 7749 7760
239. M.P. Leal, M. Assali, I. Fernández, and N. Khiar Chem Eur J 17 2011 1828 1836
240. C. Schmidtke, A.-M. Kreuziger, D. Alpers, A. Jacobsen, Y. Leshch, R. Eggers, and et al. Langmuir 29 2013 12593 12600
241. M.J. Marín, C.L. Schofield, R.A. Field, and D.A. Russell Analyst 140 2015 59 70
242. S. Gatard, L. Salmon, C. Deraedt, J. Ruiz, D. Astruc, and S. Bouquillon Eur J Inorg Chem 2014 2671 2677
243. M.J. Marín, A. Rashid, M. Rejzek, S.A. Fairhurst, S.A. Wharton, S.R. Martin, and et al. Org Biomol Chem 11 2013 7101 7107
244. Hu X.-L., Jin H.-Y., He X.-P., T.D. James, Chen G.-R., and Long Y.-T. ACS Appl Mater Interfaces 7 2015 1874 1878
245. For a recent review, see: E. Paleček, J. Tkáč, M. Bartošik, T. Bertók, V. Ostatná, and J. Paleček Chem Rev 115 2015 2045 2108
246. Wu L., and Qu X. Chem Soc Rev 44 2015 2963 2997
247. Zhao W.-W., Xu J.-J., and Chen H.-Y. Chem Soc Rev 44 2015 729 741
248. Xu J.-J., Zhao W.-W., Song S., Fan C., and Chen H.-Y. Chem Soc Rev 43 2014 1601 1611
249. Tang Y., Ge B., D. Sen, and Yu H.-Z. Chem Soc Rev 43 2014 518 529
250. Ma W., and Long Y.-T. Chem Soc Rev 43 2014 30 41
251. Chen A., and S. Chatterjee Chem Soc Rev 42 2013 5425 5438
252. Zhao J., Liu Y., H.-J. Park, J.M. Boggs, and A. Basu Bioconj Chem 23 2012 1166 1173
253. R. Roux, L. Sallet, P. Alcouffe, S. Chambert, N. Sintes-Zydowicz, E. Fleury, and et al. ACS Macro Lett 1 2012 1074 1078
254. E. Mahon, T. Aastrup, and M. Barboiu Chem Commun 46 2010 2441 2443
255. H. Freichels, V. Pourcelle, R. Auzély-Velty, J. Marchand-Brynaert, and C. Jérôme Biomacromolecules 13 2012 760 768
256. C. Grabosch, M. Kind, Y. Gies, F. Schweighöfer, A. Terfort, and T.K. Lindhorst Org Biomol Chem 11 2013 4006 4015
257. B. Gerland, A. Goudot, C. Ligeour, G. Pourceau, A. Meyer, S. Vidal, and et al. Bioconjugate Chem 25 2014 379 392
258. N. Maalouli, A. Barras, A. Siriwardena, M. Bouazaoui, R. Boukherroub, and S. Szunerits Analyst 138 2013 805 812
259. He X.-P., Wang X.-W., Jin X.-P., Zhou H., Shi X.-X., Chen G.-R., and et al. J Am Chem Soc 133 2011 3649 3657
260. Chen D., Tang L., and Li J. Chem Soc Rev 39 2010 3157 3180
261. M. Pumera Chem Soc Rev 39 2010 4146 4157
262. Guo S., and Dong S. Chem Soc Rev 40 2011 2644 2672
263. Li Z., Deng S.-S., Zang Y., Gu Z., He X.-P., Chen G.-R., and et al. Sci Rep 3 2013 2293
264. Song W., Li D.-W., Li Y.-T., and Long Y.-T. Biosens Bioelectron 26 2011 3181 3186
265. Li M., Li Y.-T., Li D.-W., and Long Y.-T. Anal Chim Acta 734 2012 31 44
266. Zhu B.-W., Cai L., He X.-P., Chen G.-R., and Long Y.-T. Chem Cent J 8 2014 67
267. Cui L., Zhu B.-W., Qu S., He X.-P., and Chen G.-R. Dyes Pigments 121 2015 312 315
268. He X.-P., Zhu B.-W., Zang Y., Li J., Chen G.-R., Tian H., and et al. Chem Sci 6 2015 1996 2001
269. M.C. Martos-Maldonado, M.B. Thygesen, K.J. Jensen, and A. Vargas-Berenguel Eur J Org Chem 2013 2793 2801
270. He X.-P., Hu X.-L., Jin H.-Y., Gan J., Zhu H., Li J., and et al. Anal Chem 87 2015 9078 9083
271. Chen N., Yu Z.-H., Zhou D., Hu X.-L., Zang Y., He X.-P., and et al. Chem Commun 52 2016 2284 2287
272. J.C. Jewett, and C.R. Bertozzi Chem Soc Rev 39 2010 1272 1279
273. C. Le Droumaguet, Wang C., and Wang Q. Chem Soc Rev 39 2010 1233 1239
274. S.-K. Ko, Chen X., J. Yoon, and I. Shin Chem Soc Rev 40 2011 2120 2130
275. S.H. Rouhanifard, L.U. Nordstrøm, Zheng T., and Wu P. Chem Soc Rev 42 2013 4284 4296
276. Yang M., Li J., and Chen P.R. Chem Soc Rev 43 2014 6511 6526
277. Zhang G., Zheng S., Liu H., and Chen P.R. Chem Soc Rev 44 2015 3405 3417
278. A. Dumont, A. Malleron, M. Awwad, S. Dukan, and B. Vauzeilles Angew Chem Int Ed 51 2012 3143 3146
279. J.M. Pons, A. Dumont, G. Sautejeau, E. Fugier, A. Baron, S. Dukan, and et al. Angew Chem Int Ed 53 2014 1275 1278
280. V.K. Tiwari, B.B. Mishra, K.B. Mishra, N. Mishra, A.S. Singh, and Chen X. Chem Rev 116 2016 3086 3240