Biofunctionalization on alkylated silicon substrate surfaces via "click" chemistry

Journal of the American Chemical Society

Volumn 132, Issue 46, 2010, Pages 16432-16441

  Qin, Guoting ^a   Santos, Catherine ^a   Zhang, Wen ^a   Li, Yan ^a   Kumar, Amit ^a   Erasquin, Uriel J ^a   Liu, Kai ^a   Muradov, Pavel ^a   Trautner, Barbara Wells ^b   Cai, Chengzhi ^a  

^a University of Houston   (United States)

^b BAYLOR COLLEGE OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNYL GROUPS; ALKYNYLS; AQUEOUS SOLUTIONS; BIO-CONJUGATION; BIOFUNCTIONALIZATION; BIOLOGICAL APPLICATIONS; DIPOLAR CYCLOADDITIONS; FUNCTIONALIZED; GOOD YIELD; HIGH DENSITY; HYDROGEN-TERMINATED SILICON; HYDROLYTIC CLEAVAGE; INTERMEDIATE LAYERS; NONSPECIFIC ADSORPTION; OLIGO(ETHYLENE GLYCOL); ORGANIC MONOLAYERS; ORGANOSILOXANE FILMS; PHOTO-ACTIVATED; SI-C BOND; SILICON SUBSTRATES; SILICON-BASED BIOSENSORS; SINGLE-STEP;

ACETYLENE; ADSORPTION; BIOSENSORS; COPPER; CYCLOADDITION; ELECTRON ENERGY LEVELS; ESCHERICHIA COLI; ETHYLENE; ETHYLENE GLYCOL; HYDROSILYLATION; LITHOGRAPHY; MONOLAYERS; OXIDE FILMS; PROTEINS; SELF ASSEMBLY; SILICON COMPOUNDS; SILICON OXIDES; SOLUTIONS;

SUBSTRATES;

ALKENE DERIVATIVE; AZIDE; BIOTIN; COPPER; FIBRINOGEN; FIMBRIA PROTEIN; GERMANIUM DERIVATIVE; GLUCOSE; HYDROGEN; MACROGOL; MANNOSE; SILICON;

ADSORPTION; ALKYLATION; AQUEOUS SOLUTION; ARTICLE; BIOFUNCTIONALIZATION; CHEMICAL MODIFICATION; CHEMICAL REACTION; CONTROLLED STUDY; DEGERMANYLATION; DENSITY; DEPROTECTION REACTION; ESCHERICHIA COLI; HYDROSILYLATION; MICROARRAY ANALYSIS; NONHUMAN;

ALKYLATION; ALKYNES; BACTERIA; BIOSENSING TECHNIQUES; MANNOSE; MICROARRAY ANALYSIS; MICROSCOPY, ATOMIC FORCE; MOLECULAR STRUCTURE; SILICON; SURFACE PROPERTIES;

EID: 78649284504     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja1025497     Document Type: Article

References (128)

1. Hamers, R. J. Annu. Rev. Anal. Chem. 2008, 1, 707-736
2. Ciampi, S. and Gooding, J. J. Chem. - Eur. J. 2010, 16, 5961-5968
3. Yang, W. S., Butler, J. E., Russell, J. N., and Hamers, R. J. Analyst 2007, 132, 296-306
4. Shalek, A. K., Robinson, J. T., Karp, E. S., Lee, J. S., Ahn, D. R., Yoon, M. H., Sutton, A., Jorgolli, M., Gertner, R. S., Gujral, T. S., MacBeath, G., Yang, E. G., and Park, H. Proc. Natl. Acad. Sci. U. S. A. 2010, 107, 1870-1875
5. Ainslie, K. M. and Desai, T. A. Lab Chip 2008, 8, 1864-1878
6. Vilan, A., Yaffe, O., Biller, A., Salomon, A., Kahn, A., and Cohen, D. Adv. Mater. 2010, 22, 140-159
7. Touahir, L., Moraillon, A., Allongue, P., Chazalviel, J. N., de Villeneuve, C. H., Ozanam, F., Solomon, I., and Gouget-Laemmel, A. C. Biosens. Bioelectron. 2009, 25, 952-955
8. Hochberg, L. R., Serruya, M. D., Friehs, G. M., Mukand, J. A., Saleh, M., Caplan, A. H., Branner, A., Chen, D., Penn, R. D., and Donoghue, J. P. Nature 2006, 442, 164-171
9. He, Y., Kang, Z. H., Li, Q. S., Tsang, C. H. A., Fan, C. H., and Lee, S. T. Angew. Chem.,Int. Ed. 2009, 48, 128-132
10. He, Y., Su, Y. Y., Yang, X. B., Kang, Z. H., Xu, T. T., Zhang, R. Q., Fan, C. H., and Lee, S. T. J. Am. Chem. Soc. 2009, 131, 4434-4438
11. Shiohara, A., Hanada, S., Prabakar, S., Fujioka, K., Lim, T. H., Yamamoto, K., Northcote, P. T., and Tilley, R. D. J. Am. Chem. Soc. 2010, 132, 248-253
12. Erogbogbo, F., Yong, K. T., Roy, I., Xu, G. X., Prasad, P. N., and Swihart, M. T. ACS Nano 2008, 2, 873-878
13. Okamoto, H., Kumai, Y., Sugiyama, Y., Mitsuoka, T., Nakanishi, K., Ohta, T., Nozaki, H., Yamaguchi, S., Shirai, S., and Nakano, H. J. Am. Chem. Soc. 2010, 132, 2710-2718
14. Orosco, M. M., Pacholski, C., Miskelly, G. M., and Sailor, M. J. Adv. Mater. 2006, 18, 1393-1396
15. Tilley, R. D. and Yamamoto, K. Adv. Mater. 2006, 18, 2053-2056
16. Rosso-Vasic, M., Spruijt, E., Popovic, Z., Overgaag, K., van Lagen, B., Grandidier, B., Vanmaekelbergh, D., Dominguez-Gutierrez, D., De Cola, L., and Zuilhof, H. J. Mater. Chem. 2009, 19, 5926-5933
17. Gao, X. P. A., Zheng, G. F., and Lieber, C. M. Nano Lett. 2010, 10, 547-552
18. Ben Ishai, M. and Patolsky, F. J. Am. Chem. Soc. 2009, 131, 3679-3689
19. Bunimovich, Y. L., Shin, Y. S., Yeo, W. S., Amori, M., Kwong, G., and Heath, J. R. J. Am. Chem. Soc. 2006, 128, 16323-16331
20. Cohen-Karni, T., Timko, B. P., Weiss, L. E., and Lieber, C. M. Proc. Natl. Acad. Sci. U.S.A. 2009, 106, 7309-7313
21. Martinez, J. A., Misra, N., Wang, Y. M., Stroeve, P., Grigoropoulos, C. P., and Noy, A. Nano Lett. 2009, 9, 1121-1126
22. Patolsky, F., Zheng, G., and Lieber, C. M. Nanomedicine 2006, 1, 51-65
23. Wang, W. U., Chen, C., Lin, K. H., Fang, Y., and Lieber, C. M. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 3208-3212
24. Alvarez, S. D., Derfus, A. M., Schwartz, M. P., Bhatia, S. N., and Sailor, M. J. Biomaterials 2009, 30, 26-34
25. Sailor, M. J. and Wu, E. C. Adv. Funct. Mater. 2009, 19, 3195-3208
26. Qu, Y. Q., Liao, L., Li, Y. J., Zhang, H., Huang, Y., and Duan, X. F. Nano Lett. 2009, 9, 4539-4543
27. Ouyang, H., Christophersen, M., Viard, R., Miller, B. L., and Fauchet, P. M. Adv. Funct. Mater. 2005, 15, 1851-1859
28. Kilian, K. A., Bocking, T., Gaus, K., Gal, M., and Gooding, J. J. Biomaterials 2007, 28, 3055-3062
29. Kilian, K. A., Bocking, T., Ilyas, S., Gaus, K., Jessup, W., Gal, M., and Gooding, J. J. Adv. Funct. Mater. 2007, 17, 2884-2890
30. Kilian, K. A., Boecking, T., and Gooding, J. J. Chem. Commun. 2009, 630-640
31. Ilic, B., Yang, Y., and Craighead, H. G. Appl. Phys. Lett. 2004, 85, 2604-2606
32. Singamaneni, S., LeMieux, M. C., Lang, H. P., Gerber, C., Lam, Y., Zauscher, S., Datskos, P. G., Lavrik, N. V., Jiang, H., Naik, R. R., Bunning, T. J., and Tsukruk, V. V. Adv. Mater. 2008, 20, 653-680
33. Yam, C. M., Xiao, Z. D., Gu, J. H., Boutet, S., and Cai, C. Z. J. Am. Chem. Soc. 2003, 125, 7498-7499
34. Gu, J. H., Xiao, Z. D., Yam, C. M., Qin, G. T., Deluge, M., Boutet, S., and Cai, C. Z. Biophys. J. 2005, 89, L31-L33
35. Jonkheijm, P., Weinrich, D., Schroder, H., Niemeyer, C. M., and Waldmann, H. Angew. Chem., Int. Ed. 2008, 47, 9618-9647
36. Cha, T., Guo, A., Jun, Y., Pei, D. Q., and Zhu, X. Y. Proteomics 2004, 4, 1965-1976
37. Nijdam, A. J., Cheng, M. M. C., Geho, D. H., Fedele, R., Herrmann, P., Killian, K., Espina, V., Petricoin, E. F., Liotta, L. A., and Ferrari, M. Biomaterials 2007, 28, 550-558
38. Domachuk, P., Tsioris, K., Omenetto, F. G., and Kaplan, D. L. Adv. Mater. 2010, 22, 249-260
39. Stern, E., Vacic, A., Rajan, N. K., Criscione, J. M., Park, J., Ilic, B. R., Mooney, D. J., Reed, M. A., and Fahmy, T. M. Nat. Nanotechnol. 2010, 5, 138-142
40. Fromherz, P. Solid-State Electron. 2008, 52, 1364-1373
41. Jo, S. and Park, K. Biomaterials 2000, 21, 605-616
42. Lee, S. W. and Laibinis, P. E. Biomaterials 1998, 19, 1669-1675
43. Dekeyser, C. M., Buron, C. C., Mc Evoy, K., Dupont-Gillain, C. C., Marchand-Brynaert, J., Jonas, A. M., and Rouxhet, P. G. J. Colloid Interface Sci. 2008, 324, 118-126
44. Harbers, G. M., Emoto, K., Greef, C., Metzger, S. W., Woodward, H. N., Mascali, J. J., Grainger, D. W., and Lochhead, M. J. Chem. Mater. 2007, 19, 4405-4414
45. Hoffmann, C. and Tovar, G. E. M. J. Colloid Interface Sci. 2006, 295, 427-435
46. Tsukagoshi, T., Kondo, Y., and Yoshino, N. Colloid Surf. B: Biointerfaces 2007, 54, 82-87
47. Lasseter, T. L., Cai, W., and Hamers, R. J. Analyst 2004, 129, 3-8
48. Wang, C., Landis, E. C., Franking, R., and Hamers, R. J. Acc. Chem. Res. 2010, 43, 1205-1215
49. Clare, T. L., Clare, B. H., Nichols, B. M., Abbott, N. L., and Hamers, R. J. Langmuir 2005, 21, 6344-6355
50. Bocking, T., Kilian, K. A., Hanley, T., Ilyas, S., Gaus, K., Gal, M., and Gooding, J. J. Langmuir 2005, 21, 10522-10529
51. Bocking, T., Killan, K. A., Gaus, K., and Gooding, J. J. Langmuir 2006, 22, 3494-3496
52. Yu, Q. K., Qin, G. T., Darne, C., Cai, C. Z., Wosik, W., and Pei, S. S. Sens. Actuators A: Phys. 2006, 126, 369-374
53. Yam, C. M., Lopez-Romero, J. M., Gu, J. H., and Cai, C. Z. Chem. Commun. 2004, 2510-2511
54. Yam, C. M., Gu, J. H., Li, S., and Cai, C. Z. J. Colloid Interface Sci. 2005, 285, 711-718
55. Gu, J. H., Yam, C. M., Li, S., and Cai, C. Z. J. Am. Chem. Soc. 2004, 126, 8098-8099
56. Qin, G. T. and Cai, C. Z. Chem. Commun. 2009, 5112-5114
57. Linford, M. R., Fenter, P., Eisenberger, P. M., and Chidsey, C. E. D. J. Am. Chem. Soc. 1995, 117, 3145-3155
58. Buriak, J. M. Chem. Rev. 2002, 102, 1271-1308
59. Cicero, R. L., Linford, M. R., and Chidsey, C. E. D. Langmuir 2000, 16, 5688-5695
60. Ciampi, S., Harper, J. B., and Gooding, J. J. Chem. Soc. Rev. 2010, 39, 2158-2183
61. Qin, G. T., Zhang, R., Makarenko, B., Kumar, A., Rabalais, W., Romero, J. M. L., Rico, R., and Cai, C. Z. Chem. Commun. 2010, 46, 3289-3291
62. Rostovtsev, V. V., Green, L. G., Fokin, V. V., and Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596-2599
63. Hein, J. E. and Fokin, V. V. Chem. Soc. Rev. 2010, 39, 1302-1315
64. Meldal, M. and Tornoe, C. W. Chem. Rev. 2008, 108, 2952-3015
65. Hong, V., Presolski, S. I., Ma, C., and Finn, M. G. Angew. Chem., Int. Ed. 2009, 48, 9879-9883
66. Wong, L. S., Khan, F., and Micklefield, J. Chem. Rev. 2009, 109, 4025-4053
67. Hudalla, G. A. and Murphy, W. L. Langmuir 2009, 25, 5737-5746
68. Le Droumaguet, C., Wang, C., and Wang, Q. Chem. Soc. Rev. 2010, 39, 1233-1239
69. Bryan, M. C., Fazio, F., Lee, H. K., Huang, C. Y., Chang, A., Best, M. D., Calarese, D. A., Blixt, C., Paulson, J. C., Burton, D., Wilson, I. A., and Wong, C. H. J. Am. Chem. Soc. 2004, 126, 8640-8641
70. Lutz, J. F. Angew. Chem., Int. Ed. 2007, 46, 1018-1025
71. Nandivada, H., Jiang, X. W., and Lahann, J. Adv. Mater. 2007, 19, 2197-2208
72. Nebhani, L. and Barner-Kowollik, C. Adv. Mater. 2009, 21, 3442-3468
73. Collman, J. P., Devaraj, N. K., and Chidsey, C. E. D. Langmuir 2004, 20, 1051-1053
74. Gallant, N. D., Lavery, K. A., Amis, E. J., and Becker, M. L. Adv. Mater. 2007, 19, 965-969
75. Fleming, D. A., Thode, C. J., and Williams, M. E. Chem. Mater. 2006, 18, 2327-2334
76. Li, H. M., Cheng, F. O., Duft, A. M., and Adronov, A. J. Am. Chem. Soc. 2005, 127, 14518-14524
77. O'Reilly, R. K., Joralemon, M. J., Wooley, K. L., and Hawker, C. J. Chem. Mater. 2005, 17, 5976-5988
78. Prakash, S., Long, T. M., Selby, J. C., Moore, J. S., and Shannon, M. A. Anal. Chem. 2007, 79, 1661-1667
79. White, M. A., Johnson, J. A., Koberstein, J. T., and Turro, N. J. J. Am. Chem. Soc. 2006, 128, 11356-11357
80. Zhang, Y., Luo, S. Z., Tang, Y. J., Yu, L., Hou, K. Y., Cheng, J. P., Zeng, X. Q., and Wang, P. G. Anal. Chem. 2006, 78, 2001-2008
81. Devadoss, A. and Chidsey, C. E. D. J. Am. Chem. Soc. 2007, 129, 5370-5371
82. Duckworth, B. P., Xu, J. H., Taton, T. A., Guo, A., and Distefano, M. D. Bioconjugate Chem. 2006, 17, 967-974
83. Sun, X. L., Stabler, C. L., Cazalis, C. S., and Chaikof, E. L. Bioconjugate Chem. 2006, 17, 52-57
84. Santos, C. M., Kumar, A., Zhang, W., and Cai, C. Z. Chem. Commun. 2009, 2854-2856
85. Kumar, A., Erasquin, U. J., Qin, G., Li, K., and Cai, C. Z. Chem. Commun. 2010, 46, 5746-5748
86. Ciampi, S., Bocking, T., Kilian, K. A., James, M., Harper, J. B., and Gooding, J. J. Langmuir 2007, 23, 9320-9329
87. Lin, P. C., Ueng, S. H., Tseng, M. C., Ko, J. L., Huang, K. T., Yu, S. C., Adak, A. K., Chen, Y. J., and Lin, C. C. Angew. Chem., Int. Ed. 2006, 45, 4286-4290
88. Rohde, R. D., Agnew, H. D., Yeo, W. S., Bailey, R. C., and Heath, J. R. J. Am. Chem. Soc. 2006, 128, 9518-9525
89. Cao, P. G., Xu, K., and Heath, J. R. J. Am. Chem. Soc. 2008, 130, 14910-14911
90. Haensch, C., Hoeppener, S., and Schubert, U. S. Nanotechnology 2008, 19
91. Giacomo, M. A., Fabrizio, C., Franco, D., Robertino, Z., Maurizio, C., and Francesca, I. M. J. Nanosci. Nanotechnol. 2010, 10, 2901-2907
92. Scriven, E. F. V. Azides and nitrenes: reactivity and utility; Academic Press: Orlando, FL, 1984.
93. Hurley, P. T., Nemanick, E. J., Brunschwig, B. S., and Lewis, N. S. J. Am. Chem. Soc. 2006, 128, 9990-9991
94. Ciampi, S., Eggers, P. K., Le Saux, G., James, M., Harper, J. B., and Gooding, J. J. Langmuir 2009, 25, 2530-2539
95. Ng, A., Ciampi, S., James, M., Harper, J. B., and Gooding, J. J. Langmuir 2009, 25, 13934-13941
96. Scheres, L., Arafat, A., and Zuilhof, H. Langmuir 2007, 23, 8343-8346
97. Cai, C. Z. and Vasella, A. Helv. Chim. Acta 1995, 78, 732-757
98. Ernst, A., Gobbi, L., and Vasella, A. Tetrahedron Lett. 1996, 37, 7959-7962
99. Dallaire, C. and Brook, M. A. Organometallics 1990, 9, 2873-2874
100. Eaborn, C. and Walton, D. R. M. J. Organomet. Chem. 1964, 2, 95-97
101. Ito, E., Oji, H., Araki, T., Oichi, K., Ishii, H., Ouchi, Y., Ohta, T., Kosugi, N., Maruyama, Y., Naito, T., Inabe, T., and Seki, K. J. Am. Chem. Soc. 1997, 119, 6336-6344
102. Alfredsson, Y., Brena, B., Nilson, K., Ahlund, J., Kjeldgaard, L., Nyberg, M., Luo, Y., Martensson, N., Sandell, A., Puglia, C., and Siegbahn, H. J. Chem. Phys. 2005, 122, 6
103. Collman, J. P., Devaraj, N. K., Eberspacher, T. P. A., and Chidsey, C. E. D. Langmuir 2006, 22, 2457-2464
104. Petrovykh, D. Y., Kimura-Suda, H., Tarlov, M. J., and Whitman, L. J. Langmuir 2004, 20, 429-440
105. Lin, P. C., Ueng, S. H., Yu, S. C., Jan, M. D., Adak, A. K., Yu, C. C., and Lin, C. C. Org. Lett. 2007, 9, 2131-2134
106. Eglinton, G. and McCrae, W. Adv. Org. Chem. 1963, 4, 225
107. Chan, T. R., Hilgraf, R., Sharpless, K. B., and Fokin, V. V. Org. Lett. 2004, 6, 2853-2855
108. Rodionov, V. O., Presolski, S. I., Gardinier, S., Lim, Y. H., and Finn, M. G. J. Am. Chem. Soc. 2007, 129, 12696-12704
109. Rodionov, V. O., Presolski, S. I., Diaz, D. D., Fokin, V. V., and Finn, M. G. J. Am. Chem. Soc. 2007, 129, 12705-12712
110. He, Y., Chang, Y., Hower, J. C., Zheng, J., Chen, S. F., and Jiang, S. Phys. Chem. Chem. Phys. 2008, 10, 5539-5544
111. Zolk, M., Eisert, F., Pipper, J., Herrwerth, S., Eck, W., Buck, M., and Grunze, M. Langmuir 2000, 16, 5849-5852
112. Qian, X. P., Metallo, S. J., Choi, I. S., Wu, H. K., Liang, M. N., and Whitesides, G. M. Anal. Chem. 2002, 74, 1805-1810
113. Barth, K. A., Coullerez, G., Nilsson, L. M., Castelli, R., Seeberger, P. H., Vogel, V., and Textor, M. Adv. Funct. Mater. 2008, 18, 1459-1469
114. Pieters, R. J. Med. Res. Rev. 2007, 27, 796-816
115. Rozhok, S., Shen, C. K. F., Littler, P. L. H., Fan, Z. F., Liu, C., Mirkin, C. A., and Holz, R. C. Small 2005, 1, 445-451
116. Burton, E. A., Sirnon, K. A., Hou, S. Y., Ren, D. C., and Luk, Y. Y. Langmuir 2009, 25, 1547-1553
117. Cheng, G., Li, G. Z., Xue, H., Chen, S. F., Bryers, J. D., and Jiang, S. Y. Biomaterials 2009, 30, 5234-5240
118. Harris, L. G., Tosatti, S., Wieland, M., Textor, M., and Richards, R. G. Biomaterials 2004, 25, 4135-4148
119. Roosjen, A., Busscher, H. J., Nordel, W., and van der Mei, H. C. Microbiology (UK) 2006, 152, 2673-2682
120. Chapman, R. G., Ostuni, E., Liang, M. N., Meluleni, G., Kim, E., Yan, L., Pier, G., Warren, H. S., and Whitesides, G. M. Langmuir 2001, 17, 1225-1233
121. Kingshott, P., Wei, J., Bagge-Ravn, D., Gadegaard, N., and Gram, L. Langmuir 2003, 19, 6912-6921
122. Ostuni, E., Chapman, R. G., Liang, M. N., Meluleni, G., Pier, G., Ingber, D. E., and Whitesides, G. M. Langmuir 2001, 17, 6336-6343
123. Andersson, P., Engberg, I., Lidinjanson, G., Lincoln, K., Hull, R., Hull, S., and Svanborg, C. Infect. Immun. 1991, 59, 2915-2921
124. Sunden, F., Hakansson, L., Ljunggren, E., and Wullt, B. Int. J. Antimicrob. Agents 2006, 28, S26-S29
125. Trautner, B. W., Hull, R. A., Thornby, J. I., and Darouiche, R. O. Infect. Control Hosp. Epidemiol. 2007, 28, 92-94
126. Trautner, B. W., Cevallos, M. E., Li, H. G., Riosa, S., Hull, R. A., Hull, S. I., Tweardy, D. J., and Darouiche, R. O. J. Infect. Dis. 2008, 198, 899-906
127. Hull, R. A., Gill, R. E., Hsu, P., Minshew, B. H., and Falkow, S. Infect. Immun. 1981, 33, 933-938
128. Tao, S.-H. and Bolger, P. M. Regul. Toxicol. Pharmacol. 1997, 25, 211-219