Boronic Acid-Based Receptors and Chemosensors

Artificial Receptors for Chemical Sensors

Volumn , Issue , 2010, Pages 169-189

  Yang, Xiaochuan ^a   Cheng, Yunfeng ^a   Jin, Shan ^a   Wang, Binghe ^a  

^a GEORGIA STATE UNIVERSITY   (United States)

Author keywords

Boronic acid based sensor; Carbohydrate sensing; Catechol sensing; Combinatorial chemistry; de novo design; Scaffold selection and design; Template directed synthesis

Indexed keywords

EID: 84885719962     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527632480.ch6     Document Type: Chapter

References (146)

1. Lorand, J.P. and Edwards, J.O. (1959) J. Org. Chem.,24, 769-774.
2. Springsteen, G. and Wang, B. (2002) Tetrahedron,58, 5291-5300.
3. Yan, J., Springsteen, G., Deeter, S., and Wang, B. (2004) Tetrahedron,60, 11205-11209.
4. Jabbour, A., Steinberg, D., Dembitsky, V.M., Moussaieff, A., Zaks, B., and Srebnik, M. (2004) J. Med. Chem.,47, 2409-2410.
5. DiCesare, N. and Lakowicz, J.R. (2002) Anal. Biochem.,301, 111-116.
6. Badugu, R., Lakowicz, J.R., and Geddes, C.D. (2005) Sensor Actuat. B-Chem.,104, 103-110.
7. Swamy, K.M.K., Lee, Y.J., Lee, H.N., Chun, J., Kim, Y., Kim, S.J., and Yoon, J. (2006) J. Org. Chem.,71, 8626-8628.
8. Oehlke, A., Auer, A.A., Jahre, I., Walfort, B., Ruffer, T., Zoufala, P., Lang, H., and Spange, S. (2007) J. Org. Chem.,72, 4328-4339.
9. Badugu, R., Lakowicz, J.R., and Geddes, C.D. (2004) Anal. Chem.,327, 82-90.
10. Badugu, R., Lakowicz, J.R., and Geddes, C.D. (2005) Dyes Pigments,64, 49-55.
11. Brindley, P.B., Gerrard, W., and Lappert, M.F. (1955) J. Chem. Soc., 2956-2958.
12. Morrison, J.D. and Letsinger, R.L. (1964) J. Org. Chem.,29, 3405-3407.
13. Matteson, D.S. and Schaumberg, G.D. (1967) J. Organomet. Chem.,8, 359-360.
14. Sienkiewicz, P.A. and Roberts, D.C. (1980) J. Inorg. Nucl. Chem.,42, 1559-1575.
15. Yoon, J. and Czarnik, A.W. (1992) J. Am. Chem. Soc.,114, 5874-5875.
16. James, T.D., Sandanayake, K.R.A.S., Iguchi, R., and Shinkai, S. (1995) J. Am. Chem. Soc.,117, 8982-8987.
17. Eggert, H., Frederiksen, J., Morin, C., and Norrild, J.C. (1999) J. Org. Chem.,64, 3846-3852.
18. Bielecki, M., Eggert, H., and Norrild, J.C. (1999) J. Chem. Soc., Perkin Trans.2, 449-455.
19. Yang,W., Fan, H.,Gao, S.,Gao, X., Ni,W., Karnati, V., Hooks, W.B., Carson, J., Weston, B., and Wang, B. (2004) Chem. Biol.,11, 439-448.
20. Asher, S.A., Alexeev, V.L., Goponenko, A.V., Sharma, A.C., Lednev, I.K., Wilcox, C.S., and Finegold, D.N. (2003) J. Am. Chem. Soc.,125, 3322-3329.
21. Wang, Z., Zhang, D.Q., and Zhu, D.B. (2005) J. Org. Chem.,70, 5729-5732.
22. Gray Jr., C.W. and Houston, T.A. (2002) J. Org. Chem.,67, 5426-5428.
23. Wiskur, S.L., Lavigne, J.L., Ait-Haddou, H., Lynch, V., Chiu, Y.H., Canary, J.W., and Anslyn, E.V. (2001) Org. Lett.,3, 1311-1314.
24. Gamsey, S., Miller, A., Olmstead, M.M., Beavers, C.M., Hirayama, L.C., Pradhan, S., Wessling, R.A., and Singaram, B. (2007) J. Am. Chem. Soc.,129, 1278-1286.
25. Cho, B.T. (2005) in Boronic Acids (ed. D.G. Hall), Wiley-VCH Verlag GmbH, Weinheim, pp. 411-439.
26. Aharoni F R, Bronstheyn, M., Jabbour, A., Zaks, B., Srebnik, M., and Steinberg, D. (2008) Bioorg. Med. Chem.,16, 1596-1604.
27. Cooper, C.R., Spencer, N., and James, T.D. (1998) Chem. Commun., 1365-1366.
28. Dennis, J.W. (1992) in Cell Surface Carbohydrates and Cell Development (ed. M. Fukuda), CRC Press, Boca Raton, pp. 161-194.
29. Fukuda, M. (1992) in Cell Surface Carbohydrates and Cell Development (ed. M. Fukuda), CRC Press, Boca Raton, pp. 127-160.
30. Culig F Z, Hittmair, A., Hobisch, A., Bartsch, G., Klocker, H., Pai, L.H., and Pastan, I. (1998) Prostate,36, 162-167.
31. Fukuda, M. (1996) Cancer Res.,56, 2237-2244.
32. Meyer, T. and Hart, I.R. (1998) Eur. J. Cancer,34, 214-221.
33. Kannagi, R., Izawa, M., Koike, T., Miyazaki, K., and Kimura, N. (2004) Cancer Sci.,95, 377-384.
34. Karlsson, K.A. (1998) Acta. Biochim. Pol.,45, 429-438.
35. Liu, J., Shriver, Z., Pope, R.M., Thorp, S.C., Duncan, M.B., Copeland, R.J., Raska, C.S., Yoshida, K., Eisenberg, R.J., Cohen, G., Linhardt, R.J., and Sasisekharan, R. (2002) J. Biol. Chem.,277, 33456-33467.
36. Hartshorn, K.L., White, M.R., Mogues, T., Ligtenberg, T., Crouch, E., and Holmskov, U. (2003) Am. J. Physiol.- Lung Cell. Mol. Physiol., 285, L1066-L1076.
37. Goodman, J.L., Nelson, C.M., Klein, M.B., Hayes, S.F., and Weston, B.W. (1999) J. Clin. Invest.,103, 407-412.
38. Thomas, R.J. and Brooks, T.J. (2004) Microb. Pathol.,36, 83-92.
39. Chiba, H., Inokoshi, J., Nakashima, H., Omura, S., and Tanaka, H. (2004) Biochem. Biophys. Res. Commun.,316, 203-210.
40. Masoud, H., Martin, A., Thibault, P., Moxon, E.R., and Richards, J.C. (2003) Biochemistry,42, 4463-4475.
41. Shroll, R.M. and Straatsma, T.P. (2002) Biopolymers.,65, 395-407.
42. Miyazaki, K., Ohmori, K., Izawa, M., Koike, T., Kumamoto, K., Furukawa, K., Ando, T., Kiso, M., Yamaji, T., Hashimoto, Y., Suzuki, A., Yoshida, A., Takeuchi, M., and Kannagi, R. (2004) Cancer Res., 64 4498-4505.
43. Zhang, J., Nakayama, J., Ohyama, C., Suzuki, M., Suzuki, A., Fukuda, M., and Fukuda, M.N. (2002) Cancer Res.,62, 4194-4198.
44. Krzeslak, A., Pomorski, L., Gaj, Z., and Lipinska, A. (2003) Cancer Lett.,196, 101-107.
45. Takano, R., Muchmore, E., and Dennis, J.W. (1994) Glycobiology,4, 665-674.
46. Peracaula, R., Royle, L., Tabares, G., Mallorqui-Fernandez, G., Barrabes, S., Harvey, D.J., Dwek, R.A., Rudd, P.M., and de Llorens, R. (2003) Glycobiology,13, 227-244.
47. Fernandez-Salas, E., Peracaula, R., Frazier, M.L., and De Llorens, R. (2000) Eur. J. Biochem.,267, 1484-1494.
48. Yan, J., Fang, H., and Wang, B. (2005) Med. Res. Rev.,25, 490-520.
49. James, T.D., Sandanayake, K.R.A.S., and Shinkai, S. (1994) Chem. Commun., 477-478.
50. Cao, H., McGill, T., and Heagy, M.D. (2004) J. Org. Chem.,69, 2959-2966.
51. DiCesare, N. and Lakowicz, J.R. (2002) Tetrahedron Lett.,43, 2615-2618.
52. Davis, C.J., Lewis, P.T., McCarroll, M.E., Read, M.W., Cueto, R., and Strongin, R.M. (1999) Org. Lett.,1, 331-334.
53. Arimori, S., Bosch, L.I., Ward, C.J., and James, T.D. (2001) Tetrahedron Lett.,42, 4553-4555.
54. Zhang, Y., Li, M., Chandrasekaran, S., Gao, X., Fang, X., Lee, H.-W., Hardcastle, K., Yang, J., and Wang, B. (2007) Tetrahedron,63, 3287-3292.
55. Lin, N., Yan, J., Huang, Z., Altier, C., Yan, J., Carrasco, N., Suyemoto, M., Johnson, L., Fang, H., Wang, Q., Wang, S., and Wang, B. (2007) Nucl. Acid Res., 35 1222-1229.
56. Manimala, J.C., Wiskur, S.L., Ellington, A.D., and Anslyn, E.V. (2004) J. Am. Chem. Soc.,126, 16515-16519.
57. Gravel, M., Kim, A., Mark Zak, T., Berube, C., and Hall, D.G. (2002) J. Org. Chem.,67, 3-15.
58. Edwards, N.Y., Sager, T.W., McDevitt, J.T., and Anslyn, E.V. (2007) J. Am. Chem. Soc.,129, 13575-13583.
59. Duggan, P.J. and Offermann, D.A. (2007) Aust. J. Chem.,60, 829-834.
60. Stones, D., Manku, S., Xiaosong, L., and Hall, D. (2004) Chem. Eur. J.,10, 92-100.
61. Zou, Y., Broughton, D.L., Bicker, K.L., Thompson, P.R., and Lavigne, J.J. (2007) ChemBiochem.,8, 2048-2051.
62. Manku, S. and Hall, D.G. (2007) Aust. J. Chem.,60, 824-828.
63. Wang, W., Gao, X., and Wang, B. (2002) Curr. Org. Chem.,6, 1285-1317.
64. Yang, W., Gao, X., and Wang, B. (2003) Med. Res. Rev.,23, 346-368.
65. James, T.D. and Shinkai, S. (2002) Top. Curr. Chem.,218, 159-200.
66. Cao, H.S. and Heagy, M.D. (2004) J. Fluoresc.,14, 569-584.
67. Striegler, S. (2003) Curr. Org. Chem.,7, 81-102.
68. Badugu, R., Lakowicz, J.R., and Geddes, C.D. (2005) Curr. Anal. Chem.,1, 157-170.
69. Kim, S.K., Kim, H.N., Xiaoru, Z., Lee, H.N., Lee, H.N., Soh, J.H., Swamyand, K.M.K., and Yoon, J. (2007) Supramol. Chem.,19, 221-227.
70. Pickup, J.C., Hussain, F., Evans, N.D., Rolinski, O.J., and Birch, D.J.S. (2005) Biosens. Bioelectron.,20, 2555-2565.
71. Mader, H.S. and Wolfbeis, O.S. (2008) Microchim. Acta,162, 1-34.
72. Norrild, J.C. and Eggert, H. (1995) J. Am. Chem. Soc.,117, 1479-1484.
73. Norrild, J.C. and Eggert, H. (1996) J. Chem. Soc. Perkin Trans. 2, 2583-2588.
74. Norrild, J.C. (2001) J. Chem. Soc. Perkin Trans. 2, 719-726.
75. Norrild, J.C. and Sotofte, I. (2001) J. Chem. Soc. Perkin Trans. 2, 727-732.
76. Hall, D.G. (ed.) (2005) Boronic Acids: Preparation and Applications in Organic Synthesis and Medicine, Wiley-VCH Verlag GmbH.
77. Springsteen, G. and Wang, B.H. (2001) Chem. Commun., 1608-1609.
78. Woods, R.J., Dwek, R.A., Edge, C.J., and Fraser-Reid, B. (1995) J. Phy. Chem.,99, 3832-3846.
79. Bras, N.F., Cerqueira, N.M.F.S.A., Fernandes, P.A., and Ramos, M.J. (2008) Int. J. Quantum. Chem.,108, 2030-2040.
80. DeMarco, M.L. and Woods, R.J. (2008) Glycobiology,18, 426-440.
81. Neumann, D., Lehr, C.M., Lenhof, H.P., and Kohlbacher, O. (2004) Adv. Drug Deliver. Rev.,56, 437-457.
82. Parrill, A.L., Mamuya, N., Dolata, D.P., andGervay, J. (1997) Glycoconjugate J.,14, 523-529.
83. Peters, T. and Pinto, B.M. (1996) Curr. Opin. Struc. Biol.,6, 710-720.
84. Woods, R.J. (1998) Glycoconjugate J.,15, 209-216.
85. Yang, W., He, H., and Drueckhammer, D.G. (2001) Angew. Chem. Int. Edit.,40, 1714-1718.
86. Alavi, A and Axford, J.S. (eds) (1995) Glycoimmunology, vol. 376. Plenum Press, New York.
87. Alexeev, V.L., Sharma, A.C., Goponenko, A.V., Das, S., Lednev, I.K., Wilcox, C.S., Finegold, D.N., and Asher, S.A. (2004) Anal. Chem.,75, 2316-2323.
88. Cooper, C.R. and James, T.D. (1998) Chem. Lett., 883-884.
89. Eggert, H., Frederiksen, J., Morin, C., and Norrild, J.C. (1999) J. Org. Chem.,64, 3846-3852.
90. Kaur, G., Fang, H., Gao, X., Li, H., and Wang, B. (2006) Tetrahedron,62, 2583-2589.
91. Nicholls, M.P. and Paul, P.K.C. (2004) Org. Biomol. Chem.,2, 1434-1441.
92. Jin, S., Li, M., Zhu, C., Tran, V., and Wang, B. (2008) ChemBiochem.,9, 1431-1438.
93. Springsteen, G. and Wang, B. (2001) Chem. Commun., 1608-1609.
94. Stack, D.E., Hill, A.L., Diffendaffer, C.B., and Burns, N.M. (2002) Org. Lett.,4, 4487-4490.
95. Zhu, L., Shabbir, S.H., Gray, M., Lynch, V.M., Sorey, S., and Anslyn, E.V. (2006) J. Am. Chem. Soc.,128, 1222-1223.
96. Sarson, L.D., Ueda, K., Takeuchi, R., and Shinkai, S. (1996) Chem. Comm.,5, 619-620.
97. Secor, K.E. and Glass, T.E. (2004) Org. Lett.,6, 3727-3730.
98. Frisch, M.J.,Trucks,G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Montgomery Jr., J.A., Vreven, T., Kudin, K.N., Burant, J.C., Millam, J.M., Iyengar, S.S., Tomasi, J., Barone, V., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G.A., Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J.E., Hratchian, H.P., Cross, J.B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Ayala, P.Y., Morokuma, K., Voth, G.A., Salvador, P., Dannenberg, J.J., Zakrzewski, V.G., Dapprich, S., Daniels, A.D., Strain, M.C., Farkas, O., Malick, D.K., Rabuck, A.D., Raghavachari, K., Foresman, J.B., Ortiz, J.V., Cui, Q., Baboul, A.G., Clifford, S., Cioslowski, J., Stefanov, B.B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Martin, R.L., Fox, D.J., Keith, T., Al- Laham, M.A., Peng, C.Y., Nanayakkara, A., Challacombe, M., Gill, P.M.W., Johnson, B., Chen, W., Wong, M.W., Gonzalez, C., and Pople, J.A. (2004) Gaussian 03, Revision C.02. Gaussian, Inc.: Wallingford, CT.
99. Langer, T. and Wolber, G. (2004) Pure Appl. Chem.,76, 991-996.
100. Dornhofer, A., Biely, M., Wolber, G., and Langer, T. (2006) A novel 2D depiction method using breadth-first ordering and an adapted 2D force field. In: Esin Aki Sener and Ismail Yalcin, editors, QSAR and Molecular Modelling in Rational Design of Bioactive Molecules, Computer Aided Drug Design & Development Society, Ankara, Turkey, pp. 421-422.
101. Gasteiger, J., Rudolph, C., and Sadowski, J. (1990) Tetrahedron Comput. Methodol.,3, 537-547.
102. Jang, Y.J., Jun, J.H., Swamy, K.M.K., Nakamura, K., Koh, H.S., Yoon, Y.J., and Yoon, J. (2005) Bull. Korean Chem. Soc.,26, 2041-2043.
103. Yoon, J.Y. and Czamik, A.W. (1993) Bioorg. Med. Chem.,1, 267-271.
104. Takeuchi, M., Yamamoto, M., and Shinkai, S. (1997) Chem. Commun., 1731-1732.
105. Diaz-Garcia, M.E., Pina-Luis, G., and Rivero, I.A. (2006) Trac-Trend Anal. Chem.,25, 112-121.
106. Potyrailo, R.A. (2004) Macromol. Rapid Commun.,25, 78-94.
107. Hermkens, P.H.H., Ottenheijm, H.C.J., and Rees, D. (1996) Tetrahedron,52, 4527-4554.
108. Potyrailo, R.A. and Mirsky, V.M. (2009) Combinatorial Methods for Chemical and Biological Sensors, Springer, New York.
109. Lam, K.S., Liu, R.W., Miyamoto, S., Lehman, A.L., and Tuscano, J.M. (2003) Acc. Chem. Res.,36, 370-377.
110. Brown, B.B., Wagner, D.S., and Geysen, H.M. (1995) Mol. Divers.,1, 4-12.
111. Basu, P.S., Majhi, R., and Batabyal, S.K. (2003) Clin. Biochem.,36, 373-376.
112. Belanger, A., van Halbeek, H., Graves, H.C., Grandbois, K., Stamey, T.A., Huang, L., Poppe, I., and Labrie, F. (1995) Prostate,27, 187-197.
113. Dudkin, V.Y., Miller, J.S., and Danishefsky, S.J. (2004) J. Am. Chem. Soc.,126, 736-738.
114. Huber, P.R., Schmid, H.P.,Mattarelli, G., Strittmatter, B., van Steenbrugge, G.J., and Maurer, A. (1995) Prostate,27, 212-219.
115. Huizen, I.V., Wu, G., Moussa, M., Chin, J.L., Fenster, A., Lacefield, J.C., Sakai, H., Greenberg, N.M., and Xuan, J.W. (2005) Clin. Cancer Res.,11, 7911-7919.
116. Jankovic, M.M. and Kosanovic, M.M. (2005) Clin. Biochem.,38, 58-65.
117. Kanoh, Y., Mashiko, T., Danbara, M., Takayama, Y., Ohtani, S., Egawa, S., Baba, S., and Akahoshi, T. (2004) Anticancer Res.,24, 3135-3139.
118. Ohyama, C., Hosono, M., Nitta, K., Oheda, M., Yoshikawa, K.,Habuchi, T., Arai, Y., and Fukuda, M. (2004) Glycobiology,14, 671-679.
119. Tabares, G., Jung, K., Reiche, J., Stephan, C., Lein, M., Peracaula, R., de Llorens, R., and Hoesel,W. (2007) Clin. Biochem.,40, 343-350.
120. Tabares, G., Radcliffe, C.M., Barrabes, S., Ramirez, M., Aleixandre, R.N., Hoesel, W., Dwek, R.A., Rudd, P.M., Peracaula, R., and de Llorens, R. (2006) Glycobiology,16, 132-145.
121. Villoutreix, B.O., Getzoff, E.D., and Griffin, J.H. (1994) Protein Sci.,3, 2033-2044.
122. Ellington, A.D. and Szostak, J.W. (1990) Nature,346, 818-822.
123. Robertson, D.L. and Joyce, G.F. (1990) Nature,344, 467-468.
124. Tuerk, C. and Gold, L. (1990) Science,249, 505-510.
125. Huisgen, R. (1963) Angew. Chem., Int. Edit.,2, 565-598.
126. Kolb, H.C., Finn, M.G., and Sharpless, K.B. (2001) Angew. Chem. Int. Edit. Engl.,40, 2004-2021.
127. Tornoe, C.W., Christensen, C., and Meldal, M. (2002) J. Org. Chem.,67, 3057-3064.
128. Yang, W., Gao, X., Springsteen, G., and Wang, B. (2002) Tetrahedron Lett.,43, 6339-6342.
129. Dickey, F.H. (1949) Proc. Natl. Acad. Sci.,35, 227-229.
130. Yan, M. and Ramstrom, O. (2005) Molecularly Imprinted Materials: Science and Technology, Marcel Dekker.
131. Zhang, H.Q., Ye, L., and Mosbach, K. (2006) J. Mol. Recognit.,19, 248-259.
132. Shea, K. (1994) Trends Polym. Sci., 2, 166.
133. Wang, W.,Gao, S., and Wang, B. (2005) in Molecularly Imprinted Materials: Science and Technology (eds M. Yan and O. Ramstrom),Marcel Dekker, pp. 701-726.
134. Wulff, G. and Schauhoff, S. (1991) J. Org. Chem.,56, 395-400.
135. Gao, S., Wang, W., and Wang, B. (2001) Bioorg. Chem.,29, 308-320.
136. Wang, W., Gao, S., and Wang, B. (1999) Org. Lett.,1, 1209-1212.
137. Miyahara, T. and Kurihara, K. (2000) Chem. Lett., 1356-1357.
138. Sallacan, N., Zayats, M., Bourenko, T., Kharitonov, A.B., and Willner, I. (2002) Anal. Chem.,74, 702-712.
139. Granot, E., Tel-Vered, R., Lioubashevski, O., and Willner, I. (2008) Adv. Funct. Mater.,18, 478-484.
140. Zayats, M., Lahav, M., Kharitonov, A.B., and Willner, I. (2002) Tetrahedron,58, 815-824.
141. Rajkumar, R.,Katterle,M.,Warsinke, A., Moehwald, H., and Scheller, F.W. (2008) Biosens Bioelectron.,23, 1195-1199.
142. Lehn, J.-M. (1999) Chem. Eur. J.,5, 2455-2463.
143. Linton, B. and Hamilton, A.D. (1999) Curr. Opin. Chem. Biol.,3, 307-312.
144. Otto, S., Furlan, R.L.E., and Sanders, J.K.M. (2002) Drug Discov. Today,7, 117-125.
145. Eliseev, A.V. and Lehn, J.M. (1999) Combinatorial Chem. Biol.,243, 159-172.
146. Alonso, H., Bliznyuk, A.A., and Gready, J.E. (2006) Med. Res. Rev.,26, 531-568.