Probing the interactions between boronic acids and cis-diol-containing biomolecules by affinity capillary electrophoresis

Analytical Chemistry

Volumn 85, Issue 4, 2013, Pages 2361-2369

  Lü, Chenchen ^a   Li, Hengye ^a   Wang, Heye ^a   Liu, Zhen ^a  

^a NANJING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACCURACY AND PRECISION; AFFINITY CAPILLARY ELECTROPHORESIS; AFFINITY INTERACTIONS; ANALYTICAL TOOL; BINDING INTERACTION; BINDING STRENGTH; BORONATE; BORONIC ACID; COMPARATIVE STUDIES; MULTIPLE INTERACTIONS;

BINDING ENERGY; CAPILLARY ELECTROPHORESIS; DRUG DELIVERY; FUNCTIONAL MATERIALS; GLUCOSE;

BIOMOLECULES;

BORONIC ACID DERIVATIVE; MONOSACCHARIDE;

ARTICLE; CAPILLARY ELECTROPHORESIS; CHEMISTRY; ISOMERISM; PH; TEMPERATURE;

BORONIC ACIDS; ELECTROPHORESIS, CAPILLARY; HYDROGEN-ION CONCENTRATION; ISOMERISM; MONOSACCHARIDES; TEMPERATURE;

EID: 84874050855     PISSN: 00032700     EISSN: 15206882     Source Type: Journal    
DOI: 10.1021/ac3033917     Document Type: Article

References (72)

1. Elstner, M.; Weisshart, K.; Müllen, K.; Schiller, A. J. Am. Chem. Soc. 2012, 134, 8098-8100
2. Liu, Y.; Deng, C.; Tang, L.; Qin, A.; Hu, R.; Sun, J. Z.; Tang, B. Z. J. Am. Chem. Soc. 2011, 133, 660-663
3. Pal, A.; Berube, M.; Hall, D. G. Angew. Chem., Int. Ed. 2010, 49, 1492-1495
4. Li, H.; Wang, H.; Liu, Y.; Liu, Z. Chem. Commun. 2012, 48, 4115-4117
5. Liu, Y.; Lu, Y.; Liu, Z. Chem. Sci. 2012, 3, 1467-1471
6. Ren, L.; Liu, Z.; Liu, Y.; Dou, P.; Chen, H.-Y. Angew. Chem., Int. Ed. 2009, 48, 6704-6707
7. Ren, L.; Liu, Y.; Dong, M.; Liu, Z. J. Chromatogr. A 2009, 1216, 8421-8425
8. Nishiyabu, R.; Kubo, Y.; James, T. D.; Fossey, J. S. Chem. Commun. 2011, 47, 1106-1123
9. Nishiyabu, R.; Kubo, Y.; James, T. D.; Fossey, J. S. Chem. Commun. 2011, 47, 1124-1150
10. Liang, L.; Liu, Z. Chem. Commun. 2011, 47, 2255-2257
11. Schumacher, S.; Katterle, M.; Hettrich, C.; Paulke, B.-R.; Hall, D. G.; Scheller, F. W.; Gajovic-Eichelmann, N. J. Mol. Recognit. 2011, 24, 953-959
12. Vlandas, A.; Kurkina, T.; Ahmad, A.; Kern, K.; Balasubramanian, K. Anal. Chem. 2010, 82, 6090-6097
13. Ali, S. R.; Parajuli, R. R.; Balogun, Y.; Ma, Y.; He, H. Sensors 2008, 8, 8423-8452
14. Ivanov, A. E.; Kumar, A.; Nilsang, S.; Aguilar, M.-R.; Mikhalovska, L. I.; Savina, I. N.; Nilsson, L.; Scheblykin, I. G.; Kuzimenkova, M. V.; Galaev, I. Y. Colloids Surf. B 2010, 75, 510-519
15. Li, H.; Liu, Z. Trends Anal. Chem. 2012, 37, 148-161
16. Kim, H.; Kang, Y. J.; Kang, S.; Kim, K. T. J. Am. Chem. Soc. 2012, 134, 4030-4033
17. Ellis, G. A.; Palte, M. J.; Raines, R. T. J. Am. Chem. Soc. 2012, 134, 3631-3634
18. Li, Y.; Xiao, W.; Xiao, K.; Berti, L.; Luo, J.; Tseng, H. P.; Fung, G.; Lam, K. S. Angew. Chem., Int. Ed. 2012, 51, 2864-2869
19. Chen, W.; Cheng, Y.; Wang, B. Angew. Chem., Int. Ed. 2012, 51, 5293-5295
20. Kelly, A. M.; Perez-Fuertes, Y.; Fossey, J. S.; Yeste, S. L.; Bull, S. D.; James, T. D. Nat. Protoc. 2008, 3, 215-219
21. Liu, A.; Peng, S.; Soo, J. C.; Kuang, M.; Chen, P.; Duan, H. Anal. Chem. 2011, 83, 1124-1130
22. Neubert, K.; Meister, S.; Moser, K.; Weisel, F.; Maseda, D.; Amann, K.; Wiethe, C.; Winkler, T. H.; Kalden, J. R.; Manz, R. A.; Voll, R. E. Nat. Med. 2008, 14, 748-755
23. Mahalingam, A.; Geonnotti, A. R.; Balzarini, J.; Kiser, P. F. Mol. Pharm. 2011, 8, 2465-2475
24. Cambre, J. N.; Sumerlin, B. S. Polymer 2011, 52, 4631-4643
25. Jay, J. I.; Lai, B. E.; Myszka, D. G.; Mahalingam, A.; Langheinrich, K.; Katz, D. F.; Kiser, P. F. Mol. Pharm. 2010, 7, 116-129
26. Berenson, J. R. Nat. Rev. Clin. Oncol. 2009, 6, 255-256
27. Paramore, A.; Frantz, S. Nat. Rev. Drug Discovery 2003, 2, 611-612
28. Yan, J.; Springsteen, G.; Deeter, S.; Wang, B. H. Tetrahedron 2004, 60, 11205-11209
29. Dowlut, M.; Hall, D. G. J. Am. Chem. Soc. 2006, 128, 4226-4227
30. Li, H.; Liu, Y.; Liu, J.; Liu, Z. Chem. Commun. 2011, 47, 8169-8171
31. Liu, Y.; Ren, L.; Liu, Z. Chem. Commun. 2011, 47, 5067-5069
32. De Guzman, J. M.; Soper, S. A.; McCarley, R. L. Anal. Chem. 2010, 82, 8970-8977
33. Ivanov, A. E.; Galaev, I. Y.; Mattiasson, B. J. Mol. Recognit. 2006, 19, 322-331
34. Henderso, W. G.; How, M. J.; Kennedy, G. R.; Mooney, E. F. Carbohydr. Res. 1973, 28, 1-12
35. Vanduin, M.; Peters, J. A.; Kieboom, A. P. G.; Vanbekkum, H.;, Tetrahedron 1984, 40, 2901-2911.
36. Chapelle, S.; Verchere, J. F. Tetrahedron 1988, 44, 4469-4482
37. Sinton, S. W. Macromolecules 1987, 20, 2430-2441
38. Springsteen, G.; Wang, B. H. Chem. Commun. 2001, 1608-1609
39. Springsteen, G.; Wang, B. H. Tetrahedron 2002, 58, 5291-5300
40. Liu, J.-T.; Chen, L.-Y.; Shih, M.-C.; Chang, Y.; Chen, W.-Y. Anal. Biochem. 2008, 375, 90-96
41. Torun, O.; Dudak, F. C.; Bas, D.; Tamer, U.; Boyaci, I. H. Sens. Actuators B 2009, 140, 597-602
42. Wiskur, S. L.; Lavigne, J. L.; Metzger, A.; Tobey, S. L.; Lynch, V.; Anslyn, E. V. Chem.-Eur. J. 2004, 10, 3792-3804
43. Nicholls, M. P.; Paul, P. K. C. Org. Biomol. Chem. 2004, 2, 1434-1441
44. Tsukagoshi, K.; Shinkai, S. J. Org. Chem. 1991, 56, 4089-4091
45. [Vlandas, V.; Karine; Schappler, J.; Veuthey, J.-L.; Carrupt, P.-A.; Martel, S. Anal. Bioanal. Chem. 2010, 398, 53-66
46. Jiang, C.; Armstrong, D. W. Electrophoresis 2010, 31, 17-27
47. Mironov, G. G.; Logie, J.; Okhonin, V.; Renaud, J. B.; Mayer, P. M.; Berezovski, M. V. J. Am. Soc. Mass. Spectrom. 2012, 23, 1232-1240
48. Parker, K. M.; Stalcup, A. M. J. Chromatogr. A 2008, 1204, 171-182
49. Zhang, B.; Li, Y. X.; Gao, H. N.; Bian, J.; Bao, J. J. Electrophoresis 2011, 32, 3589-3596
50. Bi, X.; Yu, J.; Li, L.; Jiang, H.; Huang, F.; Liu, Z. Analyst 2012, 137, 4016-4022
51. Harskamp, J.; Britz-McKibbin, P.; Wilson, J. Y. Anal. Chem. 2012, 84, 862-866
52. Li, T.; Wang, H. Anal. Chem. 2009, 81, 1988-1995
53. Berezovski, M.; Krylov, S. N. J. Am. Chem. Soc. 2002, 124, 13674-13675
54. Petrov, A. P.; Cherney, L. T.; Dodgson, B.; Okhonin, V.; Krylov, S. N. J. Am. Chem. Soc. 2011, 133, 12486-12492
55. Liu, Z.; Drabovich, A. P.; Krylov, S. N.; Pawliszyn, J. Anal. Chem. 2007, 79, 1097-1100
56. Li, N.; Zeng, S.; He, L.; Zhong, W. Anal. Chem. 2010, 82, 7460-7466
57. Fei, F.; Britz-McKibbin, P. Anal. Bioanal. Chem. 2010, 398, 1349-1356
58. Kaiser, C.; Segui-Lines, G.; D'Amaral, J. C.; Ptolemy, A. S.; Britz-McKibbin, P. Chem. Commun. 2008, 338-340
59. Jiang, Y.; Ma, Y. Anal. Chem. 2009, 81, 6474-6480
60. Ni, N.; Laughlin, S.; Wang, Y.; Feng, Y.; Zheng, Y.; Wang, B. Biorg. Med. Chem. 2012, 20, 2957-2961
61. Ostergaard, J.; Jensen, H.; Hoim, R. J. Sep. Sci. 2009, 32, 1712-1721
62. Britz-McKibbin, P.; Chen, D. D. Y. Electrophoresis 2002, 23, 880-888
63. Offord, R. E. Nature 1966, 211, 591-593
64. Tanaka, Y.; Terabe, S. J. Chromatogr. B 2002, 768, 81-92
65. Marth, J. D.; Grewal, P. K. Nat. Rev. Immunol. 2008, 8, 874-87
66. Berube, M.; Dowlut, M.; Hall, D. G. J. Org. Chem. 2008, 73, 6471-6479
67. Shoji, E.; Freund, M. S. J. Am. Chem. Soc. 2002, 124, 12486-12493
68. Otsuka, H.; Uchimura, E.; Koshino, H.; Okano, T.; Kataoka, K. J. Am. Chem. Soc. 2003, 125, 3493-3502
69. Lu, Y.; Bie, Z.; Liu, Y.; Liu, Z. Analyst 2013, 138, 290-298
70. Hall, D. G. Boronic Acids; Wiley-VCH Verlag GmbH: Weinheim, Germany, 2005; pp 9-10.
71. Byung, Y. Y.; James, S. S.; Gray, R. M. Carbohydr. Res. 1996, 287, 203-212
72. Myung, J. H.; Gajjar, K. A.; Saric, J.; Eddington, D. T.; Hong, S. Angew. Chem., Int. Ed. 2011, 50, 11769-11772