Synthetic materials capable of reporting biomolecular recognition events by chromic transition

Abstract

This article presents a survey of synthetic materials capable of reporting in real time by chromic transition the recognition event occurring between a specific ligand and a biomolecule such as a receptor or an antibody. The review focuses on conductive polymers and colloidal gold. Besides their mode of synthesis and coupling to biomolecules, it explores their physicochemical reactivity, emphasizing the mechanisms underlying the chromic transition occurring upon the biomolecular recognition event. The future prospects offered by composite materials based on these polymers and colloids are further discussed.

References

1. I. C. Kwon, Y. H. Bae and S. W. Kim, Nature, 1991, 354, 291.
2. J. P. Gosling, in Immunotechnology, eds. J. P. Gosling and D. J. Reen, Portland Press, London, 1993, p. 91.
3. C. L. Morgan, D. J. Newman and C. P. Price, Clin. Chem., 1996, 42, 193.
4. G. Chen and A. S. Hoffman, Nature, 1995, 373, 49.
5. H. S. O. Chan, S. C. Ng and S. H. Seow, Synth. Met., 1994, 66, 177.
6. R. Yoshida, K. Uchida, Y. Kaneko, K. Sakai, A. Kikuchi, Y. Sakurai and T. Okano, Nature, 1995, 374, 240.
7. Y. G. Takei, T. Aoki, K. Sanui, N. Ogata, T. Okano and Y. Sakurai, Bioconjugate Chem., 1993, 4, 42.
8. G. Chen and A. S. Hoffman, Bioconjugate Chem., 1993, 4, 509.
9. A. Chilkoti, G. Chen, P. S. Stayton and A. S. Hoffman, Bioconjugate Chem., 1994, 5, 504.
10. M. Berggren, O. Inganäs, G. Gustafsson, J. Rasmusson, M. R. Andersson, T. Hjertberg and O. Wennerström, Nature, 1994, 372, 444.
11. B. S. Kang, M. L. Seo, Y. S. Jun, C. K. Lee and S. C. Shin, Chem. Commun., 1996, 1167.
12. B. Xu and S. Holdcroft, J. Am. Chem. Soc., 1993, 115, 8447.
13. R. H. Friend, R. W. Gymer, A. B. Holmes, J. H. Burroughes, R. N. Marks, C. Taliani, D. D. C. Bradley, D. A. Dos Santos, J. L. Brédas, M. Lögdlund and W. R. Salaneck, Nature, 1999, 397, 121.
14. S. M. Barnard and D. R. Walt, Science, 1991, 251, 927.
15. P. J. Tarcha, W. Bindseil and V. P. Chu, J. Immunol. Methods, 1989, 125, 243.
16. P. S. Stayton, T. Shimoboji, C. Long, A. Chilkoti, G. Chen, J. M. Harris and A. S. Hoffman, Nature, 1995, 378, 472.
17. R. L. Greene and G. B. Street, Science, 1984, 226, 651.
18. D. Clery, Science, 1994, 263, 1700.
19. A. O. Patil, A. J. Heeger and F. Wudl, Chem. Rev., 1988, 88, 183.
20. J. L. Brédas and G. B. Street, Acc. Chem. Res., 1985, 18, 309.
21. S. Etemad, A. G. Heeger and A. G. MacDiarmid, Annu. Rev. Phys. Chem., 1982, 33, 443.
22. M. J. Nowak, S. D. D. V. Rughooputh, S. Hotta and A. J. Heeger, Macromolecules, 1987, 20, 965.
23. W.-C. Chen and S. A. Jenekhe, Polym. Prepr., 1992, 33, 204.
24. J. Yue, Z. H. Wang, K. R. Cromack, A. J. Epstein and A. G. MacDiarmid, J. Am. Chem. Soc., 1991, 113, 2665.
25. G. N. Patel, R. R. Chance and J. D. Witt, J. Chem. Phys., 1979, 70, 4387.
26. K. Y. Jen, R. Oboodi and R. L. Elsenbaumer, Polym. Mater. Sci. Eng., 1985, 53, 79.
27. J. E. Frommer, Acc. Chem. Res., 1986, 19, 2.
28. S. Hotta, S. D. D. V. Rughooputh, A. J. Heeger and F. Wudl, Macromolecules, 1987, 20, 212.
29. N. C. Foulds and C. R. Lowe, Anal. Chem., 1988, 60, 2473.
30. T. Matsue, M. Nishigawa, T. Sawaguchi and I. Uchida, J. Chem. Soc., Chem. Commun., 1991, 1029.
31. B. Fabre, G. Bidan and M. Lapkowski, J. Chem. Soc., Chem. Commun., 1994, 1509.
32. M. Mastragostino, C. Arbizzani, A. Bongini, G. Barbarella and M. Zambianchi, Electrochim. Acta, 1993, 38, 135.
33. A. O. Patil, Y. Ikenoue, F. Wudl and A. J. Heeger, J. Am. Chem. Soc., 1987, 109, 1858.
34. Y. Ikenoue, Y. Saida, M. Kira, H. Tomozawa, H. Yashima and M. Kobayachi, J. Chem. Soc., Chem. Commun., 1990, 1694.
35. T. Tatsuma, K. Ariyama and N. Oyama, Anal. Chem., 1995, 67, 283.
36. J. Roncali, Chem. Rev., 1992, 92, 711.
37. G. Barbarella and M. Zambianchi, Tetrahedron, 1994, 50, 11249.
38. S. D. D. V. Rughooputh, S. Hotta, J. Heeger and F. Wudl, J. Polym. Sci., 1987, 25, 1071.
39. R. D. McCullough, R. D. Lowe, M. Jayaraman and D. L. Anderson, J. Org. Chem., 1993, 58, 904.
40. G. Barbarella, A. Bongini and M. Zambianchi, Macromolecules, 1994, 27, 3039.
41. H. S. O. Chan, A. J. Neuendorf, S.-C. Ng, P. M. L. Wong and D. J. Young, Chem. Commun., 1998, 1327.
42. M. T. Nguyen and A. F. Diaz, Macromolecules, 1995, 28, 3411.
43. A. A. Karyakin, A. K. Strakhova and A. K. Yatsimirsky, J. Electroanal. Chem., 1994, 371, 259.
44. P. Englebienne and M. Weiland, J. Immunol. Methods, 1996, 191, 159.
45. P. Englebienne and M. Weiland, Chem. Commun., 1996, 1651.
46. B. Vincent and J. Waterson, J. Chem. Soc., Chem. Commun., 1990, 683.
47. N. Gospodinova, P. Mokreva and L. Terlemezyan, J. Chem. Soc., Chem. Commun., 1992, 923.
48. S. P. Armes and B. Vincent, J. Chem. Soc., Chem. Commun., 1987, 288.
49. Z. Qi and P. G. Pickup, Chem. Commun., 1998, 15.
50. S. Okada, S. Peng, W. Spevak and D. Charych, Acc. Chem. Res., 1998, 31, 229.
51. C. B. Gorman, E. J. Ginsburg and R. H. Grubbs, J. Am. Chem. Soc., 1993, 115, 1397.
52. R. Koncki and O. S. Wolfbeis, Anal. Chem., 1998, 70, 2544.
53. N. Nakajima and Y. Ikada, Bioconjugate Chem., 1995, 6, 123.
54. M. R. Pope, S. P. Armes and P. J. Tarcha, Bioconjugate Chem., 1996, 7, 436.
55. P. J. Tarcha, D. Misun, D. Finley, M. Wong and J. J. Donovan, in Polymer Latexes, ed. E. S. Daniels, E. Sudol and M. S. El-Aasser, American Chemical Society, 1992, p. 347.
56. I. Lévesque and M. Leclerc, J. Chem. Soc., Chem. Commun., 1995, 2293.
57. M. Leclerc and G. Daoust, J. Chem. Soc., Chem. Commun., 1990, 273.
58. J. Roncali, C. Thobie-Gautier, E. H. Elandaloussi and P. Frère, J. Chem. Soc., Chem. Commun., 1994, 2249.
59. D. H. Charych, J. O. Nagy, W. Spevak and M. D. Bednarski, Science, 1993, 261, 585.
60. J. J. Pan and D. Charych, Langmuir, 1997, 13, 1365.
61. A. Reichert, J. O. Nagy, W. Spevak and D. Charych, J. Am. Chem. Soc., 1995, 117, 829.
62. W. Spevak, J. O. Nagy and D. H. Charych, Adv. Mater., 1995, 7, 85.
63. K. Faïd and M. Leclerc, Chem. Commun., 1996, 2761.
64. L. Schoeff, Anal. Chem., 1997, 69, 206R.
65. C. S. Lee, P. Y. Huang and D. M. Ayres, Anal. Chem., 1991, 63, 464.
66. D. H. Everett, in Basic Principles of Colloid Science, Royal Society of Chemistry, London, 1988, p. 30.
67. J. L. Coffer, J. R. Shapley and H. G. Drickamer, J. Am. Chem. Soc., 1990, 112, 3736.
68. L. Ellens, G. Ameryckx and P. Englebienne, Meded. Fac. Landbouwwet. Rijksuniv. Gent, 1988, 53, 2035.
69. L. Ellens, G. Ameryckx and P. Englebienne, Int. Biotech. Lab., 1989, 7, 33.
70. J. E. Beesley, in Colloidal Gold: A New Perspective for Cytochemical Marking, Oxford University Press, Oxford, 1989, p. 5.
71. J. De Mey, in Immunochemistry: Modern Methods and Applications, ed. J. M. Polak and. I. M. Varndell, J. Wright and Sons, Bristol, 1986, p. 115.
72. W. D. Geoghegan and G. A. Ackerman, J. Histochem. Cytochem., 1977, 25, 1187.
73. W. D. Geoghegan, J. Histochem. Cytochem., 1988, 36, 401.
74. W. D. Geoghegan, J. Clin. Immunoassay, 1988, 11, 11.
75. R. Elghanian, J. J. Storhoff, R. C. Mucic, R. L. Letsinger and C. A. Mirkin, Science, 1997, 277, 1078.
76. J. H. W. Leuvering, P. J. H. M. Thal, M. van der Waart and A. H. W. M. Schuurs, J. Immunoassay, 1980, 1, 77.
77. T. J. C. Gribnau, J. H. W. Leuvering and H. van Hell, J. Chromatogr., 1986, 376, 175.
78. J. H. W. Leuvering, P. J. H. M. Thal and A. H. W. M. Schuurs, J. Immunol. Methods, 1983, 62, 175.
79. J. H. W. Leuvering, P. J. H. M. Thal, D. D. White and A. H. W. M. Schuurs, J. Immunol. Methods, 1983, 62, 163.
80. J. H. W. Leuvering, B. C. Goverde, P. J. H. M. Thal and A. H. W. M. Schuurs, J. Immunol. Methods, 1983, 60, 9.
81. J. H. W. Leuvering, P. J. H. M. Thal, M. van der Waart and A. H. W. M. Schuurs, J. Immunol. Methods, 1981, 45, 183.
82. C. A. Mirkin, R. L. Letsinger, R. C. Mucic and J. J. Storhoff, Nature, 1996, 382, 607.
83. P. Englebienne, Analyst, 1998, 123, 1599.
84. M. M. Morelock, R. H. Ingraham, R. Betageri and S. Jakes, J. Med. Chem., 1995, 38, 1309.
85. R. Nakamura, H. Muguruma, K. Ikebukuro, S. Sasaki, R. Nagata, I. Karube and H. Pedersen, Anal. Chem., 1997, 69, 4649.
86. H. Sota, Y. Hasegawa and M. Iwakura, Anal. Chem., 1998, 70, 2019.
87. G. Lowe, Chem. Soc. Rev., 1995, 24, 309.
88. G. P. Smith and V. A. Petrenko, Chem. Rev., 1997, 97, 391.
89. L. A. Lyon, M. D. Musick and M. J. Natan, Anal. Chem., 1998, 70, 5177.
90. M. Brust, M. Walker, D. Bethell, D. J. Schiffrin and R. Whyman, J. Chem. Soc., Chem. Commun., 1994, 801.
91. M. Brust, J. Fink, D. Bethell, D. J. Shiffrin and C. Kiely, J. Chem. Soc., Chem. Commun., 1995, 1655.
92. D. V. Leff, L. Brandt and J. R. Heath, Langmuir, 1996, 12, 4723.
93. M. E. Garcia, L. A. Baker and R. M. Crooks, Anal. Chem., 1999, 71, 256.
94. S. Chen, R. S. Ingram, M. J. Hostetler, J. J. Pietron, R. W. Murray, T. J. Schaaff, J. T. Khoury, M. M. Alvarez and R. L. Whetten, Science, 1998, 280, 2098.
95. H. S. Zhou, T. Wada and H. Sasabe, J. Chem. Soc., Chem. Commun., 1995, 1525.