Supramolecular analytical chemistry

Journal of Organic Chemistry

Volumn 72, Issue 3, 2007, Pages 687-699

  Anslyn, Eric V ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BODY FLUIDS; CHEMICAL SENSORS; IMAGING TECHNIQUES; INDICATORS (CHEMICAL);

CELLULAR IMAGING; DIFFERENTIAL SENSING; ENANTIOMERIC EXCESS ANALYSIS; SYNTHETIC RECEPTORS;

SUPRAMOLECULAR CHEMISTRY;

INDICATOR; RECEPTOR;

ANALYSIS; BIOASSAY; BODY FLUID; CELL STRUCTURE; CHEMICAL ANALYSIS; CROSS REACTION; ENANTIOMER; IMAGING; REVIEW; SENSOR; SUPRAMOLECULAR CHEMISTRY; SYNTHESIS;

BIOLOGICAL PRODUCTS; BIOSENSING TECHNIQUES; CATALYSIS; CHEMISTRY, ANALYTICAL; CHEMISTRY, ORGANIC; CHEMISTRY, PHARMACEUTICAL; COMBINATORIAL CHEMISTRY TECHNIQUES; INDICATORS AND REAGENTS; MODELS, BIOLOGICAL; MOLECULAR BIOLOGY; MOLECULAR MIMICRY; NEURAL NETWORKS (COMPUTER); PHARMACEUTICAL PREPARATIONS; RECEPTORS, DRUG; STEREOISOMERISM;

EID: 33846936829     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0617971     Document Type: Review

References (140)

1. Lehn, J.-M. Supramolecular Chemistry; VCH: New York, 1995.
2. Random House Webster's Unabridged Dictionary, 2nd ed.; Random House: New York, 1998.
3. Czarnik, A. W. Chem. Biol. 1995, 2, 423-428.
4. Coral, V.; Nelen, M. I.; Eliseev, A. V.; Lehn, J.-M. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 1347-1352.
5. Sijbren, O.; Ricardo, L. E.; Sanders, J. K. M. Drug Dis. Today 2002, 7, 117-125.
6. Polyakov, V. A.; Nelen, M. I.; Nazarpack-Kandlousy, N.; Ryabov, A. D.; Eliseev, A. V. J. Phys. Org. Chem. 1999, 12, 357-363.
7. Otto, S.; Furlan, R. L. E.; Sanders, J. K. M. J. Am. Chem. Soc. 2000, 122 (48), 12063-12064.
8. West, K. R.; Bake, K. D.; Otto, S. Org. Lett. 2005, 7(13), 2615-2618.
9. Boul, P. J.; Reutenauer, P.; Lehn, J.-M. Org. Lett. 2005, 7 (1), 15-18.
10. Schrader, T.; Hamilton, A. Functional Synthetic Receptors; John Wiley & Sons: New York, 2005.
11. Madsen-Rancke, E. In Indicators; Bishop, E., Ed.; International Series of Monographs In Analytical Chemistry; Pergamon Press: Oxford, UK, 1972; Vol. 51, pp 1-12.
12. Boltz von Rufach, V. Illuminirbuch künstlich alle Farben zu machen und bereyten (1566).
13. Citations in this chapter from the Danish translation, "En Ny oc Illuminer-Bog", Kiøbenhaffn, 1648.
14. Boyle, R. Experimental History of Colours; London, 1664;
15. quoted in The Works of the Hounerable Robert Boyle, London, 1744; Vol. II.
16. Gokel, G. W.; Leevy, W. M.; Weber, M. E. Chem. Rev. 2004, 104, 2723-2750.
17. (a) Cram, D. J.; Carmack, R. A.; Helgeson, R. C. J. Am. Chem. Soc. 1988, 110, 571-577.
18. (b) Molecular Probes catalog no. C36676.
19. Dyatlova, N. M.; Temikina, V. Y.; Popov, K. I. Present-day Aspects of Complexone Coordination Chemistry. In Complex Formation and Stereochemistry of Coordination Compounds; Buslaev, Y., Ed.; Nova Science: Hauppauge, NY, 1996; pp 1-48.
20. de Silva, A. P.; McCaughan, B.; McKinney, B. O. F.; Querol, M. Dalton Trans. 2003, 10, 1902-1913.
21. de Silva, A. P.; Gunaratne, H. Q. N.; Gunnlaugsson, T.; Huxley, A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97(5), 1515-1566.
22. Vance, D. H.; Czarnik, A. W. J. Am. Chem. Soc. 1994, 116, 9397-9398.
23. de Silva, A.P.; Gunaratne, H. Q. N.; Gunnalugsson, T.; Nieuwenhuizen, M. Chem. Commun. 1996, 1967-1968.
24. James, T. D.; Shinkai, S. Top. Curr. Chem. 2002, 218, 159-200.
25. Ni, W.; Kaur, G.; Springsteen, G.; Wang, B.; Franzen, S. Bioorg. Chem. 2004, 32, 571-581.
26. Zhu, L.; Shabbir, S.; Anslyn, E. V. J. Am. Chem. Soc. 2006, 128, 1222-1232.
27. Wright, A.; Zhong, Z.; Anslyn, E. V. Angew. Chem. 2005, 44, 5679-5682.
28. Grynkiewicz, G.; Poenie, M.; Tsien, R. Y. J. Biol. Chem. 1985, 260 (6), 3440-3450.
29. (a) Bornhop, D. J.; Licha, K. Biomedical Photonics Handbook; CRC Press LLC: Boca Raton, FL, 2003.
30. (b) Yang, L.; McRae, R.; Henary, M. M.; Patel, R.; Lai, B.; Stefan, V.; Fahrni, C. J. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 11179-11180.
31. (c) Ueno, T.; Urano, Y.; Kojima, H.; Nagano, T. J. Am. Chem. Soc. 2006, 128, 10640-10641.
32. (d) Wang, S.; Chang, Y.-T. J. Am. Chem. Soc. 2006, 128, 10380-10381.
33. Mohr, G. J. Chem. Eur. J. 2004, 10, 1082-1090.
34. Feuster, E. K.; Glass, T. E. J. Am. Chem. Soc. 2003, 125 (52), 16174-16175.
35. Wallace, K.; Anslyn, E. Chem Commun. 2006, 3886-3887.
36. Inouye, M.; Hashimoto, K.; Isagawa, K. J. Am. Chem. Soc. 1994, 116, 5517-5518.
37. Koh, K. N.; Araki, K.; Ikeda, A.; Otsuka, H.; Shinkai, S. J. Am. Chem. Soc. 1996, 118, 755-758.
38. Wiskur, S.; Ait-Haddou, H.; Lavigne, J.; Anslyn, E. V. Acc. Chem. Res. 2001, 34, 963-972.
39. Szejtli, J. Cyclodextrin Technology; Kluver Academic Publishers: Dordrecht, Boston, 1988; 450 pp.
40. Metzger, A.; Lynch, V. M.; Anslyn, E. V. Angew. Chem., Int. Ed. Engl. 1997, 36, 862-865.
41. Perreault, D. M.; Cabell, L. A.; Anslyn, E. V. Bioorg. Med. Chem. 1997, 36 (5), 433-450.
42. Piatek, A. M.; Bomble, Y. J.; Wiskur, S. L.; Anslyn, E. V. J. Am. Chem. Soc. 2004, 126, 6072-6077.
43. Fabbrizzi, L.; Marcotte, N.; Stomeo, F.; Taglietti, A. Angew. Chem., Int. Ed. 2002, 41 (20), 3811-3814.
44. Lavigne, J. J.; Anslyn, E. V. Angew. Chem., Int. Ed. 1999, 38 (24), 3666-3669.
45. Tobey, S. L.; Jones, B. D.; Anslyn, E. V. J. Am. Chem. Soc. 2003, 125 (14), 4026-4027.
46. Tobey, S. L.; Anslyn, E. V. J. Am. Chem. Soc. 2003, 125 (48), 14807-14815.
47. Niikura, K.; Anslyn, E. V. J. Chem. Soc. Perkin Trans. 2: Phys. Org. Chem. 1999, 12, 2769-2775.
48. Niikura, K.; Anslyn, E. V. J. Org. Chem. 2003, 68 (26), 10156-10157.
49. Niikura, K.; Metzger, A.; Anslyn, E. V. J. Am. Chem. Soc. 1998, 120 (33), 8533-8534.
50. Niikura, K.; Bisson, A. P.; Anslyn, E. V. J. Chem. Soc., Perkins Trans. 2 1999, 111-1114.
51. Zhong, Z.; Anslyn, E. V. J. Am. Chem. Soc. 2002, 124, 9014-9015.
52. Zhong, Z.; Anslyn, E. V. Angew. Chem., Int. Ed. 2003, 42 (26), 3005-3008.
53. Nguyen, B.; Anslyn, E. V. Coor. Chem. Rev. 2006, 250, 3118-3127.
54. Tobey, S. L.; Anslyn, E. V. Org. Lett. 2003, 5 (12), 2029-2031.
55. See ref 39.
56. Zhang, T.; Anslyn, E. V. Org. Lett. 2006, 8 (8), 1649-1652.
57. Pereira, C. M.; Oliveini, J. M.; Silva, R. M.; Silva, F. Anal. Chem. 2004, 76, 5547-5551.
58. Heller, A. Annu. Rev. Biomed. Eng. 1999, 01, 153-175.
59. Melendez, R. E.; Carr, A. J.; Limon, B. R.; Hamilton, A. D. Struct. Bonding (Berlin) 2000, 96, 31-61.
60. Kucharsky, J.; Safarik, L. Titrations in Non-Aqueous Solvents; Elsevier: New York, 1965.
61. Li, Z.; Lin, J.; Pu, L. Angew. Chem., Int. Ed. 2005, 44, 1690-1693.
62. Pu, L. Chem. Rev. 2004, 104, 1687-1716.
63. Kubo, Y.; Maeda, S.; Tokita, S.; Kubo, M. Nature 1996, 382, 522-524.
64. Kim, J.; Kim, S.-G.; Seong, H. R.; Ahn, K. H. J. Org. Chem. 2005, 70, 7227-7231.
65. Korbel, G. A.; Lalic, G.; Shair, M. D. J. Am. Chem. Soc. 2001, 123, 361-362.
66. Zhu, L.; Zhong, Z.; Anslyn, E. V. J. Am. Chem. Soc. 2005, 127 (12), 4260-4269.
67. Zhu, L.; Anslyn, E. V. J. Am. Chem. Soc. 2004, 126 (12), 3676-3677.
68. Folmer-Andersen, J. F.; Lynch, V. M.; Anslyn, E. V. J. Am. Chem. Soc. 2005, 127 (22), 7986-7987.
69. Folmer-Andersen, J. F.; Kitamura, M.; Anslyn, E. V. J. Am. Chem. Soc. 2006, 128 (17), 5652-5653.
70. Gennari, C.; Piarulli, U. Chem. Rev. 2003, 103 (8), 3071-3100.
71. Reetz, M. T. Angew. Chem., Int. Ed. 2002, 41 (8), 1335-1338.
72. Reetz, M. T. Angew. Chem., Int. Ed. 2001, 40 (2), 284-310.
73. Reetz, M. T.; Jaeger, K. E. Chemistry 2000, 6 (3), 407-412.
74. Jayasena, S. P. Clin. Chem. 1999, 45, 1628-1680.
75. Bunka, D. H. J.; Stockley, P. G. Nature Rev. Microbiol. 2006, 4, 588-596.
76. Lee, J. F.; Stovall, G. M.; Ellington, A. P. Curr. Opin. Chem. Biol. 2006, 10, 282-289.
77. Sidhu, S. S. Curr. Opin. Biotechnol. 2000, 11 (6), 610-616.
78. Chen, C.-T.; Wagner, H.; Still W. C. Science 1998, 279, 851-853.
79. Ryan, K.; Still, W. C. Bioorg. Med. Chem. Lett. 1999, 9, 2673-2678.
80. Iorio, E. J.; Shao, Y.; Chen, C.-T.; Wagner, H.; Still, W. C. Bioorg. Med. Chem. Lett. 2001, 11, 1635-1638.
81. Monnee, M. C. F.; Brouwer, A. J.; Liskamp, R. M. J. QSAR Combin. Sci. 2004, 23 (7), 546-559.
82. Shepherd, J.; Gale, T.; Jensen, K. B.; Kilburn, J. D. Chem. Eur. J. 2006, 12, 713-720.
83. Schneider, S. E.; O'Neil, S. N.; Anslyn, E. V. J. Am. Chem. Soc. 2000, 122 (3), 542-543.
84. Hennrich, G.; Lynch, V. M.; Anslyn, E. V. Chem. Eur. J. 2002, 8 (10), 2274-2278.
85. Lavigne, J. J.; Anslyn, E. V. Angew. Chem., Int. Ed. 2001, 40, 3118-3130.
86. Behr, J.-P., Ed. Perspectives In Supramolecular Chemistry 1; John Wiley & Sons: Chichester, 1994.
87. Lavigne, J. J.; Savoy, S.; Clevenger, M. B.; Ritchie, J. E.; McDoniel, B.; Yoo, S.-J.; Anslyn, E. V.; McDevitt, J. T.; Shear, J. B.; Neikirk, D. J. Am. Chem. Soc. 1998, 120, 6429-6430.
88. Goodey, A.; Lavigne, J. J.; Savoy, S. M.; Rodriguez, M. D.; Curey, T.; Tsao, A.; Simmons, G.; Wright, J.; Yoo, S.-J.; Sohn, Y.; Anslyn, E. V.; Shear, J. B.; Neikirk, D. P.; McDevitt, J. T. J. Am. Chem. Soc. 2001, 123 (11), 2559-2570.
89. Vo-Dinh, T.; Askari, M. Curr. Genom. 2001, 2, 399-415.
90. Jelinek, R.; Kolusheva, S. Chem. Rev. 2004, 104, 5987-6015.
91. Gu, J.; Yam, C. M.; Li, S.; Cai, C. J. Am. Chem. Soc. 2004, 126, 8098-8099.
92. Monk, D. J.; Walt, D. R. Anal. Bioanal. Chem. 2004, 378, 931-945.
93. Song, L.; Ahn, S.; Walt, D. R. Anal. Chem. 2006, 78, 1023-1033.
94. Christodoulides, N.; Floriano, P. N.; Acosta, S. A.; Ballard, K. L. M.; Weiguim, S. E.; Mohanty, S.; Dharshan, P.; Romanovicz, D.; McDevitt, J. T. Clin. Chem. 2005, 51 (12), 2391-2395.
95. Keverne, E. B. Chem. Senses 2002, 27, 159-190.
96. Horio, T. Chem. Senses 2002, 27, 159-190.
97. Taniguchi, M. Chem. Senses 2002, 27, 159-190.
98. Dalton, P.; Doolittle, N.; Nagata, H.; Breslin, P. A. S. Nat. Neurosci. 2000, 3 (5), 431-432.
99. Olender, T.; Fuchs, T.; Linhart, C.; Shamir, R.; Adams, M.; Kalush, F.; Khen, M.; Lanceta, D. Genomics 2004, 83, 361-372.
100. Firestein, S.; Given, P.; Paredes, D. Chemistry of Taste: Mechanisms, Behaviors, and Mimics 2003, Chapter 9.
101. Persaud, K.; Dodd, G. Nature 1982, 299, 352-355.
102. Hudewenz, V. Spec. Chem. Mag. 2005, 25 (1), 26-27.
103. James, D.; Scott, Simon M.; Ali, Z.; O'Hare, W. T. Microchim. Acta 2005, 149 (1-2), 1-17.
104. Deisingh, A. K.; Stone, D. C.; Thompson, M. Int. J. Food Sci. Tech. 2004, 39 (6), 587-604.
105. Kohl, C.-D. Nanoelectron. Inf. Technol. 2003, 851-864.
106. Turner, A. P.; Magan, N. Microbology 2004, 2 (2), 161-166.
107. Quotium: http://www.quotium.com. Osmetech: http://www.osmetech-.plc.uk
108. Toko, K. Meas. Sci. Technol. 1998, 9, 1919-1936.
109. Rakow, N. A.; Suslick, K. S. Nature 2000, 406, 710-713.
110. Ferguson, J. A.; Healey, B. G.; Bronk, K. S.; Barnard, S. M.; Walt, D. R. Anal. Chim. Acta 1997, 340 (1-3), 123-131.
111. http://www.illumina.com.
112. Albert, K. J.; Lewis, N. S.; Schauer, C. L.; Sotzing, G. A.; Stitzel, S. E.; Vaid, T. P.; Walt, D. R. Chem. Rev. 2000, 100 (7), 2595-2626.
113. Jurs, P. C.; Bakken, G. A.; McClelland, H. E. Chem. Rev. 2000, 100, 2649-2678.
114. Jolliffe, I. T. Principal Component Analysis, 2nd ed.: Springer-Verlag: New York, 2002.
115. (a) Haswell, S. J. Practical Guide to Chemometrics; Dekker: New York. 1992.
116. (b) Zhang, C.; Suslick, K. S. J. Am. Chem. Soc. 2005, 127, 11548-11549.
117. Bishop, C. M. Neural Networks for Pattern Recognition; Oxford University Press: Oxford, 1995.
118. Burns, J. A.; Whitesides, G. M. Chem. Rev. 1993, 93, 2583-2601.
119. Greene, N. T.; Shimizu, K. D. J. Am. Chem. Soc. 2005, 127 (15), 5695-5700.
120. Greene, N. T.; Morgan, S. L.; Shimizu, K. D. Chem. Commun. 2004, 10, 1172-1173.
121. Ait-Haddou, H.; Wiskur, S. L.; Lynch, V. M.; Anslyn, E. V. J. Am. Chem. Soc. 2001, 123 (45), 11296-11297.
122. Buryak, A.; Severin, K. J. Am. Chem. Soc. 2005, 127 (11), 3700-3701.
123. Buryak, A.; Severin, K. Angew. Chem., Int. Ed. 2004, 43 (36), 4771-4774.
124. Buryak, A.; Severin, K. Angew. Chem., Int. Ed. 2005, 44, 7935-7938.
125. Wiskur, S. L.; Anslyn, E. V. J. Am. Chem. Soc. 2001, 123 (41), 10109-10110.
126. Nishimura, K.; Matsuayama, R. Science and Technology of Whiskies; E. Longman Scientific and Technical: Essex, U.K., 1989; p 235.
127. Lavigne, J. T.; Anslyn, E. V. Angew. Chem., Int. Ed. 1999, 38, 3666-3669.
128. Wiskur, S.; Lavigne, J. T.; Metzger, A.; Tobey, S.; Lynch, V.; Anslyn, E. V. Chem. Eur. J. 2004, 16, 521-528.
129. (a) Wiskur, S.; Floriano, P.; Anslyn, E. V.; McDevitt, J. T. Angew. Chem., Int. Ed. 2003, 18, 2070-2072.
130. (b) McCleskey, S. C.; Floriano, P. N.; Wiskur, S. L.; Anslyn, E. V.; McDevitt, J. T. Tetrahedron 2003, 59, 10089-10092.
131. McCleskey, S. C.; Griffin, M. J.; Schneider, S. E.; McDevitt, J. T.; Anslyn, E. V. J. Am. Chem. Soc. 2003, 125 (5), 1114-1115.
132. Janos, P. J. Chromatogr. A 1997, 789 (1+2), 3-19.
133. Heeter, G. A.; Liapis, A. I. J. Chromatogr., A 1996, 743 (1), 3-14.
134. Baldini, L.; Wilson, A. J.; Hong, J.; Hamilton, A. D. J. Am. Chem. Soc. 2004, 126 (18), 5656-5657.
135. Zhou, H.; Baldini, L.; Hong, J.; Wilson, A. J.; Hamilton, A. D. J. Am. Chem. Soc. 2006, 128 (7), 2421-2425.
136. Wright, A. T.; Griffin, M. J.; Zhong, Z.; McCleskey, S. C.; Anslyn, E. V.; McDevitt, J. T. Angew. Chem., Int. Ed. 2005, 44 (39), 6375-6378.
137. Ciulli, A.; Williams, G.; Smith, A. G.; Blundell, T.; Abell, C. J. Med. Chem. 2006, 49, 4992-5000.
138. Folmer-Andersen, J. F.; Ait-Haddou, H.; Lynch, V. M.; Anslyn, E. V. Inorg. Chem. 2003, 42, 8674-8681.
139. Wright, A. T.; Anslyn. E. V. Org. Lett. 2004, 6 (9), 1341-1344.
140. Wright, A. T.; Anslyn, E. V.; McDevitt, J. T. J. Am. Chem. Soc. 2005, 127 (49), 17405-17411.