Sensing of carboxylate drugs in urine by a supramolecular sensor array

Journal of the American Chemical Society

Volumn 135, Issue 20, 2013, Pages 7705-7712

  Liu, Yuanli ^a   Minami, Tsuyoshi ^a   Nishiyabu, Ryuhei ^b   Wang, Zhuo ^a   Anzenbacher, Pavel ^a  

^a BOWLING GREEN STATE UNIVERSITY   (United States)

^b TOKYO METROPOLITAN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CLASSIFICATION ACCURACY; DISCRIMINATORY POWER; ENVIRONMENTAL MONITORING; LINEAR DISCRIMINANT ANALYSIS; NON-STEROIDAL ANTI-INFLAMMATORY DRUGS; PHYSIOLOGICAL ENVIRONMENT; POTENTIAL UTILITY; SUPRAMOLECULAR SENSORS;

BODY FLUIDS; CARBOXYLATION; PHYSIOLOGY; PRINCIPAL COMPONENT ANALYSIS; SUPRAMOLECULAR CHEMISTRY;

SENSORS;

CARBOXYLIC ACID DERIVATIVE; NONSTEROID ANTIINFLAMMATORY AGENT;

ARTICLE; BINDING AFFINITY; CHEMICAL STRUCTURE; DISCRIMINANT ANALYSIS; HUMAN; HYDROGEL; HYDROGEN BOND; LINEAR DISCRIMINANT ANALYSIS; PRINCIPAL COMPONENT ANALYSIS; SENSOR; SIGNAL TRANSDUCTION; SUPRAMOLECULAR CHEMISTRY; URINALYSIS;

ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; FLUORESCENT DYES; HUMANS; HYDROGELS; MOLECULAR STRUCTURE; SENSITIVITY AND SPECIFICITY;

EID: 84878251300     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja4015748     Document Type: Article

References (71)

1. Kroschwitz, J. I. and Seidel, A. Kirk-Othmer Encyclopedia of Chemical Technology, 5 th ed.; Wiley-Interscience: Hoboken, N. J.: New York, 2007; Vol. 5.
2. Ullmann, F., Gerhartz, W., Yamamoto, Y. S., Campbell, T., Pfefferkorn, R., and Rounsaville, J. F. Ullmann's Encyclopedia of Industrial Chemistry, 7 th ed.; Wiley-VCH: Weinheim, 2011.
3. Nonsteroidal Anti-Inflammatory Drugs: Mechanisms and Clinical Uses, 2 nd ed.; Lewis, A. J. and Furst, D. E., Eds. Marcel Dekker: New York, 1994
4. Lemke, T. L. and Williams, D. A. Nonsteroidal Anti-Inflammatory Drugs Foye's Principles of Medicinal Chemistry, 6 th ed.; Lippincott, Williams, & Wilkins: Philadelphia, 2008.
5. Pharmacotherapy Handbook, 8 th ed.; Wells, B. G., DiPiro, J. T., Schwinghammer, T. L., and DiPiro, C., Eds.; McGraw Hill: New York, 2012.
6. Corcoran, J.; Winter, M. J.; Tyler, C. R. Crit. Rev. Toxicol. 2010, 40, 287-304
7. http://www.epa.gov/esd/bios/daughton/book-summary.htm.
8. Li, Q.; Weina, P. Pharmaceuticals 2010, 3, 2322-2332
9. Sreekumar, A.; Poisson, L. M.; Rajendiran, T. M.; Khan, A. P.; Cao, Q.; Yu, J.; Laxman, B.; Mehra, R.; Lonigro, R. J.; Li, Y.; Nyati, M. K.; Ahsan, A.; Kalyana-Sundaram, S.; Han, B.; Cao, X.; Byun, J.; Omenn, G. S.; Ghosh, D.; Pennathur, S.; Alexander, D. C.; Berger, A.; Shuster, J. R.; Wei, J. T.; Varambally, S.; Beecher, C.; Chinnaiyan, A. M. Nature 2009, 457, 910-914
10. Wu, H.; Liu, T.; Ma, C.; Xue, R.; Deng, C.; Zeng, H.; Shen, X. Anal. Bioanal. Chem. 2011, 401, 635-646
11. Solimana, L. C.; Hui, Y.; Hewavitharan, A. K.; Chen, D. D.Y. J. Chromatogr. A 2012, 1267, 162-169
12. Miziorko, H. M. Arch. Biochem. Biophys. 2011, 505, 131-143
13. Fernstrom, J. D.; Fernstrom, M. H. J. Nutr. 2007, 137, 1539S-1547S
14. Hirai, T.; Matsumoto, S.; Kishi, I. J. Chromatogr. B 1997, 692, 375-388
15. Aresta, A.; Palmisano, F.; Zambonin, C. G. J. Pharm. Biomed. Anal. 2005, 39, 643-647
16. Maurer, H. H.; Tauvel, F. X.; Kraemer, T. J. Anal. Toxicol. 2001, 25, 237-244
17. Sessler, J. L.; Gale, P. A.; Cho, W.-S. Anion Receptor Chemistry. Monographs in Supramolecular Chemistry; Royal Society of Chemistry: Cambridge, 2006.
18. Bayly, S. R.; Beer, P. D. Struct. Bonding (Berlin) 2008, 129, 45-94
19. Valeria, A.; Fabbrizzi, L.; Mosca, L. Chem. Soc. Rev. 2010, 39, 3889-3915
20. Duke, R. M.; Veale, E. B.; Pfeffer, F. M.; Kruger, P. E.; Gunnlaugsson, T. Chem. Soc. Rev. 2010, 39, 3936-3953
21. Li, A.-F.; Wang, J.-H.; Wang, F.; Jiang, Y.-B. Chem. Soc. Rev. 2010, 39, 3729-3745
22. Wenzel, M.; Hiscock, J. R.; Gale, P. A. Chem. Soc. Rev. 2012, 41, 480-520
23. Ngo, H. T.; Liu, X.; Jolliffe, K. A. Chem. Soc. Rev. 2012, 41, 4928-4965
24. Pal, R.; Beeby, A.; Parker, D. J. Pharm. Biomed. Anal. 2011, 56, 352-358
25. Butler, S. J.; Parker, D. Chem. Soc. Rev. 2013, 42, 1652-1666
26. Gardner, J. W.; Bartlett, P. N. Electronic Noses: Principles and Applications; Oxford University Press: New York, 1999.
27. Rakow, N. A.; Suslick, K. S. Nature 2000, 406, 710-714
28. 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, 2595-2626
29. Lavigne, J. J.; Anslyn, E. V. Angew. Chem., Int. Ed. 2001, 40, 3118-3130
30. Anzenbacher, P., Jr.; Lubal, P.; Bucek, P.; Palacios, M. A.; Kozelkova, M. E. Chem. Soc. Rev. 2010, 39, 3954-3979
31. Paolesse, R.; Monti, D.; Dini, F.; Di Natale, C. Top. Curr. Chem. 2011, 300, 139-174
32. Stitzel, S. E.; Aernecke, M. J.; Walt, D. R. Annu. Rev. Biomed. Eng. 2011, 13, 1-25
33. Nelson, T. L.; O'Sullivan, C.; Greene, N. T.; Maynor, M. S.; Lavigne, J. J. J. Am. Chem. Soc. 2006, 128, 5640-5641
34. Palacios, M. A.; Nishiyabu, R.; Marquez, M.; Anzenbacher, P., Jr. J. Am. Chem. Soc. 2007, 129, 7538-7544
35. Lavigne, J. J. Nat. Mater. 2007, 6, 548-549
36. Palacios, M. A.; Wang, Z.; Montes, V. A.; Zyryanov, G. V.; Hausch, B. J.; JursIkova, K.; Anzenbacher, P., Jr. Chem. Commun. 2007, 3708-3710
37. Zyryanov, G. V.; Palacios, M. A.; Anzenbacher, P., Jr. Angew. Chem., Int. Ed. 2007, 46, 7849-7852
38. Wang, Z.; Palacios, M. A.; Zyryanov, G. V.; Anzenbacher, P., Jr. Chem.-Eur. J. 2008, 14, 8540-8546
39. Wang, Z.; Palacios, M. A.; Anzenbacher, P., Jr. Anal. Chem. 2008, 80, 7451-7459
40. Palacios, M. A.; Wang, Z.; Montes, V. A.; Zyryanov, G. V.; Anzenbacher, P., Jr. J. Am. Chem. Soc. 2008, 130, 10307-10314
41. Shabbir, S. H.; Joyce, L. A.; da Cruz, G. M.; Lynch, V. M.; Sorey, S.; Anslyn, E. V. J. Am. Chem. Soc. 2009, 131, 13125-13131
42. Suslick, B. A.; Feng, L.; Suslick, K. S. Anal. Chem. 2010, 82, 2067-2073
43. Liu, Y.; Palacios, M. A.; Anzenbacher, P., Jr. Chem. Commun. 2010, 46, 1860-1862
44. Feng, L.; Zhang, Y.; Wen, L. Y.; Chen, L.; Shen, Z.; Guan, Y. F. Chem. -Eur. J. 2011, 17, 1101-1104
45. Davey, E. A.; Zucchero, A. J.; Trapp, O.; Bunz, U. H. F. J. Am. Chem. Soc. 2011, 133, 7716-7718
46. Lin, H.; Jang, M.; Suslick, K. S. J. Am. Chem. Soc. 2011, 133, 16786-16789
47. Zhang, X.; You, L.; Anslyn, E. V.; Qian, X. Chem.-Eur. J. 2012, 18, 1102-1110
48. Anzenbacher, P., Jr.; Li, F.; Palacios, M. A. Angew. Chem., Int. Ed. 2012, 51, 2345-2348
49. Lim, J.; Nam, D.; Miljanić, O. Š. Chem. Sci. 2012, 3, 559-563
50. Minami, T.; Esipenko, N. A.; Zhang, B.; Kozelkova, M. E.; Isaacs, L.; Nishiyabu, R.; Kubo, Y.; Anzenbacher, P., Jr. J. Am. Chem. Soc. 2012, 134, 20021-20024
51. Kitamura, M.; Shabbir, S. H.; Anslyn, E. V. J. Org. Chem. 2009, 74, 4479-4489
52. Nishiyabu, R.; Anzenbacher, P., Jr. J. Am. Chem. Soc. 2005, 127, 8270-8271
53. Gale, P. A.; Anzenbacher, P., Jr.; Sessler, J. L. Coord. Chem. Rev. 2001, 222, 57-102
54. Anzenbacher, P., Jr. Top. Heterocycl. Chem. 2010, 24, 205-235
55. Anzenbacher, P., Jr. Top. Heterocycl. Chem. 2010, 24, 237-265
56. Miyaji, H.; Sato, W.; Sessler, J. L. Angew. Chem., Int. Ed. 2000, 39, 1777-1780
57. Nielsen, K. A.; Jeppesen, J. O.; Levillain, E.; Becher, J. Angew. Chem., Int. Ed. 2003, 42, 187-191
58. Nishiyabu, R.; Anzenbacher, P., Jr. Org. Lett. 2006, 8, 359-362
59. Sokkalingam, P.; Kim, D. S.; Hwang, H.; Sessler, J. L.; Lee, C.-H. Chem. Sci. 2012, 3, 1819-1824
60. Gunnlaugsson, T.; Kruger, P. E.; Jensen, P.; Tierney, J.; Ali, H. D. P.; Hussey, G. M. J. Org. Chem. 2005, 70, 10875-10878
61. Quinlan, E.; Matthews, S. E.; Gunnlaugsson, T. J. Org. Chem. 2007, 72, 7497-7503
62. Duke, R. M.; Gunnlaugsson, T. Tetrahedron Lett. 2011, 52, 1503-1505
63. The choice of DMSO and MeCN was made because the binding behavior observed in these polar organic solvents is also observed in arrays when the sensor elements are embedded in polyurethane matrixes and the anions are administered as strictly aqueous solutions. See: Palacios, M. A.; Nishiyabu, R.; Marquez, M.; Anzenbacher, P., Jr. J. Am. Chem. Soc. 2007, 129, 7538-7544
64. Jambu, M. In Exploratory and Multivariate Data Analysis; Academic Press: San Diego, 1991.
65. Beebe, K. R.; Pell, R. J.; Seasholtz, M. B. In Chemometrics: A Practical Guide; Wiley: New York, 1998.
66. Otto, M. Chemometrics, Statistics and Computer Application in Analytical Chemistry; Wiley-VCH: Chichester. 1999.
67. Carey, W.; Beebe, K.; Kowalski, B. Anal. Chem. 1986, 58, 149-153
68. Avila, F.; Myers, D.; Palmer, C. J. Chemometrics 1991, 5, 455-465
69. Green, E.; Olah, M. J.; Abramova, T.; Williams, L. R.; Stefanovic, D.; Worgall, T.; Stojanovic, M. N. J. Am. Chem. Soc. 2006, 128, 15278-15282
70. Turley, S. M. Understanding Pharmacology for Health Professionals, 3 rd ed.; Prentice Hall: New York, 2002
71. Cohen, B. J. Medical Terminology: An Illustrated Guide, 4 th ed.; Lippincott, Williams, & Wilkins: Philadelphia, 2003.