Cp*Rh-based indicator-displacement assays for the identification of amino sugars and aminoglycosides

Chemistry - A European Journal

Volumn 12, Issue 14, 2006, Pages 3928-3934

  Zaubitzer, Friederike ^a   Buryak, Andrey ^a   Severin, Kay ^a  

^a EPFL   (Switzerland)

Author keywords

Amino sugars; Amino glycosides; Organometallic complexes; Rhodium; Sensors

Indexed keywords

AMINES; ASSAYS; COMPLEXATION; ORGANOMETALLICS; RHODIUM; SENSORS; SOLUTIONS; SPECTROSCOPIC ANALYSIS;

AMINO SUGARS; AMINO-GLYCOSIDES; ORGANOMETALLIC COMPLEXES; QUANTITATIVE INFORMATION;

SUGARS;

AMINOGLYCOSIDE; AMINOSUGAR; GALLOCYANIN; ORGANOMETALLIC COMPOUND; OXAZINE DERIVATIVE; RHODIUM;

ARTICLE; CARBOHYDRATE ANALYSIS; CHEMISTRY; METHODOLOGY; MOLECULAR GENETICS; SENSITIVITY AND SPECIFICITY; ULTRAVIOLET SPECTROPHOTOMETRY;

AMINO SUGARS; AMINOGLYCOSIDES; CARBOHYDRATE SEQUENCE; CHEMISTRY, ANALYTICAL; MOLECULAR SEQUENCE DATA; ORGANOMETALLIC COMPOUNDS; OXAZINES; RHODIUM; SENSITIVITY AND SPECIFICITY; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 33646527166     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200501410     Document Type: Article

References (87)

1. For reviews, see: a) F. Mancin, E. Rampazzo, P. Tecilla, U. Tonellato, Chem. Eur. J. 2005, 12, 1844-1854;
2. b) L. Fabbrizzi, M. Licchelli, A. Taglietti, Dalton Trans. 2003, 3471-3479;
3. c) C. Suksai, T. Tuntulani, Chem. Soc. Rev. 2003, 32, 192-202;
4. d) S. L. Wiskur, H. Aït-Haddou, J. J. Lavigne, E. V. Anslyn, Acc. Chem. Res. 2001, 34, 963-972.
5. A. M. Pia̧tek, Y. J. Bomble, S. L. Wiskur, E. V. Anslyn, J. Am. Chem. Soc. 2004, 126, 6072-6077.
6. a) R. G. Hanshaw, S. M. Hilkert, J. Hua, B. D. Smith, Tetrahedron Lett. 2004, 45, 8721-8724;
7. b) S. L. Tobey, E.V. Anslyn, Org. Lett. 2003, 5, 2029-2031;
8. c) Z. Zhong, E. V. Anslyn, Angew. Chem. 2003, 115, 3113-3116;
9. Angew. Chem. Int. Ed. 2003, 42, 3005-3008;
10. d) M.S. Han, D.H. Kim, Angew. Chem. 2002, 114, 3963-3965;
11. Angew. Chem. Int. Ed. 2002, 41, 3809-3811;
12. e) L. Fabbrizzi, N. Marcotte, F. Stomeo, A. Taglietti, Angew. Chem. 2002, 114, 2665-2668;
13. Angew. Chem. Int. Ed. 2002, 41, 3811-3814.
14. a) R. G. Hanshaw, E. J. O'Neil, M. Foley, R. T. Carpenter, B. D. Smith, J. Mater. Chem. 2005, 15, 2707-2713;
15. b) T. Zhang, E.V. Anslyn, Tetrahedron 2004, 60, 11117-11124.
16. C.-F. Chow, M. H. W. Lam, W.-Y. Wong, Inorg. Chem. 2004, 43, 8387-8393.
17. a) M. H. Lim, S. J. Lippard, Inorg. Chem. 2004, 43, 6366-6370;
18. b) S. A. Hilderbrand, M. H. Lee, S. J. Lippard, J. Am. Chem. Soc. 2004, 126, 4972-4987.
19. L. Fabbrizzi, A. Leone, A. Taglietti, Angew. Chem. 2001, 113, 3156-3159;
20. Angew. Chem. Int. Ed. 2001, 40, 3066-3069.
21. a) J. F. Folmer-Andersen, V. M. Lynch, E. V. Anslyn, Chem. Eur. J. 2005, 11, 5319-5326;
22. b) C.-F. Chow, M. H. W. Lam, H. Sui, W.-Y. Wong, Dalton Trans. 2005, 475-484;
23. c) M. Bonizzoni, L. Fabbrizzi, G. Piovani, A. Taglietti, Tetrahedron 2004, 60, 11159-11162;
24. d) M. S. Han, D. H. Kim, Tetrahedron 2004, 60, 11251-11257;
25. e) C.-F. Chow, B. K. W. Chiu, M. H. W. Lam, W.-Y. Wong, J. Am. Chem. Soc. 2003, 125, 7802-7803;
26. f) M. A. Hortalá, L. Fabbrizzi, N. Marcotte, F. Stomeo, A. Taglietti, J. Am. Chem. Soc, 2003, 125, 20-21;
27. g) K. E. S. Dean, G. Klein, O. Renaudet, J.-L. Reymond, Bioorg. Med. Chem. Lett. 2003, 13, 1653-1656;
28. h) H. Aït-Haddou, S. L. Wiskur, V. M. Lynch, E. V. Anslyn, J. Am. Chem. Soc. 2001, 123, 11296-11297;
29. i) G. Klein, J.-L. Reymond, Angew. Chem. 2001, 113, 1821-1823;
30. Angew. Chem. Int. Ed. 2001, 40, 1771-1773.
31. For the colorimetric enantiodiscrimination of amino acids, see: J. F. Folmer-Andersen, V. M. Lynch, E. V. Anslyn, J. Am. Chem. Soc. 2005, 127, 7986-7987.
32. L. Fabbrizzi, F. Foti, A. Taglietti, Org. Lett. 2005, 7, 2603-2606.
33. M. Boiocchi, M. Bonizzoni, L. Fabbrizzi, G. Piovani, A. Taglietti, Angew. Chem. 2004, 116, 3935-3940;
34. Angew. Chem. Int. Ed. 2004, 43, 3847-3852.
35. D. H. Kim, M. S. Han, Bioorg. Med. Chem. Lett. 2003, 13, 2543-2546.
36. For (arene)Ru complexes that can be used to sense lithium ions, see: a) Z. Grote, R. Scopelliti, K. Severin, J. Am. Chem. Soc. 2004, 126, 16959-16972;
37. b) Z. Grote, M.-L. Lehaire, R. Scopelliti, K. Severin, J. Am. Chem. Soc. 2003, 125, 13638-13639;
38. c) H. Piotrowski, K. Severin, Proc. Natl. Acad. Sci. USA 2002, 99, 4997-5000;
39. d) H. Piotrowski, G. Hilt, A. Schulz, P. Mayer, K. Polborn, K. Severin, Chem. Eur. J. 2001, 7, 3197-3208;
40. e) H. Piotrowski, K. Polborn, G. Hilt, K. Severin, J. Am. Chem. Soc. 2001, 123, 2699-2700.
41. For a Cp*Ir complex that can be used to sense fluoride ions, see: M.-L. Lehaire, R. Scopelliti, H. Piotrowski, K. Severin, Angew. Chem. 2002, 114, 1477-1480;
42. Angew. Chem. Int. Ed. 2002, 41, 1419-1422.
43. A. Buryak, K. Severin, Angew. Chem. 2004, 116, 4875-4878;
44. Angew. Chem. Int. Ed. 2004, 43, 4771-4774.
45. A. Buryak, K. Severin, J. Am. Chem. Soc. 2005, 127, 3700-3701.
46. Despite the high binding constants, ligand-exchange reactions at the three coordination sites opposite to the Cp* ligand are relatively fast: L. Helm, A. E. Merbach, Chem. Rev. 2005, 105, 1923-1959.
47. S. B. Vakulenko, S. Mobashery, Clin. Microbiol. Rev. 2003, 16, 430-450.
48. For a review, see: D. A. Stead, J. Chromatogr. B 2000, 747, 69-93.
49. a) M. Rizk, S. S. Toubar, M. S. Abdel-Mottaleb, H. I. Ali, Bull. Fac. Pharm. 2003, 41, 141-148;
50. b) Y. El-Shabrawy, Spectrosc. Lett. 2002, 35, 99-109;
51. c) J. Kusnir, K. Barna, Z. Anal. Chem. 1974, 271, 288.
52. For the detection of aminoglycosides by HPLC in combination with a ligand displacement reaction, see: M. Yang, S. A. Tomellini, J. Chromatogr. A 2001, 939, 59-67.
53. Other indicators tested include arsenazo I, celestin blue, and Chicago sky blue. Arsenazo I was disregarded because amino sugars were not able to replace it from the Cp*Rh complex and celestin blue was rejected because of solubility problems. Chigaco sky blue is potentially suited for amino sugar IDAs, but it was found to bind more than one Cp*Rh fragment, which would complicate the analysis.
54. For reviews of sensor arrays, see: a) A. T. Wright, E. V. Anslyn, Chem. Soc. Rev. 2006, 35, 14-28;
55. b) K. L. Brogan, D. R. Walt, Curr. Opin. Chem. Biol. 2005, 9, 494-500;
56. c) D. James, S. M. Scott, Z. Ali, W.T. O'Hare, Microchim. Acta 2005, 149, 1-17;
57. d) J. J. Lavigne, E.V. Anslyn, Angew. Chem. 2001, 113, 3212-3225;
58. Angew. Chem. Int. Ed. 2001, 40, 3119-3130;
59. e) K. J. Albert, N. S. Lewis, C. L. Schauer, G. A. Sotzing, S. E. Stitzel, T. P. Vaid, D. R. Walt, Chem. Rev. 2000, 100, 2595-2626.
60. For recent publications concerning optical sensor arrays, see: a) C. Zhang, K. S. Suslick, J. Am. Chem. Soc. 2005, 127, 11548-11549;
61. b) N. A. Rakow, A. Sen, M. C. Janzen, J. B. Ponder, K. S. Suslick, Angew. Chem. 2005, 117, 4604-4608;
62. Angew. Chem. Int. Ed. 2005, 44, 4528-4532;
63. c) K. S. Suslick, N. A. Rakow, A. Sen, Tetrahedron 2004, 60, 11133-11138;
64. d) L. Baldini, A.J. Wilson, J. Hong, A.D. Hamilton, J. Am. Chem. Soc. 2004, 126, 5656-5657;
65. e) E. A. Baldauff, J. M. Buriak, Chem. Commun. 2004, 2028-2029;
66. f) M. N. Stojanovic, E. G. Green, S. Semova, D. B. Nikić, D. W. Landry, J. Am. Chem. Soc. 2003, 125, 6085-6089;
67. g) A. P. Goodey, J. T. McDevitt, J. Am. Chem. Soc. 2003, 125, 2870-2871;
68. h) A. Goodey, J. J. Lavigne, S. M. Savoy, M. D. Rodriguez, T. Curey, A. Tsao, G. Simmons, J. Wright, S.-J. Yoo, Y. Sohn, E. V. Anslyn, J. B. Shear, D. P. Neikirk, J. T. McDevitt, J. Am. Chem. Soc. 2001, 123, 2559-2570;
69. i) N. A. Rakow, K. S. Suslick, Nature 2000, 406, 710-713.
70. a) A. T. Wright, M. J. Griffin, Z. Zhong, S. C. McCleskey, E.V. Anslyn, J. T. McDevitt, Angew. Chem. 2005, 117, 6533-6536;
71. Angew. Chem. Int. Ed. 2005, 44, 6375-6378;
72. b) N. T. Greene, K. D. Shimizu, J. Am. Chem. Soc. 2005, 127, 5695-5700;
73. c) S. C. McCleskey, M. J. Griffin, S. E. Schneider, J. T. McDevitt, E. V. Anslyn, J. Am. Chem. Soc. 2003, 125, 1114-1115.
74. For the acid-base properties of aminoglycosides, see: H. Kozłowski, T. Kowalik-Jankowska, M. Jeżowska-Bojczuk, Coord. Chem. Rev. 2005, 249, 2323-2334.
75. P. C. Jurs, G. A. Bakken, H. E. McClelland, Chem. Rev. 2000, 100, 2649-2678.
76. For concentrations of more than 120 UM, a simultaneous identification and quantification was no longer possible.
77. a) G. Jaouen, Bioorganometallics, Wiley-VCH, Weinheim, 2005;
78. b) D. R. van Staveren, N. Metzler-Nolte, Chem. Rev. 2004, 104, 5931-5985;
79. c) R. H. Fish, G. Jaouen, Organometallics 2003, 22, 2166-2177;
80. d) K. Severin, Coord. Chem. Rev. 2003, 245, 3-10;
81. e) M. Salmain, G. Jaouen, C. R. Chimie 2003, 6, 249-258;
82. f) W. Beck, K. Severin, Chem. Unserer Zeit 2002, 36, 356-365;
83. g) N. Metzler-Nolte, Angew. Chem. 2001, 113, 1072-1076;
84. Angew. Chem. Int. Ed. 2001, 40, 1040-1043.
85. C. White, A. Yates, P. M. Maitlis, Inorg. Synth. 1992, 29, 228-234.
86. a) P. Mendes, Comput. Appl. Biosci. 1993, 9, 563-571;
87. b) P. Mendes, Trends Biochem. Sci. 1997, 22, 361-363.