Enzyme assays with boronic acid appended bipyridinium salts

Analytica Chimica Acta

Volumn 649, Issue 2, 2009, Pages 246-251

  Vilozny, Boaz ^a   Schiller, Alexander ^b   Wessling, Ritchie A ^a   Singaram, Bakthan ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

Author keywords

Boronic acid; Enzyme assay; Fluorescence; Saccharide; Viologen

Indexed keywords

BIPYRIDINIUM SALTS; BORONIC ACID; DETECTION LIMITS; ENZYME ASSAY; ENZYME ASSAYS; ENZYME INHIBITORS; GLUCOSE 6 PHOSPHATES; HIGH-THROUGHPUT SCREENING; IN-VITRO; MICHAELIS-MENTEN KINETIC; PHOSPHOGLUCOMUTASE; PRODUCT CONCENTRATION; REACTION VELOCITIES; SACCHARIDE; SELECTIVE RECEPTORS; SENSING SYSTEMS; TRISULFONIC ACID; VIOLOGEN; VIOLOGENS; WORKING RANGE;

ACIDS; CARBOHYDRATES; ENZYMES; FLUORESCENCE; FRUCTOSE; GLUCOSE; REACTION KINETICS; SENSORS; SUGAR (SUCROSE);

ASSAYS;

8 HYDROXYPYRENE 1,3,6 TRISULFONIC ACID TRISODIUM SALT; BIPYRIDINIUM; BORONIC ACID; EDETIC ACID; FRUCTOSE; GLUCOSE 6 PHOSPHATE; LITHIUM CHLORIDE; ORGANOBORON DERIVATIVE; PHOSPHOGLUCOMUTASE; PHOSPHORYLASE; PYRIDINIUM DERIVATIVE; SODIUM DERIVATIVE; SUCROSE PHOSPHORYLASE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; ENZYME ASSAY; FLUORESCENCE ANALYSIS; HIGH THROUGHPUT SCREENING; IN VITRO STUDY; MICHAELIS MENTEN KINETICS; PRIORITY JOURNAL; SENSITIVITY AND SPECIFICITY;

ARYLSULFONATES; BORONIC ACIDS; EDETIC ACID; FRUCTOSE; GLUCOSE-6-PHOSPHATE; GLUCOSYLTRANSFERASES; KINETICS; PHOSPHOGLUCOMUTASE; SPECTROMETRY, FLUORESCENCE; VIOLOGENS;

EID: 68749099625     PISSN: 00032670     EISSN: 18734324     Source Type: Journal    
DOI: 10.1016/j.aca.2009.07.032     Document Type: Article

References (47)

1. Dang Q., Kasibhatla S.R., Reddy K.R., Jiang T., Reddy M.R., Potter S.C., Fujitaki J.M., van Poelje P.D., Huang J., Lipscomb W.N., and Erion M.D. J. Am. Chem. Soc. 129 (2007) 15491 (and references therein)
2. Reymond J.-L. Enzyme Assays (2006), Wiley-VCH, Weinheim
3. Vermeir S., Nicolai B.M., Jans K., Maes G., and Lammertyn J. J. Agric. Food Chem. 55 (2007) 3240
4. Tang Y.L., Teng F., Yu M.H., An L.L., He F., Wang S., Li Y.L., Zhu D.B., and Bazan G.C. Adv. Mater. 20 (2008) 703
5. Wongkongkatep J., Miyahara Y., Ojida A., and Hamachi I. Angew. Chem. Int. Ed. 45 (2006) 665
6. Trebbi D., and McGrath J.M. J. Agric. Food Chem. 52 (2004) 6862
7. Greis K.D. Mass Spectrom. Rev. 26 (2007) 324
8. Liu Y., Ogawa K., and Schanze K.S. Anal. Chem. 80 (2008) 150
9. Schrenkhammer P., Rosnizeck I.C., Duerkop A., Wolfbeis O.S., and Schäferling M. J. Biomol. Screen. 13 (2008) 9
10. An L.L., Tang Y.L., Feng F.D., He F., and Wang S. J. Mater. Chem. 17 (2007) 4147
11. Liu R.R., Liew R.S., Zhou H., and Xing B.G. Angew. Chem. Int. Ed. 46 (2007) 8799
12. Klein G., and Reymond J.L. Angew. Chem. Int. Ed. 40 (2001) 1771
13. Csutora P., Karsai A., Nagy T., Vas B., Kovacs G.L., Rideg O., Bogner P., and Miseta A. Int. J. Neuropsychopharmacol. 9 (2006) 613
14. Csutora P., Strassz A., Boldizsar F., Nemeth P., Sipos K., Aiello D.P., Bedwell D.M., and Miseta A. Am. J. Phys. Cell Physiol. 289 (2005) C58
15. Rossolini G.M., and Mantengoli E. Clin. Microbiol. Infect. 11 (2005) 17
16. Naught L.E., and Tipton P.A. Arch. Biochem. Biophys. 396 (2001) 111
17. Gao H., and Leary J.A. Anal. Biochem. 329 (2004) 269
18. Cui Y., Barford J.P., and Renneberg R. Anal. Biochem. 354 (2006) 162
19. Nakata E., Wang H.X., and Hamachi I. Chembiochem 9 (2008) 25
20. Nomura K., Sugimoto K., Nishiura H., Ohdan K., Nishimura T., Hayashi H., and Kuriki T. Biosci. Biotechnol. Biochem. 72 (2008) 82
21. Sugimoto K., Nomura K., Nishiura H., Ohdan K., Nishimura T., Hayashi H., and Kuriki T. J. Biosci. Bioeng. 104 (2007) 22
22. Inoue H., Kondo S., Hinohara Y., Juni N., and Yamamoto D. Arch. Biochem. Biophys. 413 (2003) 207
23. Treptau T., Kissmehl R., Wissmann J.D., and Plattner H. Biochem. J. 309 (1995) 557
24. Goedl C., Schwarz A., Minani A., and Nidetzky B. J. Biotechnol. 129 (2007) 77
25. van den Broek L.A.M., van Boxtel E.L., Kievit R.P., Verhoef R., Beldman G., and Voragen A.G.J. Appl. Microbiol. Biotechnol. 65 (2004) 219
26. Galban J., Andreu Y., Sierra J.F., de Marcos S., and Castillo J.R. Luminescence 16 (2001) 199
27. Mader H.S., and Wolfbeis O.S. Microchim. Acta 162 (2008) 1
28. Sharrett Z., Gamsey S., Fat J., Cunningham-Bryant D., Wessling R.A., and Singaram B. Tetrahedron Lett. 48 (2007) 5125
29. Gamsey S., Miller A., Olmstead M.M., Beavers C.M., Hirayama L.C., Pradhan S., Wessling R.A., and Singaram B. J. Am. Chem. Soc. 129 (2007) 1278
30. Suri J.T., Cordes D.B., Cappuccio F.E., Wessling R.A., and Singaram B. Angew. Chem. Int. Ed. 42 (2003) 5857
31. Schiller A., Wessling R.A., and Singaram B. Angew. Chem. Int. Ed. 46 (2007) 6457
32. Schiller A., Vilozny B., Wessling R.A., and Singaram B. Anal. Acta Chim. 627 (2008) 203
33. Kermis H.R., Koslov Y., Harms P., and Rao G. Biotechnol. Prog. 18 (2002) 1047
34. Gamsey S., Baxter N.A., Sharrett Z., Cordes D.B., Olmstead M.M., Wessling R.A., and Singaram B. Tetrahedron 62 (2006) 6321
35. Weiss S., John G.T., Klimant I., and Heinzle E. Biotechnol. Prog. 18 (2002) 821
36. See supporting information for details.
37. Very few boronic acid units have yet been demonstrated to bind to nonreducing sugars and glycosides, see:. Dowlut M., and Hall D.G. J. Am. Chem. Soc. 128 (2006) 4226
38. -1.
39. Yang W.Q., Gao X.M., and Wang B.H. Med. Res. Rev. 23 (2003) 346
40. m could not be determined as it is below the detection limit for glucose-6-phosphate, see:. Naught L.E., Regni C., Beamer L.J., and Tipton P.A. Biochemistry 42 (2003) 9946
41. Silverstein R., Voet J., Reed D., and Abeles R.H. J. Biol. Chem. 242 (1967) 1338
42. Tedokon M., Suzuki K., Kayamori Y., Fujita S., and Katayama Y. Clin. Chem. 38 (1992) 512
43. Grazi E., Trombetta G., and Morisi F. J. Mol. Catal. 2 (1977) 453
44. Ray W.J., and Roscelli G.A. J. Biol. Chem. 241 (1966) 2596
45. In case of using an ex situ calibration to determine the reaction velocity, reaction rates (fluorescence intensity increase per minute) were calculated to demonstrate the rapid identification of enzyme inhibitors.
46. Ray W.J., Szymanki E.S., and Ng L. Biochim. Biophys. Acta 522 (1978) 434
47. Sharrett Z., Gamsey S., Levine P., Cunningham-Bryant D., Vilozny B., Schiller A., Wessling R.A., and Singaram B. Tetrahedron Lett. 49 (2008) 300