Disulfide symmetric dimers as stable pre-hapten forms for bioconjugation: A strategy to prepare immunoreagents for the detection of sulfophenyl carboxylate residues in environmental samples

Chemistry - A European Journal

Volumn 14, Issue 6, 2008, Pages 1906-1917

  Estévez, M Carmen ^a   Galve, Roger ^a   Sánchez Baeza, Francisco ^a   Marco, M Pilar ^a  

^a CSIC   (Spain)

Author keywords

Antibodies; Carboxylates; Immunization; Immunoassays; Resins; Solid phase synthesis; Sulfophenyl

Indexed keywords

ABS RESINS; ANTIGENS; BIOMOLECULES; MOLECULAR BIOLOGY; OLIGOMERS; POLYSTYRENES; RESINS;

ANTIBODIES; CARBOXYLATES; IMMUNIZATION; IMMUNOASSAYS; SOLID-PHASE SYNTHESIS; SULFOPHENYL;

CARBOXYLATION;

DISULFIDE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; SURFACTANT;

ARTICLE; CHEMISTRY; DIMERIZATION; ELECTROSPRAY MASS SPECTROMETRY; ENZYME LINKED IMMUNOSORBENT ASSAY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLLUTANT; SENSITIVITY AND SPECIFICITY;

DIMERIZATION; DISULFIDES; ENVIRONMENTAL POLLUTANTS; ENZYME-LINKED IMMUNOSORBENT ASSAY; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; SENSITIVITY AND SPECIFICITY; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SURFACE-ACTIVE AGENTS;

EID: 53849123337     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200701232     Document Type: Article

References (53)

1. A. Oubiña, B. Ballesteros, P. Bou, R. Galve, J. Gascón, F. Iglesias, N. Sanvicens and M.-P. Marco in Immunoassays for Environmental Analysis, Vol. 21 (Ed.: D. Barceló). Elsevier. Amsterdam, The Netherlands, 2000, pp. 289-340.
2. Y. Xu, N. Yamamoto, K. D. Janda, Bioorg. Med. Chem. 2004, 12, 5247-5268.
3. J. Emneus in Integrated Immuno Extraction Sampling and Portable Biosensor Prototype for In-field Monitoring, EC, Environmental and Climate Program ENV4-CT97-0476, Lund 1997-2000.
4. P. Schöberl, Tenside Surfactants Deterg. 1989, 26, 86-94.
5. T. P. Knepper, M. Kruse, Tenside Surfactants Deterg. 2000, 37, 41 - 47.
6. A. Marcomini, G. Pojana, A. Sfriso, J. M. Quiroga. Environ. Toxicol. Chem. 2003, 19, 2000-2007.
7. V. Andreu, Y. Picó, Anal. Chem. 2004, 76, 2878-2885.
8. V. M. Leon, A. Gomez-Parra, E. Gonzalez-Mazo, Environ. Sci. Technol. 2004, 38, 2359-2367.
9. J. A. Perales, M. A. Manzano, D. Sales, J. M. Quiroga, Int. Biodeterior. Biodegrad. 2003, 51, 187-194.
10. M. Mosche, U. Meyer, Water Res 2002, 36, 3253-3260.
11. J. Vives-Vego, R. López-Amorós, T. Guindulain, M. T. García, J. Comas, J. Sánchez-Leal, J. Surfactants Deterg. 2000, 3, 303-308.
12. P. Eichhorn, S. V. Rodrigues, W. Baumann, T. P. Knepper, Sci. Total Environ. 2002, 284, 123-134.
13. P. Eichhorn, M. E. Flavier, M. L. Paje, T. P. Knepper, Sci. Total Environ. 2001, 269, 75-85.
14. E. Gonzalez-Mazo, V. M. Leon, M. Saez, A. Gomez-Parra, Sci. Total Environ. 2002, 288, 215-226.
15. W.-H. Ding, J.-H. Lo, S.-H. Tzing. J. Chromatogr. A 1998, 818, 270-279.
16. P. Eichhorn, T. P. Knepper, F. Ventura, A. Diaz, Water Res. 2002, 36, 2179-2186.
17. E. Gonzalez-Mazo, M. Honing, D. Barcelo, A. Gomez-Parra, Environ. Sci. Technol. 1991, 31, 504-510.
18. C. A. Spinks, G. M. Wyatt, H. A. Lee, M. R. A. Morgan, Bioconjugate Chem. 1999, 10, 583-588.
19. P. Cliquet, E. Cox, W. Haasnoot, E. Schacht, B. M. Goddeeris, J. Agric. Food Chem. 2003, 51, 5835-5842.
20. C. A. Spinks, G. M. Wyatt, S. Everest, R. Jackman, M. R. A. Morgan, J. Sci. Food Agric. 2002, 82, 428-434.
21. P. Degelmann, J. Wenger, R. Niessner, D. Knopp, Environ. Sci. Technol. 2004, 38, 6795-6802.
22. V. Kolar, A. P. Deng, M. Franek, Food Agric. Immunol. 2002, 14, 91-105.
23. M.-C. Estevez, R. Galve, F. Sanchez-Baeza, M.-P. Marco, Anal. Chem. 2005, 77, 5283-5293.
24. T. Korpimaki, V. Hagren, E. C. Brockmann, M. Tuomola, Anal. Chem. 2004, 76, 3091-3098.
25. T. Korpimaki, J. Rosenberg, P. Virtanen, T. Karskela, U. Lamminmaki, M. Tuomola, M. Vehniainen, P. Saviranta, J. Agric. Food Chem. 2002, 50, 4194-4201.
26. T. Korpimaki, J. Rosenberg, P. Virtanen, U. Lamminmaki, M. Tuomola, P. Saviranta, Protein Eng. 2003, 16, 37-46.
27. T. Tsumuraya, H. Suga, S. Meguro, A. Tsunakawa, S. Masamune, J. Am. Chem. Soc. 1995, 117, 11390-11396.
28. H. Suga, O. Ersoy, S. F. Williams, T. Tsumuraya, M. N. Margolies, A. J. Sinskey. S. Masamune, J. Am. Chem. Soc. 1994, 116, 6025-6026.
29. O. Ersoy, R. Fleck, A. Sinskey, S. Masamune, J. Am. Chem. Soc. 1996, 118, 13077-13078.
30. T. Tsumuraya, N. Takazawa, A. Tsunakawa, R. Fleck, S. Masamune, Chem. Eur. J. 2001, 7, 3748-3755.
31. T. W. Green, P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley, Canada, 1999.
32. S. S. Wong, Chemistry of Protein Conjugation and Cross-linking, CRC Press, Boca Raton, Fl. 1993.
33. H. T. Clarke, G. S. Babcock, T. F. Murray, Organic Synthesis, Vol. 1, 1932.
34. P. W. Riddles, R. L. Blakeley, B. Zerner, Anal. Biochem. 1979, 94, 75-81.
35. J. T. Avers, S. R. Anderson. Synth. Commun. 1999, 29, 351-358.
36. B. Ballesteros, D. Barcelo, F. Sanchez-Baeza, F. Camps, M. P. Marco, Anal. Chem. 1998, 70, 4004-4014.
37. R. Galve, F. Camps, F. Sanchez-Baeza, M. P. Marco, Anal. Chem. 2000, 72, 2237-2246.
38. N. Sanvicens, F. Sanchez-Baeza, M. P. Marco, J. Agric. Food Chem. 2003, 51, 3924-3931.
39. M. C. Estevez, M. Kreuzer, F. Sanchez-Baeza, M. P. Marco, Environ. Sci. Technol. 2006, 40, 559-568.
40. J. Brichta, M. Hnilova, T. Viskovic, Vet. Med. 2005, 50, 231-252.
41. W. Kusharyoto, J. Pleiss, T. T. Bachmann, R. D. Schmid, Environ. Prot. Eng. 2002, 15, 233-241.
42. V. G. Omelyaneko, W. Jiskoot, J. N. Herron, Biochemistry 1993, 32, 10423-10429.
43. C. J. van Oss, Mol. Immunol. 1995, 32, 199-211.
44. J. N. Herron, D. M. Kranz, D. M. Jameson, E. W. J. Voss, Biochemistry 1986, 25, 4602-4609.
45. G. Zeder-Lutz, N. Rauffer, D. Altschuh, M. H. V. Van Regenmortel, J. Immunol. Methods 1995, 189, 131-140.
46. O. Ersoy, R. Fleck, M. J. Blanco, S. Masamune. Bioorg. Med. Chem. 1999, 7, 279-286.
47. O. Ersoy, R. Fleck, A. Sinskey, S. Masamune, J. Am. Chem. Soc. 1998, 120, 817-818.
48. O. Nielsen, O. Buchardt, Synthesis 1991, 819-821.
49. M. S. Bernatowicz, G. R. Matsueda, Anal. Biochem. 1986, 155, 95-102.
50. J. Gascón, A. Oubiõa, B. Ballesteros, D. Barceló, F. Camps, M.-P. Marco, M.-A. González-Martinez, S. Morais, R. Puchades, A. Maquiera, Anal. Chim. Acta 1997, 347, 149-162.
51. C. Wittmann, B. Hock, J. Agric. Food Chem. 1991, 39, 1194-1200.
52. B. Ballesteros, D. Barceló, F. Camps, M.-P. Marco, Anal. Chim. Acta 1997, 347, 139-147.
53. mix, and the immunochemical performance of the anlibodies under different physicochemical conditions are given in the Supporting Information.