The use of enzyme immunoassays for the detection of abzymatic activities. Application to an enantioselective thioacetal hydrolysis activity

Journal of Immunological Methods

Volumn 269, Issue 1-2, 2002, Pages 133-145

  Gauchet, Cécile ^a   Taran, Frédéric ^a   Renard, Pierre Yves ^a,b   Créminon, Christophe ^c   Grassi, Jacques ^c   Pradelles, Philippe ^c   Mioskowski, Charles ^a,d  

^a CEA SACLAY   (France)

^b CENTRE D ETUDES DU BOUCHET   (France)

^c Institut National de la Recherche Agronomique   (France)

^d UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

Catalytic antibody; High throughput screening; Thioacetal hydrolysis

Indexed keywords

ACETAL DERIVATIVE; ACETIC ACID DERIVATIVE; ACETYLCHOLINESTERASE; CATALYTIC ANTIBODY; HAPTEN; HYDROXY(3 METHOXY 4 METHYLSULFANYLMETHOXYPHENYL)ACETIC ACID; MONOCLONAL ANTIBODY; THIOACETAL; UNCLASSIFIED DRUG; VANILMANDELIC ACID;

ACCURACY; ANALYTIC METHOD; ANTIBODY DETECTION; ANTIBODY SCREENING; ARTICLE; CATALYSIS; ENANTIOMER; ENANTIOSELECTIVITY; ENZYME ACTIVITY; ENZYME IMMUNOASSAY; ENZYME LINKED IMMUNOSORBENT ASSAY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; PRIORITY JOURNAL;

ACETIC ACIDS; ACETYLCHOLINESTERASE; ANTIBODIES, CATALYTIC; ANTIBODIES, MONOCLONAL; CATALYSIS; HYDROLYSIS; IMMUNOENZYME TECHNIQUES; MANDELIC ACIDS; PROTON-TRANSLOCATING ATPASES; VANILMANDELIC ACID;

FELIS CATUS;

EID: 0036837164     PISSN: 00221759     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-1759(02)00230-2     Document Type: Article

References (59)

1. Baca M., Scanlan T.S., Stephenson R.C., Wells J.A. Phage display of a catalytic antibody to optimize affinity for transition-state analog binding. Proc. Natl. Acad. Sci. U. S. A. 94:1997;10063.
2. Badalassi F., Wahler D., Klein G., Crotti P., Reymond J.L. A versatile periodate-coupled fluorogenic assay for hydrolytic enzymes. Angew. Chem., Int. Ed. 39:2000;4067.
3. Benedetti F., Berti F., Flego M., Resmini M., Bastiani E. A competitive immunoassay for the detection of esterolytic activity of antibodies and enzymes. Anal. Biochem. 256:1998;67.
4. Braisted C., Schultz P.G. An antibody-catalyzed oxy-cope rearrangement. J. Am. Chem. Soc. 116:1994;2211.
5. Carrera M.R., Ashley J.A., Parsons L.H., Wirsching P., Koob G.F., Janda K.D. Suppression of psychoactive effects of cocaine by active immunization. Nature. 378:1995;727.
6. Chen Y.W., Reymond J.L., Lerner R.A. Antibody-catalyzed 1,2-rearrangement involving C-C bonds. Angew. Chem., Int. Ed. Engl. 33:1994;1607.
7. Corey E.J., Bock M.G. Protection of primary hydroxyl groups as (methylthio)methyl ethers. Tetrahedron Lett. 38:1975;3269.
8. Cravart B.F., Ashley J.A., Janda K.D., Boger D.L., Lerner R.A. Crossing extreme mechanistic barriers by antibody catalysis: syn elimination to a cis olefin. J. Am. Chem. Soc. 116:1994;6013.
9. Desilva B.S., Orosz G., Egodage K.L., Carlson R.G., Schowen R.L., Wilson G.S. Catalytic antibodies for complex reactions: hapten design and the importance of screening for catalysis in the generation of catalytic antibodies for the NDA/CN reaction. Appl. Biochem. Biotechnol. 83:2000;195.
10. Ellman G.L., Courtney K.D., Andres V., Featherstone R.M. A new and rapid colorimetric determination of acetylcholine esterase activity. Biochem. Pharmacol. 7:1961;88.
11. Fenniri H., Janda K.D., Lerner R.A. Encoded reaction cassette for the highly sensitive detection of the making and breaking of chemicals bonds. Proc. Natl. Acad. Sci. U. S. A. 92:1995;2278.
12. Gong B., Lesley S.A., Schultz P.G. A chromogenic assay for screening large antibody libraries. J. Am. Chem. Soc. 114:1992;1486.
13. Gouverneur V.E., Houk K.N., de Pascual-Teresa B., Beno B., Janda K.D., Lerner R.A. Control of the exo and endo pathways of the Diels-Alder reaction by antibody catalysis. Science. 262:1993;204.
14. Hilvert D. Critical analysis of antibody catalysis. Annu. Rev. Biochem. 69:2000;751.
15. Hilvert D., Hill K.W., Auditor M.T.M. Antibody catalysis of the Diels-Alder reaction. J. Am. Chem. Soc. 111:1989;9262.
16. Holton R.A., Davis R.G. Protection of phenols as methylthiomethyl ethers. Tetrahedron Lett. 40:1977;533.
17. Hua T.D., Rolland-Fulcrand V., Lazaro R., Viallefont V., Lefranc M.P., Weil M. Detection of enzyme activity at trace levels: a new perspective for the direct screening of active catalytic antibodies. Tetrahedron Lett. 37:1996;175.
18. Jaeger K.E., Reetz M.T. Directed evolution of enantioselective enzymes for organic chemistry. Curr. Opin. Chem. Biol. 4:2000;68.
19. Janda K.D., Shevlin C.G., Lerner R.A. Antibody catalysis of a disfavored chemical transformation. Science. 259:1993;490.
20. Janda K.D., Lo C.-H.L., Li T., Barbas C.F. III, Wirsching P., Lerner R.A. Direct selection for a catalytic mechanism from combinatorial antibody libraries. Proc. Natl. Acad. Sci. U. S. A. 91:1994;2532.
21. Janda K.D., Lo L.C., Lo C.-H.L., Sim M.M., Wang R., Wong C.H., Lerner R.A. Chemical selection for catalysis in combinatorial antibody libraries. Science. 275:1997;945.
22. Klein G., Reymond J.L. An enzyme assay using pM. Angew. Chem., Int. Ed. 40:2001;1771.
23. Koch A., Reymond J.L., Lerner R.A. Antibody-catalyzed activation of unfunctionalized olefins for highly enantioselective asymmetric epoxidation. J. Am. Chem. Soc. 116:1994;803.
24. Koch T., Reymond J.L., Lerner R.A. Antibody catalysis of multistep reactions: an aldol addition followed by a disfavored elimination. J. Am. Chem. Soc. 117:1995;9383.
25. Kohler G., Milstein C. Continuous cultures of fused cells secreting antibody of predefined specificity. Nature. 256:1975;495.
26. Landry D.W., Zhao K., Yang G.X.Q., Glickman M., Georgiadis T.M. Antibody-catalyzed degradation of cocaine. Science. 259:1993;1899.
27. Lane J.W., Hong X., Schwabacher A.W. Sensitive detection of catalytic species without chromophoric substrates. J. Am. Chem. Soc. 115:1993;2078.
28. MacBeath G., Hilvert D. Monitoring catalytic activity by immunoassay: implications for screening. J. Am. Chem. Soc. 116:1994;6101.
29. Mader M.M., Bartlett P.A. Binding energy and catalysis: the implications for transition-state analogs and catalytic antibodies. Chem. Rev. 97:1997;1281.
30. Massoulié J., Bon S. Affinity chromatography of acetylcholinesterase. The importance of hydrophobic interactions. Eur. J. Biochem. 68:1976;539.
31. Mets B., Winger G., Cabrera C., Seo S., Jamdar S., Yang G., Zhao K., Briscoe R.J., Almonte R., Woods J.H., Landry D.W. A catalytic antibody against cocaine prevents cocaine's reinforcing and toxic effects in rats. Proc. Natl. Acad. Sci. U. S. A. 95:1998;10176.
32. Motherwell W.B., Bingham M.J., Six Y. Recent progress in the design and synthesis of artificial enzymes. Tetrahedron. 57:2001;4663.
33. Pollack S.J., Jacobs J.W., Schultz P.G. Selective chemical catalysis by an antibody. Science. 234:1986;1570.
34. Pradelles P., Grassi J., Maclouf J. Enzyme immunoassays of eicosanoids using acetylcholine esterase as label: an alternative to radioimmunoassay. Anal. Chem. 57:1985;1170.
35. Pradelles P., Grassi J., Chabardes D., Guiso N. Enzyme immunoassays of adenosine cyclic 3′,5′-monophosphate and guanosine cyclic 3′,5′-monophosphate using acetylcholinesterase. Anal. Chem. 61:1989;447.
36. Rader C., List B. Catalytic antibodies as magic bullets. Chem. Eur. J. 6:2000;2091.
37. Reymond J.L. Catalytic antibodies for organic synthesis. Top. Curr. Chem. 200:1999;59.
38. Reymond J.L., Janda K.D., Lerner R.A. Antibody-catalyzed hydrolysis of glycosidic compounds. Angew. Chem., Int. Ed. Engl. 30:1991;1711.
39. Reymond J.L., Jahangiri G.K., Stoudt C., Lerner R.A. Antibody catalyzed hydrolysis of enol ethers. J. Am. Chem. Soc. 115:1993;3909.
40. Reymond J.L., Koch T., Schroer J., Tirney E. A general assay for antibody catalysis using acridone as a fluorescent tag. Proc. Natl. Acad. Sci. 93:1996;4251.
41. Rodbard D., Lewald J.E. Computer analysis of radioligand assay and radioimmunoassay data. Acta Endocrinol., Suppl. (Copenh.). 147:1970;79.
42. Shabat D., Itzhaky H., Reymond J.L., Kelnan E. Antibody catalysis of a reaction otherwise strongly disfavoured in water. Nature. 374:1995;143.
43. Sinha S.C., Keinan E., Reymond J.L. Antibody-catalyzed enantioselective epoxide hydrolysis. J. Am. Chem. Soc. 115:1993;4893-4894.
44. Smithrud D.B., Benkovic S.J. The state of antibody catalysis. Curr. Opin. Biotechnol. 8:1997;459.
45. Taran F., Bernard H., Valleix A., Creminon C., Grassi J., Olichon D., Deverre J.R., Pradelles P. Competitive enzyme immunoassay for urinary vanillylmandelic acid (VMA). Clin. Chim. Acta. 264:1997;177.
46. Taran F., Renard P.Y., Bernard H., Mioskowski C., Frobert Y., Pradelles P., Grassi J. Antibody-catalyzed decarboxylative oxidation of vanillylmandelic acid. J. Am. Chem. Soc. 120:1998;3332.
47. Taran F., Renard P.Y., Créminon C., Valleix A., Frobert Y., Pradelles P., Grassi J., Mioskowski C. Competitive immunoassay (Cat-EIA), a helpful technique for catalytic antibody detection; Part I and II. Tetrahedron Lett. 40:1999;. 1887 and 1891.
48. Taran F., Gauchet C., Mohar B., Meunier S., Valleix A., Renard P.Y., Créminon C., Grassi J., Wagner A., Mioskowski C. High-throughput screening of enantioselective catalysts by immunoassay. Angew. Chem. Int. Ed. 114:2002;132-135.
49. Tawfik D.S., Green S.B., Chap R., Sela M., Eshhar Z. catELISA: a facile general route to catalytic antibodies. Proc. Natl. Acad. Sci. 90:1993;373.
50. Thomas N.R. Catalytic antibodies-reaching adolescence? Nat. Prod. Rep. 13:1996;479.
51. Tramontano A., Janda K.D., Lerner R.A. Catalytic antibodies. Science. 234:1986;1566.
52. Ulrich H.D., Mundorff E., Santarsiero B.D., Driggers E.M., Stevens R.C., Schultz P.G. The interplay between binding energy and catalysis in the evolution of a catalytic antibody. Nature. 389:1997;271.
53. Vayron P., Renard P.Y., Taran F., Créminon C., Frobert Y., Grassi J., Mioskowski C. Towards antibody-catalyzed hydrolysis of organophosphorus poisons. Proc. Natl. Acad. Sci. U. S. A. 97:2000;7058.
54. Wagner J., Lerner R.A., Barbas C.F. III Efficient aldolase catalytic antibodies that use the enamine mechanism of natural enzymes. Science. 270:1995;1797.
55. Wahler D., Reymond J.L. Novel methods for biocatalyst screening. Curr. Opin. Chem. Biol. 5:2001;152.
56. Wentworth P. Jr., Janda K.D. Catalytic antibodies: structure and function. Cell Biochem. Biophys. 35:2001;63.
57. Wirtshing P., Ashley J.A., Lo C.H.-L., Janda K.D., Lerner R.A. React. Immun. Sci. 270:1995;1775.
58. Yli-Kauhaluoma J.T., Ashley J.A., Lo C.-H., Tucker L., Wolfe M.M., Janda K.D. Anti-metallocene antibodies: a new approach to enantioselective catalysis of the Diels-Alder reaction. J. Am. Chem. Soc. 117:1995;7041.
59. Zhong G.F., Hoffmann T., Lerner R.A., Danishefsky S., Barbas C.F. III Antibody-catalyzed enantioselective Robinson annulation. J. Am. Chem. Soc. 119:1997;8131.