Strategies for the selection of catalytic antibodies against organophosphorus nerve agents

Chemico-Biological Interactions

Volumn 203, Issue 1, 2013, Pages 196-201

  Smirnov, Ivan ^a,b   Belogurov Jr , Alexey ^a,c   Friboulet, Alain ^d   Masson, Patrick ^e   Gabibov, Alexander ^a,b,c,f   Renard, Pierre Yves ^f,g,h  

^a SHEMYAKIN OVCHINNIKOV INSTITUTE OF BIOORGANIC CHEMISTRY   (Russian Federation)

^b MOSCOW STATE UNIVERSITY   (Russian Federation)

^c INSTITUTE OF GENE BIOLOGY   (Russian Federation)

^d UNIVERSITÉ DE TECHNOLOGIE DE COMPIÈGNE   (France)

^e CENTRE DE RECHERCHES   (France)

^f Normandie Université   (France)

^g UNIVERSITÉ ET INSA DE ROUEN   (France)

^h CNRS Delegation Normandie   (France)

Author keywords

Anti idiotypic antibodies; Bioscavangers; Chemical warfare agents; Combinatorial libraries; Reactibodies

Indexed keywords

ANTIBODY; ANTIIDIOTYPIC ANTIBODY; CHOLINESTERASE; HAPTEN; METHYLPHOSPHONOTHIOIC ACID S (2 DIISOPROPYLAMINOETHYL) O ETHYL ESTER; MONOCLONAL ANTIBODY; ORGANOPHOSPHATE; POLYCLONAL ANTIBODY;

BIOCATALYSIS; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; COMBINATORIAL LIBRARY; CONFERENCE PAPER; CONFORMATION; ENZYME ACTIVE SITE; ENZYME BINDING; HUMAN; HYDROLYSIS; HYDROPHOBICITY; MOLECULAR MECHANICS; NONHUMAN; PHAGE DISPLAY; PHASE TRANSITION;

ANIMALS; ANTIBODIES, ANTI-IDIOTYPIC; ANTIBODIES, CATALYTIC; ANTIDOTES; BINDING SITES; CHEMICAL WARFARE AGENTS; DRUG DESIGN; HAPTENS; HUMANS; MODELS, MOLECULAR; ORGANOPHOSPHORUS COMPOUNDS; PROTEIN ENGINEERING;

EID: 84875810503     PISSN: 00092797     EISSN: 18727786     Source Type: Journal    
DOI: 10.1016/j.cbi.2012.10.011     Document Type: Conference Paper

References (76)

1. Y.C. Yang, J.A. Baker, and J.R. Ward Decontamination of chemical warfare agents Chem. Rev. 92 1992 1729 1743
2. Y.C. Yang Chemical detoxification of nerve agent VX Acc. Chem. Res. 32 1999 109 115
3. B.M. Smith Catalytic methods for the destruction of chemical warfare agents under ambient conditions Chem. Soc. Rev. 37 2008 470 478
4. L.M. Eubanks, T.J. Dickerson, and K.D. Janda Technological advancements for the detection of and protection against biological and chemical warfare agents Chem. Soc. Rev. 36 2007 458 470
5. E. Lenz, A.A. Brimfield, K.W. Hunter, H.P. Benschop, L.P.A. de Jong, C. van Dijk, and T.R. Clow Studies using a monoclonal antibody against soman Fundam. Appl. Toxicol. 4 1984 S156 S164
6. J.M. Grognet, T. Ardouin, M. Istin, A. Vandais, J.P. Noel, G. Rima, J. Satge, C. Pradel, H. Sentenac-Roumanou, and C. Lion Production and characterization of antibodies directed against organophosphorus nerve agent VX Arch. Toxicol. 67 1993 66 71
7. Y.-X. Ci, Y.-X. Zhou, Z.-Q. Guo, K.-T. Rong, and W.-B. Chang Production, characterization and application of monoclonal antibodies against the organophosphorus nerve agent VX Arch. Toxicol. 69 1995 565 567
8. P.Y. Jia, Y.Y. Wang, M. Yu, J.H. Wu, R.F. Yang, Y. Zhao, and L.J. Zhou An organophosphorus hapten used in the preparation of monoclonal antibody and as an active immunization vaccine in the detoxication of soman poisoning Toxicol. Lett. 187 2009 45 51
9. L. Pauling Molecular architecture and biological reactions Chem. Eng. News 24 1946 1375 1377
10. W.P. Jencks N.O. Kaplan, E.P. Kennedy, Current Aspects of Biochemical Energetics 1966 Academic Press New York 273 298
11. S.J. Benkovic, J.A. Adams, C.L. Borders Jr., K.D. Janda, and R.A. Lerner The enzymatic nature of antibody catalysis: development of multistep kinetic processing Science 250 1990 1135 1139
12. C. Berek, G.M. Griffiths, and C. Milstein Molecular events during maturation of the immune response to oxazolone Nature 316 1985 412 418
13. A. Belogurov Jr., A. Kozyr, N. Ponomarenko, and A. Gabibov Catalytic antibodies: balancing between Dr. Jekyll and Mr. Hyde Bioessays 31 2009 1161 1171
14. S.J. Pollack, J.W. Jacobs, and P.G. Schultz Selective chemical catalysis by an antibody Science 234 1986 1570 1573
15. A. Tramontano, K.D. Janda, and R.A. Lerner Catalytic antibodies Science 234 1986 1566 1570
16. G.M. Blackburn, A. Datta, H. Denham, and P. Wentworth Jr. Catalytic antibodies Adv. Phys. Org. Chem. 31 1998 249 392
17. P.G. Schultz, J. Yin, and R.A. Lerner The chemistry of the antibody molecule Angew. Chem. Int. Ed. 41 2002 4427 4437
18. L.H. Stockwin, and S. Holmes Antibodies as therapeutic agents: vive la renaissance ! Expert Opinion Biol. Ther. 3 2003 1133 1152
19. E. Keinan Catalytic Antibodies 2005 Wiley Weinheim
20. M. Matsushita, T.Z. Hoffman, J.A. Ashley, B. Zhou, P. Wirsching, and K.D. Janda Cocaine catalytic antibodies: the primary importance of linker effects Bioorg. Med. Chem. Lett. 11 2001 87 90
21. K.M. McKenzie, J.M. Mee, C.J. Rogers, M.S. Hixon, G.F. Kaufmann, and K.D. Janda Identification and characterization of single chain anti-cocaine catalytic antibodies J. Mol. Biol. 365 2007 722 731
22. J.B. Treweek, and K.D. Janda An antidote for acute cocaine toxicity Mol. Pharm. 9 2012 969 978
23. S.X. Deng, P. de Prada, and D.W. Landry Anticocaine catalytic antibodies J. Immunol. Methods 269 2002 299 310
24. T.J. Dickerson, N. Yamamoto, and K.D. Janda Antibody-catalyzed oxidative degradation of nicotin using riboflavin Bioorg. Med. Chem. 12 2004 4981 4987
25. A.P. Brogan, L.M. Eubanks, G.F. Koob, T.J. Dickerson, and K.D. Janda Antibody-catalyzed oxidation of D9-tetrahydrocannabinol J. Am. Chem. Soc. 129 2007 3698 3702
26. L. Zheng, J.P. Goddard, U. Baumann, and J.L. Reymond Expression improvement and mechanistic study of the retro-Diels-Alderase catalytic antibody 10F11 by site-directed mutagenesis J. Mol. Biol. 341 2004 807 814
27. P. Vayron, P.Y. Renard, F. Taran, C. Créminon, Y. Frobert, J. Grassi, and C. Mioskowski Toward antibody-catalyzed hydrolysis of organophosphorus poisons Proc. Natl. Acad. Sci. USA. 97 2000 7058 7063
28. A.V. Reshetnyak, M.F. Armentan, N.A. Ponomarenko, D. Vizzuso, O.M. Durova, R. Ziganshin, M. Serebryakova, V. Govorun, G. Gololobov, H.C. Morse 3rd, A. Friboulet, S.P. Makker, A.G. Gabibov, and A. Tramontano Routes to covalent catalysis by reactive selection for nascent protein nucleophiles J. Am. Chem. Soc. 129 2007 16175 16182
29. A. Tramontano, B. Ivanov, G. Gololobov, and S. Paul Inhibition and labeling of enzymes and abzymes by phosphonate diesters Appl. Biochem. Biotechnol. 83 2000 233 242
30. J.K. Johnson, D.M. Cerasoli, and D.E. Lenz Role of immunogen design in induction of soman-specific monoclonal antibodies Immunol. Lett. 96 2005 121 127
31. R.M. Moriarty, J. Hiratake, and K. Liu New synthetic route to unsymmetrically substituted pentacoordinated phosphorus. Hydrolytically stable chiral, monocyclic oxyphosphoranes J. Am. Chem. Soc. 112 1990 8575 8577
32. A.A. Brimfield, D.E. Lenz, D.M. Maxwell, and C.A. Broomfield Catalytic antibodies hydrolysing organophosphorus esters Chem. Biol. Interact. 87 1993 95 102
33. J. Yli-Kauholuama, T. Humppi, and A. Yliniema Hydrolysis of organophosphorus nerve agent soman by the monoclonal antibodies elicited against an oxyphosphorane hapten Acta Chem. Scand. 53 1999 473 479
34. N.R. Thomas Catalytic antibodies-reaching adolescence? Nat. Prod. Rep. 13 1996 479 511
35. P.-Y. Renard, P. Vayron, F. Taran, and C. Mioskowski Design and synthesis of haptens for antibody catalyzed hydrolysis of organophosphorus nerve agents Tetrahedron Lett. 40 1999 281 284
36. R.F. Yang, L.H. Yun, Z.L. Wong, and K.T. Rong Studies on the catalytic antibodies against soman.II.A "pro-transition-state" hapten strategy generating catalytic antibodies with large rate accelerations in hydrolysis of nerve agent soman Bull. Acad. Mil. Med. Sci. 24 2000 105 109
37. Z. Wang, K. Rong, R.F. Yang, and L. Yun γ-Hydroxyphosphonate inducing single-chain antibodies capable of catalyzing soman hydrolysis Sci. China 43 2000 649 656
38. L.A. Sternberger, V.M. Sim, W.G. Kavanagh, J.J. Cuculis, H.G. Meyers, D.E. Lenz, and D.M. Hinton A vaccine against organophosphorus poisoning Army Sci. Conference Proc. 3 1972 429 441
39. L.A. Sternberger, J.J. Cuculis, H.G. Meyer, D.E. Lenz, and W.G. Kavanagh Antibodies to organophosphorous haptens: immunity to paraoxon poisoning Fed. Proc. 33 1974 728
40. P. Vayron, P.Y. Renard, A. Valleix, and C. Mioskowski Design and synthesis of an α, α-difluorophosphinate hapten for antibody-catalyzed hydrolysis of organophosphorus nerve agents Chem. Eur. J. 6 2000 1050 1063
41. Y.C. Yang, L.L. Szafraniec, W.T. Beaudry, D.K. Rohrbaugh, L.R. Procell, and J.B. Samuel Autocatalytic hydrolysis of V-type nerve agents J. Org. Chem. 61 1996 8407 8413
42. B.J. Lavey, and K.D. Janda Catalytic antibody mediated hydrolysis of paraoxon J. Org. Chem. 61 1996 7633 7636
43. J.S. Rosenblum, L.-C. Lo, T.-Y. Li, K.D. Janda, and R.A. Lerner Antibody-catalyzed phosphate triester hydrolysis Angew. Chem. Int. Ed. 34 1995 2275 2277
44. B.J. Lavey, and K.D. Janda Antibody catalyzed hydrolysis of a phosphotriester Bioorg. Med. Chem. Lett. 6 1996 1523 1524
45. D.A. Spivak, T.Z. Hoffman, A.H. Moore, M.J. Taylor, and K.D. Janda A comparison of flexible and constrained haptens in eliciting antibody catalysts for paraoxon hydrolysis Bioorg. Med. Chem. 7 1999 1145 1150
46. R.M. Moriarty, K.M. Liu, H. Zhuang, D. Lenz, A. Brimfield, and C. Xu Synthesis of unsymmetrically substituted α-aminoalkylphosphonate esters Synth. Commun. 25 1995 2763 2773
47. R.M. Moriarty, A.P. Tao, and K.M. Liu Design and synthesis of bifunctional amino phosphonic haptens for catalytic antibody production Synth. Commun. 28 1998 1601 1610
48. J. Wagner, R.A. Lerner, and C.F. Barbas III Efficient aldolase catalytic antibodies that use the enamine mechanism of natural enzyme Science 270 1995 1797 1800
49. C.F. Barbas III, A. Heine, G. Zhong, T. Hoffmann, S. Gramatikova, R. Bjornestedt, B. List, J. Anderson, E.A. Stura, I.A. Wilson, and R.A. Lerner Immune versus natural selection: antibody aldolases with enzymic rates but broader scope Science 278 1997 2085 2092
50. H. Huang, W.-G. Han, L. Noodleman, and F. Grynszpan Multiple reactive immunization towards the hydrolysis of organophosphorous nerve agents: hapten design and synthesis Bioorg. Med. Chem. 9 2001 3185 3195
51. L. Louise-Leriche, E. Paunescu, G. Saint-André, R. Baati, A. Romieu, A. Wagner, and P.Y. Renard A HTS assay for the detection of organophosphorus nerve agent scavengers Chem. Eur. J. 16 2010 3510 3523
52. F. Jovic, L. Louise, C. Mioskowski, and P.-Y. Renard Immunologically driven antibodies chemical engineering: design and synthesis of a hapten aimed at nerve agent hydrolysis Tetrahedron Lett. 46 2005 6809 6814
53. N.K. Jerne Towards a network theory of the immune system Ann. Immunol. Paris 125 1974 373 389
54. L. Izadyar, A. Friboulet, M.H. Rémy, A. Roseto, and D. Thomas Monoclonal anti-idiotypic antibodies as functional internal images of enzyme active sites. Production of a catalytic antibody with a cholinesterase activity Proc. Natl. Acad. Sci. USA. 90 1993 8876 8880
55. G. Johnson, and S.W. Moore Idiotypic mimicry of a catalytic antibody active site Mol. Immunol. 39 2002 273 288
56. B. Avalle, D. Thomas, and A. Friboulet Fnctional mimicry: elicitation of a monoclonal anti-idiotypic antibody hydrolyzing ß-lactams FASEB J. 12 1998 1055 1060
57. R. Hu, G.Y. Xie, X. Zhang, Z.Q. Guo, and S. Jin Production and characterization of monoclonal anti-idiotypic antibody exhibiting a catalytic activity similar to carboxypeptidase A J. Biotechnol. 61 1998 109 115
58. D. Pillet, M. Paon, I.I. Vorobiev, A.G. Gabibov, D. Thomas, and A. Friboulet Idiotypic network mimicry and antibody catalysis: lessons for the elicitation of efficient anti-idiotypic protéase antibodies J. Immunol. Methods 269 2002 5 12
59. A.V. Kolesnikov, A.V. Kozyr, E.S. Alexandrova, F. Koralewski, A.V. Demin, M.I. Titov, B. Avalle, A. Tramontano, S. Paul, D. Thomas, A.G. Gabibov, and A. Friboulet Enzyme mimicry by the anti-idiotypic antibody approach Proc. Natl. Acad. Sci. USA. 97 2000 13526 13531
60. N.A. Ponomarenko, D. Pillet, M. Paon, I.I. Vorobiev, I.V. Smirnov, H. Adenier, B. Avalle, A.V. Kolesnikov, A.V. Kozyr, D. Thomas, A.G. Gabibov, and A. Friboulet Anti-idiotypic antibody mimics proteolytic function of parent antigen Biochemistry 46 2007 14598 14609
61. D. Phichith, S. Bun, S. Padiolleau-Lefèvre, S. Banh, D. Thomas, A. Friboulet, and B. Avalle Mutational and inhibitory analysis of a catalytic antibody. Implication for drug discovery Mol. Immunol. 47 2009 348 356
62. B. Avalle, A. Friboulet, and D. Thomas Screening of inhibitory monoclonal antibody. A critical step for producing anti-idiotypic catalytic antibodies Ann. N. Y. Acad. Sci. 864 1998 118 130
63. J.W. Li, L. Xia, Y. Su, H. Liu, X. Xia, Q. Lu, C. Yang, and K. Reheman Molecular imprint of enzyme active site by camel nanobodies. Rapid and efficient approach to produce abzymes with alliinase activity J. Biol. Chem. 287 2012 13713 13721
64. A.M. Shuster, G.V. Gololobov, O.A. Kvashuk, A.E. Bogomolova, I.V. Smirnov, and A.G. Gabibov DNA hydrolyzing auto antibodies Science 256 1992 665 667
65. B. Mets, G. Winger, C. Cabrera, S. Seo, S. Jamdar, G. Yang, K. Zhao, R.J. Briscoe, R. Almonte, J.H. Woods, and D.W. Landry A catalytic antibody against cocaine prevents cocaine's reinforcing and toxic effects in rats Proc. Natl. Acad. Sci. USA. 95 1998 10176 10181
66. J.B. Charbonnier, B. Golinelli-Pimpaneau, B. Gigant, D.S. Tawfik, R. Chap, D.G. Schlinder, S.H. Kim, B.S. Green, Z. Eshhar, and M. Knossow Structural convergence in the active sites of a family of catalytic antibodies Science 275 1997 1140 1142
67. P. Wirsching, J.A. Ashley, C.H.L. Lo, K.D. Janda, and R.A. Lerner Reactive immunization Science 270 1995 1775 1782
68. O.M. Durova, I.I. Vorobiev, I.V. Smirnov, A.V. Reshetnyak, G.B. Telegin, O.G. Shamborant, N.A. Orlova, D.D. Genkin, A. Bacon, N.A. Ponomarenko, A. Friboulet, and A.G. Gabibov Strategies for induction of catalytic antibodies toward HIV-1 glycoprotein gp120 in autoimmune prone mice Mol. Immunol. 47 2009 87 95
69. A.G. Gabibov, A. Friboulet, D. Thomas, A.V. Demin, N.A. Ponomarenko, I.I. Vorobiev, D. Pillet, M. Paon, E.S. Alexandrova, G.B. Telegin, O.V. Reshetnyak, A.V. Grigorieva, N.V. Gnuchev, A.A. Alishkin, and D.D. Genkin Antibody proteases: induction of catalytic response Biochemistry (Moscow) 67 2002 1168 1179
70. G.V. Gololobov, E.A. Chernova, D.V. Schourouv, I.V. Smirnov, I.A. Kudelina, and A.G. Gabibov Cleavage of supercoiled plasmid DNA by autoantibody Fab fragment: application of the flow linear dichroism technique Proc. Natl. Acad. Sci. USA. 92 1995 254 257
71. S. Lacroix-Desmazes, J. Bayry, N. Misra, M.P. Horn, S. Villard, A. Pashov, N. Stieltjes, R. d'Oiron, J.M. Saint-Remy, J. Hoebeke, M.D. Kazatchkine, J. Reinbolt, D. Mohanty, and S.V. Kaveri The prevalence of proteolytic antibodies against factor VIII in hemophilia A N. Engl. J. Med. 346 2002 662 667
72. S. Paul, D.J. Volle, C.M. Beach, D.R. Johnson, M.J. Powell, and R.J. Massey Catalytic hydrolysis of vasoactive intestinal peptide by human autoantibody Science 244 1989 1158 1162
73. I. Smirnov, E. Carletti, I. Kurkova, F. Nachon, Y. Nicolet, V. Mitkevich, H. Débat, B. Avalle, A. Belogurov, N. Kuznetsov, A. Reshetnyak, P. Masson, A. Tonevitsky, N. Ponomarenko, A.A. Makarov, A. Friboulet, A. Tramontano, and A.G. Gabibov Reactibodies generated by kinetic selection couple chemical reactivity with favorable protein dynamics Proc. Natl. Acad. Sci. USA. 108 2011 15954 15959
74. L. Xie, S. Hou, W. Yang, L. Fang, F. Zheng, C.-G. Zhan, Catalytic activities of a cocaine hydrolase engineered from human butyrylcholinesterase against (+)-and (-)-cocaine, Chem. Biol. Interact. (this issue).
75. A.N. Alexandrova, and W.L. Jorgensen Origin of the activity drop with the E50D variant of catalytic antibody 34E4 for Kemp elimination J. Phys. Chem. B 113 2 2009 497 504
76. M.E. Wales, and T.E. Reeves Organophosphorus hydrolase as an in vivo catalytic nerve agent bioscavenger Drug Testing Anal. 4 2012 271 281