Complete reaction cycle of a cocaine catalytic antibody at atomic resolution

Structure

Volumn 14, Issue 2, 2006, Pages 205-216

  Zhu, Xueyong ^a   Dickerson, Tobin J ^a   Rogers, Claude J ^a   Kaufmann, Gunnar F ^a   Mee, Jenny M ^a   McKenzie, Kathleen M ^a   Janda, Kim D ^a   Wilson, Ian A ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOIC ACID; CATALYTIC ANTIBODY; COCAINE; ECGONINE METHYL ESTER; IMMUNOGLOBULIN F(AB) FRAGMENT;

ANTIBODY STRUCTURE; ANTIGEN ANTIBODY REACTION; ANTIGEN BINDING; ARTICLE; BINDING SITE; CRYSTAL STRUCTURE; CRYSTALLIZATION; HYDROLYSIS; IMMUNOASSAY; NONHUMAN; PRIORITY JOURNAL; STATISTICAL SIGNIFICANCE;

ANTIBODIES, CATALYTIC; BENZOIC ACID; BINDING SITES, ANTIBODY; CATALYSIS; COCAINE; CRYSTALLOGRAPHY; ETHYLENE GLYCOLS; IMMUNOGLOBULIN FAB FRAGMENTS; MODELS, MOLECULAR;

EID: 32044465761     PISSN: 09692126     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.str.2005.10.014     Document Type: Article

References (46)

1. B. Al-Lazikani, A.M. Lesk, and C. Chothia Standard conformations for the canonical structures of immunoglobulins J. Mol. Biol. 273 1997 927 948
2. F.H. Allen The Cambridge Structural Database: a quarter of a million crystal structures and rising Acta Crystallogr. B 58 2002 380 388
3. M.R. Arkin, and J.A. Wells Probing the importance of second sphere residues in an esterolytic antibody by phage display J. Mol. Biol. 284 1998 1083 1094
4. A.T. Brünger, P.D. Adams, G.M. Clore, W.L. DeLano, P. Gros, R.W. Grosse-Kunstleve, J.S. Jiang, J. Kuszewski, M. Nilges, and N.S. Pannu Crystallography & NMR system: a new software suite for macromolecular structure determination Acta Crystallogr. D Biol. Crystallogr. 54 1998 905 921
5. M.R. Carrera, J.A. Ashley, L.H. Parsons, P. Wirsching, G.F. Koob, and K.D. Janda Suppression of psychoactive effects of cocaine by active immunization Nature 378 1995 727 730
6. M.R. Carrera, J.A. Ashley, B. Zhou, P. Wirsching, G.F. Koob, K.D. Janda, and L.H. Parsons Cocaine vaccines: antibody protection against relapse in a rat model Proc. Natl. Acad. Sci. USA 97 2000 6202 6206
7. J.B. Charbonnier, E. Carpenter, B. Gigant, B. Golinelli-Pimpaneau, Z. Eshhar, B.S. Green, and M. Knossow Crystal structure of the complex of a catalytic antibody Fab fragment with a transition state analog: structural similarities in esterase-like catalytic antibodies Proc. Natl. Acad. Sci. USA 92 1995 11721 11725
8. J.B. Charbonnier, B. Golinelli-Pimpaneau, B. Gigant, D.S. Tawfik, R. Chap, D.G. Schindler, 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
9. D.A. Dougherty Cation-π interactions in chemistry and biology: a new view of benzene, Phe, Tyr, and Trp Science 271 1996 163 168
10. R.M. Esnouf Further additions to MolScript version 1.4, including reading and contouring of electron-density maps Acta Crystallogr. D Biol. Crystallogr. 55 1999 938 940
11. A.R. Fersht Enzyme Structure and Mechanism 1985 W.H. Freeman New York
12. B.S. Fox, K.M. Kantak, M.A. Edwards, K.M. Black, B.K. Bollinger, A.J. Botka, T.L. French, T.L. Thompson, V.C. Schad, and J.L. Greenstein Efficacy of a therapeutic cocaine vaccine in rodent models Nat. Med. 2 1996 1129 1132
13. C. Gao, C.H. Lin, C.H. Lo, S. Mao, P. Wirsching, R.A. Lerner, and K.D. Janda Making chemistry selectable by linking it to infectivity Proc. Natl. Acad. Sci. USA 94 1997 11777 11782
14. B. Gigant, J.B. Charbonnier, Z. Eshhar, B.S. Green, and M. Knossow X-ray structures of a hydrolytic antibody and of complexes elucidate catalytic pathway from substrate binding and transition state stabilization through water attack and product release Proc. Natl. Acad. Sci. USA 94 1997 7857 7861
15. B. Golinelli-Pimpaneau Structural diversity of antibody catalysts J. Immunol. Methods 269 2002 157 171
16. A. Gutteridge, and J. Thornton Conformational change in substrate binding, catalysis and product release: an open and shut case? FEBS Lett. 567 2004 67 73
17. K.U. Harlow, and D. Lane Antibodies: A Laboratory Manual 1998 Cold Spring Harbor Press Cold Spring Harbor, NY
18. K.D. Janda, L.C. Lo, C.H. Lo, M.M. Sim, R. Wang, C.H. Wong, and R.A. Lerner Chemical selection for catalysis in combinatorial antibody libraries Science 275 1997 945 948
19. D.E. Koshland Jr. Conformational changes: how small is big enough? Nat. Med. 4 1998 1112 1114
20. O. Kristensen, D.G. Vassylyev, F. Tanaka, K. Morikawa, and I. Fujii A structural basis for transition-state stabilization in antibody-catalyzed hydrolysis: crystal structures of an abzyme at 1.8 Å resolution J. Mol. Biol. 281 1998 501 511
21. N.A. Larsen, B. Zhou, A. Heine, P. Wirsching, K.D. Janda, and I.A. Wilson Crystal structure of a cocaine-binding antibody J. Mol. Biol. 311 2001 9 15
22. N.A. Larsen, P. de Prada, S.X. Deng, A. Mittal, M. Braskett, X. Zhu, I.A. Wilson, and D.W. Landry Crystallographic and biochemical analysis of cocaine-degrading antibody 15A10 Biochemistry 43 2004 8067 8076
23. M.C. Lawrence, and P.M. Colman Shape complementarity at protein/protein interfaces J. Mol. Biol. 234 1993 946 950
24. A.B. Lindner, Z. Eshhar, and D.S. Tawfik Conformational changes affect binding and catalysis by ester-hydrolysing antibodies J. Mol. Biol. 285 1999 421 430
25. G. MacBeath, and D. Hilvert Hydrolytic antibodies: variations on a theme Chem. Biol. 3 1996 433 445
26. 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
27. I.K. McDonald, and J.M. Thornton Satisfying hydrogen bonding potential in proteins J. Mol. Biol. 238 1994 777 793
28. E.A. Merritt, and M.E.P. Murphy Raster3d version 2.0 - a program for photorealistic molecular graphics Acta Crystallogr. D Biol. Crystallogr. 50 1994 869 873
29. H domain of immunoglobulins J. Mol. Biol. 275 1998 269 294
30. G.N. Murshudov, A.A. Vagin, A. Lebedev, K.S. Wilson, and E.J. Dodson Efficient anisotropic refinement of macromolecular structures using FFT Acta Crystallogr. D Biol. Crystallogr. 55 1999 247 255
31. J. Navaza Amore - an automated package for molecular replacement Acta Crystallogr. A 50 1994 157 163
32. A. Nicholls, K.A. Sharp, and B. Honig Protein folding and association: insights from the interfacial and thermodynamic properties of hydrocarbons Proteins 11 1991 281 296
33. Z. Otwinowski, and W. Minor Processing of X-ray diffraction data collected in oscillation mode Methods Enzymol. 276 1997 307 326
34. E. Pozharski, A. Moulin, A. Hewagama, A.B. Shanafelt, G.A. Petsko, and D. Ringe Diversity in hapten recognition: structural study of an anti-cocaine antibody M82G2 J. Mol. Biol. 349 2005 570 582
35. S.N. Ruzheinikov, T.A. Muranova, S.E. Sedelnikova, L.J. Partridge, G.M. Blackburn, I.A. Murray, H. Kakinuma, N. Takahashi-Ando, K. Shimazaki, and J. Sun High-resolution crystal structure of the Fab-fragments of a family of mouse catalytic antibodies with esterase activity J. Mol. Biol. 332 2003 423 435
36. SAMHSA (Substance Abuse and Mental Health Services and Administration). (2004). Results from the 2003 National Survey on Drug Use and Health: National Findings. (Office of Applied Studies, NSDUH Series H-25, DHHS Publication No. SMA 04-3964). Rockville, MD).
37. S. Sheriff, W.A. Hendrickson, and J.L. Smith Structure of myohemerythrin in the azidomet state at 1.7/1.3 Å resolution J. Mol. Biol. 197 1987 273 296
38. M. Sofuoglu, and T.R. Kosten Novel approaches to the treatment of cocaine addiction CNS Drugs 19 2005 13 25
39. F. Tanaka Catalytic antibodies as designer proteases and esterases Chem. Rev. 102 2002 4885 4906
40. M.M. Thayer, E.H. Olender, A.S. Arvai, C.K. Koike, I.L. Canestrelli, J.D. Stewart, S.J. Benkovic, E.D. Getzoff, and V.A. Roberts Structural basis for amide hydrolysis catalyzed by the 43C9 antibody J. Mol. Biol. 291 1999 329 345
41. G.J. Wedemayer, P.A. Patten, L.H. Wang, P.G. Schultz, and R.C. Stevens Structural insights into the evolution of an antibody combining site Science 276 1997 1665 1669
42. I.A. Wilson, and R.L. Stanfield Antibody-antigen interactions Curr. Opin. Struct. Biol. 3 1993 113 118
43. G. Yang, J. Chun, H. Arakawa-Uramoto, X. Wang, M.A. Gawinowicz, K. Zhao, and D.W. Landry Anti-cocaine catalytic antibodies: A synthetic approach to improved antibody diversity J. Am. Chem. Soc. 118 1996 5881 5890
44. C.G. Zhan, and D.W. Landry Theoretical studies of competing reaction pathways and energy barriers for alkaline ester hydrolysis of cocaine J. Phys. Chem. A 105 2001 1296 1301
45. G.W. Zhou, J. Guo, W. Huang, R.J. Fletterick, and T.S. Scanlan Crystal structure of a catalytic antibody with a serine protease active site Science 265 1994 1059 1064
46. X. Zhu, A. Heine, F. Monnat, K.N. Houk, K.D. Janda, and I.A. Wilson Structural basis for antibody catalysis of a cationic cyclization reaction J. Mol. Biol. 329 2003 69 83