Catalytic activities of a cocaine hydrolase engineered from human butyrylcholinesterase against (+)- and (-)-cocaine

Chemico-Biological Interactions

Volumn 203, Issue 1, 2013, Pages 57-62

  Xue, Liu ^a   Hou, Shurong ^a   Yang, Wenchao ^a   Fang, Lei ^a   Zheng, Fang ^a   Zhan, Chang Guo ^a  

^a University of Kentucky   (United States)

Author keywords

Cholinesterase; Cocaine addiction; Drug overdose; Enzyme therapy; Hydrolase

Indexed keywords

CHOLINESTERASE; COCAINE; COCAINE HYDROLASE; HYDROLASE; UNCLASSIFIED DRUG;

CATALYSIS; CONFERENCE PAPER; CONTROLLED STUDY; ENZYME KINETICS; ENZYME SUBSTRATE COMPLEX; HYDROLYSIS; MOLECULAR MODEL;

BRAIN; BUTYRYLCHOLINESTERASE; CARBON RADIOISOTOPES; COCAINE; COCAINE-RELATED DISORDERS; HUMANS; KINETICS; MODELS, MOLECULAR; MUTAGENESIS, SITE-DIRECTED; MUTANT PROTEINS; POSITRON-EMISSION TOMOGRAPHY; PROTEIN CONFORMATION; PROTEIN ENGINEERING; RADIOPHARMACEUTICALS; RECOMBINANT PROTEINS; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 84875808463     PISSN: 00092797     EISSN: 18727786     Source Type: Journal    
DOI: 10.1016/j.cbi.2012.08.003     Document Type: Conference Paper

References (43)

1. J.H. Mendelson, and N.K. Mello Drug Therapy: management of cocaine abuse and dependence New Engl. J. Med. 334 1996 965 972
2. S. Singh Chemistry, design, and structure-activity relationship of cocaine antagonists Chem. Rev. 100 2000 925 1024
3. S. Paula, M.R. Tabet, C.D. Farr, A.B. Norman, and W.J. Ball Jr. Three-dimensional quantitative structure-activity relationship modeling of cocaine binding by a novel human monoclonal antibody J. Med. Chem. 47 2004 133 142
4. D.A. Gorelick Enhancing cocaine metabolism with butyrylcholinesterase as a treatment strategy Drug Alcohol Depend. 48 1997 159 165
5. A.D. Redish Addiction as a computational process gone awry Science 306 2004 1944 1947
6. F. Zheng, and C.-G. Zhan Enzyme-therapy approaches for the treatment of drug overdose and addiction Future Med. Chem. 3 2011 9 13
7. M.M. Meijler, G.F. Kaufmann, L.W. Qi, J.M. Mee, A.R. Coyle, and J.A. Moss Fluorescent cocaine probes: a tool for the selection and engineering of therapeutic antibodies J. Am. Chem. Soc. 127 2005 2477 2484
8. M.R.A. Carrera, G.F. Kaufmann, J.M. Mee, M.M. Meijler, G.F. Koob, and K.D. Janda From the cover: treating cocaine addiction with viruses Proc. Natl. Acad. Sci. USA 101 2004 10416 10421
9. D.W. Landry, K. Zhao, G.X-Q. Yang, M. Glickman, and T.M. Georgiadis Antibody-catalyzed degradation of cocaine Science 259 1993 1899 1901
10. C.-G. Zhan, S.-X. Deng, J.G. Skiba, B.A. Hayes, S.M. Tschampel, G.C. Shields, and D.W. Landry First-principle studies of intermolecular and intramolecular catalysis of protonated cocaine J. Comput. Chem. 26 2005 980 986
11. F. Zheng, and C.-G. Zhan Modeling of kinetics of cocaine in living system reveals the feasibility for development of enzyme therapies for drugs of abuse PLoS Comput. Biol. 8 2012 e1002610 [Epub 2012 Jul 26]
12. H. Sun, Y.P. Pang, O. Lockridge, and S. Brimijoin Re-engineering butyrylcholinesterase as a cocaine hydrolase Mol. Pharmacol. 62 2002 220 224
13. A. Hamza, H. Cho, H.-H. Tai, and C.-G. Zhan Molecular dynamics simulation of cocaine binding with human butyrylcholinesterase and its mutants J. Phys. Chem. B 109 2005 4776 4782
14. S.J. Gateley Activities of the enantiomers of cocaine and some related compounds as substrates and inhibitors of plasma butyrylcholinesterase Biochem. Pharmacol. 41 1991 1249 1254
15. S. Darvesh, D.A. Hopkins, and C. Geula Neurobiology of butyrylcholinesterase Nature Rev. Neurosci. 4 2003 131 138
16. E. Giacobini, Butyrylcholinesterase: Its Function and Inhibitors, Dunitz Martin Ltd., Great Britain, 2003.
17. J.S. Fowler, N.D. Volkow, A.P. Wolf, S.L. Dewey, D.J. Schlyer, R.R. Macgregor, R. Hitzemann, J. Logan, B. Bendriem, and S.J. Gatley Mapping cocaine binding sites in human and baboon brain in vivo Synapse 4 1989 371 377
18. S.J. Gatley, R.R. MacGregor, J.S. Fowler, A.P. Wolf, and S.L. Dewey Rapid stereoselective hydrolysis of (+)-cocaine in baboon plasma prevents its uptake in the brain: implications for behavioral studies J. Neurochem. 54 1990 720 723
19. F. Zheng, and C.-G. Zhan Recent progress in protein drug design and discovery with a focus on novel approaches to the development of anti-cocaine medications Future Med. Chem. 1 2009 515 528
20. C.-G. Zhan Novel pharmacological approaches to treatment of drug overdose and addiction Expert Rev. Clinical Pharmacol. 2 2009 1 4
21. Y. Pan, D. Gao, W. Yang, H. Cho, and C.-G. Zhan Free energy perturbation (FEP) simulation on the transition-states of cocaine hydrolysis catalyzed by human butyrylcholinesterase and its mutants J. Am. Chem. Soc. 129 2007 13537 13543
22. F. Zheng, and C.-G. Zhan Structure-and-mechanism-based design and discovery of therapeutics for cocaine overdose and addiction Org. Biomol. Chem. 6 2008 836 843
23. F. Zheng, and C.-G. Zhan Rational design of an enzyme mutant for anti- cocaine therapeutics J. Computer-Aided Mol. Design 22 2008 661 671
24. Y. Pan, D. Gao, and W. Yang Computational redesign of human butyrylcholinesterase for anti-cocaine medication Proc. Natl. Acad. Sci. USA 102 2005 16656 16661
25. D. Gao, H. Cho, W. Yang, Y. Pan, G.-F. Yang, H.-H. Tai, and C.-G. Zhan Computational design of a human butyrylcholinesterase mutant for accelerating cocaine hydrolysis based on the transition-state simulation Angew. Chem. Int. Ed. 45 2006 653 657
26. F. Zheng, W. Yang, L. Xue, S. Hou, J. Liu, and C.-G. Zhan Design of high-activity mutants of human butyrylcholinesterase against (-)-cocaine: structural and energetic factors affecting the catalytic efficiency Biochemistry 49 2010 9113 9119
27. W. Yang, Y. Pan, L. Fang, D. Gao, F. Zheng, and C.-G. Zhan Free-energy perturbation simulation on transition states and high-activity mutants of human butyrylcholinesterase for (-)-cocaine hydrolysis J. Phys. Chem. B 114 2010 10889 10896
28. Y. Pan, D. Gao, and C.-G. Zhan Modeling the catalysis of anti-cocaine catalytic antibody: competing reaction pathways and free energy barriers J. Am. Chem. Soc. 130 2008 5140 5149
29. F. Zheng, W. Yang, M.-C. Ko, J. Liu, H. Cho, D. Gao, M. Tong, H.-H. Tai, J.H. Woods, and C.-G. Zhan Most efficient cocaine hydrolase designed by virtual screening of transition states J. Am. Chem. Soc. 130 2008 12148 12155
30. W. Yang, Y. Pan, F. Zheng, H. Cho, H.-H. Tai, and C.-G. Zhan Free energy perturbation (FEP) simulation on transition states and design of high-activity mutants of human butyrylcholinesterase for accelerating cocaine metabolism Biophysical J. 96 2009 1931 1938
31. W. Yang, L. Xue, L. Fang, and C.-G. Zhan Characterization of a high-activity mutant of human butyrylcholinesterase against (-)-cocaine Chem. Biol. Interact. 187 2010 148 152
32. L. Xue, M.-C. Ko, M. Tong, W. Yang, S. Hou, F. Zheng, J.H. Woods, H.-H. Tai, and C.-G. Zhan Rational design, preparation and characterization of high-activity mutants of human butyrylcholinesterase against (-)-cocaine Mol. Pharmacol. 79 2011 290 297
33. S. Brimijoin, Y. Gao, J.J. Anker, L.A. Gliddon, D. LaFleur, R. Shah, Q. Zhao, M. Singh, and M.E. Carroll A cocaine hydrolase engineered from human butyrylcholinesterase selectively blocks cocaine toxicity and reinstatement of drug seeking in rats Neuropsychopharmacology 33 2008 2715 2725
34. Y. Gao, D. LaFleur, R. Shah, Q. Zhao, M. Singh, and S. Brimijoin An albumin-butyrylcholinesterase for cocaine toxicity and addiction: catalytic and pharmacokinetic properties Chem. Biol. Interact. 175 2008 83 87
35. Y. Gao, F.M. Orson, B. Kinsey, T. Kosten, and S. Brimijoin The concept of pharmacologic cocaine interception as a treatment for drug abuse Chem Biol Interact. 187 2010 421 424
36. C.W. Schindler, and S.R. Goldberg Accelerating cocaine metabolism as an approach to the treatment of cocaine abuse and toxicity Future Med. Chem. 4 2012 163 175
37. C.W. Schindler, Z. Justinova, D. Lafleur, D. Woods, V. Roschke, H. Hallak, L. Sklair-Tavron, G.H. Redhi, S. Yasar, J. Bergman, S.R. Goldberg, Modification of pharmacokinetic and abuse-related effects of cocaine by human-derived cocaine hydrolase in monkeys, Addict. Biol. 2012 Jan 20. http://dx.doi.org/10.1111/j.1369-1600.2011.00424.x. [Epub ahead of print].
38. Teva Pharmaceutical Industries Ltd: BChE Albumin Fusions for the Treatment of Cocaine Abuse. PCT WO2011/071926 A1.
39. F. Zheng, and C.-G. Zhan Are pharmacokinetic approaches feasible for treatment of cocaine addiction and overdose? Future Med. Chem. 4 2012 125 128
40. J. Liu, and C.-G. Zhan Reaction pathway and free energy profile for cocaine hydrolase-catalyzed hydrolysis of (-)-cocaine J. Chem. Theory Comput. 8 2012 1426 1435
41. Y. Nicolet, O. Lockridge, P. Masson, J.C. Fontecilla-Camps, and F.J. Nachon Crystal structure of human butyrylcholinesterase and of its complexes with substrate and products Biol. Chem. 278 2003 41141 41147
42. D.A. Case, T.A. Darden, T.E. Cheatham, C.L. Simmerling, J. Wang, R.E. Duke, R. Luo, K.M. Merz, B. Wang, D.A. Pearlman, M. Crowley, S. Brozell, V. Tsui, H. Gohlke, J. Mongan, V. Hornak, G. Cui, P. Beroza, C. Schafmeister, J.W. Caldwell, W.S. Ross, and P.A. Kollman AMBER11 2010 University of California San Francisco
43. H. Sun, J.E. Yazal, O. Lockridge, L.M. Schopfer, S. Brimijoin, and Y.P. Pang Predicted michaelis-menten complexes of cocaine-butyrylcholinesterase: engineering effective butyrylcholinesterase mutants for cocaine detoxication J. Biol. Chem. 276 2001 9330 9336