Probing active cocaine vaccination performance through catalytic and noncatalytic hapten design

Journal of Medicinal Chemistry

Volumn 56, Issue 9, 2013, Pages 3701-3709

  Cai, Xiaoqing ^a   Whitfield, Timothy ^a   Hixon, Mark S ^b   Grant, Yanabel ^a   Koob, George F ^a   Janda, Kim D ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b Takeda San Diego Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYTIC ANTIBODY; COCAINE; COCAINE DERIVATIVE; GNE KEYHOLE LIMPET HEMOCYANNIN VACCINE; HAPTEN; UNCLASSIFIED DRUG; VACCINE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIBODY TITER; ARTICLE; CATALYSIS; COCAINE DEPENDENCE; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; KINETICS; LOCOMOTION; MOUSE; NONHUMAN; VACCINATION;

ANIMALS; ANTIBODIES; ANTIBODY SPECIFICITY; BIOCATALYSIS; COCAINE; DRUG DESIGN; HAPTENS; IMMUNOCONJUGATES; KINETICS; LOCOMOTION; MICE; VACCINATION;

EID: 84877691189     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm400228w     Document Type: Article

References (32)

1. National Institute of Drug Abuse. National Household Survey on Drug Abuse, Population Estimates; U.S. Dept. of Health and Human Services, Rockville, MD, 2001.
2. Des Jarlais, D. C.; Friedman, S. R. AIDS and i.v. Drug Use Science 1989, 245, 578-579
3. Brody, S. L.; Slovis, C. M.; Wrenn, K. D. Cocaine-Related Medical Problems: Consecutive Series of 233 Patients Am. J. Med. 1990, 88, 325-331
4. Carrera, M. R. A.; Meijler, M. M.; Janda, K. D. Cocaine Pharmacology and Current Pharmacotherapies for Its Abuse Bioorg. Med. Chem. 2004, 12, 5019-5030
5. Moreno, A.; Janda, K. D. Immunopharmacotherapy: Vaccination Strategies as a Treatment for Drug Abuse and Dependence Pharmacol., Biochem. Behav. 2009, 92, 199-205
6. Moreno, A.; Janda, K. D. Current Challenges for the Creation of Effective Vaccines Against Drugs of Abuse Expert Rev. Vaccines 2011, 10, 1637-1639
7. Janda, K. D.; Treweek, J. B. Vaccines Targeting Drugs of Abuse: Is the Glass Half-Empty or Half-Full? Nature Rev. Immunol. 2012, 12, 67-72
8. Kosten, T. R.; Rosen, M.; Bond, J.; Settles, M.; Roberts, J. S. C.; Shields, J.; Jack, L.; Fox, B. Human Therapeutic Cocaine Vaccine: Safety and Immunogenicity Vaccine 2002, 20, 1196-1204
9. Martell, B. B.; Mitchell, E.; Poling, J.; Gonsai, K.; Kosten, T. R. Vaccine Pharmacotherapy for the Treatment of Cocaine Dependence Biol. Psychiatry 2005, 58, 158-164
10. Martell, B. A.; Orson, F. M.; Poling, J.; Mitchell, E.; Rossen, R. D.; Gardner, T.; Kosten, T. R. Cocaine Vaccine for the Treatment of Cocaine Dependence in Methadone-Maintained Patients: A Randomized, Double-Blind, Placebo-Controlled Efficacy Trial Arch. Gen. Psychiatry 2009, 66, 1116-1123
11. Haney, M.; Gunderson, E. W.; Jiang, H.; Collins, E. D.; Foltin, R. W. Cocaine-Specific Antibodies Blunt the Subjective Effects of Smoked Cocaine in Human Biol. Psychiatry 2010, 67, 59-65
12. Fox, B. S.; Kantak, K. M.; Edwards, M. A.; Black, K. M.; Bollinger, B. K.; Alison, J. B.; French, T. L.; Thompson, T. L.; Schad, V. C.; Greenstein, J. L.; Gefter, M. L.; Exley, M. A.; Swain, P. A.; Briner, T. J. Efficacy of a Therapeutic Cocaine Vaccine in Rodent Models Nature Med. 1996, 2, 1129-1132
13. Lazer, E. S.; Aggarwal, N. D.; Hite, G. J.; Nieforth, K. A.; Kelleher, R. T.; Speralman, R. D.; Schuster, C. R.; Wolverton, W. Synthesis and Biological Activity of Cocaine Analogs I: N-Alkylated Norcocaine Derivatives J. Pharm. Sci. 1978, 67, 1656-1658
14. Carrera, M. R. A.; Ashley, J. A.; Parsons, L. H.; Wirsching, P.; Koob, G. F.; Janda, K. D. Suppression of Psychoactive Effects of Cocaine by Active Immunization Nature 1995, 378, 727-730
15. Carrera, M. R. A.; Ashley, J. A.; Zhou, B.; Wirsching, P.; Koob, G. F.; Janda, K. D. Cocaine Vaccines: Antibody Protection Against Relapse in a Rat Model Proc. Natl. Acad. Sci. U. S. A. 2000, 32, 6202-6207
16. Carrera, M. R. A.; Ashley, J. A.; Wirsching, P.; Koob, G. F.; Janda, K. D. A Second-Generation Vaccine Protects Against the Psychoactive Effects of Cocaine Proc. Natl. Acad. Sci. U. S. A. 2001, 98, 1988-1992
17. Koob, G.; Hicks, M. J.; Wee, S.; Rosenburg, J. B.; De, B. P.; Kaminsky, S. M.; Moreno, A.; Janda, K. D.; Crystal, R. G. Anti-Cocaine Analog to a Disrupted Adenovirus CNS Neurol. Disord.: Drug Targets 2011, 10, 899-1992
18. Hicks, M. J.; Bishnu, P. D.; Rosenberg, J. B.; Davidson, J. T.; Moreno, A. Y.; Janda, K. D.; Wee, S.; Koob, G. F.; Hackett, N. R.; Kaminsky, S. M.; Worgall, S.; Toth, M.; Mezey, J. G.; Crystal, R. G. Cocaine Analog Coupled to Disrupted Adenovirus: A Vaccine Strategy to Evoke High-Titer Immunity Against Addictive Drugs Mol. Ther. 2011, 19, 612-619
19. Landry, D. W.; Zhao, K.; Yang, G. X.; Glickman, M.; Georgiadis, T. M. Antibody-Catalyzed Degradation of Cocaine Science 1993, 259, 1899-1901
20. Yang, G.; Chun, J.; Arakawa-Uramoto, H.; Wang, X.; Gawinowicz, M. A.; Zhao, K.; Landry, D. W. Anti-Cocaine Antibodies: A Synthetic Approach to Improved Antibody Diversity J. Am. Chem. Soc. 1996, 118, 5881-5890
21. 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. 1998, 95, 10176-10181
22. Basmadjian, G. P.; Singh, S.; Sastrodjojo, B.; Smith, B. T.; Avor, K. S.; Chang, F.; Mills, S. L.; Searle, T. W. Generation of Polyclonal Catalytic Antibodies against Cocaine Using Transition State Analogs of Cocaine Conjugated to Diphtheria Toxoid Chem. Pharm. Bull. 1995, 43, 1902-1911
23. Tanaka, F. Catalytic Antibodies as Designer Proteases and Esterases Chem. Rev. 2002, 102, 4885-4906
24. Matsushita, M.; Hoffman, T. Z.; Ashley, J. A.; Zhou, B.; Wirsching, P.; Janda, K. D. Cocaine Catalytic Antibodies: The Primary Importance of Linker Effects Bioorg. Med. Chem. Lett. 2001, 11, 87-90
25. Li, P.; Zhao, K.; Deng, S.-X.; Landry, D. W. Noenzymatic Hydrolysis of Cocaine via Intramolecular Acid Catalysis Helv. Chim. Acta 1999, 82, 85-89
26. Isomura, S.; Hoffman, T. Z.; Wirsching, P.; Janda, K. D. Synthesis, Properties, and Reactivity of Cocaine Benzoylthio Ester Possessing the Cocaine Absolute Configuration J. Am. Chem. Soc. 2001, 124, 3661-3668
27. Thomsen, M.; Caine, S. B. Psychomotor Stimulant Effects of Cocaine in Rats and 15 Mouse Strains Exp. Clin. Psychopharmacol. 2011, 19, 321-341
28. Müller, R. Determination of Affinity and Specificity of Anti-Hapten Antibodies by Competitive Radioimmunoassay Methods Enzymol. 1983, 92, 589-601
29. McKenzie, K. M.; Mee, J. M.; Rogers, C. J.; Hixon, M. S.; Kaufman, G. F.; Janda, K. D. Identification and Characterization of Single Chain Anti-Cocaine Catalytic Antibodies J. Mol. Biol. 2007, 365, 722-731
30. Zhan, C. G.; Deng, S. H.; Skiba, J. G.; Hayes, B. A.; Tschmpel, S.; Shields, G. C.; Landry, D. W. First-Principle Studies of Intermolecular and Intramolecular Catalysis of Protonated Cocaine J. Comput. Chem. 2005, 26, 980-986
31. Deng, S. X.; Bharat, N.; Fischman, M. C.; Landry, D. W. Covalent Modification of Proteins by Cocaine Proc. Natl. Acad. Sci. U. S. A. 2002, 99, 3412-3416
32. Carroll, M. E.; Zlebnik, N. E.; Anker, J. J.; Kosten, T. R.; Orson, F. M.; Shen, X.; Kinsey, B.; Parks, R. J.; Gao, Y.; Brimijoin, S. Combined Cocaine Hydrolase Gene Transfer and Anti-Cocaine Vaccine Synergistically Block Cocaine-Induced Locomotion PLoS One 2012, 7, e43536