Synthesis of mercapto-(+)-methamphetamine haptens and their use for obtaining improved epitope density on (+)-methamphetamine conjugate vaccines

Journal of Medicinal Chemistry

Volumn 54, Issue 14, 2011, Pages 5221-5228

  Carroll, F Ivy ^a   Blough, Bruce E ^a   Pidaparthi, Ramakrishna R ^a   Abraham, Philip ^a   Gong, Paul K ^a   Deng, Liu ^a   Huang, Xiaodong ^a   Gunnell, Melinda ^b   Lay, Jackson O ^c   Peterson, Eric C ^b   Owens, S Michael ^b  

^a RTI INTERNATIONAL   (United States)

^b UNIVERSITY OF ARKANSAS FOR MEDICAL SCIENCES   (United States)

^c UNIVERSITY OF ARKANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARRIER PROTEIN; COCAINE; EPITOPE; HAPTEN; MALEIMIDE; MERCAPTO METHAMPHETAMINE; METHAMPHETAMINE; METHAMPHETAMINE CONJUGATE VACCINE; MONOCLONAL ANTIBODY; MORPHINE; NICOTINE; UNCLASSIFIED DRUG; VACCINE;

ANIMAL EXPERIMENT; ARTICLE; CONTROLLED STUDY; COST EFFECTIVENESS ANALYSIS; IMMUNE RESPONSE; LARGE SCALE PRODUCTION; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; MOLECULE; MOUSE; NONHUMAN; SYNTHESIS;

ANIMALS; ANTIBODIES, MONOCLONAL; DRUG CARRIERS; EPITOPES; FEMALE; HAPTENS; MALEIMIDES; METHAMPHETAMINE; MICE; MICE, INBRED BALB C; OVALBUMIN; SERUM ALBUMIN, BOVINE; STEREOISOMERISM; SULFHYDRYL COMPOUNDS; VACCINES; VACCINES, CONJUGATE;

EID: 79960632723     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm2004943     Document Type: Article

References (22)

1. SAMHSA (Substance Abuse and Mental Health Services Administration). Results from the 2009 National Survey on Drug Use and Health; Department of Health and Human Services: Washington, DC, 2010.
2. Albertson, T. E.; Derlet, R. W.; Van Hoozen, B. E. Methamphetamine and the expanding complications of amphetamines West. J. Med. 1999, 170, 214-219 (Pubitemid 32612757)
3. Barr, A. M.; Panenka, W. J.; MacEwan, G. W.; Thornton, A. E.; Lang, D. J.; Honer, W. G.; Lecomte, T. The need for speed: an update on methamphetamine addiction J. Psychiatry Neurosci. 2006, 31, 301-313 (Pubitemid 44497427)
4. Murray, J. B. Psychophysiological aspects of amphetamine-methamphetamine abuse J. Psychol. 1998, 132, 227-237 (Pubitemid 128469739)
5. Scott, J. C.; Woods, S. P.; Matt, G. E.; Meyer, R. A.; Heaton, R. K.; Atkinson, J. H.; Grant, I. Neurocognitive effects of methamphetamine: a critical review and meta-analysis Neuropsychol. Rev. 2007, 17, 275-297 (Pubitemid 47498174)
6. Darke, S.; Kaye, S.; McKetin, R.; Duflou, J. Major physical and psychological harms of methamphetamine use Drug Alcohol Rev. 2008, 27, 253-262
7. Perez, J. A., Jr. ; Arsura, E. L.; Strategos, S. Methamphetamine-related stroke: four cases J. Emerg. Med. 1999, 17, 469-471 (Pubitemid 29226540)
8. Gentry, W. B.; Ruedi-Bettschen, D.; Owens, S. M. Development of active and passive human vaccines to treat methamphetamine addiction Hum. Vaccines 2009, 5, 206-213
9. Gentry, W. B.; Ruedi-Bettschen, D.; Owens, S. M. Anti-(+)-methamphetamine monoclonal antibody antagonists designed to prevent the progression of human diseases of addiction Clin. Pharmacol. Ther. 2010, 88, 390-393
10. Laurenzana, E. M.; Hendrickson, H. P.; Carpenter, D.; Peterson, E. C.; Gentry, W. B.; West, M.; Che, Y.; Carroll, F. I.; Owens, S. M. Functional and biological determinants affecting the duration of action and efficacy of anti-(+)-methamphetamine monoclonal antibodies in rats Vaccine 2009, 27, 7011-7020
11. Byrnes-Blake, K. A.; Carroll, F. I.; Abraham, P.; Owens, S. M. Generation of anti-(+)methamphetamine antibodies is not impeded by (+)methamphetamine administration during active immunization of rats Int. Immunopharmacol. 2001, 1, 329-338 (Pubitemid 32183731)
12. Carroll, F. I.; Abraham, P.; Gong, P. K.; Pidaparthi, R. R.; Blough, B. E.; Che, Y.; Hampton, A.; Gunnell, M.; Lay, J. O., Jr. ; Peterson, E. C.; Owens, S. M. The synthesis of haptens and their use for the development of monoclonal antibodies for treating methamphetamine abuse J. Med. Chem. 2009, 52, 7301-7309
13. Peterson, E. C.; Gunnell, M.; Che, Y.; Goforth, R. L.; Carroll, F. I.; Henry, R.; Liu, H.; Owens, S. M. Using hapten design to discover therapeutic monoclonal antibodies for treating methamphetamine abuse J. Pharmacol. Exp. Ther. 2007, 322, 30-39 (Pubitemid 46956367)
14. Owens, S. M.; Zorbas, M.; Lattin, D. L.; Gunnell, M.; Polk, M. Antibodies against arylcyclohexylamines and their similarities in binding specificity with the phencyclidine receptor J. Pharmacol. Exp. Ther. 1988, 246, 472-478
15. Davis, M. T.; Preston, J. F. A simple modified carbodiimide method for conjugation of small-molecular-weight compounds to immunoglobulin G with minimal protein crosslinking Anal. Biochem. 1981, 116, 402-407
16. Karas, M.; Hillenkamp, F. Laser desorption ionization of proteins with molecular masses exceeding 10,000 daltons Anal. Chem. 1988, 60, 2299-2301
17. Ragupathi, G.; Koide, F.; Livingston, P. O.; Cho, Y. S.; Endo, A.; Wan, Q.; Spassova, M. K.; Keding, S. J.; Allen, J.; Ouerfelli, O.; Wilson, R. M.; Danishefsky, S. J. Preparation and evaluation of unimolecular pentavalent and hexavalent antigenic constructs targeting prostate and breast cancer: a synthetic route to anticancer vaccine candidates J. Am. Chem. Soc. 2006, 128, 2715-2725 (Pubitemid 43327950)
18. Kinsey, B. M.; Jackson, D. C.; Orson, F. M. Anti-drug vaccines to treat substance abuse Immunol. Cell Biol. 2009, 87, 309-314
19. Hatsukami, D. K.; Rennard, S.; Jorenby, D.; Fiore, M.; Koopmeiners, J.; de Vos, A.; Horwith, G.; Pentel, P. R. Safety and immunogenicity of a nicotine conjugate vaccine in current smokers Clin. Pharmacol. Ther. 2005, 78, 456-467 (Pubitemid 41698900)
20. 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
21. Ishikawa, E.; Imagawa, M.; Hashida, S.; Yoshitake, S.; Hamaguchi, Y.; Ueno, T. Enzyme-labeling of antibodies and their fragments for enzyme immunoassay and immunohistochemical staining J. Immunoassay 1983, 4, 209-327 (Pubitemid 13016332)
22. Moreno, A. Y.; Mayorov, A. V.; Janda, K. D. Impact of distinct chemical structures for the development of a methamphetamine vaccine J. Am. Chem. Soc. 2011, 133, 6587-6595