Reduced antinociception of opioids in rats and mice by vaccination with immunogens containing oxycodone and hydrocodone haptens

Journal of Medicinal Chemistry

Volumn 56, Issue 3, 2013, Pages 915-923

  Pravetoni, Marco ^a,b   Le Naour, Morgan ^c   Tucker, Ashli M ^a   Harmon, Theresa M ^a   Hawley, Tara M ^a   Portoghese, Philip S ^b,c   Pentel, Paul R ^a,b  

^a MINNEAPOLIS MEDICAL RESEARCH FOUNDATION   (United States)

^b UNIVERSITY OF MINNESOTA MEDICAL SCHOOL   (United States)

^c UNIVERSITY OF MINNESOTA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HAPTEN; HYDROCODONE; HYDROCODONE HAPTEN; KEYHOLE LIMPET HEMOCYANIN; OPIATE DERIVATIVE; OXYCODONE; OXYCODONE HAPTEN; UNCLASSIFIED DRUG; VACCINE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINOCICEPTION; ARTICLE; CONTROLLED STUDY; DRUG BINDING; DRUG BRAIN LEVEL; DRUG DISTRIBUTION; DRUG EFFICACY; MALE; NONHUMAN; OPIATE ADDICTION; RAT; TREATMENT OUTCOME; VACCINATION;

ANALGESICS, OPIOID; ANIMALS; ENZYME-LINKED IMMUNOSORBENT ASSAY; HAPTENS; HYDROCODONE; MICE; OXYCODONE; RATS; VACCINES, SYNTHETIC;

EID: 84873905113     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm3013745     Document Type: Article

References (36)

1. 2008 Department of Defense Survey of Health Related Behaviors Among Active Duty Military Personnel; U.S. Department of Defence, 2009
2. National Survey on Drug Use and Health: National Findings; U.S. Department of Health and Human Services Substance Abuse and Mental Health Services Administration Office of Applied Studies, 2011
3. Compton, W. M.; Volkow, N. D. Abuse of prescription drugs and the risk of addiction Drug Alcohol Depend. 2006, 83 (Suppl 1) S4-S7
4. Compton, W. M.; Volkow, N. D. Major increases in opioid analgesic abuse in the United States: concerns and strategies Drug Alcohol Depend. 2006, 81, 103-107
5. Maxwell, J. C. The prescription drug epidemic in the United States: a perfect storm Drug Alcohol Rev. 2011, 30, 264-270
6. Oxymorphone Abuse: A Growing Threat Nationwide; EWS Report 000011; U.S. Department of Justice, 2011
7. Epidemic: Responding to America's Prescription Drug Abuse Crisis; Executive Office of the President of the United States, 2011.
8. Butler, S. F.; Black, R. A.; Cassidy, T. A.; Dailey, T. M.; Budman, S. H. Abuse risks and routes of administration of different prescription opioid compounds and formulations Harm Reduction J. 2011, 8, 29
9. Dodrill, C. L.; Helmer, D. A.; Kosten, T. R. Prescription pain medication dependence Am. J. Psychiatry 2011, 168, 466-471
10. Lofwall, M. R.; Moody, D. E.; Fang, W. B.; Nuzzo, P. A.; Walsh, S. L. Pharmacokinetics of Intranasal Crushed OxyContin and Intravenous Oxycodone in Nondependent Prescription Opioid Abusers J. Clin. Pharmacol. 2011, 52, 600-606
11. Stoops, W. W.; Hatton, K. W.; Lofwall, M. R.; Nuzzo, P. A.; Walsh, S. L. Intravenous oxycodone, hydrocodone, and morphine in recreational opioid users: abuse potential and relative potencies Psychopharmacology (Berlin) 2010, 212, 193-203
12. Walsh, S. L.; Nuzzo, P. A.; Lofwall, M. R.; Holtman, J. R., Jr. The relative abuse liability of oral oxycodone, hydrocodone and hydromorphone assessed in prescription opioid abusers Drug Alcohol Depend. 2008, 98, 191-202
13. Wu, L. T.; Woody, G. E.; Yang, C.; Blazer, D. G. How do prescription opioid users differ from users of heroin or other drugs in psychopathology: results from the National Epidemiologic Survey on Alcohol and Related Conditions J. Addict. Med. 2011, 5, 28-35
14. Wu, L. T.; Woody, G. E.; Yang, C.; Mannelli, P.; Blazer, D. G. Differences in onset and abuse/dependence episodes between prescription opioids and heroin: results from the National Epidemiologic Survey on Alcohol and Related Conditions Subst. Abuse Rehabil. 2011, 2011, 77-88
15. Haney, M.; Gunderson, E. W.; Jiang, H.; Collins, E. D.; Foltin, R. W. Cocaine-specific antibodies blunt the subjective effects of smoked cocaine in humans Biol. Psychiatry 2010, 67, 59-65
16. Hatsukami, D. K.; Jorenby, D. E.; Gonzales, D.; Rigotti, N. A.; Glover, E. D.; Oncken, C. A.; Tashkin, D. P.; Reus, V. I.; Akhavain, R. C.; Fahim, R. E.; Kessler, P. D.; Niknian, M.; Kalnik, M. W.; Rennard, S. I. Immunogenicity and smoking-cessation outcomes for a novel nicotine immunotherapeutic Clin. Pharmacol. Ther. 2011, 89, 392-399
17. 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
18. Anton, B.; Leff, P. A novel bivalent morphine/heroin vaccine that prevents relapse to heroin addiction in rodents Vaccine 2006, 24, 3232-3240
19. Bonese, K. F.; Wainer, B. H.; Fitch, F. W.; Rothberg, R. M.; Schuster, C. R. Changes in heroin self-administration by a rhesus monkey after morphine immunisation Nature 1974, 252, 708-710
20. Li, Q. Q.; Luo, Y. X.; Sun, C. Y.; Xue, Y. X.; Zhu, W. L.; Shi, H. S.; Zhai, H. F.; Shi, J.; Lu, L. A morphine/heroin vaccine with new hapten design attenuates behavioral effects in rats J. Neurochem. 2011, 119, 1271-1281
21. Pravetoni, M.; Raleigh, M. D.; Le Naour, M.; Tucker, A. M.; Harmon, T. M.; Jones, J. M.; Birnbaum, A. K.; Portoghese, P. S.; Pentel, P. R. Co-administration of morphine and oxycodone vaccines reduces the distribution of 6-monoacetylmorphine and oxycodone to brain in rats Vaccine 2012, 30, 4617-4624
22. Stowe, G. N.; Vendruscolo, L. F.; Edwards, S.; Schlosburg, J. E.; Misra, K. K.; Schulteis, G.; Mayorov, A. V.; Zakhari, J. S.; Koob, G. F.; Janda, K. D. A vaccine strategy that induces protective immunity against heroin J. Med. Chem. 2011, 54, 5195-5204
23. Wainer, B. H.; Fitch, F. W.; Rothberg, R. M.; Fried, J. Morphine-3-succinyl-bovine serum albumin: an immunogenic hapten-protein conjugate Science 1972, 176, 1143-1145
24. Findlay, J. W.; Butz, R. F.; Jones, E. C. Relationships between immunogen structure and antisera specificity in the narcotic alkaloid series Clin. Chem. 1981, 27, 1524-1535
25. Pravetoni, M.; Le Naour, M.; Harmon, T.; Tucker, A.; Portoghese, P. S.; Pentel, P. R. An oxycodone conjugate vaccine elicits oxycodone-specific antibodies that reduce oxycodone distribution to brain and hot-plate analgesia J. Pharmacol. Exp. Ther. 2012, 341, 225-232
26. Lewenstein, M. J., Morphine and codeinone derivatives. Patent GB945909 19640108, 1964.
27. Glaser, M.; Karlsen, H.; Solbakken, M.; Arukwe, J.; Brady, F.; Luthra, S. K.; Cuthbertson, A. 18F-fluorothiols: a new approach to label peptides chemoselectively as potential tracers for positron emission tomography Bioconjugate Chem. 2004, 15, 1447-1453
28. Sondergaard, K.; Kristensen, J. L.; Palner, M.; Gillings, N.; Knudsen, G. M.; Roth, B. L.; Begtrup, M. Synthesis and binding studies of 2-arylapomorphines Org. Biomol. Chem. 2005, 3, 4077-4081
29. Kotick, M. P.; Leland, D. L.; Polazzi, J. O.; Schut, R. N. Analgesic narcotic antagonists. 1. 8-beta-Alkyl-, 8-beta-acyl-, and 8-beta-(tertiary alcohol)dihydrocodeinones and -dihydromorphinones J. Med. Chem. 1980, 23, 166-174
30. Sagara, T.; Okamura, M.; Shimohigashi, Y.; Ohno, M.; Kanematsu, K. Specificity affinity labeling of μ opioid receptor in rat brain by S-activated sulfydryldihydromorphine analogs Bioorg. Med. Chem. Lett. 1995, 5, 1609-1614
31. Kolev, T.; Bakalska, R.; Seidel, R. W.; Mayer-Figge, H.; Oppel, I. M.; Spiteller, M.; Sheldrick, W. S.; Koleva, B. B. Novel codeinone derivatives via Michael addition of barbituric acids Tetrahedron: Asymmetry 2009, 20, 327-334
32. Carroll, F. I.; Blough, B. E.; Pidaparthi, R. R.; Abraham, P.; Gong, P. K.; Deng, L.; Huang, X.; Gunnell, M.; Lay, J. O., Jr.; Peterson, E. C.; Owens, S. M. Synthesis of mercapto-(+)-methamphetamine haptens and their use for obtaining improved epitope density on (+)-methamphetamine conjugate vaccines J. Med. Chem. 2011, 54, 5221-5228
33. Pravetoni, M.; Keyler, D. E.; Pidaparthi, R. R.; Carroll, F. I.; Runyon, S. P.; Murtaugh, M. P.; Earley, C. A.; Pentel, P. R. Structurally distinct nicotine immunogens elicit antibodies with non-overlapping specificities Biochem. Pharmacol. 2012, 83, 543-550
34. Janda, K. D.; Benkovic, S. J.; Lerner, R. A. Catalytic antibodies with lipase activity and R or S substrate selectivity Science 1989, 244, 437-440
35. Raleigh, M. D.; Pravetoni, M.; Harris, A. C.; Birnbaum, A. K.; Pentel, P. R., Selective effects of a morphine conjugate vaccine on heroin and metabolite distribution and heroin-induced behaviors in rats. J. Pharmacol. Exp. Ther. 2012, DOI: 10.1124/jpet.112.201194.
36. Pravetoni, M.; Keyler, D. E.; Pidaparthi, R. R.; Carroll, F. I.; Runyon, S. P.; Murtaugh, M. P.; Earley, C. A.; Pentel, P. R. Structurally distinct nicotine immunogens elicit antibodies with non-overlapping specificities Biochem. Pharmacol. 2011, 83, 543-550