Preliminary pharmacological evaluation of enantiomeric morphinans

ACS Chemical Neuroscience

Volumn 5, Issue 2, 2014, Pages 93-99

  Sromek, Anna W ^a   Provencher, Brian A ^a   Russell, Shayla ^a   Chartoff, Elena ^a   Knapp, Brian I ^b   Bidlack, Jean M ^b   Neumeyer, John L ^a  

^a MCLEAN HOSPITAL   (United States)

^b UNIVERSITY OF ROCHESTER SCHOOL OF MEDICINE AND DENTISTRY   (United States)

Author keywords

Drug abuse; enantiomer; ICSS; NMDA receptor; opioid receptor; sigma receptor

Indexed keywords

ANIMALS; HUMANS; MALE; MORPHINANS; N-METHYLASPARTATE; RATS; RATS, SPRAGUE-DAWLEY; RECEPTORS, OPIOID; RECEPTORS, SIGMA;

EID: 84894441985     PISSN: None     EISSN: 19487193     Source Type: Journal    
DOI: 10.1021/cn400205z     Document Type: Article

References (30)

1. McCurdy, C. R. and Prisinzano, T. E. (2010) Opioid Receptor Ligands. In Burger's Medicinal Chemistry, Drug Discovery, and Development (Abraham, D. J. and Rotella, D. P., Eds.), seventh ed., John Wiley and Sons, Inc., New York.
2. Pentney, R. J. W. (1991) Gratton, Effects of Local Delta and Mu Opioid Receptor Activation on Basal and Stimulated Dopamine Release in Striatum and Nucleus Accumbens of Rat: An In Vivo Electrochemical Study Neuroscience 45, 95-102
3. Shippenberg, T. S. (2009) The dynorphin/kappa opioid receptor system: a new target for the treatment of addiction and affective disorders? Neuropsychopharmacology 34, 247
4. Glick, S. D., Maisonneuve, I. M., Dickinson, H. A., and Kitchen, B. A. (2001) Comparative effects of dextromethorphan and dextrorphan on morphine, methamphetamine, and nicotine self-administraion in rats Eur. J. Pharmacol. 422, 87-90
5. Chen, L. and Huang, L.-Y. M. (1991) Sustained Potentiation of NMDA Receptor-Mediated Glutamate Responses Through Activation of Protein Kinase C by a μ Opioid Neuron 7, 319-326
6. Elliott, K., Kest, B., Man, A., Kao, B., and Inturrisi, C. E. (1995) N -Methyl- d -aspartate (NMDA) Receptors, Mu and Kappa Opioid Tolerance, and Perspectives on New Analgesic Drug Development Neuropsychopharmacology 13 (4) 347-356
7. Svingos, A. L. and Colago, E. E. O. (2002) k-Opioid and NMDA glutamate receptors are differentially targeted within rat medial prefrontal cortex Brain Res. 946, 262-271
8. Trujillo, K. A. (1995) Effects of Noncompetitive N -Methyl- d -aspartate Receptor Antagonists on Opiate Tolerance and Physical Dependence Neuropsychopharmacology 13 (4) 301-307
9. Zapata, A., Gasior, M., Geter-Douglass, B., Tortella, F. C., Newman, A. H., and Witkin, J. M. (2003) Attenuation of the stimulant and convulsant effects of cocaine by 17-substituted-3-hydroxy and 3-alkoxy derivatives of dextromethorphan Pharmacol., Biochem. Behav. 74, 313-323
10. Iijima, I., Minamikawa, J.-I., Jacobson, A. E., Brossi, A., Rice, K. C., and Klee, W. (1978) Studies in the (+)-Morphinan Series. 5. Synthesis and Biological Properties of (+)-Naloxone J. Med. Chem. 21 (4) 398-400
11. Chatterjie, N., Alexander, G. J., Sechzer, J. A., and Lieberman, K. W. (1996) Prevention of Cocaine-Induced Hyperactivity by a Naloxone Isomer with no Opiate Antagonist Activity Neurochem. Res. 21 (6) 691-693
12. Chatterjie, N., Sechzer, J. A., Lieberman, K. W., and Alexander, G. J. (1998) Dextro-Naloxone Counteracts Amphetamine-Induced Hyperactivity Pharmacol., Biochem. Behav. 59 (2) 271-274
13. Wu, H.-e., Hong, J.-S., and Tseng, L. F. (2007) Stereoselective action of (+)-morphine over (-)-morphine in attenuating the (-)-morphine-produced antinociception via the naloxone-sensitive sigma receptor in the mouse Eur. J. Pharmacol. 571, 145-151
14. Hutchinson, M. R., Northcutt, A. L., Hiranita, T., Wang, X., Lewis, S. S., Thomas, J., van Steeg, K., Kopajtic, T. A., Loram, L. C., Sfregola, C., Galer, E., Miles, N. E., Bland, S. T., Amat, J., Rozeske, R. R., Maslanik, T., Chapman, T. R., Strand, K. A., Fleshner, M., Bachtell, R. K., Somogyi, A. A., Yin, H., Katz, J. L., Rice, K. C., Maier, S. F., and Watkins, L. R. (2012) Opioid Activation of Toll-Like Receptor 4 Contributes to Drug Reinforcement J. Neurosci. 32 (33) 11187-11200
15. Neumeyer, J. L., Bidlack, J. M., Zong, R., Bakthavachalam, V., Gao, P., Cohen, D. J., Negus, S. S., and Mello, N. K. (2000) Synthesis and Opioid Receptor Affinity of Morphinan and Benzomorphan Derivatives: Mixed κ Agonists and μ Agonists/Antagonists as Potential Pharmacotherapeutics for Cocaine Dependence J. Med. Chem. 43, 114-120
16. Neumeyer, J. L., Negus, S. S., and Bidlack, J. M. (2000) Kappa Opioid Agonists as Targets for Pharmacotherapies in Cocaine Abuse Pharm. Acta. Helv. 74, 337-344
17. Bowen, C. A., Negus, S. S., Zong, R., Neumeyer, J. L., Bidlack, J. M., and Mello, N. K. (2003) Effects of Mixed-Action Kappa/Mu Opioids on Cocaine Self-Administration and Cocaine Discrimination by Rhesus Monkeys Neuropsychopharmacology 28, 1125-1139
18. Zhang, A., Vliet, S. V., and Neumeyer, J. L. (2003) Synthesis of aminothiazole derived morphinans Tetrahedron Lett. 44, 6459-6462
19. Decker, M., Si, Y. G., Knapp, B. I., Bidlack, J. M., and Neumeyer, J. L. (2010) Synthesis and Opioid Receptor Binding Affinities of 2-Substituted and 3-Aminomorphinans: Ligands for μ, κ, and δ Opioid Receptors J. Med. Chem. 53, 402-418
20. Kim, H.-C., Nabeshima, T., Jhoo, W.-K., Ko, K. H., Kim, W.-K., Shin, E.-J., Cho, M., and Lee, P. H. (2001) Anticonvulsant Effects of New Morphinan Derivatives Bioorg. Med. Chem. Lett. 11, 1651-1654
21. Peng, X., Knapp, B. I., Bidlack, J. M., and Neumeyer, J. L. (2006) Synthesis and Preliminary In vitro Investigation of Bivalent Ligands Containing Homo- and Heterodimeric Pharmacophores at μ, δ, and κ Opioid Receptors J. Med. Chem. 49, 256-262
22. Stringer, M., Makin, M. K., Miles, J., and Morley, J. S. (2000) d -Morphine, but not l -morphine, has low micromolar affinity for the non-competitive N -methyl- d -aspartate site in rat forebrain. Possible clinical implications for the management of neuropathic pain Neurosci. Lett. 295, 21-24
23. Codd, E. E., Shank, R. P., Schupsky, J. J., and Raffa, R. B. (1995) Serotonin and Norepinephrine Uptake Inhibiting Activity of Centrally Acting Analgesics: Structural Determinants and role in Antinociception J. Pharmacol. Exp. Ther. 274, 1263-1270
24. Kroemer, R. T., Koutsilieri, E., Hecht, P., Leidl, K. R., Riederer, P., and Kornhuber, J. (1998) Quantitative Analysis of the Structural Requirements for the Blockade of the N -Methyl-D-aspartate Receptor at the Phencyclidine Binding Site J. Med. Chem. 41, 393-400
25. Chou, Y.-C., Liao, J.-F., Chang, W.-Y., Lin, M.-F., and Chen, C.-F. (1999) Binding of dimemorphan to sigma-1 receptor and its anticonvulsant and locomotor effects in mice, compared with dextromethorphan and dextrorphan Brain Res. 821, 5116-519
26. Knoll, A. T. and Carlezon, W. A., Jr. (2010) Dynorphin, stress, and depression Brain Res. 1314, 56-73
27. Tomasiewicz, H. C., Todtenkopf, M. S., Chartoff, E. H., Cohen, B. M., and Carlezon, W. A., Jr. (2008) The kappa-opioid agonist U69,593 blocks cocaine-induced enhancement of brain stimulation reward Biol. Psychiatry 64, 982-988
28. Potter, D. N., Damez-Werno, D., Carlezon, W. A., Jr., Cohen, B. M., and Chartoff, E. H. (2011) Repeated exposure to the kappa-opioid receptor agonist salvinorin A modulates extracellular signal-regulated kinase and reward sensitivity Biol. Psychiatry 70, 744-753
29. Carlezon, W. A., Jr. and Chartoff, E. H. (2007) Intracranial self-stimulation (ICSS) in rodents to study the neurobiology of motivation Nat. Protoc. 2, 2987-2995
30. Provencher, B. A., Sromek, A. W., Li, W., Russell, S., Chartoff, E., Knapp, B. I., Bidlack, J. M., and Neumeyer, J. L. (2013) Synthesis and Pharmacological Evaluation Aminothiazolomorphinans at Mu and Kappa Opioid Receptors J. Med. Chem. 56, 8872-8878