Synthesis and evaluation of dimeric derivatives of 5-HT 2A receptor (5-HT 2AR) antagonist M-100907

ACS Chemical Neuroscience

Volumn 2, Issue 11, 2011, Pages 640-644

  Shashack, Matthew J ^a   Cunningham, Kathryn A ^a   Seitz, Patricia K ^a   McGinnis, Andrew ^a   Smith, Thressa D ^a   Watson, Cheryl S ^a   Gilbertson, Scott R ^b  

^a University of Texas Medical Branch School of Medicine   (United States)

^b University of Houston   (United States)

Author keywords

5 HT2AR; addiction; antagonist; dimers; Serotonin

Indexed keywords

CATECHOL; HOMODIMER; POLYETHER; VOLINANSERIN;

ARTICLE; BIOASSAY; DRUG SCREENING; DRUG SYNTHESIS; PRIORITY JOURNAL;

EID: 81455131958     PISSN: None     EISSN: 19487193     Source Type: Journal    
DOI: 10.1021/cn200077q     Document Type: Article

References (28)

1. Bockaert, J., Claeysen, S., Bécamel, C., Dumuis, A., and Marin, P. (2006) Neuronal 5-HT metabotropic receptors: fine-tuning of their structure, signaling, and roles in synaptic modulation Cell Tissue Res. 326 (2) 553-572 (Pubitemid 44435826)
2. Hoyer, D., Hannon, J. P., and Martin, G. R. (2002) Molecular, pharmacological and functional diversity of 5-HT receptors Pharmacol., Biochem. Behav. 71, 533-554 (Pubitemid 34219205)
3. Monck, N. J. T. and Kennett, G. A. (2008) 5-HT2C ligands: recent progress Prog. Med. Chem. 46, 281-390
4. Kitson, S. L. (2007) 5-Hydroxytryptamine (5-HT) receptor ligands Curr. Pharm. Des. 13 (25) 2621-2637 (Pubitemid 47430438)
5. Herrick-Davis, K., Grinde, E., and Mazurkiewicz, J. E. (2004) Biochemical and Biophysical Characterization of Serotonin 5-HT 2CReceptor Homodimers on the Plasma Membrane of Living Cells Biochemistry 43 (44) 13963-13971 (Pubitemid 39482746)
6. Herrick-Davis, K., Grinde, E., Harrigan, T. J., and Mazurkiewicz, J. E. (2005) Inhibition of serotonin 5-hydroxytryptamine2c receptor function through heterodimerization: receptor dimers bind two molecules of ligand and one G-protein J. Biol. Chem. 280 (48) 40144-40151 (Pubitemid 41779150)
7. Pellissier, L. P., Barthet, G., Gaven, F., Cassier, E., Trinquet, E., Pin, J. P., Marin, P., Dumuis, A., Bockaert, J., Baneres, J. L., and Claeysen, S. (2011) G Protein Activation by Serotonin Type 4 Receptor Dimers: Evidence That Turning on Two Protomers is More Efficient J. Biol. Chem. 286 (12) 9985-9997
8. Raymond, J. R., Mukhin, Y. V., Gelasco, A., Turner, J., Collinsworth, G., Gettys, T. W., Grewal, J. S., and Garnovskaya, M. N. (2001) Multiplicity of mechanisms of serotonin receptor signal transduction Pharmacol. Ther. 92, 179-212 (Pubitemid 34251133)
9. Lezoualc'h, F., Jockers, R., and Berque-Bestel, I. (2009) Multivalent-based drug design applied to serotonin 5-HT4 receptor oligomers Curr. Pharm. Des. 15 (6) 719-729
10. Munoz-Torrero, D. (2009) Exploiting multivalency in drug design Curr. Pharm. Des. 15 (6) 585-586
11. Krishnamurthy, V. M., Estroff, L. A., and Whitesides, G. M. (2006) Multivalency in ligand design Methods Princ. Med. Chem. 34, 11-53 (Fragment-Based Approaches in Drug Discovery)
12. Vagner, J., Handl, H. L., Gillies, R. J., and Hruby, V. J. (2004) Novel targeting strategy based on multimeric ligands for drug delivery and molecular imaging: homooligomers of alpha-MSH Bioorg. Med. Chem. Lett. 14 (1) 211-215 (Pubitemid 38010222)
13. Xu, L., Vagner, J., Josan, J., Lynch, R. M., Morse, D. L., Baggett, B., Han, H., Mash, E. A., Hruby, V. J., and Gillies, R. J. (2009) Enhanced targeting with heterobivalent ligands Mol. Cancer Ther. 8 (8) 2356-2365
14. Choi, S.-K., Green, D., Ho, A., Klein, U., Marquess, D., Taylor, R., and Turner, S. D. (2008) Designing Selective, High Affinity Ligands of 5-HT 1DReceptor by Covalent Dimerization of 5-HT 1FLigands Derived From 4-Fluoro- N -[3-(1-methyl-4-piperidinyl)-1H-indol-5-yl]benzamide J. Med. Chem. 51 (12) 3609-3616 (Pubitemid 351875016)
15. Bruno, A., Guadix, A. E., and Costantino, G. (2009) Molecular Dynamics Simulation of the Heterodimeric mGluR2/5HT 2AComplex. An Atomistic Resolution Study of a Potential New Target in Psychiatric Conditions J. Chem. Inf. Model. 49 (6) 1602-1616
16. Herth, M. M., Kramer, V., Piel, M., Palner, M., Riss, P. J., Knudsen, G. M., and Rösch, F. (2009) Synthesis and in vitro affinities of various MDL 100907 derivatives as potential 18F-radioligands for 5-HT2A receptor imaging with PET Bioorg. Med. Chem. 17 (8) 2989-3002
17. Meltzer, H. Y., Horiguchi, M., and Massey, B. W. (2011) The role of serotonin in the NMDA receptor antagonist models of psychosis and cognitive impairment Psychopharmacology (Heidelberg, Ger.) 213 (2-3) 289-305
18. Pockros, L. A., Pentkowski, N. S., Swinford, S. E., and Neisewander, J. L. (2011) Blockade of 5-HT2A receptors in the medial prefrontal cortex attenuates reinstatement of cue-elicited cocaine-seeking behavior in rats Psychopharmacology (Heidelberg, Ger.) 213 (2-3) 307-320
19. Semenova, S. and Markou, A. (2010) The alpha 2 adrenergic receptor antagonist idazoxan, but not the serotonin-2A receptor antagonist M100907, partially attenuated reward deficits associated with nicotine, but not amphetamine, withdrawal in rats Eur. Neuropsychopharmacol. 20 (10) 731-746
20. Zaniewska, M., McCreary, A. C., Wydra, K., and Filip, M. (2010) Differential effects of serotonin (5-HT)2 receptor-targeting ligands on locomotor responses to nicotine-repeated treatment Synapse (Hoboken, NJ, U.S.) 64 (7) 511-519
21. Dhonnchadha, B. A. N., Fox, R. G., Stutz, S. J., Rice, K. C., and Cunningham, K. A. (2009) Blockade of the serotonin 5-HT2A receptor suppresses cue-evoked reinstatement of cocaine-seeking behavior in a rat self-administration model Behav. Neurosci. 123 (2) 382-396
22. Zaniewska, M., McCreary, A. C., Wydra, K., and Filip, M. (2010) Effects of serotonin (5-HT)2 receptor ligands on depression-like behavior during nicotine withdrawal Neuropharmacology 58 (7) 1140-1146
23. Heinrich, T., Boettcher, H., Pruecher, H., Gottschlich, R., Ackermann, K.-A., and van Amsterdam, C. (2006) 1-(1-Phenethylpiperidin-4-yl)-1- phenylethanols as potent and highly selective 5-HT2A antagonists ChemMedChem 1 (2) 245-255 (Pubitemid 43700305)
24. Herth, M. M., Piel, M., Debus, F., Schmitt, U., Lueddens, H., and Roesch, F. (2009) Preliminary in vivo and ex vivo evaluation of the 5-HT2A imaging probe [18F]MH.MZ Nucl. Med. Biol. 36 (4) 447-454
25. Herth, M. M., Kramer, V., Piel, M., Palner, M., Riss, P. J., Knudsen, G. M., and Roesch, F. (2009) Synthesis and in vitro affinities of various MDL 100907 derivatives as potential 18F-radioligands for 5-HT2A receptor imaging with PET Bioorg. Med. Chem. 17 (8) 2989-3002
26. Ullrich, T. and Rice, K. C. (2000) A Practical Synthesis of the Serotonin 5-HT2A Receptor Antagonist MDL 100907, its Enantiomer and their 3-Phenolic Derivatives as Precursors for [11C]Labeled PET Ligands Bioorg. Med. Chem. 8 (10) 2427-2432
27. Anasatsio, N. C., Witkin, B. M., Seitz, P. K., Watson, C. S., and Cunningham, K. A. (2009) Novel medium-throughput 96-well plate assay to immunohistochemicallly detect key brain proteins in the serotonin 5-HT2C receptor-ERK pathway. Abstract 787.2. Society of Neuroscience Meeting; October 17-21, 2009.
28. Berg, K. A., Clarke, W. P., Sailstad, C., Saltzman, A., and Maayani, S. (1994) Signal transduction differences between 5-hydroxytryptamine type 2A and type 2C receptor systems Mol. Pharmacol. 46, 477-484 (Pubitemid 24296681)