A new serotonin 5-HT 6 receptor antagonist with procognitive activity - Importance of a halogen bond interaction to stabilize the binding

Scientific Reports

Volumn 7, Issue , 2017, Pages

  González Vera, Juan A ^a,d   Medina, Rocío A ^a   Martín Fontecha, Mar ^a   Gonzalez, Angel ^b   De La Fuente, Tania ^a,e   Vázquez Villa, Henar ^a   García Cárceles, Javier ^a   Botta, Joaquín ^c   McCormick, Peter J ^b   Benhamú, Bellinda ^a   Pardo, Leonardo ^b   López Rodríguez, María L ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^b UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

^c UNIVERSITY OF EAST ANGLIA   (United Kingdom)

^d UNIV MONTPELLIER   (France)

^e SAINT LOUIS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZIMIDAZOLE DERIVATIVE; HALOGEN; LIGAND; SEROTONIN 6 RECEPTOR; SEROTONIN ANTAGONIST; SEROTONIN RECEPTOR;

ANIMAL; CHEMISTRY; COGNITION; DRUG EFFECT; HUMAN; LIVER MICROSOME; METABOLISM; RAT; SITE DIRECTED MUTAGENESIS; STRUCTURAL HOMOLOGY; SYNTHESIS; TASK PERFORMANCE;

ANIMALS; BENZIMIDAZOLES; COGNITION; HALOGENS; HUMANS; LIGANDS; MICROSOMES, LIVER; MUTAGENESIS, SITE-DIRECTED; RATS; RECEPTORS, SEROTONIN; SEROTONIN ANTAGONISTS; STRUCTURAL HOMOLOGY, PROTEIN; TASK PERFORMANCE AND ANALYSIS;

EID: 85010824758     PISSN: None     EISSN: 20452322     Source Type: Journal    
DOI: 10.1038/srep41293     Document Type: Article

References (29)

1. McCorvy, J. D. & Roth, B. L. Structure and function of serotonin G protein-coupled receptors. Pharmacol. Ther. 150, 129-142 (2015).
2. Codony, X., Vela, J. M. & Ramirez, M. J. 5-HT6 receptor and cognition. Curr Opin Pharmacol 11, 94-100 (2011).
3. Fone, K. C. F. An update on the role of the 5-hydroxytryptamine6 receptor in cognitive function. Neuropharmacology 55, 1015-1022 (2008).
4. Meneses, A., Perez-Garcia, G., Ponce-Lopez, T. & Castillo, C. 5-HT6 receptor memory and amnesia: behavioral pharmacology-learning and memory processes. International review of neurobiology 96, 27-47 (2011).
5. Benhamu, B., Martin-Fontecha, M., Vazquez-Villa, H., Pardo, L. & Lopez-Rodriguez, M. L. Serotonin 5-HT6 receptor antagonists for the treatment of cognitive deficiency in Alzheimer's disease. J. Med. Chem. 57, 7160-7181 (2014).
6. Ramirez, M. J. 5-HT6 receptors and Alzheimer's disease. Alzheimers Res Ther 5 (2013).
7. Marazziti, D., Rutigliano, G., Catena-Dell'Osso, M., Baroni, S. & Dell'Osso, L. The 5-HT6 receptor antagonism approach in Alzheimer's disease. Drugs Fut. 39, 133-140 (2014).
8. López-Rodríguez, M. L. et al. A three-dimensional pharmacophore model for 5-hydroxytryptamine6 (5-HT6) receptor antagonists. J. Med. Chem. 48, 4216-4219 (2005).
9. de la Fuente, T. et al. Benzimidazole derivatives as new serotonin 5-HT6 receptor antagonists. Molecular mechanisms of receptor inactivation. J. Med. Chem. 53, 1357-1369 (2010).
10. Wang, C. et al. Structural basis for molecular recognition at serotonin receptors. Science 340, 610-614 (2013).
11. Wacker, D. et al. Structural features for functional selectivity at serotonin receptors. Science 340, 615-619 (2013).
12. Wilcken, R., Zimmermann, M. O., Lange, A., Joerger, A. C. & Boeckler, F. M. Principles and applications of halogen bonding in medicinal chemistry and chemical biology. J. Med. Chem. 56, 1363-1388 (2013).
13. Voth, A. R., Khuu, P., Oishi, K. & Ho, P. S. Halogen bonds as orthogonal molecular interactions to hydrogen bonds. Nat. Chem. 1, 74-79 (2009).
14. Chakrabarti, P. & Chakrabarti, S. C-H O hydrogen bond involving proline residues in alpha-helices. J. Mol. Biol. 284, 867-873 (1998).
15. Huang, X. P. et al. Parallel functional activity profiling reveals valvulopathogens are potent 5-hydroxytryptamine(2B) receptor agonists: Implications for drug safety assessment. Mol. Pharmacol. 76, 710-722 (2009).
16. Grychowska, K. et al. Novel 1H-pyrrolo[3, 2-c]quinoline based 5-HT6 receptor antagonists with potential application for the treatment of cognitive disorders associated with Alzheimer's disease. ACS Chem. Neurosci. 7, 972-983 (2016).
17. Froestl, W., Muhs, A. & Pfeifer, A. Cognitive enhancers (nootropics). Part 1: Drugs interacting with receptors. Update 2014. J. Alzheimers Dis. 41, 961-1019 (2014).
18. Gasbarri, A. & Pompili, A. Serotonergic 5-HT7 receptors and cognition. Rev. Neurosci. 25, 311-323 (2014).
19. King, M. V. et al. 5-HT6 receptor antagonists reverse delay-dependent deficits in novel object discrimination by enhancing consolidation-an effect sensitive to NMDA receptor antagonism. Neuropharmacology 47, 195-204 (2004).
20. Vázquez-Villa, H. et al. Development of molecular probes for the human 5-HT6 receptor. J. Med. Chem. 53, 7095-7106 (2010).
21. Valhondo, M. et al. New serotonin 5-HT1A receptor agonists endowed with antinociceptive activity in vivo. J. Med. Chem. 56, 7851-7861 (2013).
22. Mathes, C. QPatch: The past, present and future of automated patch clamp. Expert Opin. Ther. Targets 10, 319-327 (2006).
23. Marti-Renom, M. A. et al. Comparative protein structure modeling of genes and genomes. Annu. Rev. Biophys. Biomol. Struct. 29, 291-325 (2000).
24. Gonzalez, A., Cordomi, A., Caltabiano, G. & Pardo, L. Impact of helix irregularities on sequence alignment and homology modeling of G protein-coupled receptors. ChemBioChem. 13, 1393-1399 (2012).
25. Trott, O. & Olson, A. J. Software news and update AutoDock Vina: Improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading. J. Comput. Chem. 31, 455-461 (2010).
26. Hess, B., Kutzner, C., van der Spoel, D. & Lindahl, E. GROMACS 4: Algorithms for highly efficient, load-balanced, and scalable molecular simulation. J. Chem. Theory Comput. 4, 435-447 (2008).
27. Cordomi, A., Caltabiano, G. & Pardo, L. Membrane protein simulations using AMBER force field and Berger lipid parameters. J. Chem. Theory Comput. 8, 948-958 (2012).
28. Ibrahim, M. A. A. Performance assessment of semiempirical molecular orbital methods in describing halogen bonding: Quantum mechanical and quantum mechanical/molecular mechanical-molecular dynamics study. J. Chem. Inf. Model. 51, 2549-2559 (2011).
29. Ford, M. C. & Ho, P. S. Computational tools to model halogen bonds in medicinal chemistry. J. Med. Chem. 59, 1655-1670 (2016).