Novel irreversible fluorescent probes targeting the 18 kDa translocator protein: Synthesis and biological characterization

Journal of Medicinal Chemistry

Volumn 53, Issue 10, 2010, Pages 4085-4093

  Taliani, Sabrina ^a   Da Pozzo, Eleonora ^a   Bellandi, Marusca ^a   Bendinelli, Sara ^a   Pugliesi, Isabella ^a   Simorini, Francesca ^a   La Motta, Concettina ^a   Salerno, Silvia ^a   Marini, Anna Maria ^a   Da Settimo, Federico ^a   Cosimelli, Barbara ^b   Greco, Giovanni ^b   Novellino, Ettore ^b   Martini, Claudia ^a  

^a UNIVERSITY OF PISA   (Italy)

^b UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

2 PHENYLINDOLE DERIVATIVE; 4' CHLORODIAZEPAM; ISOTHIOCYANIC ACID DERIVATIVE; MITOCHONDRIAL PROTEIN; N (5 ISOTHIOCYANATO 2 PHENYLINDOL 3 YLGLYCOXYL) N' (7 NITROBENZ 2 OXA 1,3 DIAZO 4 YL) 1,6 DIAMINOHEXANE; N,N DIHEXYL [5 ISOTHIOCYANATO 2 PHENYLINDOL 3 YL)GLYOXYLAMIDE; N,N DIPROPYL [5 ISOTHIOCYANAO 2 PHENYLINDOL 3 YL)GLYOXYLAMIDE; TRANSLOCATOR PROTEIN; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CANCER CELL CULTURE; CONTROLLED STUDY; DRUG SYNTHESIS; FLUORESCENCE SPECTROSCOPY; GLIOMA; HUMAN; HUMAN CELL; HUMAN CELL CULTURE; MECHANICAL PROBE; PHYSICAL CHEMISTRY; PROTEIN BINDING;

4-CHLORO-7-NITROBENZOFURAZAN; ANIMALS; BINDING, COMPETITIVE; CARRIER PROTEINS; CELL LINE, TUMOR; CELL MEMBRANE PERMEABILITY; FLUORESCENT DYES; HUMANS; ISOTHIOCYANATES; KIDNEY; KINETICS; LIGANDS; MITOCHONDRIAL PROTEINS; PROTEIN BINDING; RADIOLIGAND ASSAY; RATS; RECEPTORS, GABA; RECEPTORS, GABA-A; SPECTROMETRY, FLUORESCENCE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 77952710965     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm100100q     Document Type: Article

References (49)

1. Papadopoulos, V.; Baraldi, M.; Guilarte, T. R.; Knudsen, T. B.; Lacapère, J. J.; Lindemann, P.; Norenberg, M. D.; Nutt, D.; Weizman, A.; Zhang, M. R.; Gavish, M. Translocator protein (18 kDa): new nomenclature for the peripheral-type benzodiazepine receptor based on its structure and molecular function Trends Pharmacol. Sci. 2006, 27, 402-409
2. Gavish, M.; Bachman, I.; Shoukrun, R.; Katz, Y.; Veenman, L.; Weisinger, G.; Weizman, A. Enigma of the Peripheral Benzodiazepine Receptor Pharmacol. Rev. 1999, 51, 619-640
3. Anholt, R. R.; Pedersen, P.L.; De Souza, E. B.; Snyder, S. H. The Peripheral-Type Benzodiazepine Receptor. Localization to the Mitochondrial Outer Membrane J. Biol. Chem. 1986, 261, 576-583
4. Antkiewicz-Michaluk, L.; Guidotti, A.; Krueger, K. E. Molecular Characterization and Mitochondrial Density of a Recognition Site for Peripheral-Type Benzodiazepine Ligands Mol. Pharmacol. 1988, 34, 272-278
5. Olson, J. M.; Ciliax, B. J.; Mancini, W. R.; Young, A. B. Presence of peripheral-type benzodiazepine binding sites on human erythrocyte membranes Eur. J. Pharmacol. 1988, 152, 47-53
6. McEnery, M. W.; Snowman, A. M.; Trifiletti, R. R.; Snyder, S. H. Isolation of the Mitochondrial Benzodiazepine Receptor: Association with the Voltage-Dependent Anion Channel and the Adenine Nucleotide Carrier Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 3170-3174
7. Casellas, P.; Galiegue, S.; Basile, A. S. Peripheral Benzodiazepine Receptors and Mitochondrial Function Neurochem. Int. 2002, 40, 475-486
8. James, M. L.; Selleri, S.; Kassiou, M. Development of Ligands for the Peripheral Benzodiazepine Receptor Curr. Med. Chem. 2006, 13, 1991-2001
9. Galiegue, S.; Tinel, N.; Casellas, P. The Peripheral Benzodiazepine Receptor: A Promising Therapeutic Drug Target Curr. Med. Chem. 2003, 10, 1563-1572
10. Papadopoulos, V.; Lecanu, L.; Brown, R. C.; Han, Z.; Yao, Z.-X. Peripheral-Type Benzodiazepine Receptor in Neurosteroid Biosynthesis, Neuropathology and Neurological Disorders Neuroscience 2006, 138, 749-756
11. Scarf, A. M.; Ittner, L. M.; Kassiou, M. The Translocator Protein (18 kDa): Central Nervous System Disease and Drug Design J. Med. Chem. 2009, 52, 581-592
12. Taliani, S.; Da Settimo, F.; Da Pozzo, E.; Chelli, B.; Martini, C. Translocator Protein Ligands as Promising Therapeutic Tools for Anxiety Disorders Curr. Med. Chem. 2009, 16, 3359-3380
13. Veenman, L.; Gavish, M. Peripheral Benzodiazepine Receptors: Their Implication in Brain Disease Drug. Dev. Res. 2000, 50, 355-370
14. Chen, M.-K.; Guilarte, R. T. Translocator Protein 18 kDa (TSPO): Molecular Sensor of Brain Injury and Repair Pharmacol. Ther. 2008, 118, 1-17
15. Papadopoulos, V.; Lecanu, L. Translocator Protein (18 kDa) TSPO: An Emerging Therapeutic Target in Neurotrauma Exp. Neurol. 2009, 219, 53-57
16. 11C]PK 11195 Challengers Eur. J. Nucl. Med. Mol. Imaging 2008, 35, 2304-2319
17. Pini, S.; Martini, C.; Abelli, M.; Muti, M.; Gesi, C.; Montali, M.; Chelli, B.; Lucacchini, A.; Cassano, G. B. Peripheral-Type Benzodiazepine Receptor Binding Sites in Platelets of Patients with Panic Disorder Associated to Separation Anxiety Symptoms Psychopharmacology 2005, 181, 407-411
18. Chelli, B.; Pini, S.; Abelli, M.; Cardini, A.; Lari, L.; Muti, M.; Gesi, C.; Cassano, G. B.; Lucacchini, A.; Martini, C. Platelet 18 kDa Translocator Protein Density Is Reduced in Depressed Patients with Adult Separation Anxiety Eur. Neuropsychopharmacol. 2008, 18, 249-254
19. DellOsso, L.; Da Pozzo, E.; Carmassi, C.; Trincavelli, M. L.; Ciapparelli, A.; Martini, C. Lifetime Manic-Hypomanic Symptoms in Post-Traumatic Stress Disorder: Relationship with the 18 kDa Mitochondrial Translocator Protein Density Psychiatry Res. 2010, 177, 139-143
20. Doorduin, J.; de Vries, E. F.; Dierckx, R. A.; Klein, H. C. PET Imaging of the Peripheral Benzodiazepine Receptor: Monitoring Disease Progression and Therapy Response in Neurodegenerative Disorders Curr. Pharm. Des. 2008, 14, 3297-3315
21. Venneti, S.; Lopresti, B. J.; Wiley, C. A. The Peripheral Benzodiazepine Receptor (Translocator Protein 18 kDa) in Microglia: from Pathology to Imaging Prog. Neurobiol. 2006, 80, 308-322
22. 11C]Methylated Quinoline-2-carboxamides as Potential Radioligands for Visualization of Peripheral Benzodiazepine Receptors J. Med. Chem. 2001, 44, 579-585
23. 11C]Methyl-Labeled Phenoxyphenyl Acetamide Derivatives as Positron Emission Tomography Ligands for the Peripheral Benzodiazepine Receptor: Radiosynthesis, Uptake, and In Vivo Binding in Brain J. Med. Chem. 2006, 49, 2735-2742
24. 131I]iodo-5-methoxybenzyl)acetamide: A Potent Iodinated Radioligand for the Peripheral-Type Benzodiazepine Receptor in Brain J. Med. Chem. 2007, 50, 848-855
25. 18F]Pyrazolo[1,5- a ]Pyrimidines for the study of the Peripheral Benzodiazepine Receptor Using Positron Emission Tomography J. Med. Chem. 2008, 51, 3700-3712
26. 11C-Labeled Aryloxyanilide Ligands for Imaging Brain Peripheral Benzodiazepine Receptors In Vivo J. Med. Chem. 2008, 51, 17-30
27. Dollé, F.; Luus, C.; Reynolds, A.; Kassiou, M. Radiolabelled Molecules for Imaging the Translocator Protein (18 kDa) Using Positron Emission Tomography Curr. Med. Chem. 2009, 16, 2899-2923
28. 18F-Labeled Ligand for Imaging Brain Peripheral Benzodiazepine Receptors with PET J. Med. Chem. 2009, 52, 688-699
29. Daly, C. J.; McGrath, J. C. Fluorescent Ligands, Antibodies, and Proteins for the Study of Receptors Pharmacol. Ther. 2003, 100, 101-118
30. Laquintana, V.; Denora, N.; Lopedota, A.; Suzuki, H.; Sawada, M.; Serra, M.; Biggio, G.; Latrofa, A.; Trapani, G.; Liso, G. N -Benzyl-2-(6,8-dichloro-2- (4-chlorophenyl)imidazo[1,2- a ]pyridin-3-yl)- N -(6-(7-nitrobenzo[ c ][1,2,5]oxadiazol-4-ylamino)hexyl)acetamide as a New Fluorescent Probe for Peripheral Benzodiazepine Receptor and Microglial Cell Visualization Bioconjugate Chem. 2007, 18, 1397-1407
31. Taliani, S.; Simorini, F.; Sergianni, V.; La Motta, C.; Da Settimo, F.; Cosimelli, B.; Abignente, E.; Greco, G.; Novellino, E.; Rossi, L.; Gremigni, V.; Spinetti, F.; Chelli, B.; Martini, C. New Fluorescent 2-Phenylindolglyoxylamide Derivatives as Probes Targeting the Peripheral-Type Benzodiazepine Receptor: Design, Synthesis, and Biological Evaluation J. Med. Chem. 2007, 50, 404-407
32. Primofiore, G.; Da Settimo, F.; Taliani, S.; Simorini, F.; Patrizi, M. P.; Novellino, E.; Greco, G.; Abignente, E.; Costa, B.; Chelli, B.; Martini, C. N, N -Dialkyl-2-phenylindol-3-ylglyoxylamides. A New Class of Potent and Selective Ligands at the Peripheral Benzodiazepine Receptor J. Med. Chem. 2004, 47, 1852-1855
33. Da Settimo, F.; Simorini, F.; Taliani, S.; La Motta, C.; Marini, A. M.; Salerno, S.; Bellandi, M.; Novellino, E.; Greco, G.; Cosimelli, B.; Da Pozzo., E.; Costa, B.; Simola, N.; Morelli, M.; Martini, C. Anxiolytic-Like Effects of N, N -Dialkyl-2-phenylindol-3-ylglyoxylamides by Modulation of Translocator Protein Promoting Neurosteroid Biosynthesis J. Med. Chem. 2008, 51, 5798-5806
34. Newman, A. H. Irreversible Ligands as Probes for Drug Receptors NIDA Res. Monogr. 1991, 112, 256-283
35. Rice, K. C.; Jacobson, A. E.; Burke, T. R., Jr.; Bajwa, B. S.; Streaty, R. A.; Klee, W. A. Irreversible Ligands with High Selectivity Toward γ or μ Opiate Receptors Science 1983, 220, 314-316
36. Burke, T. R., Jr.; Bajwa, B. S.; Jacobson, A. E.; Rice, K. C.; Streaty, R. A.; Klee, W. A. Probes for Narcotic Receptor Mediated Phenomena. 7. Synthesis and Pharmacological Properties of Irreversible Ligands Specific for μ or δ Opiate Receptors J. Med. Chem. 1984, 27, 1570-1574
37. Simonds, W. F.; Burke, T. R., Jr.; Rice, K. C.; Jacobson, A. E.; Klee, W. A. Purification of the Opiate Receptor of NG108-15 Neuroblastoma-Glioma Hybrid Cells Proc. Natl. Acad. Sci. U.S.A. 1985, 82, 4974-4978
38. Newman, A. H.; Lueddens, H. W. M.; Skolnick, P.; Rice, K. C. Novel Irreversible Ligands Specific for Peripheral Type Benzodiazepine Receptors: (±)-, (+)-, and (-)-1-(2-Chlorophenyl)- N -(1-methylpropyl)- N -(2-isothiocyanatoethyl)-3-isoquinolinecarboxamide and 1-(2-Isothiocyanatoethyl) -7-chloro-1,3-dihydro-5-(4-chlorophenyl)-2 H -1,4-benzodiazepin-2-one J. Med. Chem. 1997, 30, 1901-1905
39. Allen, M. S.; Hagen, T. J.; Trudell, M. L.; Codding, P. W.; Skolnick, P.; Cook, J. M. Synthesis of Novel 3-Substituted β-Carbolines as Benzodiazepine Receptor Ligands: Probing the Benzodiazepine Receptor Pharmacophore J. Med. Chem. 1988, 31, 1854-1861
40. Picone, R. P.; Khanolkar, A. D.; Xu, W.; Ayotte, L. A.; Thakur, G. A.; Hurst, D. P.; Abood, M. E.; Reggio, P. H.; Fournier, D. J.; Makriyannis, A. (-)-7′-Isothiocyanato-11-hydroxy-1′,1′- dimethylheptylhexahydrocannabinol (AM841), a High-Affinity Electrophilic Ligand, Interacts Covalently with a Cysteine in Helix Six and Activates the CB1 Cannabinoid Receptor Mol. Pharmacol. 2005, 68, 1623-1635
41. Selleri, S.; Bruni, F.; Costagli, C.; Costanzo, A.; Guerrini, G.; Ciciani, G.; Costa, B.; Martini, C. 2-Arylpyrazolo[1,5- a ]pyrimidin-3- ylacetamides. New Potent and Selective Peripheral Benzodiazepine Receptor Ligands Bioorg. Med. Chem. 2001, 9, 2661-2671
42. Kitz, R.; Wilson, I. B. Esters of Methanesulfonic Acid as Irreversible Inhibitors of Acetylcholinesterase J. Biol. Chem. 1962, 237, 3245-3249
43. Lueddens, H.; Newman, A. H.; Rice, K. C.; Skolnick, P. AHN 086: an Irreversible Ligand of Peripheral Benzodiazepine Receptors Mol. Pharmacol. 1986, 29, 540-545
44. 3H]Beta-Funaltrexamine Binding to μ Opioid Receptor Mol. Pharmacol. 1990, 37, 243-250
45. Hirsch, J. D.; Beyer, C. F.; Malkowitz, L.; Loullis, C. C.; Blume, A. J. Characterization of ligand binding to mitochondrial benzodiazepine receptors Mol. Pharmacol. 1989, 35, 164-172 (Pubitemid 19048646)
46. 50) of an Enzymatic Reaction Biochem. Pharmacol. 1973, 22, 3099-3108
47. 1 Binding Sites J. Neurochem. 1987, 49, 681-684
48. The CLogP, ASA and TPSA calculations were performed with the Marvin Sketch and Calculator Plugins on the Web site: http://www.chemaxon.com/demosite/ marvin/index.html.
49. Selleri, S.; Gratteri, P.; Costagli, C.; Bonaccioni, C.; Costanzo, A.; Melani, F.; Guerrini, G.; Ciciani, G.; Costa, B.; Spinetti, F.; Martini, C.; Bruni, F. Insight into 2-Phenylpyrazolo[1,5- a ]pyrimidin-3-ylacetamides as Peripheral Benzodiazepine Receptor Ligands: Synthesis, Biological Evaluation and 3D-QSAR Investigation Bioorg. Med. Chem. 2005, 13, 4821-4834