Radiolabelled quinoline derivaties for the PET imaging of peripheral benzodiazepine receptor

Current Medical Imaging Reviews

Volumn 8, Issue 4, 2012, Pages 302-307

  Lei, Ming ^a,b,c,d   Tian, Wan ^a   Zhan, Zu Jin ^a   Zhang, Hong ^b,c,d  

^a ZHEJIANG UNIVERSITY   (China)

^b THE SECOND AFFILIATED HOSPITAL OF ZHEJIANG UNIVERSITY SCHOOL OF MEDICINE   (China)

^c ZHEJIANG UNIVERSITY   (China)

^d Key Laboratory of Medical Molecular Imaging of Zhejiang Province   (China)

Author keywords

3 Isoquinolinecarboxamides; Molecular Imaging; Peripheral benzodiazepine receptor (PBR); Positron Emission Tomography (PET); Quinoline derivaties; Quinoline 2 carboxamides

Indexed keywords

ADENINE NUCLEOTIDE TRANSLOCASE; BENZODIAZEPINE RECEPTOR; CARBON 11; FLUORINE 18; N METHYL N (1 METHYLPROPYL) 1 (2 FLUORO 5 NITROPHENYL)ISOQUINOLINE 3 CARBOXAMIDE; N SEC BUTYL 1 (2 CHLOROPHENYL) N METHYL 3 ISOQUINOLINECARBOXAMIDE; PERIPHERAL BENZODIAZEPINE RECEPTOR; QUINOLINE 2 CARBOXAMIDE DERIVATIVE; QUINOLINE DERIVATIVE; RADIOLIGAND; TECHNETIUM 99M; TRACER; UNCLASSIFIED DRUG;

ALZHEIMER DISEASE; AUTOIMMUNE DISEASE; BASAL GANGLION; BINDING AFFINITY; BINDING SITE; BRAIN INJURY; DOSIMETRY; DRUG DISTRIBUTION; ENANTIOMER; GRAY MATTER; HUNTINGTON CHOREA; ISOTOPE LABELING; LIPOPHILICITY; MULTIPLE SCLEROSIS; NEOPLASM; NONHUMAN; POSITRON EMISSION TOMOGRAPHY; PRIORITY JOURNAL; PROTEIN BINDING; RADIOACTIVITY; RECEPTOR BINDING; REVIEW; STEREOCHEMISTRY; STRESS; THALAMUS; VIRUS INFECTION;

EID: 84869112546     PISSN: 15734056     EISSN: 18756506     Source Type: Journal    
DOI: 10.2174/157340512803759758     Document Type: Review

References (61)

1. Ametamey SM, Honer M, Schubiger PA. Molecular imaging with PET. Chem Rev 2008; 108: 1501-16.
2. Wester H J. Nuclear imaging probes: from bench to bedside. Clin Cancer Res 2007; 13: 3470-81.
3. Papadopoulos V, Baraldi M, Guilarte T R, et al. Translocator protein (18 kDa): new nomenclature for the peripheral-type benzodiazepine receptor based on its structure and molecular function. Trends Pharmacol Sci 2006; 27: 402-9.
4. Gavish M, Katz Y, Bar-Ami S, Weizman R. Biochemical, physiological, and pathological aspects of the peripheral benzodiazepine receptor. J Neurochem 1992; 58: 1589-1601.
5. Beurdeley-Thomas A, Miccoli L, Oudard S, Dutrillaux B, Poupon M. F. The peripheral benzodiazepine receptors: a review. J Neurooncol 2000; 46: 45-56.
6. Schweitzer P J, Fallon B A, Mann J J, Kumar J S D PET tracers for the peripheral benzodiazepine receptor and uses thereof Drug Discov Today 2010; 15: 933-42.
7. Casellas P, Galiegue S, Basile AS. Peripheral benzodiazepine receptors and mitochondrial function Neurochem Int 2002; 40: 475-86.
8. Bertomeu T, Zvereff V, Ibrahim A, et al. TLN-4601 peripheral benzodiazepine receptor (PBR/TSPO) binding properties do not mediate apoptosis but confer tumor-specific accumulation. Biochem Pharmaco 2010; 80: 1572-9.
9. Bribes E, Bourrie B, Casellas P. Ligands of the peripheral benzodiazepine receptor have therapeutic effects in pneumopathies in vivo. Immunol Lett 2003; 88: 241-7.
10. Amitani M, Zhang M R, Noguchi J, et al. Blood flow dependence of the intratumoral distribution of peripheral benzodiazepine receptor binding in intact mouse fibrosarcoma Nucl Med Biol 2006; 33: 971-5.
11. Chen M K, Baidoo K, Verina T, Guilarte T R, Brain J. Peripheral benzodiazepine receptor imaging in CNS demyelination: functional implications of anatomical and cellular localization. Neurol 2004; 127: 1379-92.
12. Maeda J, Higuchi M, Inaji M, et al. Phase-dependent roles of reactive microglia and astrocytes in nervous system injury as delineated by imaging of peripheral benzodiazepine receptor. Brain Res 2007; 1157: 100-11.
13. Raghavendra Rao, Vemuganti L, Dogan A, Bowen K K, Dempsey R J. Traumatic brain injury leads to increased expression of peripheral-type benzodiazepine receptors, neuronal death, and activation of astrocytes and microglia in rat thalamus. Exp Neurol 2000; 161: 102-14.
14. Nakamura K, Fukunishi I, Nakamoto Y, Iwahashi K, Yoshii M. Peripheral-type benzodiazepine receptors on platelets are correlated with the degrees of anxiety in normal human subjects Psychopharmacology 2002; 162: 301-3.
15. Venturini I, Alho H, Podkletnova I, et al. Increased expression of peripheral benzodiazepine receptors and diazepam binding inhibitor in human tumors sited in the liver. Life Sci 1999; 65: 2223-31.
16. Hardwick M, Fertikh D, Culty M, Li H, Vidic B, Papadopoulos V. Peripheral-type benzodiazepine receptor (PBR) in human breast cancer: correlation of breast cancer cell agressive phenotype with PBR expression, nuclear localization, and PBR-mediated cell proliferation and nuclear transport of cholesterol. Cancer Res 1999; 59: 831-42.
17. Maaser K, Grabowski P, Sutter A P, et al. Overexpression of the peripheral benzodiazepine receptor is a relevant prognostic factor in stage III colorectal cancer. Clin Cancer Res 2002; 8: 3205-9.
18. Diorio D, Welner S A, Butterworth R F, Meaney M J, Suranyi-Cadotte B E. Peripheral benzodiazepine binding sites in Alzheimer's disease frontal and temporal cortex. Neurobiol Aging 1991; 12: 255-8.
19. Vowinckel E, Reutens D, Becher B, et al. PK11195 binding to the peripheral benzodiazepine receptor as a marker of microglia activation in multiple sclerosis and experimental autoimmune encephalomyelitis. J Neurosci Res 1997; 50: 345-53.
20. 3H]Ro 5-4864 benzodiazepine binding in the kainate lesioned striatum and Huntington's diseased basal ganglia. Brain Res 1982; 248: 396-401.
21. James M L, Selleri S, Kassiou M. Development of ligands for the peripheral benzodiazepine receptor. Curr Med Chem 2006; 13: 1991-2001.
22. Kassiou M, Meikle SR, Banati RB. Ligands for peripheral benzodiazepine binding sites in glial cells Brain Res Rev 2005; 48: 207-10.
23. 11C) methyl, N-(methyl-1 propyl), (chloro-2 phenyl)-1 isoquinoleine carboxamide-3 (PK 11195): A new ligand for peripheral benzodiazepine receptors. J Label Compd Radiopharm 1984; 21: 985-91.
24. Pappata S, Cornu P, Samson Y, et al. PET Study of Carbon-11-PK 11195 Binding to peripheral type benzodiazepine sites in glioblastoma: a case report. J Nucl Med 1991; 32: 1608-10.
25. Petit-Taboué M C, Baron J C, Barré L, et al. Brain kinetics and specific binding of [C-11]PK11195 to α-3 sites in baboons positron emission tomography study. Eur J Pharmacol 1991; 200: 347-51.
26. 11C]PK11195 invivo after induction of cortical ischemic lesion. Int J Rad Appl Instrum B 1992; 19:159-66.
27. Pike VW, Halldin C, Crouzel C, et al. Radioligands for PET studies of central benzodiazepine receptors and PK(peripheral benzodiazepine) binding sites-current status. Nucl Med Biol 1993; 20: 503-25.
28. 11C]PK11195 and comparison of the behaviors as radioligands for PK binding-sites in rats. Nucl Med Biol 1994; 21: 573-81.
29. Pappata S, Levasseur M, Gunn R N, et al. Thalamic microglial activation in ischemic stroke detected in vivo by PET and [C-11]PK11195 Neurology 2000; 55: 1052-4.
30. Doorduin J, de Vries E F J, Dierckx R A, Klein H C. PET imaging of the peripheral benzodiazepine receptor: monitoring disease progression and therapy response in neurodegenerative disorders. Curr Pharm Design 2008; 14: 3297-315.
31. Garcia E F, Woolley D E. Gender differences in brain peripheral benzodiazepine receptor (PBR) expression and seizures produced by heptachlor during development. Proc West Pharmacol Soc 2008; 51: 18-22.
32. Pascali C, Luthra S K, Pike V W, et al. The radiosynthesis of [F-18]PK14105 as an alternative radioligand for peripheral-type benzodiazepine-binding sites. Appl Radiat Isot 1990; 41: 477-82.
33. Price G W, Ahier R G, Hume S P, et al. In vivo binding to peripheral benzodiazepine binding-sites in lesioned rat brain-comparison between [H-3]PK11195 and [F-18]PK14105 as markers for neuronal damage. J Neurochem 1990; 55: 175-85.
34. Junck L, Olson J M, Ciliax B J, et al. PET imaging of human gliomas with ligands for the peripheral benzodiazepine binding site. Ann Neurol 1989; 26: 752-58.
35. Chauveau F, Boutin H, Van Camp N, Dolle F, Tavitian B Nuclear imaging of neuroinflammation: a comprehensive review of [C-11]PK11195 challengers. Eur J Nucl Med Mol Imaging 2008; 35: 2304-19.
36. Junck L, Jewett D M, Kilbourn M R, Young A B, Kuhl D E. PET imaging of cerebral infarcts using a ligand for the peripheral benzodiazepine binding site. Neurology 1990; 40: 265.
37. Charbonneau P, Syrota A, Crouzel C, Valois J M, Prenant C, Crouzel M. Peripheral-type benzodiazepine receptors in the living heart characterized by positron emission tomography. Circulation 1986; 73: 476-83.
38. 3H]PK 14105. Eur J Pharmacol 1988; 148: 187-93.
39. 123I]-iodo-PK11195 for mapping peripheral-type benzodiazepine receptors (α3) in heart. Nucl Med Biol 1996; 23: 23-8.
40. Myers R. Mitochondrial Benzodiazepine Receptor Ligands as Indicator of Damage in the CNS: their Application in Positron Emission Tomography. In Peripheral Benzodiazepine Receptors. Myers R, Ed.; Academic Press: London, 1993; 235-73.
41. Groom G N, Junck L, Foster N L, Frey K A, Kuhl D E. PET of Peripheral benzodiazepine binding sites in the microgliosis of Alzheimer's disease. J Nucl Med 1995; 36: 2207-10.
42. 123I]iodo-PK11195: a possible single-photon emission tomography tracer for visualization of inflammation. Eur J Nucl Med 1999; 26: 19-9.
43. 11C] (R)-1-(2-chlorophenyl)-N-(1-methylpropyl)-3-isoquinolinecarboxamide in humans; an imaging agent for in vivo assessment of peripheral benzodiazepine receptor activity with positron emission tomography. Eur J Nucl Med Mol Imaging 2009; 36: 671-82.
44. Simonyi M, Fitos I, Visy J. Chiralty of bioactive agents in proteinbinding storage and transport processes. Trends Pharmacol Sci 1986; 7: 112-16.
45. Walle T, Walle U K. Chiralty 4. Pharmacokinetic parameters obtained with racemates. Trends Pharmacol Sci 1986; 7:155-8.
46. Testa B. Chiral sspects of drug metabolism. Trends Pharmacol Sci 1986; 7: 60-4.
47. Ariens E J. Stereochemistry-a source of problems in medical chemistry. Med Res Rev 1986; 6: 451-66.
48. Dubroeucq M C, Benavides J, Doble A, et al. Stereoselective inhibition of the binding of [H-3]PK11195 to peripheral benzodiazepine binding sites by a quinolinepropanamide derivative. Eur J Pharmacol 1986; 128: 269-72.
49. Yu W P, Wang E, Voll R J, Mille A H, Goodman M M. Synthesis, fluorine-18 radiolabeling, and in vitro characterization of 1-iodophenyl-N-methyl-N-fluoroalkyl-3-isoquinoline carboxamide derivatives as potential PET radioligands forimaging peripheral benzodiazepine receptor. Bioorg Med Chem 2008; 16: 6145-55.
50. 125I-labeled analog of PK 11195, potential agent for SPECT imaging of the peripheral benzodiazepine binding site. Int J Rad Appl Instrum B 1989; 16: 423-9.
51. Doble A, Ferris O, Burgevin M C, et al. Photoaffinity-labeling of peripheral-type benzodiazepine-binding sites. Mol Pharmacol 1987; 31: 42-9.
52. 11C]-labelled quinoline carboxamides: analogues of PK-11195 as putative radioligands for PET studies of peripheral type benzodiazepine receptors. J Label Compd Radiopharm 1999; 42: S397-S9.
53. Matarrese M, Moresco RM, Cappelli A, et al. Labeling and evaluation of N-[11C]methylated quinoline-2-carboxamides as potential radioligands for visualization of peripheral benzodiazepine receptors. J Med Chem 2001; 44: 579-85.
54. Belloli S, Moresco R M, Matarrese M, et al. Evaluation of three quinoline-carboxamide derivatives as potential radioligands for the in vivo pet imaging of neurodegeneration. Neurochem Int 2004; 44: 433-40.
55. Cappelli A, Matarrese M, Moresco RM, et al. Synthesis, labeling, and biological evaluation of halogenated quinoline-2-carboxamides as potential radioligands for visualization of peripheral benzodiazepine receptors. Bioorg Med Chem 2006; 14: 4055-66.
56. Cappelli A, Pericot Mohr G, Gallelli A, et al. Structure-activity relationships in carboxamide derivatives based on the targeted delivery of radionuclides and boron atoms by means of peripheral benzodiazepine receptor ligands. J Med Chem 2003; 46: 3568-71.
57. Schwochau K. Technetium. Chemistry and radiopharmaceutical applications. Wiley-VCH: Weinheim, Germany, 2000.
58. Fritzberg A R, Abrams P G, Beaumier P L, et al. Specific and stable labeling of antibodies with technetium-99m with a diamide dithiolate chelating agent. Proc Natl Acad Sci USA 1988; 85: 4025-9.
59. Cappelli A, Mancini A, Sudati F, et al. Synthesis and Biological Characterization of Novel 2-Quinolinecarboxamide Ligands of the Peripheral Benzodiazepine Receptors Bearing Technetium-99m or Rhenium Bioconjugate Chem 2008; 19: 1143-53.
60. Anzini M, Cappelli A, Vomero S, et al. Mapping and fitting the peripheral benzodiazepine receptor binding site by carboxamide derivatives. Comparison of different approaches to quantitative ligand-receptor interaction modeling. J Med Chem 2001; 44: 1134-50.
61. Cagnin A, Gerhard A, Banati RB. In vivo imaging of neuroinflammation. Eur. Neuropsychopharmaco 2002; 12: 581-6.