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Volumn 92, Issue , 2015, Pages 554-564

Synthesis, radiolabeling and evaluation of novel 4-oxo-quinoline derivatives as PET tracers for imaging cannabinoid type 2 receptor

Author keywords

Autoradiography; Cannabinoid receptor type 2; Neuroinflammation; Positron emission tomography; Radiolabeling

Indexed keywords

1 (2 ETHOXYETHYL) 8 METHOXY 4 OXO N PHENETHYL 1,4 DIHYDROQUINOLINE 3 CARBOXAMIDE C 11; 1 (2 ETHOXYETHYL) N (3 HYDROXYADAMANTAN 1 YL) 8 METHOXY 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXAMIDE C 11; 1 BUTYL N (CYCLOPROPYLMETHYL) 8 METHOXY 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXAMIDE C 11; 1 BUTYL N CYCLOPENTYL 8 METHOXY 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXAMIDE C 11; 4 OXO QUINOLINE C 11 DERIVATIVE; CANNABINOID 1 RECEPTOR; CANNABINOID 2 RECEPTOR; LIPOPOLYSACCHARIDE; N (1 ADAMANTYL) 1 (2 ETHOXYETHYL) 8 HYDROXY 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXAMIDE C 11; N (1 ADAMANTYL) 1 (2 ETHOXYETHYL) 8 METHOXY 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXAMIDE C 11; N (1 ADAMANTYL) 1 BUTYL 8 METHOXY 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXAMIDE C 11; N (TERT BUTYL) 1 (3 FLUOROPROPYL) 8 METHOXY 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXAMIDE C 11; N (TERT BUTYL) 1 BUTYL 8 METHOXY 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXAMIDE C 11; QUINOLINE DERIVATIVE; RADIOPHARMACEUTICAL AGENT; UNCLASSIFIED DRUG; ADAMANTANE; CARBON; QUINOLONE DERIVATIVE; RS-016;

EID: 84921358298     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2015.01.028     Document Type: Article
Times cited : (58)

References (35)
  • 1
    • 0025325535 scopus 로고
    • Structure of a cannabinoid receptor and functional expression of the cloned cDNA
    • L.A. Matsuda, S.J. Lolait, M.J. Brownstein, A.C. Young, T.I. Bonner, Structure of a cannabinoid receptor and functional expression of the cloned cDNA, Nature 346 (1990) 561e564.
    • (1990) Nature , vol.346 , pp. 561-564
    • Matsuda, L.A.1    Lolait, S.J.2    Brownstein, M.J.3    Young, A.C.4    Bonner, T.I.5
  • 2
    • 0027515373 scopus 로고
    • Molecular characterization of a peripheral receptor for cannabinoids
    • S. Munro, K.L. Thomas, M. Abu-Shaar, Molecular characterization of a peripheral receptor for cannabinoids, Nature 365 (1993) 61e65.
    • (1993) Nature , vol.365 , pp. 61-65
    • Munro, S.1    Thomas, K.L.2    Abu-Shaar, M.3
  • 3
    • 33645774927 scopus 로고    scopus 로고
    • Distribution of cannabinoid receptors in the central and peripheral nervous system
    • K. Mackie, Distribution of cannabinoid receptors in the central and peripheral nervous system, Handb. Exp. Pharmacol. (2005) 299e325.
    • (2005) Handb. Exp. Pharmacol. , pp. 299-325
    • MacKie, K.1
  • 4
    • 84898976737 scopus 로고    scopus 로고
    • Prospective therapeutic agents for obesity: Molecular modification approaches of centrally and peripherally acting selective cannabinoid 1 receptor antagonists
    • M.K. Sharma, P.R. Murumkar, A.M. Kanhed, R. Giridhar, M.R. Yadav, Prospective therapeutic agents for obesity: molecular modification approaches of centrally and peripherally acting selective cannabinoid 1 receptor antagonists, Eur. J. Med. Chem. 79 (2014) 298e339.
    • (2014) Eur. J. Med. Chem. , vol.79 , pp. 298-339
    • Sharma, M.K.1    Murumkar, P.R.2    Kanhed, A.M.3    Giridhar, R.4    Yadav, M.R.5
  • 5
    • 26844504226 scopus 로고    scopus 로고
    • Identification and functional characterization of brainstem cannabinoid CB2 receptors
    • M.D. Van Sickle, M. Duncan, P.J. Kingsley, A. Mouihate, P. Urbani, et al., Identification and functional characterization of brainstem cannabinoid CB2 receptors, Science 310 (2005) 329e332.
    • (2005) Science , vol.310 , pp. 329-332
    • Van Sickle, M.D.1    Duncan, M.2    Kingsley, P.J.3    Mouihate, A.4    Urbani, P.5
  • 6
    • 33244493807 scopus 로고    scopus 로고
    • Expression of the cannabinoid CB2 receptor in the rat cerebellum: An immunohistochemical study
    • J.C. Ashton, D. Friberg, C.L. Darlington, P.F. Smith, Expression of the cannabinoid CB2 receptor in the rat cerebellum: an immunohistochemical study, Neurosci. Lett. 396 (2006) 113e116.
    • (2006) Neurosci. Lett. , vol.396 , pp. 113-116
    • Ashton, J.C.1    Friberg, D.2    Darlington, C.L.3    Smith, P.F.4
  • 7
    • 56549089453 scopus 로고    scopus 로고
    • Postsynaptic localization of CB2 cannabinoid receptors in the rat hippocampus
    • A. Brusco, P. Tagliaferro, T. Saez, E.S. Onaivi, Postsynaptic localization of CB2 cannabinoid receptors in the rat hippocampus, Synapse 62 (2008) 944e949.
    • (2008) Synapse , vol.62 , pp. 944-949
    • Brusco, A.1    Tagliaferro, P.2    Saez, T.3    Onaivi, E.S.4
  • 9
    • 71749104726 scopus 로고    scopus 로고
    • Cannabinoid receptors in brain: Pharmacogenetics, neuropharmacology, neurotoxicology, and potential therapeutic applications
    • E.S. Onaivi, Cannabinoid receptors in brain: pharmacogenetics, neuropharmacology, neurotoxicology, and potential therapeutic applications, Int. Rev. Neurobiol. 88 (2009) 335e369.
    • (2009) Int. Rev. Neurobiol. , vol.88 , pp. 335-369
    • Onaivi, E.S.1
  • 10
    • 33947278309 scopus 로고    scopus 로고
    • The CB2 cannabinoid agonist AM-1241 prolongs survival in a transgenic mouse model of amyotrophic lateral sclerosis when initiated at symptom onset
    • J.L. Shoemaker, K.A. Seely, R.L. Reed, J.P. Crow, P.L. Prather, The CB2 cannabinoid agonist AM-1241 prolongs survival in a transgenic mouse model of amyotrophic lateral sclerosis when initiated at symptom onset, J. Neurochem. 101 (2007) 87e98.
    • (2007) J. Neurochem. , vol.101 , pp. 87-98
    • Shoemaker, J.L.1    Seely, K.A.2    Reed, R.L.3    Crow, J.P.4    Prather, P.L.5
  • 11
    • 33645224970 scopus 로고    scopus 로고
    • COX-2, CB2 and P2X7-immunoreactivities are increased in activated microglial cells/ macrophages of multiple sclerosis and amyotrophic lateral sclerosis spinal cord
    • Y. Yiangou, P. Facer, P. Durrenberger, I.P. Chessell, A. Naylor, et al., COX-2, CB2 and P2X7-immunoreactivities are increased in activated microglial cells/ macrophages of multiple sclerosis and amyotrophic lateral sclerosis spinal cord, BMC Neurol. 6 (2006) 12.
    • (2006) BMC Neurol. , vol.6 , pp. 12
    • Yiangou, Y.1    Facer, P.2    Durrenberger, P.3    Chessell, I.P.4    Naylor, A.5
  • 12
    • 0027164824 scopus 로고
    • Mutations in Cu/Zn superoxide dismutase gene are associated with familial amyotrophic lateral sclerosis
    • D.R. Rosen, Mutations in Cu/Zn superoxide dismutase gene are associated with familial amyotrophic lateral sclerosis, Nature 364 (1993) 362.
    • (1993) Nature , vol.364 , pp. 362
    • Rosen, D.R.1
  • 13
    • 79954608945 scopus 로고    scopus 로고
    • Emerging targets and treatments in amyotrophic lateral sclerosis
    • L. Zinman, M. Cudkowicz, Emerging targets and treatments in amyotrophic lateral sclerosis, Lancet Neurol. 10 (2011) 481e490.
    • (2011) Lancet Neurol. , vol.10 , pp. 481-490
    • Zinman, L.1    Cudkowicz, M.2
  • 14
    • 77349114038 scopus 로고    scopus 로고
    • Progressive changes in microglia and macrophages in spinal cord and peripheral nerve in the transgenic rat model of amyotrophic lateral sclerosis
    • D.J. Graber, W.F. Hickey, B.T. Harris, Progressive changes in microglia and macrophages in spinal cord and peripheral nerve in the transgenic rat model of amyotrophic lateral sclerosis, J. Neuroinflamm. 7 (2010) 8.
    • (2010) J. Neuroinflamm. , vol.7 , pp. 8
    • Graber, D.J.1    Hickey, W.F.2    Harris, B.T.3
  • 15
    • 52949103699 scopus 로고    scopus 로고
    • The endocannabinoid system in amyotrophic lateral sceloris
    • L.G. Bilsland, The endocannabinoid system in amyotrophic lateral sceloris, Curr. Pharm. Des. 14 (2006) 2306e2316.
    • (2006) Curr. Pharm. Des. , vol.14 , pp. 2306-2316
    • Bilsland, L.G.1
  • 16
    • 84893842477 scopus 로고    scopus 로고
    • 1,2-Dihydro-2-oxopyridine-3-carboxamides: The C-5 substituent is responsible for functionality switch at CB2 cannabinoid receptor
    • V. Lucchesi, T. Parkkari, J.R. Savinainen, A.M. Malfitano, M. Allara, et al., 1,2-Dihydro-2-oxopyridine-3-carboxamides: the C-5 substituent is responsible for functionality switch at CB2 cannabinoid receptor, Eur. J. Med. Chem. 74 (2014) 524e532.
    • (2014) Eur. J. Med. Chem. , vol.74 , pp. 524-532
    • Lucchesi, V.1    Parkkari, T.2    Savinainen, J.R.3    Malfitano, A.M.4    Allara, M.5
  • 17
    • 84880331685 scopus 로고    scopus 로고
    • Whole-body biodistribution and radiation dosimetry of the cannabinoid type 2 receptor ligand [C]-NE40 in healthy subjects
    • R. Ahmad, M. Koole, N. Evens, K. Serdons, A. Verbruggen, et al., Whole-body biodistribution and radiation dosimetry of the cannabinoid type 2 receptor ligand [C]-NE40 in healthy subjects, Mol. Imaging Biol 15 (2013) 384e390.
    • (2013) Mol. Imaging Biol , vol.15 , pp. 384-390
    • Ahmad, R.1    Koole, M.2    Evens, N.3    Serdons, K.4    Verbruggen, A.5
  • 18
    • 84883143252 scopus 로고    scopus 로고
    • Radiolabeling and in vitro/in vivo evaluation of N-(1-Adamantyl)-8-methoxy-4-oxo-1-phenyl-1,4-dihydroquinoline-3-carboxamide as a PET probe for imaging cannabinoid type 2 receptor
    • L. Mu, D. Bieri, R. Slavik, K. Drandarov, A. Muller, et al., Radiolabeling and in vitro/in vivo evaluation of N-(1-Adamantyl)-8-methoxy-4-oxo-1-phenyl-1,4-dihydroquinoline-3-carboxamide as a PET probe for imaging cannabinoid type 2 receptor, J. Neurochem. 126 (2013) 616e624.
    • (2013) J. Neurochem. , vol.126 , pp. 616-624
    • Mu, L.1    Bieri, D.2    Slavik, R.3    Drandarov, K.4    Muller, A.5
  • 19
    • 67349092220 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of carbon-11-And fluorine-18-labeled 2-oxoquinoline derivatives for type 2 cannabinoid receptor positron emission tomography imaging
    • N. Evens, G.G. Muccioli, N. Houbrechts, D.M. Lambert, A.M. Verbruggen, et al., Synthesis and biological evaluation of carbon-11-And fluorine-18-labeled 2-oxoquinoline derivatives for type 2 cannabinoid receptor positron emission tomography imaging, Nucl. Med. Biol. 36 (2009) 455e465.
    • (2009) Nucl. Med. Biol. , vol.36 , pp. 455-465
    • Evens, N.1    Muccioli, G.G.2    Houbrechts, N.3    Lambert, D.M.4    Verbruggen, A.M.5
  • 20
    • 77955323562 scopus 로고    scopus 로고
    • Synthesis and biodistribution of [11C] A-836339, a new potential radioligand for PET imaging of cannabinoid type 2 receptors (CB2)
    • A.G. Horti, Y. Gao, H.T. Ravert, P. Finley, H. Valentine, et al., Synthesis and biodistribution of [11C]A-836339, a new potential radioligand for PET imaging of cannabinoid type 2 receptors (CB2), Bioorg. Med. Chem. 18 (2010) 5202e5207.
    • (2010) Bioorg. Med. Chem. , vol.18 , pp. 5202-5207
    • Horti, A.G.1    Gao, Y.2    Ravert, H.T.3    Finley, P.4    Valentine, H.5
  • 21
    • 79960563429 scopus 로고    scopus 로고
    • Syn thesis in vitro and in vivo evaluation of fluorine-18 labelled FEGW405833 as a PET tracer for type 2 cannabinoid receptor imaging
    • N. Evens, C. Vandeputte, G.G. Muccioli, D.M. Lambert, V. Baekelandt, et al., Synthesis, in vitro and in vivo evaluation of fluorine-18 labelled FEGW405833 as a PET tracer for type 2 cannabinoid receptor imaging, Bioorg. Med. Chem. 19 (2011) 4499e4505.
    • (2011) Bioorg. Med. Chem. , vol.19 , pp. 4499-4505
    • Evens, N.1    Vandeputte, C.2    Muccioli, G.G.3    Lambert, D.M.4    Baekelandt, V.5
  • 22
    • 79960324391 scopus 로고    scopus 로고
    • A PET brain reporter gene system based on type 2 cannabinoid receptors
    • C. Vandeputte, N. Evens, J. Toelen, C.M. Deroose, B. Bosier, et al., A PET brain reporter gene system based on type 2 cannabinoid receptors, J. Nucl. Med. 52 (2011) 1102e1109.
    • (2011) J. Nucl. Med. , vol.52 , pp. 1102-1109
    • Vandeputte, C.1    Evens, N.2    Toelen, J.3    Deroose, C.M.4    Bosier, B.5
  • 23
    • 84883205385 scopus 로고    scopus 로고
    • Cannabinoid receptor type 2 (CB2)-selective N-Aryl-oxadiazolyl-propionamides: Syn thesis, radiolabelling, molecular modelling and biological evaluation
    • T. Ruhl, W. Deuther-Conrad, S. Fischer, R. Gunther, L. Hennig, et al., Cannabinoid receptor type 2 (CB2)-selective N-Aryl-oxadiazolyl-propionamides: synthesis, radiolabelling, molecular modelling and biological evaluation, Org. Med. Chem. Lett. 2 (2012) 32.
    • (2012) Org. Med. Chem. Lett. , vol.2 , pp. 32
    • Ruhl, T.1    Deuther-Conrad, W.2    Fischer, S.3    Gunther, R.4    Hennig, L.5
  • 24
    • 84891495922 scopus 로고    scopus 로고
    • Synthesis and preliminary evaluation of a new fluorine-18 labelled triazine derivative for PET imaging of cannabinoid CB2 receptor
    • L. Hortala, J. Arnaud, P. Roux, D. Oustric, L. Boulu, et al., Synthesis and preliminary evaluation of a new fluorine-18 labelled triazine derivative for PET imaging of cannabinoid CB2 receptor, Bioorg. Med. Chem. Lett. 24 (2014) 283e287.
    • (2014) Bioorg. Med. Chem. Lett. , vol.24 , pp. 283-287
    • Hortala, L.1    Arnaud, J.2    Roux, P.3    Oustric, D.4    Boulu, L.5
  • 25
    • 77955866101 scopus 로고    scopus 로고
    • Investigations on the 4-quinolone-3-carboxylic acid motif 3 Syn thesis, structure-Affinity relationships, and pharmacological characterization of 6-substituted 4-quinolone-3-carboxamides as highly selective cannabinoid-2 receptor ligands
    • S. Pasquini, A. Ligresti, C. Mugnaini, T. Semeraro, L. Cicione, et al., Investigations on the 4-quinolone-3-carboxylic acid motif. 3. Synthesis, structure-Affinity relationships, and pharmacological characterization of 6-substituted 4-quinolone-3-carboxamides as highly selective cannabinoid-2 receptor ligands, J. Med. Chem. 53 (2010) 5915e5928.
    • (2010) J. Med. Chem. , vol.53 , pp. 5915-5928
    • Pasquini, S.1    Ligresti, A.2    Mugnaini, C.3    Semeraro, T.4    Cicione, L.5
  • 27
    • 0344121272 scopus 로고    scopus 로고
    • Determination of lipophilicity and its use as a predictor of blood-brain barrier penetration of molecular imaging agents
    • R.N. Waterhouse, Determination of lipophilicity and its use as a predictor of blood-brain barrier penetration of molecular imaging agents, Mol. Imaging Biol. 5 (2003) 376e389.
    • (2003) Mol. Imaging Biol. , vol.5 , pp. 376-389
    • Waterhouse, R.N.1
  • 28
    • 25844495011 scopus 로고    scopus 로고
    • Medicinal chemical properties of successful central nervous system drugs
    • H. Pajouhesh, G.R. Lenz, Medicinal chemical properties of successful central nervous system drugs, NeuroRx 2 (2005) 541e553.
    • (2005) NeuroRx 2 , pp. 541-553
    • Pajouhesh, H.1    Lenz, G.R.2
  • 29
    • 20144388149 scopus 로고    scopus 로고
    • Pharmacological and pharmacokinetic characterization of the cannabinoid receptor 2 agonist GW405833 utilizing rodent models of acute and chronic pain anxiety ataxia and catalepsy
    • K.J. Valenzano, L. Tafesse, G. Lee, J.E. Harrison, J.M. Boulet, et al., Pharmacological and pharmacokinetic characterization of the cannabinoid receptor 2 agonist, GW405833, utilizing rodent models of acute and chronic pain, anxiety, ataxia and catalepsy, Neuropharmacology 48 (2005) 658e672.
    • (2005) Neuropharmacology , vol.48 , pp. 658-672
    • Valenzano, K.J.1    Tafesse, L.2    Lee, G.3    Harrison, J.E.4    Boulet, J.M.5
  • 30
    • 0029094470 scopus 로고
    • Expression of central and peripheral cannabinoid receptors in human immune tissues and leukocyte subpopulations
    • S. Galiegue, S. Mary, J. Marchand, D. Dussossoy, D. Carriere, et al., Expression of central and peripheral cannabinoid receptors in human immune tissues and leukocyte subpopulations, Eur. J. Biochem. 232 (1995) 54e61.
    • (1995) Eur. J. Biochem. , vol.232 , pp. 54-61
    • Galiegue, S.1    Mary, S.2    Marchand, J.3    Dussossoy, D.4    Carriere, D.5
  • 31
    • 33847759064 scopus 로고    scopus 로고
    • Systemic LPS causes chronic neuroinflammation and progressive neurodegeneration
    • L. Qin, X. Wu, M.L. Block, Y. Liu, G.R. Breese, et al., Systemic LPS causes chronic neuroinflammation and progressive neurodegeneration, Glia 55 (2007) 453e462.
    • (2007) Glia , vol.55 , pp. 453-462
    • Qin, L.1    Wu, X.2    Block, M.L.3    Liu, Y.4    Breese, G.R.5
  • 32
    • 0030425575 scopus 로고    scopus 로고
    • Evaluation of binding in a transfected cell line expressing a peripheral cannabinoid receptor (CB2): Identification of cannabinoid receptor subtype selective ligands
    • V.M. Showalter, D.R. Compton, B.R. Martin, M.E. Abood, Evaluation of binding in a transfected cell line expressing a peripheral cannabinoid receptor (CB2): identification of cannabinoid receptor subtype selective ligands, J. Pharmacol. Exp. Ther. 278 (1996) 989e999.
    • (1996) J. Pharmacol. Exp. Ther. , vol.278 , pp. 989-999
    • Showalter, V.M.1    Compton, D.R.2    Martin, B.R.3    Abood, M.E.4
  • 33
    • 0015861774 scopus 로고
    • Relationship between the inhibition constant (K1) and the concentration of inhibitor which causes 50 per cent inhibition I50) of an enzymatic reaction
    • Y. Cheng, W.H. Prusoff, Relationship between the inhibition constant (K1) and the concentration of inhibitor which causes 50 per cent inhibition (I50) of an enzymatic reaction, Biochem. Pharmacol. 22 (1973) 3099e3108.
    • (1973) Biochem. Pharmacol. , vol.22 , pp. 3099-3108
    • Cheng, Y.1    Prusoff, W.H.2
  • 34
    • 0035255404 scopus 로고    scopus 로고
    • An admonition when measuring the lipophilicity of radiotracers using counting techniques
    • A.A. Wilson, L. Jin, A. Garcia, J.N. DaSilva, S. Houle, An admonition when measuring the lipophilicity of radiotracers using counting techniques, Appl. Radiat. Isot. 54 (2001) 203e208.
    • (2001) Appl. Radiat. Isot. , vol.54 , pp. 203-208
    • Wilson, A.A.1    Jin, L.2    Garcia, A.3    Dasilva, J.N.4    Houle, S.5
  • 35
    • 84903305166 scopus 로고    scopus 로고
    • Towards non-invasive imaging of vulnerable atherosclerotic plaques by targeting co-stimulatory molecules
    • A. Müller, L. Mu, R. Meletta, K. Beck, Z. Rancic, et al., Towards non-invasive imaging of vulnerable atherosclerotic plaques by targeting co-stimulatory molecules, Int. J. Cardiol. 174 (2014) 503e515.
    • (2014) Int. J. Cardiol. , vol.174 , pp. 503-515
    • Müller, A.1    Mu, L.2    Meletta, R.3    Beck, K.4    Rancic, Z.5


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