메뉴 건너뛰기




Volumn 39, Issue 4, 2012, Pages 593-600

Synthesis and preliminary evaluation of [ 18F]-labeled 2-oxoquinoline derivatives for PET imaging of cannabinoid CB 2 receptor

Author keywords

18F 2 oxoquinoline derivatives; Cannabinoid receptor CB 2; Positron emission tomography

Indexed keywords

4 CYANO N,N,N TRIMETHYLANILINIUM TRIFLATE; 7 METHOXY 8 ALKOXY 2 OXO 1,2 DIHYDROQUINOLINE 3 CARBOXYLIC ACID (4 FLUOROBENZYL)AMIDE F 18; CANNABINOID 1 RECEPTOR; CANNABINOID 2 RECEPTOR; DIAGNOSTIC AGENT; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

EID: 84860317168     PISSN: 09698051     EISSN: 18729614     Source Type: Journal    
DOI: 10.1016/j.nucmedbio.2011.10.019     Document Type: Article
Times cited : (34)

References (27)
  • 1
    • 74849084874 scopus 로고    scopus 로고
    • Indol-3-ylcycloalkyl ketones: effects of N1 substituted indole side chain variations on CB2 cannabinoid receptor activity
    • Frost J.M., Dart M.J., Tietje K.R., Garrison T.R., Grayson G.K., Daza A.V., et al. Indol-3-ylcycloalkyl ketones: effects of N1 substituted indole side chain variations on CB2 cannabinoid receptor activity. J Med Chem 2010, 53:295-315.
    • (2010) J Med Chem , vol.53 , pp. 295-315
    • Frost, J.M.1    Dart, M.J.2    Tietje, K.R.3    Garrison, T.R.4    Grayson, G.K.5    Daza, A.V.6
  • 2
    • 24744436637 scopus 로고    scopus 로고
    • Synthesis and structure-activity relationship of a novel series of aminoalkylindoles with potential for imaging the neuronal cannabinoid receptor by positron emission tomography
    • Willis P.G., Pavlova O.A., Chefer S.I., Vaupel D.B., Mukhin A.G., Horti A.G. Synthesis and structure-activity relationship of a novel series of aminoalkylindoles with potential for imaging the neuronal cannabinoid receptor by positron emission tomography. J Med Chem 2005, 48:5813-5822.
    • (2005) J Med Chem , vol.48 , pp. 5813-5822
    • Willis, P.G.1    Pavlova, O.A.2    Chefer, S.I.3    Vaupel, D.B.4    Mukhin, A.G.5    Horti, A.G.6
  • 3
    • 0027515373 scopus 로고
    • Molecular characterization of a peripheral receptor for cannabinoids
    • Munro S., Thomas K.L., Abushaar M. Molecular characterization of a peripheral receptor for cannabinoids. Nature 1993, 365:61-65.
    • (1993) Nature , vol.365 , pp. 61-65
    • Munro, S.1    Thomas, K.L.2    Abushaar, M.3
  • 6
    • 77952623444 scopus 로고    scopus 로고
    • CB2: a cannabinoid receptor with an identity crisis
    • Atwood B.K., Mackie K. CB2: a cannabinoid receptor with an identity crisis. Br J Pharmacol 2010, 160:467-479.
    • (2010) Br J Pharmacol , vol.160 , pp. 467-479
    • Atwood, B.K.1    Mackie, K.2
  • 7
    • 66449088967 scopus 로고    scopus 로고
    • Synthesis of quinolinyl and isoquinolinyl phenyl ketones as novel agonists for the cannabinoid
    • Reux B., Nevalainen T., Raitio K.H., Koskinen A.M.P. Synthesis of quinolinyl and isoquinolinyl phenyl ketones as novel agonists for the cannabinoid. Bioorg Med Chem 2009, 17:4441-4447.
    • (2009) Bioorg Med Chem , vol.17 , pp. 4441-4447
    • Reux, B.1    Nevalainen, T.2    Raitio, K.H.3    Koskinen, A.M.P.4
  • 8
    • 77957293945 scopus 로고    scopus 로고
    • Receptors: implications for neuropsychiatric disorders
    • Roche M., Finn D.P. Receptors: implications for neuropsychiatric disorders. Pharmaceuticals 2010, 3:2517-2553.
    • (2010) Pharmaceuticals , vol.3 , pp. 2517-2553
    • Roche, M.1    Finn, D.P.2
  • 9
    • 16444375370 scopus 로고    scopus 로고
    • Cannabinoid receptor as a novel target for the treatment of prostate cancer
    • Sarfaraz S., Afaq F., Adhami V.M., Mukhtar H. Cannabinoid receptor as a novel target for the treatment of prostate cancer. Cancer Res 2005, 65:1635-1641.
    • (2005) Cancer Res , vol.65 , pp. 1635-1641
    • Sarfaraz, S.1    Afaq, F.2    Adhami, V.M.3    Mukhtar, H.4
  • 10
    • 18444386531 scopus 로고    scopus 로고
    • Targeting the cannabinoid CB2 receptor: mutations, modeling and development of CB2 selective ligands
    • Raitio K.H., Salo O.M.H., Nevalainen T., Poso A., Jaervinen T. Targeting the cannabinoid CB2 receptor: mutations, modeling and development of CB2 selective ligands. Curr Med Chem 2005, 12:1217-1237.
    • (2005) Curr Med Chem , vol.12 , pp. 1217-1237
    • Raitio, K.H.1    Salo, O.M.H.2    Nevalainen, T.3    Poso, A.4    Jaervinen, T.5
  • 11
    • 21044458324 scopus 로고    scopus 로고
    • Current knowledge on the antagonists and inverse agonists of cannabinoid receptors
    • Muccioli G.G., Lambert D.M. Current knowledge on the antagonists and inverse agonists of cannabinoid receptors. Curr Med Chem 2005, 12:1361-1394.
    • (2005) Curr Med Chem , vol.12 , pp. 1361-1394
    • Muccioli, G.G.1    Lambert, D.M.2
  • 12
    • 0036669789 scopus 로고    scopus 로고
    • From cannabis to cannabinergics: new therapeutic opportunities
    • Goutopoulos A., Makriyannis A. From cannabis to cannabinergics: new therapeutic opportunities. Pharmacol Ther 2002, 95:103-117.
    • (2002) Pharmacol Ther , vol.95 , pp. 103-117
    • Goutopoulos, A.1    Makriyannis, A.2
  • 13
    • 0033624042 scopus 로고    scopus 로고
    • The search for selective ligands for the CB2 receptor
    • Huffman J.W. The search for selective ligands for the CB2 receptor. Curr Pharm Des 2000, 6:1323-1337.
    • (2000) Curr Pharm Des , vol.6 , pp. 1323-1337
    • Huffman, J.W.1
  • 14
    • 34547411013 scopus 로고    scopus 로고
    • Hargreaves RJ [18F]MK-9470, a positron emission tomography (PET) tracer for in vivo human PET brain imaging of the cannabinoid-1 receptor
    • Burns H.D., Van Laere K., Sanabria-Bohórquez S., Hamill G.T., Bormans G., Eng W.S., et al. Hargreaves RJ [18F]MK-9470, a positron emission tomography (PET) tracer for in vivo human PET brain imaging of the cannabinoid-1 receptor. PNAS 2007, 104:9800-9805.
    • (2007) PNAS , vol.104 , pp. 9800-9805
    • Burns, H.D.1    Van Laere, K.2    Sanabria-Bohórquez, S.3    Hamill, G.T.4    Bormans, G.5    Eng, W.S.6
  • 15
    • 43149098070 scopus 로고    scopus 로고
    • Radiolabeling of a high potency cannabinoid subtype-1 receptor ligand, N-(4-fluoro-benzyl)-4-(3-(piperidin-1-yl)-indole-1-sulfonyl)benzamide (PipISB), with carbon-11 or fluorine-18
    • Donohue S.R., Halldin C., Schou M., Hong J., Phebus L., Chernet E., et al. Radiolabeling of a high potency cannabinoid subtype-1 receptor ligand, N-(4-fluoro-benzyl)-4-(3-(piperidin-1-yl)-indole-1-sulfonyl)benzamide (PipISB), with carbon-11 or fluorine-18. J Labelled Compd Radiopharm 2008, 51:146-152.
    • (2008) J Labelled Compd Radiopharm , vol.51 , pp. 146-152
    • Donohue, S.R.1    Halldin, C.2    Schou, M.3    Hong, J.4    Phebus, L.5    Chernet, E.6
  • 16
    • 34547559603 scopus 로고    scopus 로고
    • Discovery of N-{(1S,2S)-2-(3-cyanophenyl)- 3-[4-(2-[18F]fluoroethoxy)phenyl]-1-methylpropyl}-2-methyl-2-[(5-methylpyridin-2-yl)oxy]propanamide, a cannabinoid-1 receptor positron emission tomography tracer suitable for clinical use
    • Liu P., Lin L.S., Hamill T.G., Jewell J.P., Lanza T.J., Gibson R.E., et al. Discovery of N-{(1S,2S)-2-(3-cyanophenyl)- 3-[4-(2-[18F]fluoroethoxy)phenyl]-1-methylpropyl}-2-methyl-2-[(5-methylpyridin-2-yl)oxy]propanamide, a cannabinoid-1 receptor positron emission tomography tracer suitable for clinical use. J Med Chem 2007, 50:3427-3430.
    • (2007) J Med Chem , vol.50 , pp. 3427-3430
    • Liu, P.1    Lin, L.S.2    Hamill, T.G.3    Jewell, J.P.4    Lanza, T.J.5    Gibson, R.E.6
  • 17
    • 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
    • Evens N., Muccioli G.G., Houbrechts N., Lambert D.M., Verbruggen A.M., Van Laere K., 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 2009, 36:455-465.
    • (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    Van Laere, K.6
  • 18
    • 53249151675 scopus 로고    scopus 로고
    • Labelling and biological evaluation of [11C]methoxy-Sch225336: a radioligand for the cannabinoid-type 2 receptor
    • Evens N., Bosier B., Lavey B.J., Kozlowski J.A., Vermaelen P., Baudemprez L., et al. Labelling and biological evaluation of [11C]methoxy-Sch225336: a radioligand for the cannabinoid-type 2 receptor. Nucl Med Biol 2008, 35:793-800.
    • (2008) Nucl Med Biol , vol.35 , pp. 793-800
    • Evens, N.1    Bosier, B.2    Lavey, B.J.3    Kozlowski, J.A.4    Vermaelen, P.5    Baudemprez, L.6
  • 19
    • 33645423157 scopus 로고    scopus 로고
    • Synthesis and SAR studies of 2-oxoquinoline derivatives as CB2 receptor inverse agonists
    • Raitio K.H., Savinainen J.R., Vepsalainen J., Laitinen J.T., Poso A., Jarvinen T., et al. Synthesis and SAR studies of 2-oxoquinoline derivatives as CB2 receptor inverse agonists. J Med Chem 2006, 49:2022-2027.
    • (2006) J Med Chem , vol.49 , pp. 2022-2027
    • Raitio, K.H.1    Savinainen, J.R.2    Vepsalainen, J.3    Laitinen, J.T.4    Poso, A.5    Jarvinen, T.6
  • 20
    • 77649235665 scopus 로고    scopus 로고
    • Synthesis and in vitro biological evaluation of carbon-11-labeled quinoline derivatives as new candidate PET radioligands for cannabinoid CB2 receptor imaging
    • Gao M., Wang M., Miller K.D., Hutchins G.D., Zheng Q.H. Synthesis and in vitro biological evaluation of carbon-11-labeled quinoline derivatives as new candidate PET radioligands for cannabinoid CB2 receptor imaging. Bioorg Med Chem 2010, 18:2099-2106.
    • (2010) Bioorg Med Chem , vol.18 , pp. 2099-2106
    • Gao, M.1    Wang, M.2    Miller, K.D.3    Hutchins, G.D.4    Zheng, Q.H.5
  • 21
    • 29144462516 scopus 로고    scopus 로고
    • Aspects of positron emission tomography radiochemistry as relevant for food chemistry
    • Wuest F. Aspects of positron emission tomography radiochemistry as relevant for food chemistry. Amino Acids 2005, 29:323-339.
    • (2005) Amino Acids , vol.29 , pp. 323-339
    • Wuest, F.1
  • 22
    • 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)
    • Horti A.G., Gao Y., Ravert H.T., Finley P., Valentine H., Wong D.F., 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 2010, 18:5202-5207.
    • (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    Wong, D.F.6
  • 24
    • 80052604108 scopus 로고    scopus 로고
    • Fluorinated cannabinoid CB2 receptor ligands: synthesis and in vitro binding characteristics of 2-oxo-quinoline derivatives
    • Turkman N., Shavrin A., Ivanov R.A., Rabinovich B., Volgin A., Gelovani J.G., et al. Fluorinated cannabinoid CB2 receptor ligands: synthesis and in vitro binding characteristics of 2-oxo-quinoline derivatives. Bioorg Med Chem 2011, 19:5698-5707.
    • (2011) Bioorg Med Chem , vol.19 , pp. 5698-5707
    • Turkman, N.1    Shavrin, A.2    Ivanov, R.A.3    Rabinovich, B.4    Volgin, A.5    Gelovani, J.G.6
  • 25
    • 0033794909 scopus 로고    scopus 로고
    • General method to label antisense oligonucleotides with radioactive halogens for pharmacological and imaging studies
    • Kuhnast B., Dolle F., Terrazzino S., Rousseau B., Loc'h C., Vaufrey F., et al. General method to label antisense oligonucleotides with radioactive halogens for pharmacological and imaging studies. Bioconj Chem 2000, 11:627-636.
    • (2000) Bioconj Chem , vol.11 , pp. 627-636
    • Kuhnast, B.1    Dolle, F.2    Terrazzino, S.3    Rousseau, B.4    Loc'h, C.5    Vaufrey, F.6
  • 27
    • 0033381793 scopus 로고    scopus 로고
    • 3-(10,10-Dimethylbutyl)-1-deoxy-δ8-THC and related compounds: synthesis of selective ligands for the CB2 receptor
    • Huffman J.W., John Liddle J., Shu Yu S., Aung M.M., Abood M.E., Wiley JL, et al. 3-(10,10-Dimethylbutyl)-1-deoxy-δ8-THC and related compounds: synthesis of selective ligands for the CB2 receptor. Bioor Med Chem 1999, 7:2905-2914.
    • (1999) Bioor Med Chem , vol.7 , pp. 2905-2914
    • Huffman, J.W.1    John Liddle, J.2    Shu Yu, S.3    Aung, M.M.4    Abood, M.E.5    Wiley, J.L.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.