메뉴 건너뛰기




Volumn 39, Issue 7, 2012, Pages 1058-1067

The synthesis and in vivo evaluation of [18F]PF-9811: A novel PET ligand for imaging brain fatty acid amide hydrolase (FAAH)

Author keywords

FAAH; Fluorine 18; Molecular imaging; PET ligand; Positron emission tomography; Rats

Indexed keywords

FATTY ACID AMIDASE; FATTY ACID AMIDASE INHIBITOR; PF 04457845; PF 9811; PF 9811 F 18; RADIOLIGAND; UNCLASSIFIED DRUG;

EID: 84866013018     PISSN: 09698051     EISSN: 18729614     Source Type: Journal    
DOI: 10.1016/j.nucmedbio.2012.03.011     Document Type: Article
Times cited : (28)

References (36)
  • 1
    • 44849141696 scopus 로고    scopus 로고
    • Enzymatic pathways that regulate endocannabinoid signaling in the nervous system
    • Ahn K., McKinney M.K., Cravatt B.F. Enzymatic pathways that regulate endocannabinoid signaling in the nervous system. Chem Rev 2008, 108:1687-1707.
    • (2008) Chem Rev , vol.108 , pp. 1687-1707
    • Ahn, K.1    McKinney, M.K.2    Cravatt, B.F.3
  • 2
    • 43249100162 scopus 로고    scopus 로고
    • Targeting the endocannabinoid system: to enhance or reduce?
    • Di Marzo V. Targeting the endocannabinoid system: to enhance or reduce?. Nat Rev Drug Discov 2008, 7:438-455.
    • (2008) Nat Rev Drug Discov , vol.7 , pp. 438-455
    • Di Marzo, V.1
  • 3
    • 34447575641 scopus 로고    scopus 로고
    • Endocannabinoids and related compounds: walking back and forth between plant natural products and animal physiology
    • Di Marzo V., Bisogno T., De Petrocellis L. Endocannabinoids and related compounds: walking back and forth between plant natural products and animal physiology. Chem Biol 2007, 14:741-756.
    • (2007) Chem Biol , vol.14 , pp. 741-756
    • Di Marzo, V.1    Bisogno, T.2    De Petrocellis, L.3
  • 4
    • 33748703859 scopus 로고    scopus 로고
    • The endocannabinoid system as an emerging target of pharmacotherapy
    • Pacher P., Batkai S., Kunos G. The endocannabinoid system as an emerging target of pharmacotherapy. Pharmacol Rev 2006, 58:389-462.
    • (2006) Pharmacol Rev , vol.58 , pp. 389-462
    • Pacher, P.1    Batkai, S.2    Kunos, G.3
  • 5
    • 0027078685 scopus 로고
    • Isolation and structure of a brain constituent that binds to the cannabinoid receptor
    • Devane W.A., Hanus L., Breuer A., Pertwee R.G., Stevenson L.A., Griffin G., et al. Isolation and structure of a brain constituent that binds to the cannabinoid receptor. Science 1992, 258:1946-1949.
    • (1992) Science , vol.258 , pp. 1946-1949
    • Devane, W.A.1    Hanus, L.2    Breuer, A.3    Pertwee, R.G.4    Stevenson, L.A.5    Griffin, G.6
  • 6
    • 0029904838 scopus 로고    scopus 로고
    • Molecular characterization of an enzyme that degrades neuromodulatory fatty-acid amides
    • Cravatt B.F., Giang D.K., Mayfield S.P., Boger D.L., Lerner R.A., Gilula N.B. Molecular characterization of an enzyme that degrades neuromodulatory fatty-acid amides. Nature 1996, 384:83-87.
    • (1996) Nature , vol.384 , pp. 83-87
    • Cravatt, B.F.1    Giang, D.K.2    Mayfield, S.P.3    Boger, D.L.4    Lerner, R.A.5    Gilula, N.B.6
  • 7
    • 22244484464 scopus 로고    scopus 로고
    • Structure and function of fatty acid amide hydrolase
    • McKinney M.K., Cravatt B.F. Structure and function of fatty acid amide hydrolase. Ann Rev Biochem 2005, 74:411-432.
    • (2005) Ann Rev Biochem , vol.74 , pp. 411-432
    • McKinney, M.K.1    Cravatt, B.F.2
  • 9
    • 0036216311 scopus 로고    scopus 로고
    • The palmitoylethanolamide family: a new class of anti-inflammatory agents?
    • Lambert D.M., Vandevoorde S., Jonsson K.O., Fowler C.J. The palmitoylethanolamide family: a new class of anti-inflammatory agents?. Curr Med Chem 2002, 9:663-674.
    • (2002) Curr Med Chem , vol.9 , pp. 663-674
    • Lambert, D.M.1    Vandevoorde, S.2    Jonsson, K.O.3    Fowler, C.J.4
  • 10
    • 67650732783 scopus 로고    scopus 로고
    • Fatty acid amide hydrolase as a potential therapeutic target for the treatment of pain and CNS disorders
    • Ahn K., Johnson D.S., Cravatt B.F. Fatty acid amide hydrolase as a potential therapeutic target for the treatment of pain and CNS disorders. Expert Opin Drug Discov 2009, 4:763-784.
    • (2009) Expert Opin Drug Discov , vol.4 , pp. 763-784
    • Ahn, K.1    Johnson, D.S.2    Cravatt, B.F.3
  • 11
    • 57349170752 scopus 로고    scopus 로고
    • Discovery and development of fatty acid amide hydrolase (FAAH) inhibitors
    • Seierstad M., Breitenbucher J.G. Discovery and development of fatty acid amide hydrolase (FAAH) inhibitors. J Med Chem 2008, 51:7327-7343.
    • (2008) J Med Chem , vol.51 , pp. 7327-7343
    • Seierstad, M.1    Breitenbucher, J.G.2
  • 12
    • 20144377098 scopus 로고    scopus 로고
    • Discovery of a potent, selective, and efficacious class of reversible alpha-ketoheterocycle inhibitors of fatty acid amide hydrolase effective as analgesics
    • Boger D.L., Miyauchi H., Du W., Hardouin C., Fecik R.A., Cheng H., et al. Discovery of a potent, selective, and efficacious class of reversible alpha-ketoheterocycle inhibitors of fatty acid amide hydrolase effective as analgesics. J Med Chem 2005, 48:1849-1856.
    • (2005) J Med Chem , vol.48 , pp. 1849-1856
    • Boger, D.L.1    Miyauchi, H.2    Du, W.3    Hardouin, C.4    Fecik, R.A.5    Cheng, H.6
  • 13
    • 4744354729 scopus 로고    scopus 로고
    • Cyclohexylcarbamic acid 3'- or 4'-substituted biphenyl-3-yl esters as fatty acid amide hydrolase inhibitors: synthesis, quantitative structure-activity relationships, and molecular modeling studies
    • Mor M., Rivara S., Lodola A., Plazzi P.V., Tarzia G., Duranti A., et al. Cyclohexylcarbamic acid 3'- or 4'-substituted biphenyl-3-yl esters as fatty acid amide hydrolase inhibitors: synthesis, quantitative structure-activity relationships, and molecular modeling studies. J Med Chem 2004, 47:4998-5008.
    • (2004) J Med Chem , vol.47 , pp. 4998-5008
    • Mor, M.1    Rivara, S.2    Lodola, A.3    Plazzi, P.V.4    Tarzia, G.5    Duranti, A.6
  • 14
    • 36048978697 scopus 로고    scopus 로고
    • Novel mechanistic class of fatty acid amide hydrolase inhibitors with remarkable selectivity
    • Ahn K., Johnson D.S., Fitzgerald L.R., Liimatta M., Arendse A., Stevenson T., et al. Novel mechanistic class of fatty acid amide hydrolase inhibitors with remarkable selectivity. Biochemistry 2007, 46:13019-13030.
    • (2007) Biochemistry , vol.46 , pp. 13019-13030
    • Ahn, K.1    Johnson, D.S.2    Fitzgerald, L.R.3    Liimatta, M.4    Arendse, A.5    Stevenson, T.6
  • 15
    • 64749114255 scopus 로고    scopus 로고
    • Discovery and characterization of a highly selective FAAH inhibitor that reduces inflammatory pain
    • Ahn K., Johnson D.S., Mileni M., Beidler D., Long J.Z., McKinney M.K., et al. Discovery and characterization of a highly selective FAAH inhibitor that reduces inflammatory pain. Chem Biol 2009, 16:411-420.
    • (2009) Chem Biol , vol.16 , pp. 411-420
    • Ahn, K.1    Johnson, D.S.2    Mileni, M.3    Beidler, D.4    Long, J.Z.5    McKinney, M.K.6
  • 16
    • 79956311523 scopus 로고    scopus 로고
    • Discovery and molecular basis of potent noncovalent inhibitors of fatty acid amide hydrolase (FAAH)
    • Min X., Thibault S.T., Porter A.C., Gustin D.J., Carlson T.J., Xu H., et al. Discovery and molecular basis of potent noncovalent inhibitors of fatty acid amide hydrolase (FAAH). Proc Natl Acad Sci USA 2011, 108:7379-7384.
    • (2011) Proc Natl Acad Sci USA , vol.108 , pp. 7379-7384
    • Min, X.1    Thibault, S.T.2    Porter, A.C.3    Gustin, D.J.4    Carlson, T.J.5    Xu, H.6
  • 17
    • 59449100866 scopus 로고    scopus 로고
    • Synthesis and evaluation of benzothiazole-based analogues as novel, potent, and selective fatty acid amide hydrolase inhibitors
    • Wang X., Sarris K., Kage K., Zhang D., Brown S.P., Kolasa T., et al. Synthesis and evaluation of benzothiazole-based analogues as novel, potent, and selective fatty acid amide hydrolase inhibitors. J Med Chem 2009, 52:170-180.
    • (2009) J Med Chem , vol.52 , pp. 170-180
    • Wang, X.1    Sarris, K.2    Kage, K.3    Zhang, D.4    Brown, S.P.5    Kolasa, T.6
  • 18
    • 51349143217 scopus 로고    scopus 로고
    • Structure-guided inhibitor design for human FAAH by interspecies active site conversion
    • Mileni M., Johnson D.S., Wang Z., Everdeen D.S., Liimatta M., Pabst B., et al. Structure-guided inhibitor design for human FAAH by interspecies active site conversion. Proc Natl Acad Sci USA 2008, 105:12820-12824.
    • (2008) Proc Natl Acad Sci USA , vol.105 , pp. 12820-12824
    • Mileni, M.1    Johnson, D.S.2    Wang, Z.3    Everdeen, D.S.4    Liimatta, M.5    Pabst, B.6
  • 19
    • 77954385220 scopus 로고    scopus 로고
    • Crystal structure of fatty acid amide hydrolase bound to the carbamate inhibitor URB597: discovery of a deacylating water molecule and insight into enzyme inactivation
    • Mileni M., Kamtekar S., Wood D.C., Benson T.E., Cravatt B.F., Stevens R.C. Crystal structure of fatty acid amide hydrolase bound to the carbamate inhibitor URB597: discovery of a deacylating water molecule and insight into enzyme inactivation. J Mol Biol 2010, 400:743-754.
    • (2010) J Mol Biol , vol.400 , pp. 743-754
    • Mileni, M.1    Kamtekar, S.2    Wood, D.C.3    Benson, T.E.4    Cravatt, B.F.5    Stevens, R.C.6
  • 20
    • 79959506821 scopus 로고    scopus 로고
    • Mechanistic and pharmacological characterization of PF-04457845: a highly potent and selective fatty acid amide hydrolase inhibitor that reduces inflammatory and noninflammatory pain
    • Ahn K., Smith S.E., Liimatta M.B., Beidler D., Sadagopan N., Dudley D.T., et al. Mechanistic and pharmacological characterization of PF-04457845: a highly potent and selective fatty acid amide hydrolase inhibitor that reduces inflammatory and noninflammatory pain. J Pharmacol Exp Ther 2011, 338:114-124.
    • (2011) J Pharmacol Exp Ther , vol.338 , pp. 114-124
    • Ahn, K.1    Smith, S.E.2    Liimatta, M.B.3    Beidler, D.4    Sadagopan, N.5    Dudley, D.T.6
  • 21
    • 79951518976 scopus 로고    scopus 로고
    • Discovery of PF-04457845: a highly potent, orally bioavailable, and selective urea FAAH inhibitor
    • Johnson D.S., Stiff C., Lazerwith S.E., Kesten S.R., Fay L.K., Morris M., et al. Discovery of PF-04457845: a highly potent, orally bioavailable, and selective urea FAAH inhibitor. ACS Med Chem Lett 2011, 2:91-96.
    • (2011) ACS Med Chem Lett , vol.2 , pp. 91-96
    • Johnson, D.S.1    Stiff, C.2    Lazerwith, S.E.3    Kesten, S.R.4    Fay, L.K.5    Morris, M.6
  • 22
    • 0030590440 scopus 로고    scopus 로고
    • Isolation and measurement of the endogenous cannabinoid receptor agonist, anandamide, in brain and peripheral tissues of human and rat
    • Felder C.C., Nielsen A., Briley E.M., Palkovits M., Priller J., Axelrod J., et al. Isolation and measurement of the endogenous cannabinoid receptor agonist, anandamide, in brain and peripheral tissues of human and rat. FEBS Lett 1996, 393:231-235.
    • (1996) FEBS Lett , vol.393 , pp. 231-235
    • Felder, C.C.1    Nielsen, A.2    Briley, E.M.3    Palkovits, M.4    Priller, J.5    Axelrod, J.6
  • 23
    • 84866030602 scopus 로고    scopus 로고
    • The discovery and characterization of [11C]MK-3168, a novel PET tracer for imaging fatty acid amide hydrolase (FAAH)
    • Li W., Sanabria-Bohórquez S., Joshi A., Cook J., Holahan M., Posavec D., et al. The discovery and characterization of [11C]MK-3168, a novel PET tracer for imaging fatty acid amide hydrolase (FAAH). J Labelled Comp Radiopharm 2011, 54:S38.
    • (2011) J Labelled Comp Radiopharm , vol.54
    • Li, W.1    Sanabria-Bohórquez, S.2    Joshi, A.3    Cook, J.4    Holahan, M.5    Posavec, D.6
  • 24
    • 77953811861 scopus 로고    scopus 로고
    • PET imaging of fatty acid amide hydrolase in the brain: synthesis and biological evaluation of an 11C-labelled URB597 analogue
    • Wyffels L., Muccioli G.G., Kapanda C.N., Labar G., De Bruyne S., De Vos F., et al. PET imaging of fatty acid amide hydrolase in the brain: synthesis and biological evaluation of an 11C-labelled URB597 analogue. Nucl Med Biol 2010, 37:665-675.
    • (2010) Nucl Med Biol , vol.37 , pp. 665-675
    • Wyffels, L.1    Muccioli, G.G.2    Kapanda, C.N.3    Labar, G.4    De Bruyne, S.5    De Vos, F.6
  • 25
    • 79551684090 scopus 로고    scopus 로고
    • [11C]CURB: Evaluation of a novel radiotracer for imaging fatty acid amide hydrolase by positron emission tomography
    • Wilson A.A., Garcia A., Parkes J., Houle S., Tong J., Vasdev N. [11C]CURB: Evaluation of a novel radiotracer for imaging fatty acid amide hydrolase by positron emission tomography. Nucl Med Biol 2011, 38:247-253.
    • (2011) Nucl Med Biol , vol.38 , pp. 247-253
    • Wilson, A.A.1    Garcia, A.2    Parkes, J.3    Houle, S.4    Tong, J.5    Vasdev, N.6
  • 26
    • 84874251045 scopus 로고    scopus 로고
    • Assessment of the pharmacology and tolerability of PF-04457845, an irreversible inhibitor of fatty acid amide hydrolase-1, in healthy subjects
    • Ling G.L., Winter H., Arends R., Jay G.W., Le V., Young T., et al. Assessment of the pharmacology and tolerability of PF-04457845, an irreversible inhibitor of fatty acid amide hydrolase-1, in healthy subjects. Br J Clin Pharm 2011.
    • (2011) Br J Clin Pharm
    • Ling, G.L.1    Winter, H.2    Arends, R.3    Jay, G.W.4    Le, V.5    Young, T.6
  • 27
    • 78650495439 scopus 로고    scopus 로고
    • Superfamily-wide portrait of serine hydrolase inhibition achieved by library-versus-library screening
    • Bachovchin D.A., Ji T., Li W., Simon G.M., Blankman J.L., Adibekian A., et al. Superfamily-wide portrait of serine hydrolase inhibition achieved by library-versus-library screening. Proc Natl Acad Sci USA 2010, 107:20941-20946.
    • (2010) Proc Natl Acad Sci USA , vol.107 , pp. 20941-20946
    • Bachovchin, D.A.1    Ji, T.2    Li, W.3    Simon, G.M.4    Blankman, J.L.5    Adibekian, A.6
  • 28
    • 50649112213 scopus 로고    scopus 로고
    • Activity-based protein profiling: from enzyme chemistry to proteomic chemistry
    • Cravatt B.F., Wright A.T., Kozarich J.W. Activity-based protein profiling: from enzyme chemistry to proteomic chemistry. Annu Rev Biochem 2008, 77:383-414.
    • (2008) Annu Rev Biochem , vol.77 , pp. 383-414
    • Cravatt, B.F.1    Wright, A.T.2    Kozarich, J.W.3
  • 29
    • 0033593013 scopus 로고    scopus 로고
    • Activity-based protein profiling: the serine hydrolases
    • Liu Y., Patricelli M.P., Cravatt B.F. Activity-based protein profiling: the serine hydrolases. Proc Natl Acad Sci USA 1999, 96:14694-14699.
    • (1999) Proc Natl Acad Sci USA , vol.96 , pp. 14694-14699
    • Liu, Y.1    Patricelli, M.P.2    Cravatt, B.F.3
  • 30
    • 0032494704 scopus 로고    scopus 로고
    • A new perspective on cannabinoid signaling: complementary localization of fatty acid amide hydrolase and the CB1 receptor in rat brain
    • Egertova M., Giang D.K., Cravatt B.F. A new perspective on cannabinoid signaling: complementary localization of fatty acid amide hydrolase and the CB1 receptor in rat brain. Proc Biol Sci 1998, 265:2081-2085.
    • (1998) Proc Biol Sci , vol.265 , pp. 2081-2085
    • Egertova, M.1    Giang, D.K.2    Cravatt, B.F.3
  • 31
    • 0031469972 scopus 로고    scopus 로고
    • Fatty acid amide hydrolase, the degenerative enzyme for anandamide and oleamide, has selective distribution within the rat central nervous system
    • Thomas E.A., Cravatt B.F., Danielson P.E., Gilula N.B., Sutcliffe J.G. Fatty acid amide hydrolase, the degenerative enzyme for anandamide and oleamide, has selective distribution within the rat central nervous system. J Neuroscience Res 1997, 50:1047-1052.
    • (1997) J Neuroscience Res , vol.50 , pp. 1047-1052
    • Thomas, E.A.1    Cravatt, B.F.2    Danielson, P.E.3    Gilula, N.B.4    Sutcliffe, J.G.5
  • 33
    • 0344121272 scopus 로고    scopus 로고
    • Determination of lipophilicity and its use as a predictor of blood-brain barrier penetration of molecular imaging agents
    • Waterhouse R.N. Determination of lipophilicity and its use as a predictor of blood-brain barrier penetration of molecular imaging agents. Mol Imaging Biol 2003, 3:376-389.
    • (2003) Mol Imaging Biol , vol.3 , pp. 376-389
    • Waterhouse, R.N.1
  • 34
    • 0028903996 scopus 로고
    • Anandamide amidohydrolase activity in rat brain microsomes: identification and partial characterization
    • Desarnaud F., Cadas H., Piomelli D. Anandamide amidohydrolase activity in rat brain microsomes: identification and partial characterization. J Biol Chem 1995, 270:6030-6035.
    • (1995) J Biol Chem , vol.270 , pp. 6030-6035
    • Desarnaud, F.1    Cadas, H.2    Piomelli, D.3
  • 36
    • 0035255404 scopus 로고    scopus 로고
    • An admonition when measuring the lipophilicity of radiotracers using counting techniques
    • Wilson A.A., Jin L., Garcia A., DaSilva J.N., Houle S. An admonition when measuring the lipophilicity of radiotracers using counting techniques. Appl Radiat Isot 2001, 54:203-208.
    • (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


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.