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Volumn 36, Issue 2, 2009, Pages 147-153

Fluorine-18 labeling and biodistribution studies on peroxisome proliferator-activated receptor-γ ligands: potential positron emission tomography imaging agents

Author keywords

Fluorine 18; Iodonium salt; Nucleophilic aromatic substitution; Peroxisome proliferator activated receptor ; PPAR ; Ullmann coupling

Indexed keywords

(2 BENZOYLPHENYLAMINO) 3 [4 [2 [2 (4 FLUOROPHENYL) 5 METHYLOXAZOL 4 YL]ETHOXY]PHENYL]PROPIONIC ACID F 18; 2 (4 FLUOROBENZOYL)PHENYLAMINO 3 [4 [2 (5 METHYL 2 PHENYLOXAZOL 4 YL)ETHOXY]PHENYL]PROPIONIC ACID; 2 IODO 4' FLUOROBENZOPHENONE F 18; BENZOPHENONE; CONTRAST MEDIUM; FARGLITAZAR; FLUORINE 18; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR GAMMA; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR GAMMA AGONIST; UNCLASSIFIED DRUG;

EID: 59649109169     PISSN: 09698051     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.nucmedbio.2008.11.002     Document Type: Article
Times cited : (29)

References (31)
  • 1
    • 0029152375 scopus 로고
    • Isolation of the human peroxisome proliferator activated receptor gamma cDNA: expression in hematopoietic cells and chromosomal mapping
    • Greene M.E., Blumberg B., McBride O.W., et al. Isolation of the human peroxisome proliferator activated receptor gamma cDNA: expression in hematopoietic cells and chromosomal mapping. Gene Expr 4 (1995) 281-299
    • (1995) Gene Expr , vol.4 , pp. 281-299
    • Greene, M.E.1    Blumberg, B.2    McBride, O.W.3
  • 2
    • 0025132245 scopus 로고
    • Activation of a member of the steroid hormone receptor superfamily by peroxisome proliferators
    • Issemann I., and Green S. Activation of a member of the steroid hormone receptor superfamily by peroxisome proliferators. Nature 347 (1990) 645-650
    • (1990) Nature , vol.347 , pp. 645-650
    • Issemann, I.1    Green, S.2
  • 3
    • 0029731662 scopus 로고    scopus 로고
    • Peroxisome proliferator-activated receptors: a nuclear receptor signaling pathway in lipid physiology
    • Lemberger T., Desvergne B., and Wahli W. Peroxisome proliferator-activated receptors: a nuclear receptor signaling pathway in lipid physiology. Annu Rev Cell Dev Biol 12 (1996) 335-363
    • (1996) Annu Rev Cell Dev Biol , vol.12 , pp. 335-363
    • Lemberger, T.1    Desvergne, B.2    Wahli, W.3
  • 4
    • 0030062325 scopus 로고    scopus 로고
    • The structure-activity relationship between peroxisome proliferator-activated receptor γ agonism and the anti-hyperglycemic activity of thiazolidinediones
    • Willson T.M., Cobb J.E., Cowan D.J., et al. The structure-activity relationship between peroxisome proliferator-activated receptor γ agonism and the anti-hyperglycemic activity of thiazolidinediones. J Med Chem 39 (1996) 665-668
    • (1996) J Med Chem , vol.39 , pp. 665-668
    • Willson, T.M.1    Cobb, J.E.2    Cowan, D.J.3
  • 5
    • 0028972026 scopus 로고
    • A prostaglandin J2 metabolite binds peroxisome proliferator-activated receptor γ and promotes adipocyte differentiation
    • Kliewer S.A., Lenhard J.M., Willson T.M., et al. A prostaglandin J2 metabolite binds peroxisome proliferator-activated receptor γ and promotes adipocyte differentiation. Cell 83 (1995) 813-819
    • (1995) Cell , vol.83 , pp. 813-819
    • Kliewer, S.A.1    Lenhard, J.M.2    Willson, T.M.3
  • 6
    • 0343855442 scopus 로고    scopus 로고
    • Effects of ligand activation of peroxisome proliferator-activated receptor γ in human prostate cancer
    • Mueller E., Smith M., Sarraf P., et al. Effects of ligand activation of peroxisome proliferator-activated receptor γ in human prostate cancer. Proc Natl Acad Sci U S A 97 (2000) 10990-10995
    • (2000) Proc Natl Acad Sci U S A , vol.97 , pp. 10990-10995
    • Mueller, E.1    Smith, M.2    Sarraf, P.3
  • 7
    • 0037899628 scopus 로고    scopus 로고
    • Use of the peroxisome proliferator-activated receptor (PPAR) γ ligand troglitazone as treatment for refractory breast cancer: a Phase II study
    • Burstein H.J., Demetri G.D., Mueller E., et al. Use of the peroxisome proliferator-activated receptor (PPAR) γ ligand troglitazone as treatment for refractory breast cancer: a Phase II study. Breast Cancer Res Treat 79 (2003) 391-397
    • (2003) Breast Cancer Res Treat , vol.79 , pp. 391-397
    • Burstein, H.J.1    Demetri, G.D.2    Mueller, E.3
  • 8
    • 0348149135 scopus 로고    scopus 로고
    • Therapeutic potential of thiazolidinediones as anticancer agents
    • Panigrahy D., Shen L.Q., Kieran M.W., et al. Therapeutic potential of thiazolidinediones as anticancer agents. Expert Opin Investig Drugs 12 (2003) 1925-1937
    • (2003) Expert Opin Investig Drugs , vol.12 , pp. 1925-1937
    • Panigrahy, D.1    Shen, L.Q.2    Kieran, M.W.3
  • 9
    • 0033616795 scopus 로고    scopus 로고
    • Induction of solid tumor differentiation by the peroxisome proliferator-activated receptor-gamma ligand troglitazone in patients with liposarcoma
    • Demetri G.D., Fletcher C.D., Mueller E., et al. Induction of solid tumor differentiation by the peroxisome proliferator-activated receptor-gamma ligand troglitazone in patients with liposarcoma. Proc Natl Acad Sci U S A 96 (1999) 3951-3956
    • (1999) Proc Natl Acad Sci U S A , vol.96 , pp. 3951-3956
    • Demetri, G.D.1    Fletcher, C.D.2    Mueller, E.3
  • 10
    • 0031993322 scopus 로고    scopus 로고
    • Terminal differentiation of human breast cancer through PPAR γ
    • Mueller E., Sarraf P., Tontonoz P., et al. Terminal differentiation of human breast cancer through PPAR γ. Mol Cell 1 (1998) 465-470
    • (1998) Mol Cell , vol.1 , pp. 465-470
    • Mueller, E.1    Sarraf, P.2    Tontonoz, P.3
  • 11
    • 4143115845 scopus 로고    scopus 로고
    • The increased expression of peroxisome proliferator-activated receptor-γ1 in human breast cancer is mediated by selective promoter usage
    • Wang X., Southard R.C., and Kilgore M.W. The increased expression of peroxisome proliferator-activated receptor-γ1 in human breast cancer is mediated by selective promoter usage. Cancer Res 64 (2004) 5592-5596
    • (2004) Cancer Res , vol.64 , pp. 5592-5596
    • Wang, X.1    Southard, R.C.2    Kilgore, M.W.3
  • 13
    • 0035011748 scopus 로고    scopus 로고
    • Fluorine-substituted ligands for the peroxisome proliferator-activated receptor gamma (PPARγ): potential imaging agents for metastatic tumors
    • Kim S.-H., Jonson S.D., Welch M.J., et al. Fluorine-substituted ligands for the peroxisome proliferator-activated receptor gamma (PPARγ): potential imaging agents for metastatic tumors. Bioconjug Chem 12 (2001) 439-450
    • (2001) Bioconjug Chem , vol.12 , pp. 439-450
    • Kim, S.-H.1    Jonson, S.D.2    Welch, M.J.3
  • 14
    • 0034611678 scopus 로고    scopus 로고
    • Towards a molecular understanding of adaptive thermogenesis
    • Lowell B.B., and Spiegelman B.M. Towards a molecular understanding of adaptive thermogenesis. Nature 404 (2000) 652-660
    • (2000) Nature , vol.404 , pp. 652-660
    • Lowell, B.B.1    Spiegelman, B.M.2
  • 16
    • 7844232968 scopus 로고    scopus 로고
    • N-(2-Benzoylphenyl)-l-tyrosine PPARgamma agonists: 3. Structure-activity relationship and optimization of the N-aryl substituent
    • Cobb J.E., Blanchard S.G., Boswell E.G., et al. N-(2-Benzoylphenyl)-l-tyrosine PPARgamma agonists: 3. Structure-activity relationship and optimization of the N-aryl substituent. J Med Chem 41 (1998) 5055-5069
    • (1998) J Med Chem , vol.41 , pp. 5055-5069
    • Cobb, J.E.1    Blanchard, S.G.2    Boswell, E.G.3
  • 17
    • 7844226652 scopus 로고    scopus 로고
    • N-(2-Benzoylphenyl)-l-tyrosine PPARγ agonists: 2. Structure-activity relationship and optimization of the phenyl alkyl ether moiety
    • Collins J.L., Blanchard S.G., Boswell G.E., et al. N-(2-Benzoylphenyl)-l-tyrosine PPARγ agonists: 2. Structure-activity relationship and optimization of the phenyl alkyl ether moiety. J Med Chem 41 (1998) 5037-5054
    • (1998) J Med Chem , vol.41 , pp. 5037-5054
    • Collins, J.L.1    Blanchard, S.G.2    Boswell, G.E.3
  • 18
    • 7844224790 scopus 로고    scopus 로고
    • N-(2-Benzoylphenyl)-l-tyrosine PPARγ agonists: 1. Discovery of a novel series of potent antihyperglycemic and antihyperlipidemic agents
    • Henke B.R., Blanchard S.G., Brackeen M.F., et al. N-(2-Benzoylphenyl)-l-tyrosine PPARγ agonists: 1. Discovery of a novel series of potent antihyperglycemic and antihyperlipidemic agents. J Med Chem 41 (1998) 5020-5036
    • (1998) J Med Chem , vol.41 , pp. 5020-5036
    • Henke, B.R.1    Blanchard, S.G.2    Brackeen, M.F.3
  • 19
    • 0033998334 scopus 로고    scopus 로고
    • The PPARs: from orphan receptors to drug discovery
    • Willson T.M., Brown P.J., Sternbach D.D., et al. The PPARs: from orphan receptors to drug discovery. J Med Chem 43 (2000) 527-550
    • (2000) J Med Chem , vol.43 , pp. 527-550
    • Willson, T.M.1    Brown, P.J.2    Sternbach, D.D.3
  • 20
    • 33644667556 scopus 로고    scopus 로고
    • Synthesis and biodistribution of (11)C-GW7845, a positron-emitting agonist for peroxisome proliferator-activated receptor-{gamma}
    • Mathews W.B., Foss C.A., Stoermer D., et al. Synthesis and biodistribution of (11)C-GW7845, a positron-emitting agonist for peroxisome proliferator-activated receptor-{gamma}. J Nucl Med 46 (2005) 1719-1726
    • (2005) J Nucl Med , vol.46 , pp. 1719-1726
    • Mathews, W.B.1    Foss, C.A.2    Stoermer, D.3
  • 21
    • 14444281382 scopus 로고    scopus 로고
    • Identification of high-affinity binding sites for the insulin sensitizer rosiglitazone (BRL-49653) in rodent and human adipocytes using a radioiodinated ligand for peroxisomal proliferator-activated receptor γ
    • Young P.W., Buckle D.R., Cantello B.C.C., et al. Identification of high-affinity binding sites for the insulin sensitizer rosiglitazone (BRL-49653) in rodent and human adipocytes using a radioiodinated ligand for peroxisomal proliferator-activated receptor γ. J Pharmacol Exp Ther 284 (1998) 751-759
    • (1998) J Pharmacol Exp Ther , vol.284 , pp. 751-759
    • Young, P.W.1    Buckle, D.R.2    Cantello, B.C.C.3
  • 22
    • 33947704129 scopus 로고    scopus 로고
    • Strategies for the labeling of halogen-substituted peroxisome proliferator-activated receptor gamma ligands: potential positron emission tomography and single photon emission computed tomography imaging agents
    • Lee B.C., Lee K.C., Lee H., et al. Strategies for the labeling of halogen-substituted peroxisome proliferator-activated receptor gamma ligands: potential positron emission tomography and single photon emission computed tomography imaging agents. Bioconjug Chem 18 (2007) 514-523
    • (2007) Bioconjug Chem , vol.18 , pp. 514-523
    • Lee, B.C.1    Lee, K.C.2    Lee, H.3
  • 23
    • 33947704130 scopus 로고    scopus 로고
    • Synthesis and binding affinity of a fluorine-substituted peroxisome proliferator-activated gamma (PPARgamma) ligand as a potential positron emission tomography (PET) imaging agent
    • Lee B.C., Lee K.C., Lee H., et al. Synthesis and binding affinity of a fluorine-substituted peroxisome proliferator-activated gamma (PPARgamma) ligand as a potential positron emission tomography (PET) imaging agent. Bioconjug Chem 18 (2007) 507-513
    • (2007) Bioconjug Chem , vol.18 , pp. 507-513
    • Lee, B.C.1    Lee, K.C.2    Lee, H.3
  • 24
    • 0013458416 scopus 로고
    • New methodology in iodonium salt synthesis. Reactions of [hydroxy(tosyloxy)iodo]arenes with aryltrimethylsilanes
    • Koser G.F., Wettach R.H., and Smith C.S. New methodology in iodonium salt synthesis. Reactions of [hydroxy(tosyloxy)iodo]arenes with aryltrimethylsilanes. J Org Chem 45 (1980) 1543-1544
    • (1980) J Org Chem , vol.45 , pp. 1543-1544
    • Koser, G.F.1    Wettach, R.H.2    Smith, C.S.3
  • 25
    • 33748619802 scopus 로고    scopus 로고
    • Facile synthesis of substituted diaryliodonium tosylates by treatment of aryltributylstannanes with Koser's reagent
    • Pike V.W., Butt F., Shah A., et al. Facile synthesis of substituted diaryliodonium tosylates by treatment of aryltributylstannanes with Koser's reagent. J Chem Soc Perkin Trans 1 (1999) 245-248
    • (1999) J Chem Soc Perkin Trans , vol.1 , pp. 245-248
    • Pike, V.W.1    Butt, F.2    Shah, A.3
  • 27
    • 0001625530 scopus 로고
    • Conversion of diaryliodonium salts to aryl fluorides
    • Van der Puy M. Conversion of diaryliodonium salts to aryl fluorides. J Fluorine Chem 21 (1982) 385-392
    • (1982) J Fluorine Chem , vol.21 , pp. 385-392
    • Van der Puy, M.1
  • 28
    • 0034847422 scopus 로고    scopus 로고
    • Synthesis of SB-214857 using copper catalyzed amination of aryl bromides with l-aspartic acid
    • Clement J.-B., Hayes J.F., Sheldrake H.M., et al. Synthesis of SB-214857 using copper catalyzed amination of aryl bromides with l-aspartic acid. Synlett (2001) 1423-1427
    • (2001) Synlett , pp. 1423-1427
    • Clement, J.-B.1    Hayes, J.F.2    Sheldrake, H.M.3
  • 29
    • 0032501446 scopus 로고    scopus 로고
    • Accelerating effect induced by the structure of α-amino acid in the copper-catalyzed coupling reaction of aryl halides with α-amino acids. Synthesis of benzolactam-V8
    • Ma D., Zhang Y., Yao J., et al. Accelerating effect induced by the structure of α-amino acid in the copper-catalyzed coupling reaction of aryl halides with α-amino acids. Synthesis of benzolactam-V8. J Am Chem Soc 120 (1998) 12459-12467
    • (1998) J Am Chem Soc , vol.120 , pp. 12459-12467
    • Ma, D.1    Zhang, Y.2    Yao, J.3
  • 30
    • 1142276334 scopus 로고    scopus 로고
    • Efficient palladium/copper-cocatalyzed C-N coupling reaction of unactivated aryl bromide or iodide with amino acid under microwave heating
    • Xu L.-W., Xia C.G., Li J.W., et al. Efficient palladium/copper-cocatalyzed C-N coupling reaction of unactivated aryl bromide or iodide with amino acid under microwave heating. Catal Commun 5 (2004) 121-123
    • (2004) Catal Commun , vol.5 , pp. 121-123
    • Xu, L.-W.1    Xia, C.G.2    Li, J.W.3
  • 31
    • 27144462242 scopus 로고    scopus 로고
    • Techniques necessary for multiple tracer quantitative small-animal imaging studies
    • Sharp T.L., Dence C.S., Engelbach J.A., et al. Techniques necessary for multiple tracer quantitative small-animal imaging studies. Nucl Med Biol 32 (2005) 875-884
    • (2005) Nucl Med Biol , vol.32 , pp. 875-884
    • Sharp, T.L.1    Dence, C.S.2    Engelbach, J.A.3


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