Synthesis and evaluation of 18F-labeled bile acid compound: A potential PET imaging agent for FXR-related diseases

Nuclear Medicine and Biology

Volumn 41, Issue 6, 2014, Pages 495-500

  Jia, Lina ^a,b   Jiang, Dawei ^a,b   Hu, Pengcheng ^c   Li, Xiao ^c   Shi, Hongcheng ^c   Cheng, Dengfeng ^c   Zhang, Lan ^b  

^a SHANGHAI INSTITUTE OF APPLIED PHYSICS   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

^c FUDAN UNIVERSITY   (China)

Author keywords

Bile acid; CDCA; Click chemistry; FXR; PET imaging

Indexed keywords

ALKYNE; AZIDE; BILE ACID; BILE ACID COMPOUND F 18; CHENODEOXYCHOLIC ACID; FARNESOID X RECEPTOR; LIGAND; TRACER; UNCLASSIFIED DRUG; CELL RECEPTOR; FARNESOID X-ACTIVATED RECEPTOR; FLUORINE;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BIOACCUMULATION; BLADDER; BRAIN; CANCER DIAGNOSIS; CLICK CHEMISTRY; CONTROLLED STUDY; CYCLOADDITION; DRUG ACTIVITY; DRUG METABOLISM; DRUG PURITY; DRUG SCREENING; DRUG STABILITY; DRUG SYNTHESIS; DRUG UPTAKE; EARLY DIAGNOSIS; GALLBLADDER; HEART; IN VITRO STUDY; IN VIVO STUDY; INTESTINE; ISOTOPE LABELING; LIVER; LIVER DISEASE; MALE; MOUSE; NONHUMAN; NUDE MOUSE; PET SCANNER; POSITRON EMISSION TOMOGRAPHY; RADIOACTIVITY; ANIMAL; CHEMICAL PHENOMENA; CHEMISTRY; COMPUTER ASSISTED TOMOGRAPHY; DIAGNOSTIC USE; METABOLISM; PROCEDURES; RADIOCHEMISTRY; RADIOGRAPHY; SCINTISCANNING; SYNTHESIS;

ANIMALS; BILE ACIDS AND SALTS; CHEMISTRY TECHNIQUES, SYNTHETIC; FLUORINE RADIOISOTOPES; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; LIVER DISEASES; MICE; POSITRON-EMISSION TOMOGRAPHY; RADIOCHEMISTRY; RECEPTORS, CYTOPLASMIC AND NUCLEAR; TOMOGRAPHY, X-RAY COMPUTED;

EID: 84901281300     PISSN: 09698051     EISSN: 18729614     Source Type: Journal    
DOI: 10.1016/j.nucmedbio.2014.03.016     Document Type: Article

References (46)

1. Dowling R.H., Mack E., Small D.M. Effects of controlled interruption of the enterohepatic circulation of bile salts by biliary diversion and by ileal resection on bile salt secretion, synthesis, and pool size in the rhesus monkey. J Clin Invest 1970, 49:232-242.
2. Hofmann A.F., Hagey L.R. Bile acids: Chemistry, pathochemistry, biology, pathobiology, and therapeutics. Cell Mol Life Sci 2008, 65:2461-2483.
3. Rao Y.P., Vlahcevic Z.R., Stravitz R.T., Mallonee D.H., Mullick J., Avadhani N.G., et al. Down-regulation of the rat hepatic sterol 27-hydroxylase gene by bile acids in transfected primary hepatocytes: possible role of hepatic nuclear factor 1 alpha. J Steroid Biochem Mol Biol 1999, 70:1-14.
4. Inagaki T., Choi M., Moschetta A., Peng L., Cummins C.L., McDonald J.G., et al. Fibroblast growth factor 15 functions as an enterohepatic signal to regulate bile acid homeostasis. Cell Metab 2005, 2:217-225.
5. Yu C.D., Wang F., Jin C.L., Huang X.Q., McKeehan W.L. Independent repression of bile acid synthesis and activation of c-Jun N-terminal kinase (JNK) by activated hepatocyte fibroblast growth factor receptor 4 (FGFR4) and bile acids. J Biol Chem 2005, 280:17707-17714.
6. Chawla A., Repa J.J., Evans R.M., Mangelsdorf D.J. Nuclear receptors and lipid physiology: Opening the X-files. Science 2001, 294:1866-1870.
7. Maruyama T., Miyamoto Y., Nakamura T., Tamai Y., Okada H., Sugiyama E., et al. Identification of membrane-type receptor for bile acids (M-BAR). Biochem Biophys Res Commun 2002, 298:714-719.
8. Kawamata Y., Fujii R., Hosoya M., Harada M., Yoshida H., Miwa M., et al. A G protein-coupled receptor responsive to bile acids. J Biol Chem 2003, 278:9435-9440.
9. Gioiello A., Macchiarulo A., Carotti A., Filipponi P., Costantino G., Rizzo G., et al. Extending SAR of bile acids as FXR ligands: Discovery of 23-N-(carbocinnamyloxy)-3alpha, 7alpha-dihydroxy-6 alpha-ethyl-24-nor-5 beta-cholan-23-amine. Bioorg Med Chem 2011, 19:2650-2658.
10. Zhang Y.Q., Kast-Woelbern H.R., Edwards P.A. Natural structural variants of the nuclear receptor farnesoid X receptor affect transcriptional activation. J Biol Chem 2003, 278:104-110.
11. Pircher P.C., Kitto J.L., Petrowski M.L., Tangirala R.K., Bischoff E.D., Schulman I.G., et al. Farnesoid X receptor regulates bile acid-amino acid conjugation. J Biol Chem 2003, 278:27703-27711.
12. Huang W.D., Ma K., Zhang J., Qatanani M., Cuvillier J., Liu J., et al. Nuclear receptor-dependent bile acid signaling is required for normal liver regeneration. Science 2006, 312:233-236.
13. Kim I., Morimura K., Shah Y., Yang Q., Ward J.M., Gonzalez F.J. Spontaneous hepatocarcinogenesis in farnesoid X receptor-null mice. Carcinogenesis 2007, 28:940-946.
14. Yang F., Huang X.F., Yi T.S., Yen Y., Moore D.D., Huang W.D. Spontaneous development of liver tumors in the absence of the bile acid receptor farnesoid X receptor. Cancer Res 2007, 67:863-867.
15. Kim I., Ahn S.H., Inagaki T., Choi M., Ito S., Guo G.L., et al. Differential regulation of bile acid homeostasis by the farnesoid X receptor in liver and intestine. J Lipid Res 2007, 48:2664-2672.
16. Maran R.R.M., Thomas A., Roth M., Sheng Z.H., Esterly N., Pinson D., et al. Farnesoid X Receptor Deficiency in Mice Leads to Increased Intestinal Epithelial Cell Proliferation and Tumor Development. J Pharmacol Exp Ther 2009, 328:469-477.
17. Moschetta A., Bookout A.L., Mangelsdorf D.J. Prevention of cholesterol gallstone disease by FXR agonists in a mouse model. Nat Med 2004, 10:1352-1358.
18. Stedman C., Liddle C., Coulter S., Sonoda J., Alvarez J.G., Evans R.M., et al. Benefit of farnesoid X receptor inhibition in obstructive cholestasis. Proc Natl Acad Sci U S A 2006, 103:11323-11328.
19. Guo G.L., Santamarina-Fojo S., Akiyama T.E., Amar M.J.A., Paigen B.J., Brewer B., et al. Effects of FXR in foam-cell formation and atherosclerosis development. Biochim Biophys Acta Mol Cell Biol Lipids 2006, 1761:1401-1409.
20. Modica S., Petruzzelli M., Bellafante E., Murzilli S., Salvatore L., Celli N., et al. Selective Activation of Nuclear Bile Acid Receptor FXR in the Intestine Protects Mice Against Cholestasis. Gastroenterology 2012, 142:355-365.
21. Zhang L.S., Wang Y.D., Chen W.D., Wang X.C., Lou G.Y., Liu N., et al. Promotion of Liver Regeneration/Repair by Farnesoid X Receptor in Both Liver and Intestine in Mice. Hepatology 2012, 56:2336-2343.
22. Chen F., Ananthanarayanan M., Emre S., Neimark E., Bull L.N., Knisely A.S., et al. Progressive familial intrahepatic cholestasis, type 1, is associated with decreased farnesoid X receptor activity. Gastroenterology 2004, 126:756-764.
23. De Gottardi A., Touri F., Maurer C.A., Perez A., Maurhofer O., Ventre G., et al. The bile acid nuclear receptor FXR and the bile acid binding protein IBABP are differently expressed in colon cancer. Dig Dis Sci 2004, 49:982-989.
24. Takahara Y., Takahashi M., Zhang Q.W., Wagatsuma H., Mori M., Tamori A., et al. Serial changes in expression of functionally clustered genes in progression of liver fibrosis in hepatitis C patients. World J Gastroenterol 2008, 14:2010-2022.
25. Fickert P., Fuchsbichler A., Moustafa T., Wagner M., Zollner G., Halilbasic E., et al. Farnesoid X Receptor Critically Determines the Fibrotic Response in Mice but Is Expressed to a Low Extent in Human Hepatic Stellate Cells and Periductal Myofibroblasts. Am J Pathol 2009, 175:2392-2405.
26. Wolfe A., Thomas A., Edwards G., Jaseja R., Guo G.L., Apte U. Increased Activation of the Wnt/beta-Catenin Pathway in Spontaneous Hepatocellular Carcinoma Observed in Farnesoid X Receptor Knockout Mice. J Pharmacol Exp Ther 2011, 338:12-21.
27. Lax S., Schauer G., Prein K., Kapitan M., Silbert D., Berghold A., et al. Expression of the nuclear bile acid receptor/farnesoid X receptor is reduced in human colon carcinoma compared to nonneoplastic mucosa independent from site and may be associated with adverse prognosis. Int J Cancer 2012, 130:2232-2239.
28. Meng Z.P., Wang X.Q., Gan Y.C., Zhang Y.F., Zhou H., Van Ness C., et al. Deletion of IFN gamma enhances hepatocarcinogenesis in FXR knockout mice. J Hepatol 2012, 57:1004-1012.
29. Elsharkawy A.M., Mann D.A. Nuclear factor-kappa B and the hepatic inflammation-fibrosis-cancer axis. Hepatology 2007, 46:590-597.
30. Liu N.A., Meng Z.P., Lou G.Y., Zhou W.P., Wang X.Q., Zhang Y.F., et al. Hepatocarcinogenesis in FXR-/- Mice Mimics Human HCC Progression That Operates through HNF1 alpha Regulation of FXR Expression. Mol Endocrinol 2012, 26:775-785.
31. Vavassori P., Mencarelli A., Renga B., Distrutti E., Fiorucci S. The Bile Acid Receptor FXR Is a Modulator of Intestinal Innate Immunity. J Immunol 2009, 183:6251-6261.
32. Fiorucci S., Cipriani S., Mencarelli A., Renga B., Distrutti E., Baldelli F. Counter-Regulatory Role of Bile Acid Activated Receptors in Immunity and Inflammation. Curr Mol Med 2010, 10:579-595.
33. Frisch K., Jakobsen S., Sorensen M., Munk O.L., Alstrup A.K.O., Ott P., et al. N-Methyl-C-11 Cholylsarcosine, a Novel Bile Acid Tracer for PET/CT of Hepatic Excretory Function: Radiosynthesis and Proof-of-Concept Studies in Pigs. J Nucl Med 2012, 53:772-778.
34. Anelli P.L., Lattuada L., Lorusso V., Lux G., Morisetti A., Morosini P., et al. Conjugates of gadolinium complexes to bile acids as hepatocyte-directed contrast agents for magnetic resonance Imaging. J Med Chem 2004, 47:3629-3641.
35. Makishima M., Okamoto A.Y., Repa J.J., Tu H., Learned R.M., Luk A., et al. Identification of a nuclear receptor for bile acids. Science 1999, 284:1362-1365.
36. Wang H.B., Chen J., Hollister K., Sowers L.C., Forman B.M. Endogenous bile acids are ligands for the nuclear receptor FXR BAR. Mol Cell 1999, 3:543-553.
37. Parks D.J., Blanchard S.G., Bledsoe R.K., Chandra G., Consler T.G., Kliewer S.A., et al. Bile acids: Natural ligands for an orphan nuclear receptor. Science 1999, 284:1365-1368.
38. Pellicciari R., Gioiello A., Costantino G., Sadeghpour B.M., Rizzo G., Meyer U., et al. Back door modulation of the farnesoid X receptor: Design, synthesis, and biological evaluation of a series of side chain modified chenodeoxycholic acid derivatives. J Med Chem 2006, 49:4208-4215.
39. Marik J., Sutcliffe J.L. Click for PET: rapid preparation of F-18 fluoropeptides using Cu-I catalyzed 1,3-dipolar cycloaddition. Tetrahedron Lett 2006, 47:6681-6684.
40. Smith G., Sala R., Carroll L., Behan K., Glaser M., Robins E., et al. Synthesis and evaluation of nucleoside radiotracers for imaging proliferation. Nucl Med Biol 2012, 39:652-665.
41. Jia L.N., Cheng Z., Shi L.L., Li J.B., Wang C., Jiang D.W., et al. Fluorine-18 labeling by click chemistry: Multiple probes in one pot. Appl Radiat Isot 2013, 75:64-70.
42. Baumann C.A., Mu L.J., Wertli N., Kramer S.D., Honer M., Schubiger P.A., et al. Syntheses and pharmacological characterization of novel thiazole derivatives as potential mGluR5 PET ligands. Bioorg Med Chem 2010, 18:6044-6054.
43. Betebenner D.A., Carney P.L., Zimmer A.M., Kazikiewicz J.M., Brucher E., Sherry A.D., et al. Hepatobiliary delivery of polyaminopolycarboxylate chelates-synthesis and characterization of a cholic-acid conjugate of EDTA and biodistribution and imaging studies with its In-111 chelate. Bioconjug Chem 1991, 2:117-123.
44. Majer F., Salomon J.J., Sharma R., Etzbach S.V., Najib M.N.M., Keaveny R., et al. New fluorescent bile acids: Synthesis, chemical characterization, and disastereoselective uptake by Caco-2 cells of 3-deoxy 3-NBD-amino deoxycholic and ursodeoxycholic acid. Bioorg Med Chem 2012, 20:1767-1778.
45. Bock V.D., Hiemstra H., van Maarseveen J.H. Cu-I-catalyzed alkyne-azide "click" cycloadditions from a mechanistic and synthetic perspective. Eur J Org Chem 2005, 51-68.
46. Meldal M., Tornoe C.W. Cu-catalyzed azide-alkyne cycloaddition. Chem Rev 2008, 108:2952-3015.