Synthesis and validation of fatty acid analogs radiolabeled by nonisotopic substitution

Journal of Nuclear Cardiology

Volumn 14, Issue 3 SUPPL., 2007, Pages

  Eckelman, William C ^a   Babich, John W ^b  

^a Molecular Tracer LLC   (United States)

^b A Subsidiary of Lantheus Holdings   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

16 FLUOROPALMITIC ACID F 18; 3 METHYL 17 FLUOROHEPTADECANOIC ACID F 18; 3,3 DIMETHYL IODOPHENYL PENTADECANOIC ACID; 4 IODOPHENYLPALMITIC ACID; 5 METHYL 17 FLUOROHEPTADECANOIC ACID F 18; BETA METHYL 4 IODOPHENYLPALMITIC ACID; CARBON 11; DECANOIC ACID DERIVATIVE; FATTY ACID; FATTY ACID DERIVATIVE; FLUORODEOXYGLUCOSE F 18; GLUCOSE DERIVATIVE; IODINE 123; PALMITIC ACID; PALMITIC ACID DERIVATIVE; RADIOPHARMACEUTICAL AGENT; TECHNETIUM 99M; UNCLASSIFIED DRUG;

ARTICLE; CARDIAC PATIENT; CELL ENERGY; DIAGNOSTIC IMAGING; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; FATTY ACID METABOLISM; FATTY ACID OXIDATION; FATTY ACID TRANSPORT; HEART FAILURE; HEART MUSCLE; HEART MUSCLE ISCHEMIA; HUMAN; IMAGE QUALITY; ISOTOPE LABELING; MEMBRANE TRANSPORT; NONHUMAN; PRIORITY JOURNAL; SINGLE PHOTON EMISSION COMPUTER TOMOGRAPHY; VALIDATION PROCESS;

CARDIOMYOPATHIES; DRUG DESIGN; FATTY ACIDS; HEART; HUMANS; ISOTOPE LABELING; MYOCARDIUM; RADIOPHARMACEUTICALS; TOMOGRAPHY, EMISSION-COMPUTED, SINGLE-PHOTON;

EID: 34249737891     PISSN: 10713581     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.nuclcard.2007.02.014     Document Type: Article

References (52)

1. Tamaki N., Morita K., Kuge Y., and Tsukamoto E. The role of fatty acids in cardiac imaging. J Nucl Med 41 (2000) 1525-1534
2. Sack M.N., and Kelly D.P. The energy substrate switch during development of heart failure: gene regulatory mechanisms (review). Int J Mol Med 1 (1998) 17-24
3. Febbraio M., Guy E., Coburn C., et al. The impact of over-expression and deficiency of fatty acid translocase (FAT)/CD36. Mol Cell Biochem 239 (2002) 193-197
4. Knapp Jr. F.F., and Kropp J. BMIPP-design and development. Int J Card Imaging 15 (1999) 1-9
5. Knapp Jr. F.F., Kropp J., Franken P.R., et al. Pharmacokinetics of radioiodinated fatty acid myocardial imaging agents in animal models and human studies. Q J Nucl Med 40 (1996) 252-269
6. Herrero P., and Gropler R.J. Imaging of myocardial metabolism. J Nucl Cardiol 12 (2005) 345-358
7. Krohn K.A., Mankoff D.A., Muzi M., Link J.M., and Spence A.M. True tracers: comparing FDG with glucose and FLT with thymidine. Nucl Med Biol 32 (2005) 663-671
8. Gropler R.J. Is BMIPP a sensitive marker for myocardial ischaemic stress?. Against. Eur J Nucl Med Mol Imaging 31 (2004) 1033-1037
9. Takahashi T., Nishimura S., Ido T., Ishiwata K., and Iwata R. Biological evaluation of 5-methyl-branched-chain omega-[18F]fluorofatty acid: a potential myocardial imaging tracer for positron emission tomography. Nucl Med Biol 23 (1996) 303-308
10. Curry S., Mandelkow H., Brick P., and Franks N. Crystal structure of human serum albumin complexed with fatty acid reveals an asymmetric distribution of binding sites. Nat Struct Biol 5 (1998) 827-835
11. Petitpas I., Grune T., Bhattacharya A.A., and Curry S. Crystal structures of human serum albumin complexed with monounsaturated and polyunsaturated fatty acids. J Mol Biol 314 (2001) 955-960
12. Knapp Jr. F.F., Goodman M.M., Kirsch G., et al. Both total chain length and position of dimethyl-branching effect the myocardial uptake and retention of radioiodinated analogues of 15-(p-iodophenyl)-3,3-dimethylpentadecanoic acid (DMIPP). Ann Nucl Med 10 (1996) 19-32
13. Brinkmann J.F.F., Abumrad N.A., Ibrahimi A., van der Vusse G.R., and Glatz J.F.C. New insights into long-chain fatty acid uptake by heart muscle: a crucial role for fatty acid translocase/CD36. Biochem J 367 (2002) 561-570
14. Coburn C.T., Knapp Jr. F.F., Febbraio M., et al. Defective uptake and utilization of long chain fatty acids in muscle and adipose tissues of CD36 knockout mice. J Biol Chem 275 (2000) 32523-32529
15. Abumrad N.A., Coburn C.T., and Ibrahimi A. Membrane proteins implicated in long-chain fatty acid uptake by mammalian cells: CD36, FATP and FABPm. Biochim Biophys Acta 1441 (1999) 4-13
16. Watanabe K., Miyajima S., Kusano Y., Tanabe N., and Hirokawa Y. Hypertrophic cardiomyopathy showing no 123I-BMIPP myocardial accumulation with type I CD36 deficiency. [in Japanese]. Kaku Igaku 34 (1997) 481-486
17. Koonen D.P., Glatz J.F., Bonen A., and Luiken J.J. Long-chain fatty acid uptake and FAT/CD36 translocation in heart and skeletal muscle. Biochim Biophys Acta 1736 (2005) 163-180
18. Evans J.R., Gunton R.W., Baker R.G., et al. Use of radioiodinated fatty acids for photoscans of the heart. Circ Res 16 (1965) 1-10
19. Livni E., Elmaleh D.Z.R., Levy S., Brownell G., and Strauss H.W. Beta methyl [1-11C] heptadecanoic acid: a new myocardial metabolic tracer for positron emission tomography. J Nucl Med 23 (1982) 169-175
20. Knapp Jr. F.F., Ambrose K.R., Callahan A.P., Ferren L.A., Grigsby R.A., and Irgolic K.J. Effects of chain length and tellurium position on the myocardial uptake of Te-123m fatty acids. J Nucl Med 22 (1981) 988-993
21. DeGrado T.R., Coenen H.H., and Stocklin G. 14(R,S)-[18F]fluoro-6-thia-heptadecanoic acid (FTHA): evaluation in mouse of a new probe of myocardial utilization of long chain fatty acids. J Nucl Med 32 (1991) 1888-1896
22. Eisenhut M., Lehmann W.D., Hull W.E., et al. Trapping and metabolism of radioiodinated PHIPA 3-10 in the rat myocardium. J Nucl Med 38 (1997) 1864-1869
23. Goldstein R.A., Klein M.S., Welch M.J., and Sobel B.E. External assessment of myocardial metabolism with C-11 palmitate in vivo. J Nucl Med 21 (1980) 342-348
24. 11C]polyhomoallylic acids. J Labelled Comp Radiopharm 33 (1993) 541-546
25. Buckman B.O., VanBrocklin H.F., Dence C.S., et al. Synthesis and tissue biodistribution of [omega-11C]palmitic acid. A novel PET imaging agent for cardiac fatty acid metabolism. J Med Chem 37 (1994) 2481-2485
26. Collier T.L., Hwang Y., Ramasamy R., et al. Synthesis and initial evaluation of 17-(11)C-heptadecanoic acid for measurement of myocardial fatty acid metabolism. J Nucl Med 43 (2002) 1707-1714
27. Schmall B., Finn R.D., Rapoport S.I., et al. Synthesis of a fluorinated fatty acid, dl-erythro-9,10-[18F]difluoropalmitic acid, and biodistribution studies in rats. Int J Rad Appl Instrum B 17 (1990) 805-809
28. Takahashi T., Mizuno T., Ido T., Iwata R., and Watanabe K. Improved synthesis of pure [18F]fluoro-compounds for PET studies from bromo-compounds. Appl Radiat Isot 58 (2003) 557-566
29. Ebert A., Herzog H., Stocklin G.L., et al. Kinetics of 14(R,S)-fluorine-18-fluoro-6-thia-heptadecanoic acid in normal human hearts at rest, during exercise, and after dipyridamole injection. J Nucl Med 35 (1994) 51-56
30. DeGrado T.R., Wang S., Holden J.E., et al. Synthesis and preliminary evaluation of 18F-labeled 4-thia palmitate as a PET tracer of myocardial fatty acid oxidation. Nucl Med Biol 27 (2000) 221-231
31. Shoup T.M., Elmaleh D.R., Bonab A.A., and Fischman A.J. Evaluation of trans-9-18F-fluoro-3,4-methyleneheptadecanoic acid as a PET tracer for myocardial fatty acid imaging. J Nucl Med 46 (2005) 297-304
32. Machulla H.J., Marsmann M., and Dutschka K. Biochemical concept and synthesis of a radioiodinated phenylfatty acid for in vivo metabolic studies of the myocardium. Eur J Nucl Med 5 (1980) 171-173
33. Corbett J.R. Fatty acids for myocardial imaging. Semin Nucl Med 29 (1999) 237-258
34. Goodman M.M., Kirsch G., and Knapp Jr. F.F. Synthesis and evaluation of radioiodinated terminal p-iodophenyl-substituted alpha- and beta-methyl-branched fatty acids. J Med Chem 27 (1984) 390-397
35. Knapp Jr. F.F., Goodman M.M., Callahan A.P., and Kirsch G. Radioiodinated 15-(p-iodophenyl)-3,3-dimethylpentadecanoic acid: a useful new agent to evaluate myocardial fatty acid uptake. J Nucl Med 27 (1986) 521-531
36. Knapp Jr. F.F., and Kropp J. Iodine-123-labeled fatty acids for myocardial single photon emission tomography: current status and future perspectives. Eur J Nucl Med 22 (1995) 361-381
37. Ambrose K.R., Owen B.A., Goodman M.M., and Knapp Jr. F.F. Evaluation of the metabolism in rat hearts of two new radioiodinated 3-methyl-branched fatty acid myocardial imaging agents. Eur J Nucl Med 12 (1987) 486-491
38. Dilsizian V., Bateman T.M., Bergmann S.R., et al. Metabolic imaging with beta-methyl-p-[(123)I]-iodophenyl-pentadecanoic acid identifies ischemic memory after demand ischemia. Circulation 112 (2005) 2169-2174
39. Eckelman W.C., and Coursey B.M. Technetium-99m generators. Chemistry and preparation of radiopharmaceuticals (special issue). Int J Appl Radiat Isot 33 (1982) 793-951
40. 3]+ from [99mTcO4] in aqueous solution and its reaction with a bifunctional ligand. J Am Chem Soc 120 (1998) 7987-7988
41. Karesh S.M., Eckelman W.C., and Reba R.C. Biological distribution of chemical analogues of fatty acids and long chain hydrocarbons containing a strong chelating agent. J Pharm Sci 66 (1977) 225-228
42. Astheimer L., Linse K.H., Ramamoorthy N., and Schwochau K. Synthesis, characterization and evaluation of 99Tc/99mTc DIARS and DMPE complexes containing pentadecanoic acid. Int J Rad Appl Instrum B 14 (1987) 545-553
43. Mach R.H., Kung H.F., Jungwiwattanaporn P., and Guo Y.Z. Synthesis and biodistribution of a new class of 99mTc-labeled fatty acid analogues for myocardial imaging. Int J Rad Appl Instrum B 18 (1991) 215-226
44. Jones Jr. G.S., Elmaleh D.R., Strauss H.W., and Fischman A.J. Synthesis and biodistribution of a new 99mtechnetium fatty acid. Nucl Med Biol 21 (1994) 117-123
45. Jones Jr. G.S., Elmaleh D.R., Strauss H.W., and Fischman A.J. 7,10-Bis(2-mercapto-2-methyl)propyl-7,10-diazapalmitic acid: a novel, N2S2 ligand for technetium-99m. Bioorg Med Chem Lett 6 (1996) 2399-2404
46. Banerjee S.R., Maresca K.P., Francesconi L., Valliant J., Babich J.W., and Zubieta J. New directions in the coordination chemistry of 99mTc: a reflection on technetium core structures and a strategy for new chelate design. Nucl Med Biol 32 (2005) 1-20
47. Maresca K.P., Shoup T.M., Femia F.J., et al. Synthesis, characterization, and biodistribution of a Technetium-99m '3+1' fatty acid derivative. The crystal and molecular structures of a series of oxorhenium model complexes. Inorganica Chim Acta 338 (2002) 149-156
48. Jung C.M., Kraus W., Leibnitz P., Pietzsch H.-J., Kropp J., and Spies H. Syntheses and first crystal structures of rhenium complexes derived from omega-functionalized fatty acids as model compounds of technetium tracers for myocardial metabolism imaging. Eur J Inorg Chem 5 (2002) 1219-1225
49. Yamamura N., Magata Y., Arano Y., et al. Technetium-99m-labeled medium-chain fatty acid analogues metabolized by beta-oxidation: radiopharmaceutical for assessing liver function. Bioconjug Chem 10 (1999) 489-495
50. Magata T., Kawaguchi M., Ukon N., et al. A Tc-99m-labeled long chain fatty acid derivative for myocardial imaging. Bioconjug Chem 15 (2004) 389-393
51. Chu T., Zhang Y., Liu X., Wang Y., Hu S., and Wang X. Synthesis and biodistribution of 99mTc-carbonyl technetium labeled fatty acids. Appl Radiat Isot 60 (2004) 845-850
52. Kataoka K., Nohara R., Hosokawa R., et al. Myocardial lipid metabolism in compensated and advanced stages of heart failure: evaluation by canine pacing model with BMIPP. J Nucl Med 42 (2001) 124-129