Synthesis, uptake mechanism characterization and biological evaluation of 18F labeled fluoroalkyl phenylalanine analogs as potential PET imaging agents

Nuclear Medicine and Biology

Volumn 38, Issue 1, 2011, Pages 53-62

  Wang, Limin ^a   Qu, Wenchao ^a   Lieberman, Brian P ^a   Plössl, Karl ^a   Kung, Hank F ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

18F; Imaging agent; LATs; PET; Phenylalanine derivatives

Indexed keywords

2 (2 FLUOROETHYL)TYROSINE; 4 (2 FLUOROETHYL)LPHENYLALANINE F 18; 4 (3 FLUOROPROPYL)LPHENYLALANINE F 18; RADIOPHARMACEUTICAL AGENT; TRACER; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BIOLOGICAL ACTIVITY; CONTROLLED STUDY; DEPROTECTION REACTION; DRUG ACCUMULATION; DRUG DISTRIBUTION; DRUG EXCRETION; DRUG PURITY; DRUG SELECTIVITY; DRUG SPECIFICITY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG UPTAKE; ENANTIOMER; FLUORINATION; GLIOMA CELL; IMAGE ANALYSIS; IN VITRO STUDY; IN VIVO STUDY; ISOTOPE LABELING; NONHUMAN; NUCLEOPHILICITY; POSITRON EMISSION TOMOGRAPHY; RAT; RAT STRAIN; SIGNAL NOISE RATIO; STRUCTURE ACTIVITY RELATION; TUMOR XENOGRAFT;

ANIMALS; BIOLOGICAL TRANSPORT; CELL LINE, TUMOR; FLUORINE RADIOISOTOPES; LIGANDS; PHENYLALANINE; POSITRON-EMISSION TOMOGRAPHY; RATS;

EID: 78650987788     PISSN: 09698051     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.nucmedbio.2010.07.005     Document Type: Article

References (38)

1. Plathow C., Weber W.A. Tumor cell metabolism imaging. J Nucl Med 2008, 49(Suppl 2):43S-63S.
2. van Waarde A., Elsinga P.H. Proliferation markers for the differential diagnosis of tumor and inflammation. Curr Pharm Des 2008, 14:3326-3339.
3. McConathy J., Goodman Mark M. Non-natural amino acids for tumor imaging using positron emission tomography and single photon emission computed tomography. Cancer Metastasis Rev 2008, 27:555-573.
4. Jager P.L., Vaalburg W., Pruim J., de Vries E.G., Langen K.J., Piers D.A. Radiolabeled amino acids: basic aspects and clinical applications in oncology. J Nucl Med 2001, 42:432-445.
5. Ganapathy V., Thangaraju M., Prasad P.D. Nutrient transporters in cancer: relevance to Warburg hypothesis and beyond. Pharmacol Ther 2009, 1:29-40.
6. Fujibayashi Y., Kawai K., Yonekura Y., Matsumoto K., Konishi J., Yokoyama A. Problems of [S-methyl-11C]-l-methionine as a protein synthesis marker in the pancreas. Ann Nucl Med 1990, 4:29-33.
7. Ishiwata K., Enomoto K., Sasaki T., Elsinga P.H., Senda M., Okazumi S., et al. A feasibility study on l-[1-carbon-11]tyrosine and l-[methyl-carbon-11]methionine to assess liver protein synthesis by PET. J Nucl Med 1996, 37:279-285.
8. Willemsen A.T., van Waarde A., Paans A.M., Pruim J., Luurtsema G., Go K.G., et al. In vivo protein synthesis rate determination in primary or recurrent brain tumors using l-[1-11C]-tyrosine and PET. J Nucl Med 1995, 36:411-419.
9. Heiss P., Mayer S., Herz M., Wester H.J., Schwaiger M., Senekowitsch-Schmidtke R. Investigation of transport mechanism and uptake kinetics of O-(2-[18F]fluoroethyl)-l-tyrosine in vitro and in vivo. J Nucl Med 1999, 40:1367-1373.
10. Inoue T., Tomiyoshi K., Higuichi T., Ahmed K., Sarwar M., Aoyagi K., et al. Biodistribution studies on l-3-[fluorine-18]fluoro-alpha-methyl tyrosine: a potential tumor-detecting agent. J Nucl Med 1998, 39:663-667.
11. Yu W., Williams L., Camp V.M., Olson J.J., Goodman M.M. Synthesis and biological evaluation of anti-1-amino-2-[18F]fluoro-cyclobutyl-1-carboxylic acid (anti-2-[18F]FACBC) in rat 9L gliosarcoma. Bioorg Med Chem Lett 2010, 20:2140-2143.
12. Prante O., Deichen J.T., Hocke C., Kuwert T. Characterization of uptake of 3-[(131)I]iodo-alpha-methyl-l-tyrosine in human monocyte-macrophages. Nucl Med Biol 2004, 31:365-372.
13. Couturier O., Luxen A., Chatal J.F., Vuillez J.P., Rigo P., Hustinx R. Fluorinated tracers for imaging cancer with positron emission tomography. Eur J Nucl Med Mol Imaging 2004, 31:1182-1206.
14. Fowler J.S., Ding Y.S., Volkow N.D. Radiotracers for positron emission tomography imaging. Semin Nucl Med 2003, 33:14-27.
15. Laverman P., Boerman O.C., Corstens F.H., Oyen W.J. Fluorinated amino acids for tumour imaging with positron emission tomography. Eur J Nucl Med Mol Imaging 2002, 29:681-690.
16. Hyde R., Taylor P.M., Hundal H.S. Amino acid transporters: roles in amino acid sensing and signalling in animal cells. Biochem J 2003, 373:1-18.
17. Palacin M., Estevez R., Bertran J., Zorzano A. Molecular biology of mammalian plasma membrane amino acid transporters. Physiol Rev 1998, 78:969-1054.
18. Christensen H.N. Role of amino acid transport and countertransport in nutrition and metabolism. Physiol Rev 1990, 70:43-77.
19. Yanagida O., Kanai Y., Chairoungdua A., Kim D.K., Segawa H., Nii T., et al. Human l-type amino acid transporter 1 (LAT1): characterization of function and expression in tumor cell lines. Biochim Biophys Acta 2001, 1514:291-302.
20. Fuchs B.C., Bode B.P. Amino acid transporters ASCT2 and LAT1 in cancer: partners in crime? Semin Cancer Biol 2005, 15:254-266.
21. Saier M.H., Daniels G.A., Boerner P., Lin J. Neutral amino acid transport systems in animal cells: potential targets of oncogene action and regulators of cellular growth. J Membr Biol 1988, 104:1-20.
22. Bodoy S., Martin L., Zorzano A., Palacin M., Estevez R., Bertran J. Identification of LAT4, a novel amino acid transporter with system L activity. J Biol Chem 2005, 280:12002-12011.
23. Kaira K., Oriuchi N., Imai H., Shimizu K., Yanagitani N., Sunaga N., et al. l-type amino acid transporter 1 and CD98 expression in primary and metastatic sites of human neoplasms. Cancer Sci 2008, 99:2380-2386.
24. Nawashiro H., Otani N., Shinomiya N., Fukui S., Ooigawa H., Shima K., et al. l-type amino acid transporter 1 as a potential molecular target in human astrocytic tumors. Int J Cancer 2006, 119:484-492.
25. Kaira K., Oriuchi N., Imai H., Shimizu K., Yanagitani N., Sunaga N., et al. Prognostic significance of l-type amino acid transporter 1 expression in resectable stage I-III nonsmall cell lung cancer. Br J Cancer 2008, 98:742-748.
26. Sakata T., Ferdous G., Tsuruta T., Satoh T., Baba S., Muto T., et al. l-type amino-acid transporter 1 as a novel biomarker for high-grade malignancy in prostate cancer. Pathol Int 2009, 59:7-18.
27. Langen K.J., Hamacher K., Weckesser M., Floeth F., Stoffels G., Bauer D., et al. O-(2-[18F]fluoroethyl)-l-tyrosine: uptake mechanisms and clinical applications. Nucl Med Biol 2006, 33:287-294.
28. Pauleit D., Stoffels G., Schaden W., Hamacher K., Bauer D., Tellmann L., et al. PET with O-(2-18F-Fluoroethyl)-l-tyrosine in peripheral tumors: first clinical results. J Nucl Med 2005, 46:411-416.
29. Lau E.W., Drummond K.J., Ware R.E., Drummond E., Hogg A., Ryan G., et al. Comparative PET study using F-18 FET and F-18 FDG for the evaluation of patients with suspected brain tumour. J Clin Neurosci 2010, 17:43-49.
30. Hellwig D., Ketter R., Romeike B.F., Sell N., Schaefer A., Moringlane J.R., et al. Validation of brain tumour imaging with p-[123I]iodo-l-phenylalanine and SPECT. Eur J Nucl Med Mol Imaging 2005, 32:1041-1049.
31. Shreve P.D., Anzai Y., Wahl R.L. Pitfalls in oncologic diagnosis with FDG PET imaging: physiologic and benign variants. Radiographics 1999, 19:61-77. quiz 150-1.
32. Ahlstrom H., Malmstrom P.U., Letocha H., Andersson J., Langstrom B., Nilsson S. Positron emission tomography in the diagnosis and staging of urinary bladder cancer. Acta Radiol 1996, 37:180-185.
33. Tsukada H., Sato K., Fukumoto D., Kakiuchi T. Evaluation of d-isomers of O-F-18-fluoromethyl, O-F-18-fluoroethyl and O-F-18-fluoropropyl tyrosine as tumour imaging agents in mice. Eur J Nucl Med Mol Imaging 2006, 33:1017-1024.
34. Tomi M., Mori M., Tachikawa M., Katayama K., Terasaki T., Hosoya K. l-Type amino acid transporter 1-mediated l-leucine transport at the inner blood-retinal barrier. Invest Ophthalmol Vis Sci 2005, 46:2522-2530.
35. Rossier G., Meier C., Bauch C., Summa V., Sordat B., Verrey F., et al. LAT2, a new basolateral 4F2hc/CD98-associated amino acid transporter of kidney and intestine. J Biol Chem 1999, 274:34948-34954.
36. Kersemans V., Cornelissen B., Kersemans K., Bauwens M., Dierckx R.A., De Spiegeleer B., et al. 123/125I-labelled 2-iodo-L-phenylalanine and 2-iodo-D-phenylalanine: comparative uptake in various tumour types and biodistribution in mice. Eur J Nucl Med Mol Imaging 2006, 33:919-927.
37. Urakami T., Sakai K., Asai T., Fukumoto D., Tsukada H., Oku N. Evaluation of O-[(18)F]fluoromethyl-d-tyrosine as a radiotracer for tumor imaging with positron emission tomography. Nucl Med Biol 2009, 36:295-303.
38. Lee T.S., Ahn S.H., Moon B.S., Chun K.S., Kang J.H., Cheon G.J., et al. Comparison of 18F-FDG, 18F-FET and 18F-FLT for differentiation between tumor and inflammation in rats. Nucl Med Biol 2009, 36:681-686.