Fluorine-18 labeled amino acids for oncologic imaging with positron emission tomography

Current Topics in Medicinal Chemistry

Volumn 13, Issue 8, 2013, Pages 871-891

  Huang, Chaofeng ^a   McConathy, Jonathan ^a  

^a WASHINGTON UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Amino acid transport; Amino acids; Fluorine 18; PET; Radiosynthesis; Tumor imaging

Indexed keywords

2 FLUOROMETHYL L PHENYLALANINE F 18; 3 FLUORO 1 AMINO CYCLOBUTANE 1 CARBOXYLIC ACID F 18; 4 (2 3 FLUOROPROPYL) L PHENYLALANINE F 18; 4 FLUORO L PROLINE F 18; 4 FLUOROBENZYLAZIDE F 18; 4 FLUOROGLUTAMIC ACID F 18; 4 FLUOROMETHYL L PHENYLALANINE F 18; 5 (2 FLUOROETHOXY) L TRYPTOPHAN F 18; 6 FLUORO 3,4 DIHYDROXY L PHENYLALANINE F 18; AMINO ACID F 18; ANTI 1 AMINO 2 FLUOROCYCLOBUTYL 1 CARBOXYLIC ACID F 18; ANTI 1 AMINO 2 FLUOROCYCLOPENTYL 1 CARBOXYLIC ACID F 18; GLUTAMATE TRANSPORTER; HISTIDINE F 18; O (2 FLUOROETHYL) L TYROSINE F 18; O FLUOROMETHYL L TYROSINE F 18; PROSTATE SPECIFIC ANTIGEN; RADIOPHARMACEUTICAL AGENT; UNCLASSIFIED DRUG;

AMINO ACID TRANSPORT; BILE DUCT CARCINOMA; BIOLOGICAL ACTIVITY; BRAIN TUMOR; BREAST CANCER; COMPUTER ASSISTED TOMOGRAPHY; ELECTROPHILICITY; GLIOMA; HUMAN; LIVER CELL CARCINOMA; LUNG CANCER; NEUROENDOCRINE TUMOR; NEUROIMAGING; NONHUMAN; NUCLEAR MAGNETIC RESONANCE IMAGING; NUCLEOPHILICITY; ONCOLOGY; POSITRON EMISSION TOMOGRAPHY; PROSTATE CANCER; PROTEIN SYNTHESIS; REVIEW; SENSITIVITY AND SPECIFICITY; SINGLE PHOTON EMISSION COMPUTER TOMOGRAPHY; STOMACH CANCER;

AMINO ACIDS; DIAGNOSTIC IMAGING; FLUORINE RADIOISOTOPES; HUMANS; NEOPLASMS; POSITRON-EMISSION TOMOGRAPHY;

EID: 84878779098     PISSN: 15680266     EISSN: 18734294     Source Type: Journal    
DOI: 10.2174/1568026611313080002     Document Type: Review

References (154)

1. Pauleit, D.; Stoffels, G.; Bachofner, A.; Floeth, F. W.; Sabel, M.; Herzog, H.; Tellmann, L.; Jansen, P.; Reifenberger, G.; Hamacher, K.; Coenen, H. H.; Langen, K. J. Comparison of (18)F-FET and (18)F-FDG PET in brain tumors. Nucl Med Biol, 2009, 36(7) 779-787.
2. Chen, W. Clinical applications of PET in brain tumors. J Nucl Med, 2007, 48(9) 1468-1481.
3. 18FFDG PET and evaluation of diagnostic accuracy. J Nucl Med, 2006, 47(6) 904-911.
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(3) 432-445.
5. 111In-capromab pendetide SPECT/CT. Radiology, 2011, 259(3) 852-861.
6. 18Ffluorocyclobutane-1-car boxylic acid with PET/CT in prostate carcinoma. J Nucl Med, 2007, 48(1) 56-63.
7. Montravers, F.; Grahek, D.; Kerrou, K.; Ruszniewski, P.; de Beco, V.; Aide, N.; Gutman, F.; Grange, J. D.; Lotz, J. P.; Talbot, J. N. Can fluorodihydroxyphenylalanine PET replace somatostatin receptor scintigraphy in patients with digestive endocrine tumors? J Nucl Med, 2006, 47(9) 1455-1462.
8. 18F-FDOPA PET. J Nucl Med, 2004, 45(7) 1161-1167.
9. 18F-fluorodihydroxy phenylalanine PET in neuroendocrine tumors: basic aspects and emerging clinical applications. J Nucl Med, 2008, 49(4) 573-586.
10. Murphy, C. D.; Schaffrath, C.; O'Hagan, D. Fluorinated natural products: the biosynthesis of fluoroacetate and 4-fluorothreonine in Streptomyces cattleya. Chemosphere, 2003, 52(2) 455-461.
11. Langen, K. J.; Broer, S. Molecular transport mechanisms of radiolabeled amino acids for PET and SPECT. J Nucl Med, 2004, 45(9) 1435-1436.
12. 18F]fluorotyrosine in tumor bearing mice. Nucl Med Biol, 1993, 20(8) 895-899.
13. Hediger, M. A.; Romero, M. F.; Peng, J. B.; Rolfs, A.; Takanaga, H.; Bruford, E. A. The ABCs of solute carriers: physiological, pathological and therapeutic implications of human membrane transport proteinsIntroduction. Pflugers Arch, 2004, 447(5) 465-468.
14. Popperl, G.; Kreth, F. W.; Mehrkens, J. H.; Herms, J.; Seelos, K.; Koch, W.; Gildehaus, F. J.; Kretzschmar, H. A.; Tonn, J. C.; Tatsch, K. FET PET for the evaluation of untreated gliomas: correlation of FET uptake and uptake kinetics with tumour grading. Eur J Nucl Med Mol Imaging, 2007, 34(12) 1933-1942.
15. 18F-fluoroethyl)-L-tyro sine PET and MRI in low-grade glioma. J Nucl Med, 2007, 48(4) 519-527.
16. 18F]fluoroethyl)-Ltyrosine: uptake mechanisms and clinical applications. Nucl Med Biol, 2006, 33(3) 287-294.
17. 18F]fluorethyl)-L-tyrosine PET in the clinical evaluation of primary brain tumours. Eur J Nucl Med Mol Imaging, 2005, 32(4) 422-429.
18. Tripathi, M.; Sharma, R.; D'Souza, M.; Jaimini, A.; Panwar, P.; Varshney, R.; Datta, A.; Kumar, N.; Garg, G.; Singh, D.; Grover, R. K.; Mishra, A. K.; Mondal, A. Comparative evaluation of F-18 FDOPA, F-18 FDG, and F-18 FLT-PET/CT for metabolic imaging of low grade gliomas. Clin Nucl Med, 2009, 34(12) 878-883.
19. 18F] fluoro-L-phenylalanine positron emission tomography in patients with central motor disorders and in evaluation of brain and other tumors. Semin Nucl Med, 2007, 37(6) 440-450.
20. Verrey, F.; Closs, E. I.; Wagner, C. A.; Palacin, M.; Endou, H.; Kanai, Y. CATs and HATs: the SLC7 family of amino acid transporters. Pflugers Arch, 2004, 447(5) 532-542.
21. Yu, W.; McConathy, J.; Williams, L.; Camp, V. M.; Malveaux, E. J.; Zhang, Z.; Olson, J. J.; Goodman, M. M. Synthesis, radiolabeling, and biological evaluation of (R) and (S)-2-amino-3-[(18)F]fluoro-2-methylpropanoic acid (FAMP) and (R) and (S)-3-[(18)F]fluoro-2-methyl-2-N-(methylamino)propanoic acid (NMeFAMP) as potential PET radioligands for imaging brain tumors. J Med Chem, 2010, 53(2) 876-886.
22. 18F]fluoro-2-methyl-2-(methylamino) propanoic acid. J Med Chem, 2002, 45(11) 2240-2249.
23. Mackenzie, B.; Erickson, J. D. Sodium-coupled neutral amino acid (System N/A) transporters of the SLC38 gene family. Pflugers Arch, 2004, 447(5) 784-795.
24. Gaccioli, F.; Huang, C. C.; Wang, C.; Bevilacqua, E.; Franchi-Gazzola, R.; Gazzola, G. C.; Bussolati, O.; Snider, M. D.; Hatzoglou, M. Amino acid starvation induces the SNAT2 neutral amino acid transporter by a mechanism that involves eukaryotic initiation factor 2alpha phosphorylation and cap-independent translation. J Biol Chem, 2006, 281(26) 17929-17940.
25. Franchi-Gazzola, R.; Dall'Asta, V.; Sala, R.; Visigalli, R.; Bevilacqua, E.; Gaccioli, F.; Gazzola, G. C.; Bussolati, O. The role of the neutral amino acid transporter SNAT2 in cell volume regulation. Acta Physiol (Oxf), 2006, 187(1-2) 273-283.
26. 18F-(2S,4R)4fluoroglutamine. J Nucl Med, 2011, 52(12) 1947-1955.
27. 18F]fluoroglutamic acid (BAY 85-8050), a new amino acid radiotracer for PET imaging of tumors: synthesis and in vitro characterization. J Med Chem, 2011, 54(1) 406-410.
28. 18F]fluoroethyl) 1H-[1,2,3]Triazol-4-yl]Propanoic Acid for Brain Tumor Imaging with Positron Emission Tomography. Mol Imaging, 2010, 9(6) 329-342.
29. Kanai, Y.; Hediger, M. A. The glutamate/neutral amino acid transporter family SLC1: molecular, physiological and pharmacological aspects. Pflugers Arch, 2004, 447(5) 469-479.
30. Lewerenz, J.; Hewett, S.; Huang, Y.; Lambros, M.; Gout, P. W.; Kalivas, P.; Massie, A.; Smolders, I.; Methner, A.; Pergande, M.; Smith, S. B.; Ganapathy, V.; Maher, P. The Cystine/Glutamate Antiporter System xcin Health and Disease: From Molecular Mechanisms to Novel Therapeutic Opportunities. Antioxidants & redox signaling, 2012,
31. Kanai, Y.; Hediger, M. A. The glutamate and neutral amino acid transporter family: physiological and pharmacological implications. Eur J Pharmacol, 2003, 479(1-3) 237-247.
32. Chen, N. H.; Reith, M. E.; Quick, M. W. Synaptic uptake and beyond: the sodiumand chloride-dependent neurotransmitter transporter family SLC6. Pflugers Arch, 2004, 447(5) 519-531.
33. Ichinoe, M.; Mikami, T.; Yoshida, T.; Igawa, I.; Tsuruta, T.; Nakada, N.; Anzai, N.; Suzuki, Y.; Endou, H.; Okayasu, I. High expression of L-type amino-acid transporter 1 (LAT1) in gastric carcinomas: comparison with non-cancerous lesions. Pathol Int, 2011, 61(5) 281-289.
34. Sakata, T.; Ferdous, G.; Tsuruta, T.; Satoh, T.; Baba, S.; Muto, T.; Ueno, A.; Kanai, Y.; Endou, H.; Okayasu, I. L-type amino-acid transporter 1 as a novel biomarker for high-grade malignancy in prostate cancer. Pathol Int, 2009, 59(1) 7-18.
35. Kaira, K.; Oriuchi, N.; Imai, H.; Shimizu, K.; Yanagitani, N.; Sunaga, N.; Hisada, T.; Ishizuka, T.; Kanai, Y.; Nakajima, T.; Mori, M. Prognostic significance of L-type amino acid transporter 1 (LAT1) and 4F2 heavy chain (CD98) expression in stage I pulmonary adenocarcinoma. Lung Cancer, 2009, 66(1) 120-126.
36. Kaira, K.; Oriuchi, N.; Imai, H.; Shimizu, K.; Yanagitani, N.; Sunaga, N.; Hisada, T.; Ishizuka, T.; Kanai, Y.; Endou, H.; Nakajima, T.; Mori, M. Prognostic significance of L-type amino acid transporter 1 (LAT1) and 4F2 heavy chain (CD98) expression in early stage squamous cell carcinoma of the lung. Cancer science, 2009, 100(2) 248-254.
37. Kaira, K.; Oriuchi, N.; Imai, H.; Shimizu, K.; Yanagitani, N.; Sunaga, N.; Hisada, T.; Tanaka, S.; Ishizuka, T.; Kanai, Y.; Endou, H.; Nakajima, T.; Mori, M. Prognostic significance of L-type amino acid transporter 1 expression in resectable stage I-III nonsmall cell lung cancer. Br J Cancer, 2008, 98(4) 742-748.
38. Nawashiro, H.; Otani, N.; Shinomiya, N.; Fukui, S.; Ooigawa, H.; Shima, K.; Matsuo, H.; Kanai, Y.; Endou, H. L-type amino acid transporter 1 as a potential molecular target in human astrocytic tumors. Int J Cancer, 2006, 119(3) 484-492.
39. Ross, D. T.; Kim, C. Y.; Tang, G.; Bohn, O. L.; Beck, R. A.; Ring, B. Z.; Seitz, R. S.; Paik, S.; Costantino, J. P.; Wolmark, N. Chemosensitivity and stratification by a five monoclonal antibody immunohistochemistry test in the NSABP B14 and B20 trials. Clin Cancer Res, 2008, 14(20) 6602-6609.
40. Fan, X.; Ross, D. D.; Arakawa, H.; Ganapathy, V.; Tamai, I.; Nakanishi, T. Impact of system L amino acid transporter 1 (LAT1) on proliferation of human ovarian cancer cells: a possible target for combination therapy with anti-proliferative aminopeptidase inhibitors. Biochem Pharmacol, 2010, 80(6) 811-818.
41. Shennan, D. B.; Thomson, J. Inhibition of system L (LAT1/ CD98hc) reduces the growth of cultured human breast cancer cells. Oncol Rep, 2008, 20(4) 885-889.
42. Ohkawa, M.; Ohno, Y.; Masuko, K.; Takeuchi, A.; Suda, K.; Kubo, A.; Kawahara, R.; Okazaki, S.; Tanaka, T.; Saya, H.; Seki, M.; Enomoto, T.; Yagi, H.; Hashimoto, Y.; Masuko, T. Oncogenicity of L-type amino-acid transporter 1 (LAT1) revealed by targeted gene disruption in chicken DT40 cells: LAT1 is a promising molecular target for human cancer therapy. Biochem Biophys Res Commun, 2011, 406(4) 649-655.
43. Ohno, Y.; Suda, K.; Masuko, K.; Yagi, H.; Hashimoto, Y.; Masuko, T. Production and characterization of highly tumor-specific rat monoclonal antibodies recognizing the extracellular domain of human L-type amino-acid transporter 1. Cancer science, 2008, 99(5) 1000-1007.
44. Fuchs, B. C.; Bode, B. P. Amino acid transporters ASCT2 and LAT1 in cancer: partners in crime? Semin Cancer Biol, 2005, 15(4) 254-266.
45. Fuchs, B. C.; Finger, R. E.; Onan, M. C.; Bode, B. P. ASCT2 silencing regulates mammalian target-of-rapamycin growth and survival signaling in human hepatoma cells. Am J Physiol Cell Physiol, 2007, 293(1) C55-63.
46. Nicklin, P.; Bergman, P.; Zhang, B.; Triantafellow, E.; Wang, H.; Nyfeler, B.; Yang, H.; Hild, M.; Kung, C.; Wilson, C.; Myer, V. E.; MacKeigan, J. P.; Porter, J. A.; Wang, Y. K.; Cantley, L. C.; Finan, P. M.; Murphy, L. O. Bidirectional transport of amino acids regulates mTOR and autophagy. Cell, 2009, 136(3) 521-534.
47. Kondoh, N.; Imazeki, N.; Arai, M.; Hada, A.; Hatsuse, K.; Matsuo, H.; Matsubara, O.; Ohkura, S.; Yamamoto, M. Activation of a system A amino acid transporter, ATA1/SLC38A1, in human hepatocellular carcinoma and preneoplastic liver tissues. Int J Oncol, 2007, 31(1) 81-87.
48. Sidoryk, M.; Matyja, E.; Dybel, A.; Zielinska, M.; Bogucki, J.; Jaskolski, D. J.; Liberski, P. P.; Kowalczyk, P.; Albrecht, J. Increased expression of a glutamine transporter SNAT3 is a marker of malignant gliomas. Neuroreport, 2004, 15(4) 575-578.
49. Yu, W. L.; Cong, W. M.; Zhang, Y.; Chen, Y.; Wang, F.; Yu, G. Overexpression of ATA1/SLC38A1 Predicts Future Recurrence and Death in Chinese Patients with Hilar Cholangiocarcinoma. J Surg Res, 2010,
50. Tozlu, S.; Girault, I.; Vacher, S.; Vendrell, J.; Andrieu, C.; Spyratos, F.; Cohen, P.; Lidereau, R.; Bieche, I. Identification of novel genes that co-cluster with estrogen receptor alpha in breast tumor biopsy specimens, using a large-scale real-time reverse transcription-PCR approach. Endocr Relat Cancer, 2006, 13(4) 1109-1120.
51. 0,+ (SLC6A14) in colorectal cancer and metastasis in humans. Biochim Biophys Acta, 2005, 1741(1-2) 215-223.
52. Gupta, N.; Prasad, P. D.; Ghamande, S.; Moore-Martin, P.; Herdman, A. V.; Martindale, R. G.; Podolsky, R.; Mager, S.; Ganapathy, M. E.; Ganapathy, V. Up-regulation of the amino acid transporter ATB(0,+) (SLC6A14) in carcinoma of the cervix. Gynecol Oncol, 2006, 100(1) 8-13.
53. Savaskan, N. E.; Eyupoglu, I. Y. xCT modulation in gliomas: relevance to energy metabolism and tumor microenvironment normalization. Annals of anatomy = Anatomischer Anzeiger: official organ of the Anatomische Gesellschaft, 2010, 192(5) 309-313.
54. Guo, W.; Zhao, Y.; Zhang, Z.; Tan, N.; Zhao, F.; Ge, C.; Liang, L.; Jia, D.; Chen, T.; Yao, M.; Li, J.; He, X. Disruption of xCT inhibits cell growth via the ROS/autophagy pathway in hepatocellular carcinoma. Cancer Lett, 2011, 312(1) 55-61.
55. Christensen, H. N.; Oxender, D. L.; Liang, M.; Vatz, K. A. The use of N-methylation to direct route of mediated transport of amino acids. J Biol Chem, 1965, 240(9) 3609-3616.
56. 11C] methylaminoisobutyric acid, a tracer for PET studies on system A amino acid transport in vivo. Eur J Nucl Med, 2001, 28(7) 847-854.
57. 18F]fluorotyrosine, a new PET tracer of protein synthesis. J Nucl Med, 1989, 30(8) 1367-1372.
58. 18F]fluoro-L-dopa and its metabolism in vivo--a critical review. Int J Rad Appl Instrum B, 1992, 19(2) 149-158.
59. Christensen, H. N.; Oxender, D. L. The Acid Strength of the Amino Group as a Factor in the Transport of Amino Acids. Biochim Biophys Acta, 1963, 74 386-391.
60. Mach, R. H.; Schwarz, S. W. Challenges for Developing PET Tracers: Isotopes, Chemistry, and Regulatory Aspects. PET Clin, 2010, 5(131-153.
61. 18F]fluoro-L-dopa. J. Nucl. Med., 1984, 25(11) 1228-1233.
62. Misaki, S. Direct fluorination of aryl oxygen compounds. J. Fluorine Chem., 1982, 21(2) 191-199.
63. 18F]F2. Journal of Labelled Compounds and Radiopharmaceuticals, 1986, 23(1101-1102.
64. Chirakal, R.; Sayer, B. G.; Firnau, G.; Garnett, E. S. Synthesis of F18 labeled fluoromelatonins and 5-hydroxyfluorotryptophans. J. Labelled Compd. Radiopharm., 1988, 25(1) 63-71.
65. Coenen, H. H.; Franken, K.; Kling, P.; Stoecklin, G. Direct electrophilic radiofluorination of phenylalanine, tyrosine and dopa. Appl. Radiat. Isot., 1988, 39(12) 1243-1250.
66. 18F-alpha-methylty rosine using a separation and purification system. Nucl Med Commun, 1997, 18(2) 169-175.
67. 18F]-F2 and [18F]-CH3CO2F and Regioselective Preparation of L-p-[18F] Fluorophenylalanine. Journal of Labelled Compounds & Radiopharmaceuticals, 1986, 23(10-12) 1179-1181.
68. Hess, E.; Sichler, S.; Kluge, A.; Coenen, H. H. Synthesis of 2 [18F]fluoro-L-tyrosine via regiospecific fluoro-de-stannylation. Appl. Radiat. Isot., 2002, 57(2) 185-191.
69. de Vries, E. F. J.; Luurtsema, G.; Brussermann, M.; Elsinga, P. H.; Vaalburg, W. Fully automated synthesis module for the high yield one-pot preparation of 6-[F-18]fluoro-L-DOPA. Applied Radiation and Isotopes, 1999, 51(4) 389-394.
70. 18F]fluoro-L-DOPA. Appl. Radiat. Isot., 2003, 58(5) 575-578.
71. 18F]-Labeled phenylalanines. J. Nucl. Med., 1971, 12(6) 280-286.
72. 18F]fluoroaromatic substituted amino acids: no carrier added L-p-[18F]fluorophenylalanine. Appl. Radiat. Isot., 1987, 38(12) 1033-1038.
73. Damhaut, P.; Lemaire, C.; Plenevaux, A.; Brihaye, C.; Christiaens, L.; Comar, D. No-carrier-added asymmetric synthesis ofmethyl-amino acids labeled with fluorine-18. Tetrahedron, 1997, 53(16) 5785-5796.
74. 18F]Fluoro-L-dopa by Chiral Phase-Transfer Alkylation. European Journal of Organic Chemistry, 2004, 2004(13) 2899-2904.
75. Wagner, F. M.; Ermert, J.; Coenen, H. H. Three-step, one-pot radiosynthesis of 6-fluoro-3,4-dihydroxy-L-phenylalanine by isotopic exchange. J. Nucl. Med., 2009, 50(10) 1724-1729.
76. Hoefling, S. B.; Hultsch, C.; Wester, H.-J.; Heinrich, M. R. Radiochemical 18F-fluoroarylation of unsaturated -, and-amino acids, application to a radiolabeled analog of baclofen. Tetrahedron, 2008, 64(52) 11846-11851.
77. 18F]fluoroethyl)-L-tyrosine for tumor imaging. J Nucl Med, 1999, 40(1) 205-212.
78. 18F]fluoroethylty rosine for cancer imaging: simple, fast, and high yielding automated synthesis. Bioorg Med Chem, 2009, 17(21) 7441-7448.
79. Bourdier, T.; Greguric, I.; Roselt, P.; Jackson, T.; Faragalla, J.; Katsifis, A. Fully automated one-pot radiosynthesis of O-(2-[18F]fluoroethyl)-L-tyrosine on the TracerLab FX(FN) module. Nucl Med Biol, 2011, 38(5) 645-651.
80. 18F-fluoroethoxy)-L-tryptophan as a substrate of system L transport for tumor imaging by PET. J Nucl Med, 2012, 53(3) 434-442.
81. 18F fluoroethyl-L-tyrosine. Appl Radiat Isot, 2002, 57(6) 853-856.
82. 18F]fluoromethyl-Ltyrosine as potential PET tracers for imaging amino acid transport. J. Labelled Compd. Radiopharm., 2003, 46(6) 555-566.
83. 18F]fluoropropyl)-L-tyrosine as an oncologic PET tracer. Nucl Med Biol, 2003, 30(7) 733-739.
84. 18F]fluoromethyl-L-phenylalanine, a new tumor tracer, during radiosynthesis and radiopharmaceutical formulation. Nucl. Med. Biol., 2008, 35(4) 425-432.
85. Kersemans, K.; Mertens, J.; Caveliers, V. Radiosynthesis of 4-[18F]fluoromethyl-L-phenylalanine and [18F]FET via a same strategy and automated synthesis module. J. Labelled Compd. Radiopharm., 2009, 53(2) 58-62.
86. 18F-labeled fluoroalkyl phenylalanine derivatives as tumor imaging agents. Nucl Med Biol, 2011, 38(3) 301-312.
87. 18F]fluoroethyl)-L-tyrosine via a novel type of chiral enantiomerically pure precursor, NiII complex of a (S)-tyrosine Schiff base. Bioorg. Med. Chem., 2008, 16(9) 4994-5003.
88. 18F]fluoro-Lproline, radiotracers for pet-investigation of disordered matrix protein synthesis. J. Labelled Compd. Radiopharm., 1999, 42(12) 1135-1144.
89. Wester, H.-J.; Herz, M.; Senekowitsch-Schmidtke, R.; Schwaiger, M.; Stocklin, G.; Hamacher, K. Preclinical evaluation of 4-[18F]fluoroprolines: diastereomeric effect on metabolism and uptake in mice. Nucl. Med. Biol., 1999, 26(3) 259-265.
90. 11C-1aminocyclopentanecarboxy lic acid, a potential agent for cancer detection. J Nucl Med, 1976, 17(8) 748-751.
91. 11C] carboxylic acid: preliminary clinical trials with single-photon detection. J Nucl Med, 1977, 18(12) 1215-1221.
92. Washburn, L. C.; Sun, T. T.; Anon, J. B.; Hayes, R. L. Effect of structure on tumor specificity of alicyclic alpha-amino acids. Cancer Res, 1978, 38(8) 2271-2273.
93. 18F]1-amino-3-fluorocyclobutane-1carboxylic acid to image brain tumors. J Nucl Med, 1999, 40(2) 331-338.
94. Shoup, T. M.; Goodman, M. M. Synthesis of [F-18]-1-amino-3-fluorocyclobutane-1-carboxylic acid (FACBC): A PET tracer for tumor delineation. Journal of Labelled Compounds & Radiopharmaceuticals, 1999, 42(3) 215-225.
95. 18F]FACBC: improved preparation of labeling precursor and automated radiosynthesis. Appl Radiat Isot, 2003, 58(6) 657-666.
96. 18F]fluorocyclobutyl-1-carboxylic acid as a potential positron emission tomography brain tumor imaging agent. Bioorg Med Chem, 2009, 17(5) 1982-1990.
97. Martarello, L.; McConathy, J.; Camp, V. M.; Malveaux, E. J.; Simpson, N. E.; Simpson, C. P.; Olson, J. J.; Bowers, G. D.; Goodman, M. M. Synthesis of synand anti-1-amino-3-[18F]fluoromethyl-cyclobutane-1-carboxylic acid (FMACBC), potential PET ligands for tumor detection. J Med Chem, 2002, 45(11) 2250-2259.
98. Qu, W.; Zha, Z.; Ploessl, K.; Lieberman, B. P.; Zhu, L.; Wise, D. R.; Thompson, C. B.; Kung, H. F. Synthesis of optically pure 4-fluoro-glutamines as potential metabolic imaging agents for tumors. J Am Chem Soc, 2011, 133(4) 1122-1133.
99. 18F]Fluoroglutamic Acid (BAY 85-8050), a New Amino Acid Radiotracer for PET Imaging of Tumors: Synthesis and in Vitro Characterization. J. Med. Chem., ACS ASAP.
100. Melenedz, R. E.; Lubell, W. D. Synthesis and reactivity of cyclic sulfamidites and sulfamidates. Tetrahedron, 2003, 59(15) 2581-2616.
101. Boulton, L. T.; Stock, H. T.; Raphy, J.; Horwell, D. C. Generation of unnatural alpha,alpha-disubstituted amino acid derivatives from cyclic sulfamidates. Journal of the Chemical Society-Perkin Transactions 1, 1999, 11) 1421-1429.
102. Posakony, J. J.; Tewson, T. J. Substitution reactions of hindered cyclic sulfamidates. Synthesis-Stuttgart, 2002, 7) 859-864.
103. Posakony, J. J.; Grierson, J. R.; Tewson, T. J. New routes to Nalkylated cyclic sulfamidates. Journal of Organic Chemistry, 2002, 67(15) 5164-5169.
104. Yu, W.; McConathy, J.; Williams, L.; Camp, V. M.; Malveaux, E. J.; Zhang, Z.; Olson, J. J.; Goodman, M. M. Synthesis, Radiolabeling, and Biological Evaluation of (R) and (S)-2-Amino-3-[18F]Fluoro-2-Methylpropanoic Acid (FAMP) and (R) and (S)-3-[18F]Fluoro-2-Methyl-2-N-(Methylamino)propanoic Acid (NMe-FAMP) as Potential PET Radioligands for Imaging Brain Tumors. J. Med. Chem., 2010, 53(2) 876-886.
105. Jarkas, N.; Voll, R. J.; Williams, L.; Camp, V. M.; Goodman, M. M. (R,S)-anti-1-Amino-2-[F-18]Fluorocyclopentyl-1-carboxylic Acid: Synthesis from Racemic 2-Benzyloxycyclopentanone and Biological Evaluation for Brain Tumor Imaging with Positron Emission Tomography. Journal of Medicinal Chemistry, 2010, 53(18) 6603-6607.
106. 18F]FACBC) in rat 9L gliosarcoma. Bioorg. Med. Chem. Lett., 20(7) 2140-2143.
107. Moses, J. E.; Moorhouse, A. D. The growing applications of click chemistry. Chem Soc Rev, 2007, 36(8) 1249-1262.
108. 18f]fluoroethylazide for positron emission tomography. Bioconjug Chem, 2007, 18(3) 989-993.
109. Marik, J.; Sutcliffe, J. L. Click for PET: rapid preparation of [F-18]fluoropeptides using Cu-I catalyzed 1,3-dipolar cycloaddition. Tetrahedron Letters, 2006, 47(37) 6681-6684.
110. Thonon, D.; Kech, C.; Paris, J.; Lemaire, C.; Luxen, A. New strategy for the preparation of clickable peptides and labeling with 1-(azidomethyl)-4-[(18)F]-fluorobenzene for PET. Bioconjug Chem, 2009, 20(4) 817-823.
111. Demko, Z. P.; Sharpless, K. B. An intramolecular [2 + 3] cycloaddition route to fused 5-heterosubstituted tetrazoles. Org Lett, 2001, 3(25) 4091-4094.
112. 18F-fluorocyclobutanecarboxylic acid in human prostate cancer. J Nucl Med, 2011, 52(5) 822-829.
113. Ricci, P. E.; Karis, J. P.; Heiserman, J. E.; Fram, E. K.; Bice, A. N.; Drayer, B. P. Differentiating recurrent tumor from radiation necrosis: time for re-evaluation of positron emission tomography? AJNR Am J Neuroradiol, 1998, 19(3) 407-413.
114. Wyss, M.; Hofer, S.; Bruehlmeier, M.; Hefti, M.; Uhlmann, C.; Bartschi, E.; Buettner, U. W.; Roelcke, U. Early metabolic responses in temozolomide treated low-grade glioma patients. J Neurooncol, 2009, 95(1) 87-93.
115. Plotkin, M.; Blechschmidt, C.; Auf, G.; Nyuyki, F.; Geworski, L.; Denecke, T.; Brenner, W.; Stockhammer, F. Comparison of F-18 FET-PET with F-18 FDG-PET for biopsy planning of non-contrastenhancing gliomas. Eur Radiol, 2010, 20(10) 2496-2502.
116. Weber, D. C.; Zilli, T.; Buchegger, F.; Casanova, N.; Haller, G.; Rouzaud, M.; Nouet, P.; Dipasquale, G.; Ratib, O.; Zaidi, H.; Vees, H.; Miralbell, R. [(18)F]Fluoroethyltyrosinepositron emission tomography-guided radiotherapy for high-grade glioma. Radiat Oncol, 2008, 3(44.
117. 18F]fluoro-L-proline. Nucl Med Biol, 2004, 31(1) 67-75.
118. Popperl, G.; Kreth, F. W.; Mehrkens, J. H.; Herms, J.; Seelos, K.; Koch, W.; Gildehaus, F. J.; Kretzschmar, H. A.; Tonn, J. C.; Tatsch, K. FET PET for the evaluation of untreated gliomas: correlation of FET uptake and uptake kinetics with tumour grading. Eur J Nucl Med Mol Imaging, 2007, 34(12) 1933-1942.
119. 18F-FET PET for grading of recurrent gliomas: is evaluation of uptake kinetics superior to standard methods? J Nucl Med, 2006, 47(3) 393-403.
120. Jansen, N. L.; Graute, V.; Armbruster, L.; Suchorska, B.; Lutz, J.; Eigenbrod, S.; Cumming, P.; Bartenstein, P.; Tonn, J. C.; Kreth, F. W.; la Fougere, C. MRI-suspected low-grade glioma: is there a need to perform dynamic FET PET? Eur J Nucl Med Mol Imaging, 2012, 39(6) 1021-1029.
121. 18F]fluoroethyl)-L-tyrosine (F-18 FET) PET for glioma grading: assessment of individual probability of malignancy. Clin Nucl Med, 2011, 36(10) 841-847.
122. 18F-fluoro-L-dopa PET uptake with proliferation and tumor grade in newly diagnosed and recurrent gliomas. J Nucl Med, 2010, 51(10) 1532-1538.
123. 18F-FDOPA kinetics in brain tumors. J Nucl Med, 2007, 48(10) 1651-1661.
124. 18F-Fluoroethyl)-L-Tyrosine PET for Differentiation of Local Recurrent Brain Metastasis from Radiation Necrosis. J Nucl Med, 2012,
125. Sundin, A.; Garske, U.; Orlefors, H. Nuclear imaging of neuroendocrine tumours. Best Pract Res Clin Endocrinol Metab, 2007, 21(1) 69-85.
126. 131I-metaiodobenzylguanidine therapy of neuroblastoma and other neuroendocrine tumors. Semin Nucl Med, 2010, 40(2) 153-163.
127. Graham, M. M.; Menda, Y. Radiopeptide imaging and therapy in the United States. J Nucl Med, 2011, 52 Suppl 2(56S-63S.
128. 68Ga-DOTATOC PET-CT in the diagnosis and staging of pancreatic neuroendocrine tumours. Eur Radiol, 2011,
129. Breeman, W. A.; de Blois, E.; Sze Chan, H.; Konijnenberg, M.; Kwekkeboom, D. J.; Krenning, E. P. (68)Ga-labeled DOTA-peptides and (68)Ga-labeled radiopharmaceuticals for positron emission tomography: current status of research, clinical applications, and future perspectives. Semin Nucl Med, 2011, 41(4) 314-321.
130. 18F]fluoro-3,4-dihydroxy-L-phenylalanine accumulation in neuroendocrine tumor cells. Cancer Res, 2008, 68(17) 7183-7190.
131. Yakemchuk, V. N.; Jager, P. L.; Chirakal, R.; Reid, R.; Major, P.; Gulenchyn, K. Y. PET/CT using (18)F-FDOPA provides improved staging of carcinoid tumor patients in a Canadian setting. Nucl Med Commun, 2012, 33(3) 322-330.
132. 123I-MIBG scintigraphy in stage 3 and 4 neuroblastoma: a pilot study. Eur J Nucl Med Mol Imaging, 2012, 39(1) 57-71.
133. 18F-DOPA PET/CT in neuroblastoma: comparison of conventional imaging with CT/MR. Clin Nucl Med, 2012, 37(4) e73-78.
134. Siegel, R.; Desantis, C.; Virgo, K.; Stein, K.; Mariotto, A.; Smith, T.; Cooper, D.; Gansler, T.; Lerro, C.; Fedewa, S.; Lin, C.; Leach, C.; Cannady, R. S.; Cho, H.; Scoppa, S.; Hachey, M.; Kirch, R.; Jemal, A.; Ward, E. Cancer treatment and survivorship statistics, 2012. CA: a cancer journal for clinicians, 2012, 62(4) 220-241.
135. 11C-choline. J Nucl Med, 2011, 52(1) 81-89.
136. Oka, S.; Okudaira, H.; Yoshida, Y.; Schuster, D. M.; Goodman, M. M.; Shirakami, Y. Transport mechanisms of trans-1-amino-3-fluoro[1-(14)C]cyclobutanecarboxylic acid in prostate cancer cells. Nucl Med Biol, 2012, 39(1) 109-119.
137. 18F-FET uptake in experimental soft tissue infection. Eur J Nucl Med Mol Imaging, 2002, 29(5) 648-654.
138. 18F-FLT for differentiation between tumor and inflammation in rats. Nucl Med Biol, 2009, 36(6) 681-686.
139. 18F-FDG PET and CT in patients with head and neck cancer. J Nucl Med, 2006, 47(2) 256-261.
140. Conti, P. S.; Sordillo, P. P.; Schmall, B.; Benua, R. S.; Bading, J. R.; Bigler, R. E.; Laughlin, J. S. Tumor imaging with carbon-11 labeled alpha-aminoisobutyric acid (AIB) in a patient with advanced malignant melanoma. Eur J Nucl Med, 1986, 12(7) 353-356.
141. Schmall, B.; Conti, P. S.; Bigler, R. E.; Zanzonico, P. B.; Reiman, R. E.; Benua, R. S.; Yeh, S. D.; Dahl, J. R.; Lee, R.; Laughlin, J. S. Imaging studies of patients with malignant fibrous histiocytoma using C-11-alpha-aminoisobutyric acid (AIB). Clin Nucl Med, 1987, 12(1) 22-26.
142. 11C]alpha-methylaminoisobutyric acid in untreated head and neck cancer studied by PET. Eur J Nucl Med Mol Imaging, 2003, 30(1) 72-77.
143. McConathy, J.; Yu, W. P.; Jarkas, N.; Seo, W.; Schuster, D. M.; Goodman, M. M. Radiohalogenated nonnatural amino acids as PET and SPECT tumor imaging agents. Medicinal Research Reviews, 2012, 32(4) 868-905.
144. 18F-FMT uptake seen within primary cancer on PET helps predict outcome of non-small cell lung cancer. J Nucl Med, 2009, 50(11) 1770-1776.
145. Wise, D. R.; Thompson, C. B. Glutamine addiction: a new therapeutic target in cancer. Trends in biochemical sciences, 2010, 35(8) 427-433.
146. DeBerardinis, R. J.; Lum, J. J.; Hatzivassiliou, G.; Thompson, C. B. The biology of cancer: metabolic reprogramming fuels cell growth and proliferation. Cell metabolism, 2008, 7(1) 11-20.
147. Delage, B.; Fennell, D. A.; Nicholson, L.; McNeish, I.; Lemoine, N. R.; Crook, T.; Szlosarek, P. W. Arginine deprivation and argininosuccinate synthetase expression in the treatment of cancer. Int J Cancer, 2010,
148. Wheatley, D. N. Arginine deprivation and metabolomics: important aspects of intermediary metabolism in relation to the differential sensitivity of normal and tumour cells. Semin Cancer Biol, 2005, 15(4) 247-253.
149. Lind, D. S. Arginine and cancer. J Nutr, 2004, 134(10 Suppl) 2837S-2841S; discussion 2853S.
150. Ascierto, P. A.; Scala, S.; Castello, G.; Daponte, A.; Simeone, E.; Ottaiano, A.; Beneduce, G.; De Rosa, V.; Izzo, F.; Melucci, M. T.; Ensor, C. M.; Prestayko, A. W.; Holtsberg, F. W.; Bomalaski, J. S.; Clark, M. A.; Savaraj, N.; Feun, L. G.; Logan, T. F. Pegylated arginine deiminase treatment of patients with metastatic melanoma: results from phase I and II studies. J Clin Oncol, 2005, 23(30) 7660-7668.
151. Izzo, F.; Marra, P.; Beneduce, G.; Castello, G.; Vallone, P.; De Rosa, V.; Cremona, F.; Ensor, C. M.; Holtsberg, F. W.; Bomalaski, J. S.; Clark, M. A.; Ng, C.; Curley, S. A. Pegylated arginine deiminase treatment of patients with unresectable hepatocellular carcinoma: results from phase I/II studies. J Clin Oncol, 2004, 22(10) 1815-1822.
152. Ensor, C. M.; Holtsberg, F. W.; Bomalaski, J. S.; Clark, M. A. Pegylated arginine deiminase (ADI-SS PEG20,000 mw) inhibits human melanomas and hepatocellular carcinomas in vitro and in vivo. Cancer Res, 2002, 62(19) 5443-5450.
153. Nabeyama, A.; Kurita, A.; Asano, K.; Miyake, Y.; Yasuda, T.; Miura, I.; Nishitai, G.; Arakawa, S.; Shimizu, S.; Wakana, S.; Yoshida, H.; Tanaka, M. xCT deficiency accelerates chemically induced tumorigenesis. Proc Natl Acad Sci U S A, 2010, 107(14) 6436-6441.
154. 125I-iodo-alphamethyl-L-tyrosine membrane transport in human L-type amino acid transporters. J Nucl Med, 2003, 44(2) 244-246.